We’re approaching the one-year mark of this blog. My original target was 2 posts a week when I’m not on vacation, which would have netted me around 90 a year. I’m currently at 78 posts. My biking accident¹ along with some family struggles are my rationale for missing this target. Regardless of coming up short, I have greatly enjoyed the process and the results (“Celebrate progress though short of perfection”), so this blog will live on. But I am making a fundamental change …

I want to thank the paying subscribers for helping to fund the bootstrapping of my uplevel pro business. It was valuable funding during this transition. But at the one year mark for my business, I have been evaluating the different revenue streams, and have concluded that the uplevel pro blog is much better as a free asset than as paid content. This blog has been more successful as an onramp to my coaching and university work than as a separate revenue stream. And by removing the paywalls, that will only increase the onramp potential.

So before your annual subscription payments come up for renewal, I’m canceling all paid subscriptions and removing all paywalls. The uplevel pro blog will be free to everyone. Enjoy … and share broadly!

This blog will be quiet for the rest of June while I take a few vacations. See you all here in July.

Happy Birthday, uplevel pro!

Footnotes

1. “Life is what happens to you while you’re busy making other plans”¹

There are no shortage of articles (including a few of my own¹) that call out this dilemma:

AI is easily the most powerful tool we’ve ever worked with. AI is incredibly versatile, and can help us in nearly every aspect of our lives. So it’s easy to see why people are so impressed with the technology. But AI has fundamental limitations that people are losing sight of, resulting in an overreliance on a digital brain and an underreliance on their own human brain.

Collectively, we’re all trying to get to a clearer articulation of the optimal partnership between human and AI. This is my latest attempt, and I have Arthur Brooks to thank for planting the right seed in my brain.

In “The Meaning of Your Life”², Arthur Brooks makes an important distinction between Complex and Complicated. “Complex challenges in life are easy to understand but impossible to solve, so they can only be lived and understood. This is in contrast to the complicated parts of life, which can be hard to understand but are solvable once and for all.”

Arthur establishes this difference early in his book to set up a deep dive into the search for meaning in your life, which comes down to intentionally spending more time on the Complex. We are bombarded with Complicated, such that it grows to fill all available space. One great example he uses is the lack of boredom in modern lives. Boredom used to come when none of your friends were around, when were in line at the grocery store checkout, or you had just finished your final exams for the year. But now, at the first hint of boredom, we reach for our phones or dive into a streaming show. Whew, what a relief, we don’t have to sit idle. The problem is that this boredom is where our big ideas come from. Boredom is when we ponder, and wonder.³

This framing resonated with me, and reminded of my annual retreats that are intentional periods of boredom binging. I’m certainly going to be covering gems from Arthur’s book in later posts once I’ve finished reading it and incorporating it into my Grand Synthesis.⁴ For now, I want to use Arthur’s Complex/Complicated framing to help better distinguish AI strengths and human strengths, in hopes of making you less likely to cognitively surrender to AI. Let’s explore.

Comparing Complex and Complicated

The best way to define Complex and Complicated is through a comparison. “The Meaning of Your Life” gave me a handful of comparisons to begin with, then I added a set of comparisons on my own. My final step was to brainstorm with Copilot and polish the table. Here is the result of our joint effort:

Read through this table several times, slowly. Once you’re at the point where you are seeing this dividing line clearly enough that you hopefully add another row or two of your own, then you’re ready to move on.

Making time for the Complex

Arthur claims that we are spending too much time on the left side of this table. Through our own busyness, and not having the space for reflection, we’re not wrestling with the big problems. And it makes sense when you see the above comparisons. Complex problems are ill-defined. They’re ambiguous. Rather than being rewarded with a final answer, Complex problems have evolving solutions, that will require even more pondering. Why bother?

I Heart Huckabees is one of my favorite movies (#3 on my top ten list, to be exact), and one of my favorite scenes from this movie is when the main characters are guests for dinner with a family that they don’t know.⁵ Albert explains that he’s working with an existential detective and the kids ask what that is. He gives a couple of examples of questions he’s been wrestling with, “If the forms of this world die, which is more real, the me that dies or the me that is infinite? Can I trust my habitual mind, or do I need to learn to look beneath those things?” One of the kids at the table asks, “We don’t have to ask those kinds of questions, do we mommy?” Mom calmly replies, “No honey.”

The Complex problems are essential to wrestle with. It’s what makes us human. But they’re easily dismissed, as this family does at the dinner table. Maybe Albert’s examples are pretty extreme, but how about a more common Complex problem like, “What am I doing here?” That’s a fun one to entertain.

When I realized for myself that I wasn’t giving the Complex enough attention, I forced myself out of the Complicated auto-pilot and took my first retreat (in April of 2001). What followed was a nine month overdosing on the Complex. I don’t recommend that approach, but it was what I needed, and the result was literally and completely life changing. The good news is that the reset was a one-time disruption. Now I just regularly give the Complex time, and am okay with the answers slowly evolving. I’m living, intentionally.

AI knows Complicated

Look back at the comparison table, and then think about your last dozen exchanges with AI. Where were you and AI operating: in the Complicated domain or in the Complex domain? You may have been moving between these two domains, but make no mistake about it, AI was only working in the Complicated domain.

The sum total of what AI knows is what it has read. Complicated things are easier to explicitly articulate than Complex things. It stands to reason that far more Complicated ideas have been written down than Complex ideas. So, AI’s knowledge base is skewed heavily on the side of Complicated.

Further, what the Complex side of this table shows is that Complex is far less about knowing and far more about pondering. Arthur gave an example of Koko the gorilla, who accomplished the impressive feat of learning more than a thousand words in sign language over four decades. But Arthur pointed out that in all the conversations with Koko, the gorilla never asked a single question. Similarly, AI is waiting for you to ask the questions. AI never starts the inquiry. Does AI wonder? Or, as Philip Dick asks in the title of his novel, “Do Androids Dream of Electric Sheep?”

Tune your partnership with AI

AI can help us with the Complicated. Complicated problems are in AI’s wheelhouse. Deferring Complicated work to AI frees up more time for us to do Complex work. This partnership maximizes the payoff of AI while reminding us through the experience itself what us humans are good at, and good for. This division of labor helps you more clearly answer, “How do I uniquely add value?”⁶

When I was done with my exchange with AI on this Complicated vs. Complex topic, I wasn’t saying “what’s the point of me being here? AI can do all of this.” I was celebrating the partnership, where I had ideas and thoughts that AI helped me sharpen.

In my “AI’s Love Language is Precision”^1b post, I called out four Kettering quotes that point us towards the right balance to have with AI. I want to replay the last of those four quotes here: “There is a great difference between knowing and understanding: you can know a lot about something and not really understand it.” AI knows a ton, but it doesn’t understand it.

My three favorite Copilot gems⁷ from our collaboration for this post are:

• “AI is extremely strong at knowledge. AI approximates understanding.” “AI knows a lot, and sounds like it understands.” - Copilot is telling us why we get fooled, and reminding us to not be fooled. AI sounds like it understands. The eloquence and the verbosity of AI responses hypnotize us. Snap out of it.

• “It has pattern knowledge of tacit domains, but not situated participation in them“ “AI doesn’t just know explicit things—it learns statistical echoes of tacit knowledge—but without the real-world grounding that makes human expertise reliable.” - I love the phrase “statistical echoes of tacit knowledge.” You have feelings inside of you that come from a profoundly rich base of tacit knowledge. AI has 1s and 0s inside of it. Celebrate your depth, and bring that depth to your AI collaborations. Going back to the I Heart Huckabees dinner scene, how could AI ever know “what happens when you stand in a meadow at dusk?” 🙂

• “Complex problems aren’t solvable until you make them complicated.” - This is the pure gold line for me. This captures the serious work involved in tackling Complex problems, and highlights where AI can best help. Just like with the table that started this post. I had been struggling to fully articulate this dividing line. I took the start that I had and an explanation of where I was trying to go. And in so doing, I made this piece of the Complex problem Complicated, at which point AI can add its value: (1) broad knowledge and (2) rigor.

You make progress on your Complex problems by iteratively turning ambiguity into structure. You move one aspect from ill-defined to well-defined. And then AI helps you rapidly and effectively polish that well-defined piece. Then you tackle another aspect, and another.

Use AI to accelerate and enrich your Complicated work, so that you have more time to fully commit yourself to your Complex work. That’s when you’re uniquely adding value. That’s when you’re contributing a verse. And that’s why you’re here.

Footnotes

1. 3 examples:

   1. Actual Intelligence + Artificial Intelligence = 🥇🏆🎉: Partner with AI; Don’t Defer to it

   2. AI’s Love Language is Precision: “A problem well stated is a problem half-solved”

   3. Touch Grass: Your AI agents don’t need breaks, but you do

2. The Meaning of Your Life, Arthur C. Brooks (Goodreads)

3. Boredom is the Mother of Reflection

4. You Are a Grand Synthesis

5. I Heart Huckabees What Happens In The Meadow At Dusk

6. I have referenced this fundamental question, that came out of my first retreat, in several posts:

   1. The “Spiritual Capacity” description in Revving Your Energy Flywheel

   2. The “Everyone is a Subject Matter Expert of Something” section of Lifelong Student-Teacher

   3. The introduction of Triage Shield

7. Mining for Gems

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In The Seven Habits of Highly Effective People¹, Stephen Covey divides seven habits into two spheres: private victory and public victory². The first three habits help move you from dependent to independent to become a more effective individual. This is your private victory. The next three habits help move you from independent to interdependent to become a more effective member of society. This is your public victory. The seventh habit is renewal, where you regularly revisit and hone the other six habits, iteratively raising your overall effectiveness.

In his introduction of the public victory habits, Stephen introduces the term “Emotional Bank Account”, which he defines as “the amount of trust that’s been built up in a relationship.” Relationships are complex and varied, making them very hard to assess. That’s not really a problem, because we spend less time evaluating relationships than we do experiencing relationships. Nonetheless, having tools to help measure both the health and value of a relationship can be helpful to periodically assess the give and take of a relationship.

With an Emotional Bank Account, you are making deposits when you invest in the relationship and build energy and trust, and you are making withdrawals when you sap that energy or betray that trust. Your strongest relationships have a high balance in their accounts, while your weakest relationships are the ones that are at risk of being overdrawn, or perhaps already are.

I like the metaphor of a bank account to represent the stockpiled energy and trust in a relationship, and I’d like to expand on this. Emotional Bank Accounts are very specific, with each account relating to a single relationship. A person can have a highly positive balance for one relationship while running negative for another relationship. Your public victory comes from intentionally managing all of your Emotional Bank Accounts … your overall Emotional Credit Rating.

This isn’t about keeping score, but about raising your own awareness³ on how you show up in your relationships. You can use these insights to invest strategically in your relationship portfolio, becoming a more effective individual and a more effective member of society.

Here’s how to measure and manage your own Emotional Credit Rating.

Computing your Emotional Credit Rating

In The Meaning of Your Life⁴, Arthur Brooks describes another approach to measuring a relationship: by depth. In Nicomachean Ethics, Aristotle defines three levels of depth in relationships:

1. Friendships of utility - Individuals are useful to each other for something they each want. Arthur describes such friendships as, “There’s nothing wrong with these friendships, but they don’t bring significance, because they aren’t about your being, only your doing.”

2. Friendships of pleasure - These are friendships based on the pleasure you bring to each other. Arthur says, “These are very nice relationships to have, but they can’t give you a sense of meaning because, once again, they are about doing, not being.”

3. Friendships of virtue - These relationships are based on mutual respect and admiration. Arthur calls these, “The relationships that bring true meaning—they define why your life matters … They love your being and you love theirs.”

This depth framing sets up an Arthur exercise. “Make a list of the ten people with whom you spend the most hours each week—colleagues, family members, acquaintances. This includes in person or virtually. Put them in order of time spent with each. After each name, write utility, pleasure, or virtue. Of course, some are more than just one. Write the highest level, not the lowest. But be honest with yourself. If your partner only likes you because you are physically beautiful, this is not a virtuous friendship.”

Once you’ve done this exercise, you just need to add one more step to get to your Emotional Credit Rating. For each relationship, write down the Emotional Bank Account balance for that relationship, a number in the range of -10 to 10. -10 means completely overdrawn, 0 means even, and 10 means couldn’t be any higher. Then add a short explanation for that number. Is the give and take even or one-sided? Is it more of an energy giver or an energy taker⁵?

Now you have a clearer picture of your current Emotional Credit Rating. Are you happy with the rating or do you want to take steps to improve it? Here are some options to consider.

1. Add a friendship. Do you feel like you have more to give … and more to get? This exercise may make you realize you’re not connecting with others enough. Put yourself out there more to discover new friendships. As your elementary school teachers told you, “A stranger is just a friend you haven’t met yet.” 😜Is there a running group you could connect with? Is there a volunteer opportunity that resonates with you? There are countless ways to create more connection opportunity. Just a word of caution: more time on social media won’t equate to more friendships.

2. Upgrade a friendship. Is there a friendship that you want to promote to a friendship of virtue? Or maybe you’re already there, but you don’t get enough time together. Recognize the potential of these stronger friendships and invest more in them. This just happened with me, when I was visiting a colleague at Microsoft last week. Earlier in our careers, we were part of a philosophy discussion group where we saw each other monthly. Now, we had only seen each other twice in the last year. At the end of our meeting last week, he said, “it’s conversations like this that have me wanting to do this more.” I agreed, and now we’re comparing calendars to find a monthly 1:1 slot.

3. Downgrade a friendship. Has a friendship run its course at the current depth? Should it be demoted to a pleasure friendship or a utility friendship? Be honest with yourself and ask if the friendship has run its course and should just be removed entirely. Entertaining this question is a good test, as it may reveal hidden value you hadn’t realized. But if it doesn’t, then let it go. Remember this: “I have an infinite capacity to love, but a finite time in which to demonstrate that love.”⁶ Choose wisely.

4. Change the energy. Relationships take work. It’s not just about happy times together. A friendship of pleasure may be a complete energy giver, but a friendship of virtue is going to come with some energy taking along with the energy giving. But check the overall energy balance. Has a relationship become too much of an energy taker? If that’s from your own side, then how can you be more of an energy giver to the friend? If that’s from the other side, can you bring that to their attention to see if they can make some intentional change? If not, then consider option #3 above.

5. Check your Emotional Energy Flywheel⁵. All things considered, are you feeling revved by the collective energy of all of these relationships? There are times when you may be putting yourself out there too much, to the point where you are threatening your own emotional well-being. “Remember to put your own mask on first before helping those around you.”⁷ You will be a better long-term friend to more people if you are keeping your own energy up.

Diversification

Just as your financial credit rating improves with more “active credit”, so does your Emotional Credit Rating. Don’t rely on one Emotional Bank Account for your entire credit rating.

My parents were of the generation where they liened on each other as needed, but kept others at arm’s length. They had friends, but in Aristotle’s terms, they were predominantly utility friends and pleasure friends. As Pop started to struggle both cognitively and physically, my Mom went into her own private hell cave. She remained hesitant to share the difficulties she was having even with her own children. We continually encouraged Mom to share the load with us, but old habits die hard.

This underscored the importance to me of having a diversity of deep friendships. Not only does it give me a larger pool of wisdom to draw from, but it also prevents me from burying one person in all of my liening. My Mom’s experience with my Dad changed how I viewed my own marriage, for the better. I love Charu, and it’s no surprise that our relationship tops my list in Arthur’s exercise above: I rated our Emotional Bank Account balance at the highest rating of 9 (I don’t give 10 because I believe there’s always room for improvement). But with other virtuous friendships in the mix, I don’t over-rely on Charu. We are interdependent, not codependent.

The “World” Account

In addition to the Emotional Bank Accounts you have for each of your friendships, there is also a general bank account that you should be more aware of: the account for your relationship with the world. Just as there are times when you can thank the individuals in your life for the help they’ve given you, there are those times when the world helps you out. You may call this karma. Or, for those who were part of the “Practice Random Acts of Kindness and Acts of Senseless Beauty” movement from the 80s, you may call it intentional randomness.

I grew up in Richmond, Virginia, where we had several tolled roads: Powhite Parkway, Downtown Expressway, I-95, and the Boulevard Bridge (nicknamed “the Nickel Bridge” … and then updated to “the Two-Nickel Bridge” when I was a kid). And for the younger readers, tolls back then went coins tossed in a basket (or given to the toll operator) to lift the gate. No fast pass electronic scanning.

When my family would go on a road trip, it often involved a small caravan of cars -- a family of 7 kids + 2 parents + relatives didn’t easily fit in one vehicle. When we’d reach the toll booth, dad would be in the lead car. He would tell the toll booth attendant that he was paying for the two cars behind him as well. Then he would stick his arm up for us to see, hold up two fingers, and then point forward, telling us he had paid for us already. We would then drive straight through, with the operator waving us by.

Shortly after I was driving age, and I found myself more commonly going through these toll booths, I was reminded of my dad doing this. Being someone who looked for opportunities to make a routine event more fun, I decided to start paying for the person behind me. It was an extra quarter (in most places), which was a cheap cost to feel good. And it did make me feel good. So I kept doing it. My friends asked me why I did it and I just answered, “I’m going to keep doing it until someone does it to me, because then I’ll know the idea has caught on.” And so I kept right on paying for the person behind me.

I did get several people tracking me down after the toll booth, racing up to catch me (no small task given my general driving speed) and honking or waving in thanks. But I never got my toll paid for me by a stranger. But 30-some years later, at a Starbucks drive thru in Wenatchee, Washington, I was given a withdrawal from my World Bank Account. We got to the window and the Starbucks employee handed me the tea, saying, “The person in front of you just paid for your tea.” I immediately asked, “Well can I pay for the person behind me to keep this going?” He responded, “They paid for them, too.” I said, “Sweet,” and drove off, with a very big smile on my face.

You do good for other people, and other people will do good for you.

Footnotes

1. The 7 Habits of Highly Effective People, Stephen Covey (Goodreads)

2. References to Public & Private victory in previous posts

3. Raising Your Own Awareness

4. The Meaning of Your Life, Arthur C. Brooks (Goodreads)

5. Revving Your Energy Flywheel

6. Love It Or Leave It

7. Short Term Selfishness Enables Long Term Selflessness

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Charles F. Kettering¹ was an inventor in the early ages of electrified work. He invented the electric starter, worked at General Motors, and created Delco. As an engineer, Charles valued precision in work, and saw communication as a key component to work. Hence his quote, “A problem well stated is a problem half-solved.” More than 100 years after Kettering coined that phrase, it is more applicable than ever, especially in the AI space. AI can do wonders and AI can fail miserably, and the single biggest determining factor of the outcomes of AI’s work is the precision of the prompt that AI was given.

Prompt engineering is the latest manifestation of engineering’s all-important technical communication skill. In an earlier post, I shared my encounter with how my technical communication was tested in my Microsoft interview, as I tried to explain to my interviewer the process of “driving a car from point A to point B.”² Technical communication is obviously important in engineering fields, but it is also powerful in any field. Engineering or otherwise, a dialogue between two people can easily become technical. Recognize the value of precision in your communication, and you will be a more effective communicator in all aspects of your life, from changing a smoke detector battery to hosting a great party.

AI is perhaps the best instructor of technical communication, through trial and error (and error and error). Embrace this opportunity and engage with AI to sharpen your communication. Spend quality time with AI and you’ll be rewarded for it. Build a relationship with your AI. Not a creepy relationship that has you convinced you’re falling in love with bits and bytes, but a relationship of mutual understanding through effective sharing. AI’s love language is precision, and as you build your muscle of effectively communicating your thoughts to AI, you will be rewarded with results from AI that are closer to your desired outcome, and that take less work for you and AI to co-create.

There are three other Kettering gems that I want to expand on as well, as they relate to this building of your technical communication muscle in an AI world.

• “The biggest job we have is to teach a newly hired employee how to fail intelligently. We have to train them to experiment over and over and to keep on trying and failing until they learn what will work.”

• “Inventing is a combination of brains and materials. The more brains you use, the less material you need.”

• “There is a great difference between knowing and understanding: you can know a lot about something and not really understand it.”

Experiment over and over

This came up in my most recent visit to Microsoft. Across conversations with several colleagues there, a theme was developing: they were describing a fundamental divide, between those employees that were successfully using AI to accelerate their work, and those stuck in the dabbling stage. It seems that some form of escape velocity is needed to move you from dabbling to all-in. This is where Charles’ quote provides solid advice. “The biggest job we have is to teach a newly hired employee how to fail intelligently. We have to train them to experiment over and over and to keep on trying and failing until they learn what will work.”

Fail intelligently. Don’t just keep running your head into a wall with AI. Step back from the action to observe³ what is working and what isn’t. Did AI hallucinate because you failed to provide important guardrails, such as “all references that you provide must be real artifacts available on the internet”? A bad AI output is an invitation to sharpen the precision of your communication. You can even leverage AI to help you get more precise. Ask AI to be your prompt engineer teacher in the context of your current dialogue with it.

Experiment over and over. If you’re not seeing AI as your partner in just about every aspect of your work, you’re missing opportunities to develop this important (non-creepy) relationship. Just as continued conversations with a colleague accelerates both the rate of exchange of information and the quality of that exchange, your repeated attempts to partner with AI will give both you and the AI a better understanding of each other. Over time, communication shorthands will naturally develop between you and your AI.

One signal to watch for in your experiments is the “pedantic trap”. You have to be far more explicit with AI than you would have to be with just about any human you are interacting with. The level of pedanticness that you need to demonstrate can quickly fatigue and frustrate you. The solution is to capture your favorite guardrails in boilerplate form, saved off and then readily applied to all of your conversations with AI. You can measure the maturity of your relationship with AI by how rich your boilerplate prompt is.

You escape the pedantic trap by upleveling the conversation. You reach escape velocity in your AI partnership by advancing from chat exchanges to agent creation, where you move from asking for a single thing to describing a responsibility for AI to take on. Build a varied set of agents that you use to offload more of the mundane aspects of your responsibilities, and you will begin to see the value of creating an overarching managing agent. Agents in depth is an impressive display of how clearly you can articulate what you need and how you need it.

More brains used == less materials needed

When Kettering said, “Inventing is a combination of brains and materials. The more brains you use, the less material you need,” he had no idea that one potential “material” would be “AI token count.” But his general statement applies perfectly. The number of tokens involved in an AI exchange is the measurable unit of conversation complexity. All up, this count is a rough signal of how deeply you are working with AI. Other similar signals are SLOC (Source Lines of Code) for a software engineer and chat count for a friend. You should never focus directly on maximizing token count, SLOC, or chat count. They are just signals that can help assess engagement level.

Some of my best friends require the fewest chats, because we are so in sync. And as any software engineer experiences through the progression of their own coding skills, you tend to have higher SLOC as a novice than you do as a professional, because you have learned how to more optimally reduce your ideas to code. So it goes with your AI conversations. With more precise prompts, the AI has to do less work for the desired result.

And when you find yourself playing in the context engineering space, you are further contributing to the escape velocity of your AI partnership. “Context” is the AI equivalent of a human’s working memory. This is everything that AI has “paged in” to work on a more involved exchange. When you are having an especially long conversation with AI, and you notice that it is beginning to forget some of the things you had said earlier, its context may have maxed out, at which point the AI did some compacting of context. Prompt engineering is helping you craft clearer prompts, and context engineering is helping you make sure you don’t stress AI’s working memory.

“It ain’t all that”

The final Kettering quote I want to expand on is his one of Charles’ more cautionary quotes: “There is a great difference between knowing and understanding: you can know a lot about something and not really understand it.” Kettering precisely captures the most important “great difference” to keep in mind when collaborating with AI.

We are a species that tries hard to understand things. But we all individually vary in what we can learn and how we can learn it. Us humans like to pretend, and it is sadly quite common for us to mask a lack of understanding with pretending to understand. This is why critical thinking is so critical for effective communication with each other. “Trust but verify” is a critical thinking tool. When you are working with someone, demonstrating trusting in their abilities will empower them to step up. But to ensure your trust is not misplaced, you need to occasionally verify that what they are delivering is meeting your expectations.

The better someone is at pretending to understand, the more you will unconsciously defer to trusting. Critical thinking demands that you consciously force the “but verify” piece to the top of mind. You can also take an “innocent until proven guilty” approach here where you trust until someone shows a reason to not trust, at which point you add the verify step to your interactions with that individual. “Fool me once, shame on you. Fool me twice, shame on me.”

I have come across a handful of pathological liars in my career. I am thankful that the number has been small, because they were all pretty devastating experiences for me. These individuals were so successful in capturing my trust that they tricked me out of the verify step, for way longer than I ever should have. Deliverables were missed, management was upset, and customers were lost. The long term learning for me was to realize that verifying is always needed, and should never be seen as an insult. Verifying is part of being professional.

As good as humans are at pretending to understand, AI makes them all look like amateur actors. AI’s mastery of language and delivery combined with the volume of its communications can fool anybody. So keep Kettering’s quote on hand, and refer to it regularly to build your verify muscle. AI knows more than any of us can know, as it has direct access to everything captured in binary form. But AI doesn’t understand any of that.

Don’t be fooled. The results can be devastating.

Footnotes

1. Biography and Innovations of Charles F Kettering (FixQuotes)

2. How We Should Interview

3. Raising Your Own Awareness

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On a team of 200 developers, breaking the build was a bad thing. You blocked testing, self-hosting, and further development. Everyone tried to be careful, but inevitably, amongst hundreds of check-ins, someone would break the build. The original solution was some shaming device. One team had a “fruit of questionable freshness” that was passed around from breaker to breaker. This had the added “benefit” of making breaks in the build later in the product cycle more of a punishment, because the fruit sitting on your desk would be increasingly questionable in its freshness. Whoever had the fruit of questionable freshness would actively be hoping for another build break so that they could unload their desk trophy.

That was fun, and had a bit of a “family ribbing each other” nature to it. But it wasn’t all that productive. The team members were all living in fear of getting some badge of shame if they broke the build. So it was a very welcome change when, over time, this shaming approach was replaced with an explaining approach.

Our software development practices have steadily moved in the direction of becoming software engineering practices. When we started viewing ourselves and our work more through an engineering lens, we got more structured … and more professional. One valuable maturation was our adopting of engineering’s Root Cause Analysis (RCA) approach. When a bad bug was discovered and repaired, management could request a root cause analysis of the bug.

The person who repaired the bug would then perform this analysis, guided by a form that they had to fill out detailing the problem statement, the timeline, the root cause of the problem, the immediate corrective action taken, and then the mitigation plan to reduce the likelihood of recurrence.

We weren’t shaming the person. The person was educating themselves in the process, and then educating management with the report. The motivation behind the RCA approach was to collectively get better by learning from our mistakes. And it worked great for that.

Outside of software engineering, this lesson is still valuable. Telling someone you’re sorry may be kind, but it’s far less meaningful than explaining why it happened and the steps you’ve taken to have it not happen again.

“You can stuff your sorries in a sack, mister”¹

As a kid, I loved saying “sorry.” I used that word so often that at one point my father scolded me, “Stop saying sorry all the time.” To which I reflexively replied, “Sorry.” Obviously, that encounter didn’t immediately cure me. But it did happen at a good point in my life, and with my father’s typical deft timing, it left a mental mark. I thought it was a good thing to say “sorry.” But here I was being reprimanded for using it. After the defensiveness wore off, I thought about the “all the time” part of Pop’s message, and realized it wasn’t that sorry was a bad statement, it was that I was overusing it, thereby diluting the effectiveness of any of my apologies.

At work, in a management role, I experienced the same frustration as my dad had felt with me. I found apologies from my reports to be very empty. Not because they weren’t sincere, but because, in our professional setting, I couldn’t do anything with them. So I tried to model a better behavior. I showed my team that I was human by screwing up, and then showed them a healthier way to move forward from the mistake. I would apologize first, and then I would talk about the changes I made in my own approach to prevent it from happening again.

The shorthand for this approach is called “Don’t apologize … analyze.” To be clear, it’s not that you don’t say the word “sorry” anymore, it’s just that you focus your attention on the lessons learned and the changes to be made.

Making mistakes, professionally

We’re all professionals, so we should behave professionally. When you make a mistake, don’t hide from your team. Don’t avoid calls or text threads with them. Don’t lower the blinds and close your door. Recognize that it was a mistake, and do a 5-minute informal RCA on the experience. Then share that with your team.

It’s understandable to have an internal shaming response to your mistake. But push through that. When you do it repeatedly, you will find this shaming voice gets quieter. This is an Actor/Observer² moment, where the Observer Self healthily distances themselves from the Actor Self. You ask yourself the question, “What was I thinking?”, not pejoratively but objectively. You are detached enough from the event to not have the amygdala kick in and raise a defensive wall. You take yourself less seriously, in a very good way.

The ick feeling you get from messing up is good … in moderation. A healthy amount of ick generates productive guilt, that will drive you to want to change to avoid that situation from happening again. Productive guilt results in you Working the Problem³. Too much ick will lead to paralyzing guilt, which will just drive you to curl up in the fetal position, being no help to yourself or to any of your team.

Still there’s the stigma

It’s one thing for you as the leader to embrace this objective analysis for yourself, and another thing to have the team comfortably adopt it for themselves. Framing makes all the difference. In the documentation of our RCA process, as well as at the start of every RCA meeting, we said the following: “Thank you all for taking the time to do this RCA analysis. You’re not on the hot seat today. You’re not in trouble. You are here to share how we can improve as a team. Thank you for taking this seriously.”

It’s not about trying to embarrass or shame people. It’s about the potential for improvement. We are learning as we go. We all make mistakes. In fact, mistakes are better learning opportunities than successes. Analyzing why a failure happened improves critical thinking and problem-solving. We become more aware of gaps in our knowledge base. You are better for the RCA, and the team is better for the RCA.

Footnotes

1. Stuff your sorries in a sack!, Seinfeld (YouTube)

2. Raising Your Own Awareness

3. Work the Problem

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My brother-in-law Rishi didn’t coin the phrase “Embrace the Suck”, but he preached it. Certainly he’d say this to his colleagues at his CrossFit sessions, but he also leveraged it more broadly, including shortly after he was admitted into the cancer treatment center and began his extended hospital stay:

“I look at it this way, regardless of how all this turns out, which is out of my control, my hope is that how Ritu and I approach this life-altering obstacle will help shape Ayanna and Jax as they move forward in their lives.

I have had zero hardship in my life; loving parents who are still together, college paid for, no real struggles academically and socially. I have a great wife, great family, great friends, great career. The first time I have to deal with real adversity I’m not going to back down and I will embrace the suck.“

We lost Rishi three months later. We continue to keep his memory fresh in our minds and in our hearts, with the assistance of several strategically placed memorials. The two that I see the most often are the above “Embrace the Suck” faux neon sign that we made for our workout room, and the “What Would Rishi Do?” purple and gold bumper sticker that I put, appropriately, on my bike.

“Embrace the Suck” rose out of the military as an articulation of the mindset that helps you persevere through unavoidably unpleasant situations, and even celebrates this challenging environment that leads to your own growth. Focus on the task at hand, and push through the physical and mental pain, and you’ll be a better person for it.

There are two other places where I’ve more recently seen this theme emerge. The first was in my reading of The War of Art, by Steven Pressfield¹, and the second was in an episode of the Huberman Lab² podcast. The suck they both talk about doesn’t come from physical challenges; their suck is an ever-present mental challenge that you have to intentionally and repeatedly battle. Pressfield uses the term “resistance” and Huberman uses the term “friction”, but they’re both talking about the “suck” worth facing, because it betters you.

Resistance: creator’s block

In The War of Art, Steven Pressfield describes the biggest challenge to you creating anything: your own self-imposed resistance. “Resistance is not a peripheral opponent. Resistance arises from within. It is self-generated and self-perpetuated. Resistance is the enemy within.” Resistance is the voice inside of your head that’s telling you that you can’t do it, or that what you have to say isn’t valuable, or that you should be doing something else, or that you can always do this tomorrow. It is an ever-changing and ever-present enemy. “The battle must be fought anew every day.”

Pressfield’s solution completely resonates with me because I found this same solution probably ten years ago, and have been reaping the rewards ever since. When I talk being Habit-Propelled³ and my need to Timebox Everything⁴, those are two key pieces of my Workout Mentality⁵ that forces me into the present tense, and builds momentum through compounding interest. Steven frames it Stoically: “This very moment, we can change our lives. There never was a moment, and never will be, when we are without the power to alter our destiny. This second, we can turn the tables on Resistance. This second, we can sit down and do our work.” “The most important thing about art is to work. Nothing else matters except sitting down every day and trying.”

The War of Art emphasizes the need to Play the Long Game⁶. “The professional … understands delayed gratification.” “He conserves his energy. He prepares his mind for the long haul. He sustains himself with the knowledge that if he can just keep those huskies mushing, sooner or later the sled will pull in to Nome.” “He is prepared, each day, to confront his own self-sabotage.”

Steven also covers purpose, explaining that whatever it is that you are trying to create is you sharing your own native genius, your unique value proposition. This is you “contributing a verse” to the “powerful play”⁷. “Our job in this lifetime is not to shape ourselves into some ideal we imagine we ought to be, but to find out who we already are and become it.” What you are creating matters because it is the result of your own Grand Synthesis⁸.

Tying it back to the theme of this post, the struggle to create is where real growth happens. “The instinct that pulls us toward art is the impulse to evolve, to learn, to heighten and elevate our consciousness.” The war against your own resistance is most definitely a battle worth fighting. Recognize what the potential payoff will be and get to work. Embrace the resistance.

Friction: growing your will to live

David Goggins is a motivational speaker, and the story he tells is very much his own inspirational story. He went from being too overweight to join the military to being the only US Armed Forces member to complete Navy SEAL training, Army Ranger School, and Air Force Tactical Air Controller training. He is also an ultramarathoner that has run 240-mile runs. David has embraced the suck to get to where he is now, and he continues to embrace the suck to push himself further.

Andrew Huberman is a neuroscientist who runs the Huberman Lab podcast. I have learned a lot of fascinating science listening to this podcast. Andrew had David on his podcast to talk about inner strength. What I loved the most about this episode was David talking very practically about his approach, and then Andrew explaining to him the science behind why that works for David. The whole episode is worth watching, but if you’re short on time, I want to direct your attention to a 13-minute absolute gem⁹ within this episode: a scientific explanation of willpower².

(language disclaimer: The full episodes includes the disclaimer at the beginning that there’s going to be a lot of cursing. That’s good to point out. I would call it effective cursing because (a) it’s not directed at anyone and (b) it is appropriate to the setting. David describes a lot of the inner dialogue that you will have as you fight for the willpower. Whether you verbalize that or not, that inner dialogue is sure to be profane … it’s the most unfiltered conversation with yourself. Gloves off. No holds barred.)

Andrew introduces the concept of the anterior midcingulate cortex (aMCC). “There’s a brain structure called the anterior midcingulate cortex. What’s interesting about this brain area is there’s now a lot of data showing that when people do something … that they don’t want to do, it’s not about adding more work, it’s about adding more work that you don’t want to do, this brain area gets bigger… The anterior midcingulate cortex is smaller in obese people, it gets bigger when they diet. It’s larger in athletes, it’s especially large or grows larger in people that see themselves as challenged and overcome some challenge. And in people that live a very long time, this area keeps its size. In many ways, scientists are starting to think of the anterior midcingulate cortex not just as one of the seats of willpower, but perhaps actually the seat of the will to live.”

David responds simply with, “Now we’re talkin’!” I think whenever you get David to say that, it’s an “achievement unlocked” moment.

Andrew completes his framing, “Friction is the critical ingredient. People think ‘oh, if it’s the effort, then I’m getting better.’ That’s part of it, necessary, but not sufficient, as we say in science. But the suck part, … the stick, the friction, being haunted, it’s the suck part that grows this anterior midcingulate cortex.”

Learning this science raises my awareness¹⁰ of the value of suck in my growth and in my desire to keep growing. I become less interested in trying to avoid the friction. In fact, immediately after listening to this episode I got on my bike and went for a ride, and where I normally would have chosen a flatter route for my return, I opted to add two more climbs¹¹. Thanks David and Andrew!

There are two key lines in this podcast that capture the importance of regularly returning to the suck. Andrew shares a quote from his friend, “The amazing thing about addiction is there’s a cure. The problem is, it only works one day at a time.” And David says, “Even the richest of the rich, who have everything, they always ask me this question, ‘I feel like I’m missing something.’ … You’ll never hear me say I’m missing something. I found it years ago. You find it in the suck. And you find it repeatedly in the suck.”

Embrace the friction.

Footnotes

1. The War of Art, Steven Pressfield (Goodreads)

2. How to Build Extreme Willpower, David Goggins & Dr. Andrew Huberman (YouTube) (Full Episode: How to Build Immense Inner Strength, David Goggins & Dr. Andrew Huberman (YouTube) - @0:46:09)

3. Habit-Propelled

4. Timebox Everything

5. Workout Mentality

6. Play the (Really) Long Game

7. O Me! O Life!, Walt Whitman (The Poetry Foundation)

8. You Are a Grand Synthesis

9. Mining for Gems

10. Raising Your Own Awareness

11. Embrace the Suck (Strava)

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In college, before the internet and before smart phones, a common hang out was to watch TV together. Sports, sit coms, or MTV (yes, that’s how old we’re talking). Commercials created social opportunity intervals amidst the watching, when we could replay the highlights of the last 15 minutes or catch up on whatever random topic.

But watching TV at Shawna’s place had a very different vibe. Shawna watched TV with the remote on her lap, and whenever a commercial came on, she would immediately grab the remote and start cycling through the channels. There would be an occasional short pause (<5 seconds) on a channel and then she’d be off again. Rather than socializing during the commercials, we were all trying our best to keep up with Shawna as she quickly ran through the channels.

Early on in this experience, one of the friends in our group asked, “Why do you keep doing that?” Shawna responded, “There might be something better on another channel, so I’m just making sure I’m not missing it.” This was our introduction to FOMO, well before that acronym was ever established. Shawna was ahead of her time, modeling “Fear of Missing Out” for us in the ‘80s.

In the modern era (😜) where we are surrounded by smart connected devices, FOMO is far more prevalent. A ding or buzz from your phone at dinner can pull you into whatever news flash you just got. A three minute wait at the checkout line is an opportunity to scroll through your social media. In the car you can make calls and catch up with your friends.

No single example above presents a problem. It’s the aggregate effect of FOMO that creates the problem. It feeds into a state of constant distraction. Being regularly randomized by external inputs is now the norm.

FOMO sabotages your focus. The solution is to replace that bad fear with a far more motivational fear: FOLM, Fear of Losing Momentum. It takes a lot of work to build the momentum in your Energy Flywheel¹. Once you’ve got that humming, you don’t want to lose it. This momentum supplies us with energy that increases our overall output, and helps us power through the more challenging parts of our work.

Develop your FOLM to the point where it will win out over your FOMO.

The importance of momentum

The Webster dictionary’s definition of momentum is pretty bland. But the ChatGPT definition of momentum paints a much more vivid picture: “Momentum is a fundamental concept in physics that describes the motion of an object. It is a vector quantity, meaning it has both magnitude and direction. Momentum quantifies how much motion an object has and how difficult it is to stop it.” I want to highlight three elements from this:

• Magnitude - It’s not simply about having momentum; it’s about how much momentum you have.

• Direction - Not all momentum is helpful. You have to make sure that you’re pointing the right direction. I called this out in what my sister Sue taught me²: “Interest compounds … but so does debt. You can stack good on good, for your own longevity. Or you can stack bad on bad, for your own demise. So make sure you point your ship in the right direction, otherwise every action is taking you farther away from your own ideal.”

• How difficult it is to stop it - Momentum propels you forward. Your past contributions to your flywheel carry you through the energy-sucking times.

Your momentum is your life force put into action.

To underscore how broadly leveraged momentum is, here are all the different places across uplevel pro (so far) where I’ve called out momentum’s contribution to your individual progress, as well as your team’s progress:

1. About - Uplevel Pro - This sharing is the motivation behind Uplevel Pro. The articles here are my Grand Synthesis: the wisdom I’ve gathered from my own journey and from the many teachers who helped me along the way. I hope they spark reflection, conversation, and momentum.

2. Habit-Propelled - The more habits I established, the more my day-over-day momentum built, propelling me through any challenge I encountered.

3. Energizing Leisure - Just as you optimize and intentionally organize your work energy givers and takers, there is value and momentum to be had by similarly giving attention to how your energy givers and takers are organized outside of work.

4. Finite Time - This added momentum will then carry you forward, with your “I got all that done in 25 minutes” reflection leading you to the belief that “I can get that much done in any 25 minutes that I have … when I give it my undivided attention.”

5. Actual Intelligence + Artificial Intelligence = 🥇🏆🎉 - For every type of brainstorming that I’ve ever done, pairwise brainstorming has been the most fruitful for me. It’s two people riffing off of each other, and as the brainstorming continues, the collective momentum builds.

6. How Do I Stand Out?- It is far less about what you can accomplish on your own and more about what you can bring to a team environment to contribute to the momentum and the output of a group of people.

7. Play Your Part - Far more leadership is coming from below. Everyone else from first line employees up through middle management demonstrate bottom-up leadership. They initiate grassroots efforts that start at the bottom of the organization and, through progressive successes, gain momentum to be propelled up the organizational hierarchy.

8. Maximize Smiles per Dollar - Other team members could then readily add their own thoughts to that topic, building momentum and depth for that topic.

9. Progressing Your Pitch - As each team moved, this built momentum for increasing trust. The more teams that moved to Splash, the more the remaining teams could see it working out, and more easily believe it would also work for them.

10. Lifelong Student-Teacher - This “Learn-it-all” push was the necessary first step that opened the doors to much more investment in Microsoft’s culture. And once we had enough Learn-it-all momentum, I became an advocate for its complement, “Teach-it-all”.

11. “We’ll See” - One of the most commonly occurring failures of leadership is over-indexing on the bright shiny object and sucking momentum from meaningful investments. Fight for yours.

12. Compartmentalization - Maintaining momentum amidst powerful setbacks.

FOMO has its place

FOMO drives you to pay more attention to the world around you. If you’re walled off in your own little world, it’s not healthy for you in the long run. When FOMO is telling you that you’ve fallen too far out of contact, heed it. Just don’t let it take over. FOMO has its place … in cleanly timeboxed slots on your calendar.

Here are the three main components that satisfy your FOMO.

• Social media - I’ve already detailed my own timeboxing of social media. Use this as a guide as you set up your own routine. “My updated morning routine includes a 20-minute block for checking all of my social media (5min Strava, 3min Facebook, 2min Instagram, 5min X, 5min LinkedIn).”³

• News - News continues to get more and more blended with social media, but there’s value in creating a separate timebox for news. I have a 25-minute block for reading news over lunch. And Charu and I have a 30-minute block to watch the news as we’re preparing dinner. The key here is to record the news and watch it just after, so that you can skip the ads and the boring bits of the news.

• Friends - I’m not suggesting at all that you limit your friends. This is just about establishing “at a minimum” touchpoints with family and friends. If you’re in a “heads down” period where it’s hard to find the time to Touch Grass⁴, these will ensure that you’re maintaining connection. The cadence of check-ins are different for each friend. And group chats are convenient ways to connect at scale.

With your FOMO successfully contained, you can let your FOLM take over. Momentum makes the world go ‘round. 🙂

Footnotes

1. Revving Your Energy Flywheel

2. Rest in Peace, Dear Sis

3. Nuance and Generosity

4. Touch Grass

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What does snorting cocaine and working with AI have in common? The non-stop rush. After a week in Virginia, talking with students, faculty, and industry professionals, it felt like I’d traveled back in time to Miami in the 80s. There was the normal population behaving, well, normal. And then there were these individuals that were completely racing, all the time.

Obviously, the fundamental flaw in this comparison is that there is no upside to cocaine, but there is plenty of incredible benefit to AI usage. That is why people who get a taste of this new wonder drug are so quickly hooked. Your productivity accelerates astronomically. And the more time you spend tuning your work with AI, the more productive you get. When you build an app in one day that would’ve taken weeks before, you get a huge dopamine hit. And when you discover how to effectively use an agent to help drive your workflow, you get another hit. Articulate your playbook for triaging bugs, and you get another hit.

Your Energy Flywheel¹ is spinning faster with every AI hit you take. In all of my workout mentality focus on revving your Energy Flywheel, I never thought there was such a thing as running your flywheel too hot. But AI is like adding nitrous oxide into the system. It’s dangerously fast. Unchecked, your AI-accelerated flywheel can spin so fast that it’s stressing the infrastructure that’s holding the flywheel in place. The centripetal stress is threatening to tear the wheel itself apart. The bearings are reaching their functional limits. One slight change in any part of the system can lead to a catastrophe.

You can’t run nitrous through your engine continuously. The engine needs to cool down. So too do you need breaks from AI-injection to keep your flywheel sane.

No manager or colleague is going to talk you out of taking more AI hits. You’re all together at the “party”. You have to self-regulate, for your long term sanity.

Here are some key comments from my conversations last week that raise warning flags for me. Have you found yourself saying any (or perhaps all) of these? We’ll dive into each in more detail below.

1. “I feel guilty not working when my AI is.”

2. “I’m simultaneously exhilarated and exhausted.”

3. “I’m learning a ton, but I feel like I don’t know anything.”

Race against the machine

“I feel guilty not working when my AI is.”

Feeling guilty about your contribution level to your team’s output is a pretty typical experience. You’re working with your colleagues and noticing day after day that they all seem to be working more intensely than you. It’s not that they’re staying later than you or taking shorter lunch breaks, it’s just that when they are sitting at their desks working, they seem to be focusing more than you are and moving through their work faster.

This is something that I experienced in my first open space working environment, and it actually helped my productivity. My colleagues were all modeling this behavior, so I knew it was possible. And I found a renewed focus when I felt the pressure of letting my peers down.

Human to human, peer pressure can be a positive. But when that peer is a machine, you need to keep in mind the biological and physiological differences at play. It’s a losing proposition to try to keep up with a machine that never needs to eat, drink, rest, or sleep.

Set more humanly realistic expectations, using a Play the Long Game² mindset that ensures your routines are sustainable. To avoid “losing the plot entirely”³, put checks in your system. One professional I talked with last week has a “Touch Grass” status on his Slack, to let his team know he was outside taking it all in. In these breaks, remind yourself of how much more productive you are, and congratulate yourself for being productive enough.

You’re never going to outpace AI, but you will always outdream AI. Remind yourself that your uniqueness is what is most valuable, and give yourself the needed down time for actual dreaming.

“Don’t stop me now …”

“… Because I’m having a good time, having a good time.”⁴

When I hear, “I’m simultaneously exhilarated and exhausted,” it reminds me of my first experience managing a multi-geo team. Most of my feature teams were in Washington, but I had two feature teams in India, 13 hours ahead of us. We would crank all day in Seattle, and then while we were sleeping our colleagues in Hyderabad were cranking away. Any given day, the volume of visible progress was exhilarating.

When my team was all local in Seattle, there were a few members that would end up staying later at work. As the early riser, I would arrive at work the morning after with a manageable amount of work to get up to speed on what had progressed the evening before. I would quickly catch up and then start setting things up for my team for the day ahead.

With my multi-geo team, I arrived in the morning to find 10 people’s worth of progress (and questions and follow-ups) that I needed to catch up on. I struggled to contain my morning catch-up routine, and eventually tried to solve this by bringing my laptop home at night and checking mail before I went to bed. It was exhausting.

The solution was to uplevel my approach to the management of my team such that I wasn’t robbing energy from tomorrow to get through today. That same upleveling mindset can help make your partnership with AI more sustainable.

Where is frustration highest with your AI agents? What additional guidance can you give the agent that will lessen this frustration? What new agents can you introduce to offload some of your duties? If the volume of work that the agent is generating is becoming overwhelming for you to review, construct a reviewing agent and evolve it to the point where it produces an accurate and succinct report for you to digest.

The “AI accelerated workflow” space is still in its infancy. The downside is that there aren’t yet many hard and fast best practices. But the good news is that new ideas are coming constantly. Keep your eyes and ears open for them. Brainstorming with colleagues about their AI flows is a great way to riff off of each other. Make it a conversation over a team lunch and you’ll be tuning your system while you’re touching grass.

Let the learning sink deep

AI accelerates learning and makes it more engaging. AI can tailor instruction to your exact base of knowledge to ensure that you are efficiently learning new material in a way that relates to your own frame of reference. And the fact that the generated lesson plan is uniquely yours will increase your own interest level in the learning experience.

In the movie The Matrix, you see a futuristic learning ideal, where the computer feeds you new knowledge via a direct neural link. In seconds of transfer, Neo wakes up and declares, “I know Kung Fu.”

AI isn’t there yet, but the dopamine rush from the current just-in-time, tailored-to-me education is already more than enough to leave you hungry for more. It’s easy to just learn one more thing. In The Matrix, once Neo experiences this lightning fast learning, he can’t stop. Tank tells Morpheus, “Ten hours straight. He’s a machine.”

“I’m learning a ton, but I feel like I don’t know anything,” captures the gap between The Matrix ideal and the AI reality. AI is helping to present the information to us in a way that eases absorption. But how do we make sure it sticks? There have been a number of studies on AI’s impact on “durable knowledge” and “deeper semantic processing,” warning of the potential for AI to create “cognitive offloading and superficial learning.”⁵

In 2011, well before today’s AI boom, there was a study on the “Google effect”⁶, where convenient 24/7 access to searching the vast internet led people to rely less on independent retrieval of information. “Why do I need to remember important dates from the Civil War when I can just ask Google whenever the need arises?” There is a lot of truth to this, but if there isn’t enough knowledge in your brain for independent retrieval, we create an overreliance on the computer.

Spontaneous thoughts are the gems delivered to you compliments of your own Default Mode Network (DMN)⁷. Your DMN has no access to Google (well, not until Neuralink pulls this off). Your brain, independently and marginally directionally, is constantly processing and synthesizing all of the knowledge it has accumulated. This leads to novel thought where you can experience “A-ha!” moments, big and small.

Give yourself down time between each learning experience. In 15 minutes, you can create very meaningful space for learning reinforcement. Here’s the full progression of the Learning Reflection habit.

• Crawl: Record (2 minutes) - when you’ve completed a learning exchange with AI, create a page in your External Brain⁸ and copy all the relevant links and dialogue to that page.

• Walk: Summarize (3 minutes) - add a short summary of that learning experience to the top of the page. Don’t let AI write that summary for you!

• Run: Reflect (5 minutes) - Re-read the entire page once more and update the summary with anything you missed. Then set a 2min timer, close your eyes, and just think about that.

• Fly: Uplevel your Learning (5 minutes) - Pop the stack and reflect not on the material you learned, but on the learning experience itself. Did you become a better learner? What new learning device or strategy did you discover? Add these insights to a “How I Learn” page or section in your External Brain.

Footnotes

1. Revving Your Energy Flywheel

2. Play the (Really) Long Game

3. When Using AI Leads to “Brain Fry”, Julie Bedard et al (HBR)

4. Don’t Stop Me Now, Queen (Spotify)

5. The Impact of Artificial Intelligence on Learners’ Memory: A Systematic Review, Siavash Rokhsari (CEE Journal)

6. Google Effects on Memory: Cognitive Consequences of Having Information at Our Fingertips (Science)

7. Boredom is the Mother of Reflection

8. External Brain

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At Microsoft. there is training that managers go through around handling delicate situations and the processes to follow. Within that training is the escalation path to follow with HR (Human Resources) if you as a manager witness or are told about any inappropriate behavior, more precisely termed an “HR violation.” So I knew what needed to be done the first time I was put in this situation … and had to report myself to HR.

Daniel sent me an email at 7pm, titled “not so funny”. I read this mail at 8pm (this was from an earlier time in my career before I’d established my Inviolates¹ and my Triage Shield² that would have had me reading this mail during my workday). The mail detailed an incident when I told an insensitive joke to members of the team I was leading. I immediately felt bad. Daniel went on to share their family history that made the joke especially hurtful. Now I felt even worse. And then came the worst part of all: the mail gave the date of the incident … two years ago.

I experienced a horrible sadness. I had hurt someone close to me. And I had obviously created an environment where that person didn’t feel comfortable telling me about it when it happened. How much additional pain did that cause this employee as they tried to bottle it up? Was every interaction with me in the intervening time a reminder of this incident? What else had I done to my team that they had kept inside? I had prided myself on my dedication to my team and the “2nd family feel” that I always tried to nurture. In an instant that was replaced with complete doubt. I felt helpless, ashamed, and depressed.

Everything stopped.

But when you are a manager for 50 people, “stopped” is not an option. In coaching sessions with new managers, a phrase I commonly use is, “When you have a bad day, your team has a bad day.” Bad things happen, and you need to give them due space and attention. But you also need to contain it, boxing it in as best you can, so that life outside of that event can proceed, and you can be part of it. You need to develop your Compartmentalization muscle; to avoid “stopped”.

I knew that. I replied to Daniel asking for a 1:1 the following day, which they agreed to. I then “powered through” the next morning with this weight. At 1pm, I had an in-depth 1:1 with Daniel. Immediately afterwards, I wrote-up a recounting of our conversation which I shared with Daniel … and then raised to my management and the HR department. Then, at 2pm, I closed my office door and closed my relight blinds (a shut door meant you were busy; a shut door with shut blinds next to it meant you were seriously busy). I sat down in my comfy meeting chair, laid my head against the chair back, closed my eyes, and let the full internalization happen: sadness, anger, second-guessing, regret, failure, disbelief, embarrassment, disappointment, …

About 30 minutes later, I opened my eyes, stood up, grabbed a dry erase marker, and started writing. It was a total stream-of-consciousness, attempting to articulate every thought bouncing around in my head. When I filled up one whiteboard, I moved on to the next whiteboard. When all three whiteboards were full, I started writing on my windows. When I felt that I had gotten everything out, I stepped back and did a re-read of everything written. I took pictures of what I wrote, selected a few thoughts as “keepers” and erased the rest. Four of the six keepers had been written on my windows. I transferred the two that were on my whiteboards over to the windows.

This one-hour exercise was my “immediate closure” that allowed me to feel satisfied I had given this issue the short-term attention it needed. I could now mentally park this for later exploration, with those keepers on my window in my field of vision from my desk to prompt further rumination at a later date. I opened my door and blinds and resumed my manager role.

I gave this incident its due time over the course of the two weeks that followed. And then I erased the keepers from my windows. There were fundamental changes to “how I show up” as a manager after that incident. It was a very impactful “lesson learned” moment in my management career.

But in the moment of this event, on the day I had the talk with Daniel and in the two weeks of post-processing that following, if you were to have asked any of my employees if I was checked out, preoccupied, or inattentive, I’m certain no one would have said they noticed. Compartmentalization was my success amidst my failure. I had a bad day, without my team having a bad day.

Compartmentalization as a skill

Psychology Today defines Compartmentalization as “a defense mechanism in which people mentally separate conflicting thoughts, emotions, or experiences to avoid the discomfort of contradiction.”³ Psychology Today goes on to talk about “Compartmentalization in Everyday Life”, where they capture the balance necessary to keep the compartmentalization helpful and healthy. I want to focus on Compartmentalization as a skill, much like I had talked about the skill of Embracing Angst⁴. So my thoughts here center around the healthy attributes of Compartmentalization.

There are the slow burns in your everyday life. Your child is struggling in school. Your parent is deteriorating in health. You’re wrestling with your own career growth. Long term pressures like these are a fact of life for adults, and thus this is where we most naturally develop our Compartmentalization skill, steadily over time, bit by bit.

And then there are the explosions, where something out of the blue hits you hard. Your child has a fight with a student on the playground. Your parent breaks their arm. The work project you’ve devoted the last two years to gets cut. With these events, our responses tend to be more all-consuming. Of course there are associated immediate actions with these explosions (e.g. visit principal, visit hospital, meet with team), but then there is also the emotional cloud that lingers. Dealing with what lingers requires what I consider to be a more advanced level of Compartmentalization.

Here is the pep talk I give myself when Compartmentalization is needed:

Life isn’t easy, and you’ve just found yet another reminder of this.
You need to give this some attention, but you can’t let it consume you.
You have responsibilities and accountabilities, first and foremost to the individuals on your team.
Remember, when a leader has a bad day, their team has a bad day.
Don’t let this win.
Repeat “Everything is always okay” a few times. (I’ll dive into this one below)

Another aspect of this pep talk is to hang on to your biggest Compartmentalization success and bring that memory to the forefront when you are faced with another Compartmentalization opportunity. This will make this daunting task feel doable. And, most of the time, it will provide an “at least your current challenge isn’t this bad” relief.

“Everything is always okay”

Most of the coaching I received at Microsoft was from fellow employees. But there were three occasions where I leveraged outsourced career coaches, with terrific lasting improvements each time. Craig May was my first coach, and I met him at a relative low point in my career. It came at the end of “the Splash run”, a five year period (2007 - 2012) that yielded two of my top three favorite products (Zune and Windows Phone) while building a dream feature team of 12 developers working in concert with a dream partner feature team of another 10 developers. The 22 of us were the Splash team that provided a state-of-the-art UI platform that enabled some of the most captivating user experiences of the time.

The Splash run ended after Windows Phone 8 shipped, when an ill-designed reorg left my incredibly strong feature team blowing in the wind. We tried for several months to integrate into our new team, but it was a “donor host rejection” experience that drove half of my team to seek jobs elsewhere.

As I looked back at the steps that led to this complete implosion, and tried to reason about ways it could have been avoided, there was an incredible amount of anger, guilt, and sadness for my responsibility in the whole affair, and for letting my team down in a mega way.

Conveniently, as part of the leadership program that I was in at the time, I had already been working with Craig May, an executive coach, on my professional development. So I turned to Craig for guidance as I worked my way through this problem. It was probably a month of personal struggle, during which Craig gave a lot of helpful insights. He told me the importance of keeping things in perspective, and how central of a theme that was for him, to the point that it was incorporated into his family’s mission statement. Craig shared the exact line from this mission statement: “Everything is always okay.” He said that he and his family used this phrase as a calming chant when they hit a bad patch.

You could say that this line represents denial. And that’s entirely possible if used in an “ignorance is bliss” way. But I have used it, instead, at times when the negative has me stuck. This line unsticks me. It forces me to focus on the positives and incentivizes me to act so that the negative doesn’t grow. Work the Problem⁵ to move more things towards “okay”.

You could say that this line is dismissive. I remember one time when I shared this line with my team at an all hands meeting when we were discussing an upcoming big change, and my PM counterpart quickly added, “… until it’s not.” to help counter the potential dismissiveness of this line. That made me realize that this line is best shared in a “for future reference” context, meant to arm people with a tool they can use themselves when they are personally struggling, and need help Compartmentalizing so that they can make forward progress.

Compartmentalization is an even deeper application of Timebox Everything⁶. The alternative is being consumed by the negativity to the point that your Energy Flywheel⁷ grinds to a halt.

Footnotes

1. Triage Shield and, more specifically, Managing Email

2. Inviolates

3. Compartmentalization (Psychology Today)

4. Suffering = Pain x Resistance

5. Work the Problem

6. Timebox Everything

7. Revving Your Energy Flywheel

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My sister Sue passed away on Easter Sunday. The non-medical cause of death was a broken heart. She lost her husband John on Easter Sunday last year, and a year without him was long enough for Sue.¹

The Good

I have a unique and special relationship with each of my seven siblings. Sue was my partner in clown. We all had fun as a family, but Sue and I took it to another level, mostly for the amusement of each other. As much as I enjoyed the buzz of our larger family get togethers, Sue and I enjoyed withdrawing as a pair and sharing a laugh. Sue is a blunt, even crass, individual, and I picked up a healthy amount of irreverence from my 3rd sister. Jokes were welcome on all solemn occasions, even funerals. It wasn’t meant in disrespect, but rather about building our bond and helping each other through the awkwardness of the situation.

Sue was my movie buddy. Good movies were better with Sue. In Star Wars, both Sue and I fell in love with Harrison Ford (Sue’s crush on Sean Cassidy had run its course, and she was looking for a new crush. My love of the Lone Ranger had run its course, and I was looking for a better hero.) So when Raiders of the Lost Ark came out, Sue and I were first in line. “Gusts of wind and tongues of fire” was a phrase I kept saying after the movie, referring to the ark of the covenant scene. And Sue teased me about it ever since. (My final words to my sister included that line with a laugh. 🤗)

Bad movies became funny movies with Sue. Jaws 3D and Streets of Fire were quite painful movies to sit through. But thanks to Sue, they left a hilarious mark. As Sue’s body began to fail, with me being too far away to get to her in time, my solution was to make a Sue playlist and start playing it. And when Streets of Fire’s “Nowhere Fast” came on, I tried to belt it out the way Sue and I had done every time we listened to it together … sadly, I only got through the first line. 😢

Christmas and Easter were two holidays that excited me beyond sleep. Sue was my guaranteed all-nighter companion, huddled together in either of our bedrooms quietly sharing stories so that Santa Claus and the Easter Bunny didn’t hear us. Eventually I would pass out, and (I’m sure relieved), Sue would happily finally get some rest.

When Sue’s husband passed away, I went home for the funeral, and then spent several days with Sue, along with my brother John and sister-in-law Christine. Among our adventures during this time was a walk through our old neighborhood together. This is the last walk I ever took with my sister, because the next time I came to town was six months later, and her health had already quickly deteriorated. At her passing, I said the same thing that I said about Hobbes: fast beats slow.

I miss my sister, but I know she’s in a better place … and resting in peace.

The Great

I have already talked about the appreciation I have for my seven siblings². “If you want to go fast, go alone. If you want to go far, go together.” There are countless instances of our siblings calling us together in our adulthood, perhaps the earliest being the construction of my sister Beth’s deck on her brand new townhouse in Maryland, followed by a family get together.

If my siblings had just given me a great childhood, I would have already been thankful beyond words. But what I continue to get is the gift of a living and growing family bond that gets stronger every year. We do our share of reminiscing, but we are also constantly building new memories.

My brother John started a tradition (accidentally?) by calling us all together to surprise brother joe for his 50th birthday. 14 years later, that particular tradition ended when I reached my 50th … and then we moved on to the next tradition.

Relationships are living things. Nurture them and they grow. What I have with my seven siblings (now six 😢) has carried me through some very tough times. What Sue’s passing has reinforced with me is the need to double down on this, and savor it even more than I already do.

A week after Sue’s passing, six of the remaining seven of us got together for a family wedding of one of our 15 offspring. As I climbed aboard the flight to return to Seattle, I texted the “Bogdan Sibs” group: “Such a great weekend, family. Every visit with you is a true gift. Love you all.”

Be the architect of moments that matter³. As Peterson said, “Keep the relationship alive. Living things die, after all, without attention.”⁴ Never take long term relationships for granted. They are your foundation, whether you realize it or not.

The Sad

The first two sections of this post were the easy part. I sat down and wrote those in 30 minutes. But my weeklong writer’s block that followed Sue’s passing was due to this third section. Sue’s story would be incomplete without this section. So I kept pushing on the block and, eventually (at 9pm on a plane after my Bogdan family visit), I broke through.

I lost Sue finally at 1am on Sunday, April 5, 2026. But I lost Sue initially at 3pm on some afternoon in 1999 (or maybe it was 2000) … when she fell down the stairs in her townhouse and ended up in the ER. I visited her a few weeks later when she was rehabbing in cognitive care. The good news is that this low point didn’t last too long. The bad news is that the full Sue never returned.

Sue was an alcoholic, and given the healthy dose of stubbornness that runs in our family’s genes, there was nothing and no one that could stop her. Despite the excessive drinking that led to her fall down the stairs, she was not dissuaded from continued drinking. Lying in the ICU in her final hours, she was asking for alcohol.

Sue and I created thousands of memories over our first 30 years together. After her fall, all we ever did was reminisce. Our relationship wasn’t a living thing anymore; it was in stasis. Sue stalled. It may be crass for me to speak this, but given that Sue taught me irreverence, it seems fitting: I lost my Sue decades before she breathed her last breath.

Every sibling birthday party was accompanied by the drama of Sue’s arrival. She missed exits, turned herself around, got herself frazzled, and inevitably we had to talk her down and guide her in for the landing. And our time together with Sue was fine up until the moment that it wasn’t. And no one, including Sue, had any idea when that was coming.

The lesson that Sue taught me in all of this is the significance of compounding effects. Interest compounds … but so does debt. You can stack good on good, for your own longevity. Or you can stack bad on bad, for your own demise. So make sure you point your ship in the right direction, otherwise every action is taking you farther away from your own ideal.

Addiction is lethal in the slowest and most painful way. Addiction is individual bad decisions, compounding to bury you in their aggregate. You focus on the combined weight of thousands of bad decisions, but the fundamental shift is to focus on stopping the next bad decision. That’s the only winnable fight.

My sister never asked for help, and rejected our offers of advice. Addiction lures you into isolation. And to the extent that stubbornness is involved, this isolation can be strengthened to the point of it being an unfortunate fortress of solitude. It’s not weak to ask for help. It’s strong.

I’ve been missing most of my sister for the last three decades. Now I’m missing the rest of her.

“I’m not afraid to die. I’m not afraid to live. And when I’m flat on my back, I hope to feel like I did.” - U2, “Kite”

“Get busy living, or get busy dying.” - Andy Dufrane, “The Shawshank Redemption”

Footnotes

1. Susan B. Clayborn Obituary (Affinity)

2. The “Share a love story” section of Lead with Love

3. The Power of Moments, Chip and Dan Heath (Goodreads)

4. The “Love is a verb” section of Love It Or Leave It

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I’m going to attempt to reference a political movie without making this a political post. Wish me luck. While the connections from this movie and the current Middle East events are obvious, I assure you that is not the motivation behind this post.

In Charlie Wilson’s War¹, Gust Avrakotos is a CIA agent who partners with Charlie Wilson, a US Congressman representing Texas. The movie details how a small group of individuals in various circles join forces and leverage their influence to fund rebels who are fighting the Soviet army in Afghanistan in the early 80s. The final scene in the movie is at a party celebrating the rebels’ success in driving the Soviets out of their land. The movie closes with a private exchange between Charlie and Gust out on the balcony.

Gust: “Do you know the story about the Zen master and the little boy? …
There’s a little boy, and on his 14th birthday he gets a horse, and everyone in the village says, ‘How wonderful, the boy got a horse.’
And the Zen master says, ‘We’ll see.’
Two years later the boy falls off the horse and breaks his leg, and everyone in the village says, ‘How terrible.’
Then the Zen master says, ‘We’ll see.’
Then a war breaks out and all the young men have to go off to fight but the boy can’t because his leg’s all messed up, and everyone in the village says, ‘How wonderful.’”
Charlie: “Then the Zen master says, ‘We’ll see.’”
Gust: “So you get it.”
Charlie: “No … ‘cuz I’m stupid.”
Gust: “You’re not stupid, you’re just in Congress.”
Charlie: “Send ‘em money?”
Gust: “You’re gonna start with the roads, move on to the schools, factories. Restock the sheep herds, give ‘em jobs. Give ‘em hope.”
Charlie: “I’m trying.”
Gust: “Yeah well try harder.”
Charlie: “I’m fightin’ for every dollar. I took you from 5 million to a billion. I got a Democratic Congress in lock step behind a Republican president.”
Gust: “Well that’s not good enough, because I’m gonna hand you a covert classified NIA right now and it’s gonna tell you that the crazies have started rolling into Kandahar like it’s a f*cking bathtub drain.”
Charlie: “Jesus Gust, you could depress a bride on her wedding day.”
Gust: “Hey, listen to what I’m telling you.”
Charlie: “You did a hell of a job for the son of a soda pop maker.”
Gust: “We’ll see … Said the Zen master.”

This is great story about the importance of playing the long game². Gust has been steadily raising Charlie’s awareness³ on the situation in Afghanistan. And at a moment when it seems that their work is done, Gust tries to create yet another moment of insight by telling the Zen master story.

You have certainly experienced your own Charlie moment, where you think your work is done, only to find that, as Gust says, it’s not good enough. The more complex the mission, the more likely you’re going to encounter this phase, perhaps even repeatedly, during the execution. This is the benefit of the iterative planning approach, where you keep yourself open to the suprises to come.

Let’s explore the components to a successful extended mission.

• Define long-term success

• Establish an initial best guess plan

• Follow-up: Course correct regularly

• Follow-through: Keep your eye on the prize and drive success

Define long-term success

Any manager can manager a team. A leader will grow that team, evolve that team, transform that team. Leadership is about making meaningful change. And that doesn’t come easy. It’s far simpler and straightforward to give a man a fish. Teaching that man to fish takes work. As a leader, embrace this investment.

When you identify a change worth making, your next step is to define what long-term success looks like. Good: Reduce team’s issue triaging time by 25%. Better: Customer satisfaction is up by 25%. The ultimate goal is improved customer satisfaction. One implementation (of several possible) is improved triage time. That customer-focused success metric creates an openness to many potential implementations.

Having the right success metrics will help with everything downstream of them: the initial plan and all the iterations during execution.

Establish an initial best guess plan

With clear focus on your idea of success, now it’s time to construct a plan. This will be your pitch⁴. It doesn’t have to be complete. It just has to account for all that is known: the “known knowns” and the “known unknowns”⁵. And then, to plant the right seed in your mindset, recognize the potential for “unknown unknowns”. You don’t know what to do about them, because you don’t know them at the time of planning. Accept that … and be open to that. This will serve you well in the later stages of execution.

Follow-up: Course correct regularly

Once you’ve gotten buy off on your plan, you’re ready to establish your execution plan. The key here is regular checkpoints. The Scrum methodology includes repeated “sprints” of regular intervals, with each sprint ending with a “retrospective.” The retrospective is a chance to assess how you’ve done in the last sprint and what you want to change going forward.

This is where any “unknown unknowns” that become “known unknowns” are revealed. By baking checkpoints into the plan, you are intentionally opening yourself up to the possibility of change. This is when you can capitalize on that openness and embrace the challenge. You are far less likely to dismiss this new information as scope creep or “not my problem”.

Assign a “threat level” to each discovery:

• High: It blows your original plan out of the water, and you need to fundamentally rethink your approach.

• Mid: The original plan is still solid, but there may be changes needed in resources or funding.

• Low: a tweak to the plan will address it.

You had already set expectations that some surprises were inevitable. That makes them far less surprising. Stay logical. Stay practical. Work the problem⁶. Call out these discoveries, along with your adjustments to the plan to account for them. You now have something concrete to present the stakeholders to explain the need for change.

Follow-through: keep your eye on the prize and drive success

With your plan, and with your course corrections, now all you have to do is follow-through. As Henry David Thoreau said, “Advance confidently in the direction of your dreams with no concept of failure.”

There are any number of inputs trying to distract you from your goal. Follow-through is not automatic. This is why Gust demands, “Hey, listen to what I’m telling you.”

In the tech industry, we talk about “bright shiny object syndrome”, where some new cool thing comes along that demands attention. Certainly it can be a bad idea to fully dismiss the new object: “Not now AI, I’m busy.” We need to remain vigilant, but of equal importance is maintaining perspective. One of the most commonly occurring failures of leadership is over-indexing on the bright shiny object and sucking momentum from meaningful investments. Fight for yours.

Teachers note

Returning to my movie reference from the start of this post, there’s another scene much earlier in this movie that is worth calling out for all the student-teachers⁷ in the audience. The first time Gust and Charlie meet in the movie, Gust tries to tell Charlie the Zen master story. But they keep getting interrupted, and eventually Gust stops trying to tell it.

Gust completely makes the right call by stopping. He recognizes two things in that moment. First, more than not having Charlie’s attention, Gust doesn’t have Charlie’s earned trust⁸ yet, which makes it far more likely that this story will quickly be forgotten by Charlie. Second, the timing of the story is important. This story is meant for when more of the “unknown unknowns” are revealed, which can only happen after Charlie reaches a certain checkpoint in the operation. Charlie had far more basic things to learn before the Zen master story would fit in.

Teach the right lessons. And time your lessons well.

Footnotes

1. Charlie Wilson’s War (IMDb)

2. Play the (Really) Long Game

3. Raising Your Own Awareness

4. Progressing Your Pitch

5. Rumsfeld Matrix (The Uncertainty Project)

6. Work the Problem

7. Lifelong Student-Teacher

8. Earning Trust

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Stephen Covey’s 3rd habit² is “Put First Things First.” In his presentations, he had a “big rocks” demonstration that involved a volunteer from the audience, a large clear bucket, a large jar of pebbles labeled “small things”, and ten big rocks that are each labeled:

1. “planning and prevention”

2. “relationships & family”

3. “key employment issue”

4. “major project”

5. “big opportunity”

6. “sharpen the saw”

7. “service, community, and church”

8. “vacation”

9. “block of time just for yourself”

10. “mental”

He begins by asking the somewhat rhetorical question, “Do you ever feel like you get bogged down in the thick of thin things?” Then he begins to pour the huge jar of pebbles into the clear bucket, “All these little, small things that tend to fill our lives, and little by little they just accumulate.” When the jar is empty, the pebbles almost entirely fill the bucket, with only a small space left at the top.

Stephen then asks the volunteer to try to fit all the big rocks in that bucket, without going over the top of the bucket. They can typically only fit four or five of the big rocks in.

Stephen calls out some of the big rocks they’ve left behind, “You’ve given up your ‘vacation’, and you have no ‘special block of time just for yourself’.” Then he brings out a second clear bucket and tells the volunteer, “You could take a completely different approach. You could work out of a new paradigm.”

The epiphany that most people have at that moment is to put the big rocks in first. After placing all ten of the big rocks, the bucket looks full. But you can see there’s lots of room between the rocks. When they pour all the pebbles in, these “small things” freely slide in and around the big rocks. And when the pouring is complete, everything fits.

Stephen Covey’s “big rocks” demonstration from 1994

“Put the big rocks in first” is about prioritization. If you don’t intentionally do this, then all the pebbles will fill your day, your week, your month, … And you’ll starve the big rocks.

What are your big rocks? Step back from the “day to day grind” so that you can take in the big picture. What things are most important to you? What Stephen calls big rocks I call Inviolates, because you need to hold them sacred, and protect them at all costs. When it comes to any planning you are doing, you need to prioritize the Inviolates. They may seem skippable in the moment, but in the aggregate, you’re going nowhere without them.

In 7 Habits, Covey says, “The key is not to prioritize what’s on your schedule, but to schedule your priorities.”

Here’s how to identify, nurture, and protect your own Inviolates.

The architected calendar

This is what my weekly calendar looked like at the height of my Group Engineering Manager role.

This was the starting point for each work week, as everything listed here are the recurring meetings on my schedule. So for other people to grab time with me, this is what we have to work around. If this seems stressful, you should’ve seen what it looked like before I architected my calendar.

Yes, I only have 9 hours of unscheduled time per week, but every single meeting here is an established touchpoint for the people and the projects that I oversee. So those 9 hours are for the surprises, not for normal operation. And, over the years, that has proven to be more than enough space.

This calendar of perfectly placed blocks was the result of many meeting negotiations⁴:

1. “Does the meeting need to happen?” What warrants in person discussion vs. what can happen over mail?

2. “Do I need to be there?” Check your FOMO; and think about effective delegation.

3. “Does the meeting need to be that often?” Could you get away with meeting every other week?

4. “Does it need to be as long as it is?” Could you get away with meeting for 25 minutes instead of 50?

5. “Does it need to be at that time?” Can you request a different time that would be more ideal for you?

And, from an Energy Flywheel standpoint, I have made sure that the energy givers and energy takers are properly interleaved to rev my flywheel and keep it humming all day and all week.

Put the Inviolates in first

Do you think that it just magically worked out that all of my Inviolates fit around this schedule? Of course not! My Inviolates are sacred, so I bend my schedule to fit around all of my Inviolates.

Establish a daily pattern. Mine was simple at the time of this snapshot, because my boys were all grown up so there wasn’t the varying home schedule for school drop off and pick-ups or for the various after school sports and activities they were involved in. Mark all home hours as unavailable. And respect that. I got to work at 6:10 every morning and left at 6. And work never followed me home.

This creates the canvas that you can start your architecting inside of. Now you add the Inviolates.

• Journal & Blog - I start each day with writing. Sitting in a quiet office with no movement happening in the hallways yet, it is the perfect way to start my day. I still have this on my post-Microsoft calendar, it’s just 90 minutes now instead of 50.

• Eat, E-mail, Map out Day - Grab something to eat while I Triage all my Comms⁴. Now I have all necessary context paged in and I’m ready to map out my day. What do I absolutely need to address today, and where can I place it on my calendar (moving meetings if necessary)?

• QII - An hour every day dedicated to Quadrant II⁵ work. Never starve your proactive, planful mode.

• Lunch, Home Check-in, E-mail - Grab something to eat, check phone for texts and email from family and friends to see if anything needs addressing, and then Triage all my Comms again.

• ToDo transfer, Mail wrap-up - Make sure all of my newly noted ToDo’s find the right home in my External Brain⁶, do a final Comms Triage for the day, and then head home.

Identifying your own Inviolates

My calendar and my Inviolates are just examples. What you choose for your Inviolates and where you put them on your calendar is entirely up to you. Here are my pro-tips on how to identify your Inviolates and where to put them in your day.

1. Start small. I reached the point of three contiguous hours of Inviolates in my morning, but I didn’t start there. Keep Admiral McRaven’s words in mind as you embark on your Inviolates journey: “If you want to change the world, start off by making your bed.”⁷ The first step for me was a 30 minute “email & map out day” Inviolate. My days felt more in control and productive with just this small regular investment. As you add more to your Inviolates, you should notice your Energy Flywheel getting a predictable boost with each iteration.

2. Front load proactiveness. The further into the day you go, the more that the “small things” will begin to pile up and demand your attention. Embrace the quiet of the morning (both in your mind and in your office). The first Inviolate to add to your schedule should be at the start of your day.

3. Have proactive bookends to your day. After you’ve established a start-of-day Inviolate, it’s time to add an end-of-day Inviolate. Here you reflect on how the day played out for you, what went well, and what didn’t go so well. Then pick one item you want to try to improve the next day. This brings closure to your workday, and your reflections here are notes to your future self, to be read at your next start-of-day Inviolate.

4. Embrace a midday pause. The next level Inviolate is the proactive pause you use to split your day. As a Group Engineer Manager, my midday pause was an opportunity to catch my breath as well as course correct for the day. And, in divide and conquer fashion, it changed my calendar from one large chunk to two manageable chunks. This further revved my Energy Flywheel daily. When I pivoted to my Director of Learning and Development role, where I had far fewer meetings and far more deep work blocks (yay!), my midday break became a 50 minute bike ride around campus.⁸ It was my midday meditation on wheels.

Keep nurturing your Inviolates, and they may just take over your calendar, in the best kind of way.

Footnotes

1. The “Be the architect of your day” section of Revving Your Energy Flywheel

2. The 7 Habits of Highly Effective People, Stephen Covey (Goodreads)

3. The “Creating space on your calendar” section of Revving Your Energy Flywheel

4. Triage Shield, Managing Email, and Herding Chats

5. The “Important vs. Urgent” section of Play the (Really) Long Game

6. External Brain

7. Admiral McRaven’s commencement speech @4:44 - 6:12

8. Fortuitous FlyBy (Strava)

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My brother John is a retired Army Colonel, and over the years he and I have spent a lot of time sharing leadership pro-tips from our respective jobs. He told me several times about the Right Seat and Left Seat Ride Program that he participated in on each change of command. Right Seat refers to the role of passenger. Left Seat refers to the role of driver.

Here are the relevant excerpts from USAREC Regulation 350-1, Training and Leader Development¹:

• “The Right Seat and Left Seat Ride Program gives new leaders an opportunity to accompany departing leaders through their operational area prior to the change of command or transfer of authority/responsibility. The program provides an excellent opportunity for training and mentoring incoming leaders.”

• “The Right Seat and Left Seat Ride Program ensures continuity and the passage of knowledge between outgoing and incoming leaders. The program is normally 10 days in duration, which consists of 5 days riding in the right seat and 5 days riding in the left seat.”

• “The program is flexible and represents the normal day-to-day activities of a company commander. The departing commander is the trainer for the Right Seat and Left Seat Ride Program. During the first 5 days, the outgoing commander will conduct normal operations with the new commander observing from the right seat. During the last 5 days, the new commander will take the left seat with the outgoing commander serving as an observer and mentor. The outgoing leader will provide their expertise and guidance.”

When John walked me through this, I loved the sound of it and thought about how smooth of a transition this would provide versus the normal role transitions I experienced at Microsoft: (a) leader leaves, (b) there is an interim leader, (c) we hire a replacement leader. I have experienced so much disruption in this latter approach that I was in search of the opportunity to apply this Right Seat / Left Seat procedure.

That opportunity came with my transition into the Director of Learning and Development role I created². Being an entirely new role, there was no time pressure to get me into the new job immediately. My role had been Software Engineering Manager overseeing a team of 60 people. My team had been purring along, and I wanted to keep it that way.

I talked to Neil, my replacement, about this and he was on board. Then I shared this process with my team in the form of a blog post before the transition started. For the first week, Neil shadowed me to every meeting and stood over my shoulder while I worked through my mail, repo tracking, and OKR tracking processes. The second week I shadowed Neil and stood over his shoulder. It worked beautifully, with Neil saying he felt more prepared than he ever had for a new role.

Putting it into practice

The military has an excellent Team External Brain³. They are very good about writing processes down, so my studying of the Right Seat and Left Seat Ride Program was eased by the documentation that I could readily find online. Beyond reading about the process itself, I also found the Army’s one page form that is used by the transitioning leaders⁴. The straightforward form states two steps, with free form responses from both leaders.

• STEP 1: Incoming leaders ride with outgoing leaders for the first five days of the program. The outgoing leader conducts normal operations with the incoming leader observing from the right seat. (Cover what went GOOD, BAD, and what needs IMPROVING)

• STEP 2: Incoming leaders assume the left seat, with the outgoing leader serving as an observer and mentor for the last five days of the program. The outgoing leader will provide expertise and guidance as needed. (Cover what went GOOD, BAD, and what needs IMPROVING)

In my implementation, Neil and I didn’t use this exact form. But there was definitely plenty of notetaking. I had been cultivating our Team External Brain for years, so my notes mostly took the form of direct updates to our knowledge base. Whenever we spotted a shortcoming in the process, I would just update the documentation in real time.

Neil tracked his own observations outside of this documentation. These were his own personal notes for what stood out to him in this role that he would need to pay special attention to. For instance, in his old team, their focus had been entirely on internal source code, so his new team’s involvement in open source would be a new experience for Neil.

Continuity book

Despite the Army’s excellent record of documentation and formalizing their processes, I discovered a very interesting aspect of the Right Seat and Left Seat Ride Program that is outside of formal procedure. Soldiers are encouraged to create and maintain a Continuity Book for each role they have. This book includes duties, responsibilities, procedures, points of contact, and personnel and equipment data. It’s the soldier’s External Brain⁵. And then the soldier leaves that role, they give their Continuity Book to their replacement.

Retired Colonel Leonel Nascimento recognized the value of the Continuity Book, not only for your own efficiency, but for the ramp-up and long term efficiency of those who follow you. Nascimento, as a Captain, included these pro-tips in his detailed write-up⁶ (his reference to “computer disks” gives you an indication of when he originally wrote this advice 🙂):

• Start Now and Keep Revising It. The continuity book should not be put together the week before the replacement takes over. In fact, the departing soldier should begin assembling it when he first assumes his position. This will allow him to begin recording continuity information during his time in that position and will ensure that the data in the book is accurate and detailed. Moreover, the developmental process involved in putting together the document will greatly increase the author’s own familiarity with his duty position.

• Use It Daily. The author should assemble the book with an eye to making it relevant and useful for himself. He will know he has achieved this when he refers to it to accomplish routine activities. This technique has two advantages. First and foremost, the soldier developing the document can use it as a handy reference. A second advantage, one that is important to both the unit and the replacement soldier, is that the book is tested by the author on a daily basis for relevance and usefulness.

• Make the Continuity Book One of the Goals and Objectives in the Author’s NCOER Checklist or OER Support Form. A soldier and the soldier’s rater should agree on the importance of developing the document during the rating period. This ensures that the author is both afforded the time and given the credit for producing it.

• Make the Document Revision-Friendly. With the current ease of accessibility to computers in both the workplace and at home, soldiers should assemble information for the continuity book using computers. This allows the author to quickly update old information. Additionally, he/she can save the data on computer disks. This allows a replacement to further revise and update the information to pass on to future replacements. However, remember to save the data in a manner which allows the replacement soldier to access it. Normally, the optimal method of doing this is to save it on a computer disk using a software program (pay attention to the version) that the replacement can access using the computer at the unit.

To summarize his advice: Don’t start your transition document when the transition is about to happen. No doubt you will forget stuff. Instead, start building it the day you start the role. It will be your own cheat sheet to make you more efficient, and your regular use of it will validate its accuracy. Creating a success metric for the management of your Continuity Book is a great way to hold yourself accountable. And having it stored electronically allows for easy access, updating, and sharing.

Going one step further on this last point, there is a huge uplevel opportunity that comes from comparing Continuity Books across team members. Whatever you discover to be leverageable across the team is an opportunity to promote External Brain information to the Team External Brain.

As Stephen Covey’s 2nd habit⁷ states: “Begin with the end in mind.” For every role that you take, you’re going to be handing it off at some point. Make that hand off as smooth as possible. Model this behavior enough and you may even experience the payoff of having a Continuity Book waiting for you when you take a new role.

Footnotes

1. UR 350-1.pdf (army.mil)

2. The introduction of Maximize Smiles per Dollar

3. Your Team’s External Brain

4. USAREC Form 350-1.8 AAR (Templateroller)

5. External Brain

6. Building a Useful Continuity Book, Captain Leonel Nascimento

7. The 7 Habits of Highly Effective People, Stephen Covey (Goodreads) … (7 inception 🙂)

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Andy Weir tells a good story. After Drew and Charu read his first novel, The Martian¹, they got the four of us to go see the movie when it came out. When Project Hail Mary² came out, Drew, Charu, and I read it and loved it. So last week, we got the family back together to go watch Project Hail Mary. It was very well done. Highly recommend!

No spoilers here. I just want to share the premise of each of these two stories. In The Martian, they’re trying to figure out how to get Mark Watney, a stranded astronaut, off of Mars and back to Earth. In Project Hail Mary, an isolated Ryland Grace is trying to figure out how to research black matter in a distant galaxy and send his findings home to save Earth from this same black matter.

Both of these stories center around intense and extended problem solving. Both Mark and Ryland have their pity party moments, but in Finite Bitching³ fashion, they are quick to turn their attention to the task at hand and begin to Work the Problem. Once Mark groks the gravity (no pun intended) of his situation, he says, “In the face of overwhelming odds, I’m left with only one option: I’m gonna have to science the shit out of this.” Well said. Little problems require a little science. Big problems require a shit ton of science. Work the shit out of the problem.

“Work the Problem” is a phrase perhaps most famously used by Gene Kranz, lead flight director for NASA’s Apollo 13 mission. 55 hours and 55 minutes into the Apollo 13 mission, there was a major failure on the spacecraft. At the same time that commander Jim Lovell radioed, “Houston, we’ve had a problem,” mission control was already reacting to a whole bunch of simultaneous alerts flashing on screens around the room.

The panic was building, so Gene Kranz worked to settle people down, “Let’s work the problem, people. Let’s not make things worse by guessing.” Gene went on to highlight how to keep focused on the problem. “Okay, now let’s everybody keep cool. We got the LM [Lunar Module] still attached. The LM spacecraft’s good, so if we need, to get back home we’ve got a LM to do a good portion of it with.”⁴

For the next 87 hours, mission control and the astronauts worked together to solve the problem. Gene later described the flow as, “Everybody seemed to be moving in the right direction without being directed.” Lovell celebrated the victory of “Initiative to think outside of the box. When things go wrong, how do we repair them?” These are articulations of Work the Problem at its finest.

Space is probably the most unforgiving environment, so the Martian and Apollo examples are extreme, but the Work the Problem lessons here are broadly applicable. You can probably even put yourself at ease when you encounter any problem by telling yourself, “This can’t be as hard as Watney’s or Kranz’s problem, so I’m sure I can figure it out.”

You have a problem in front of you, and you have time working against you. Focus on the problem at hand, and get to work.

Divide and conquer

In the movie Unstrung Heroes⁵, John Turturro plays Sid Lidz, a father who prides himself on his love of science. He is constantly exploring, and enthusiastically involving his family in the running of his experiments. When Sid’s son Steven faces a challenge (running for class president), Sid jumps at the opportunity to walk Steven through his own approach to Working the Problem. “Now the first thing we have to do is make two lists, see. One list you call ‘Possible ideas.’ The other list, ‘Available materials.’”

This is a great way to approach the problem. What do you have to work with, and how can you creatively leverage those materials to solve the problem? By answering these questions, you’re beginning to break your large and scary problem down into manageable chunks.

At the end of The Martian, Watney captures the incremental nature of Work the Problem. “This is space. It does not cooperate. At some point, everything is going to go South on you. Everything is going to go South and you’re going to say, ‘This is it. This is how I end.’ Now you can either accept that, or you can get to work. That’s all it is. You just begin. You do the math. You solve one problem, then you solve the next one, and then the next. And if you solve enough problems, you get to come home.”

Build your problem solving muscle

My dad didn’t use the same terms as Sid Lidz, but he was a master problem solver. I saw him fix our cars and fix our house. Regardless of the problem, he would resolve it. He wasn’t born with that. His problem solving proficiency came over years of learning. Problem solving is a muscle you build. I have aspired to be as well-versed at working the problem as Pop was.

When you encounter a problem at a scale that is daunting to you, lean into the experience. Break the problem down, work through the possible ideas and available materials, and solve it. The more success you have at large scale problems, the more confidence you have that you can fix even larger problems.

The goal state is the belief that you can fix any problem you set your mind to. This isn’t about arrogance or about self-delusion. This is about having a level of confidence that comes from your battle-tested approach to problem solving.

My measure of success for the building of my own problem solving muscle was to get as excited as my dad would get at the opportunity to solve a problem. I realized I had achieved that during a Crucial Conversations training I took several years ago. The instructor said, “It’s five o’clock on a Friday and you’re just about to walk out the door when a colleague steps into your office and says, ‘You and I have a problem. Can we talk?’ What’s your first reaction?”

People began giving what I imagine are the more expected responses: “Oh no.” “Here it comes.” “Yikes.” My response was, “YES !!!” and it wasn’t a joke. The Work the Problem mindset is all about optimism: visualizing a better future and then taking steps to get there. So while the timing of this colleague’s visit is unfortunate, the opportunity for us to be better on the other side of it has me excited to engage.

A slight tweak of Teddy Roosevelt’s gem is perfect for this. “Far and away the best prize that life has to offer is the chance to work hard at problems worth solving.“ Choose your problems, and then get to work on fixing them.

Don’t get married to your solutions

There is a phrase made popular by Uri Levine: “Fall in love with the problem, not the solution.” I think a more precise phrase would be “Fall in love with the solving, not the solution.” When I’m presented with a problem, my excitement doesn’t come from the problem itself, but from my belief that I can solve it. And when I do solve it, I don’t find myself missing the problem, longing for its return. So, I wouldn’t say that I love the problem. I love the problem solving itself.

That clarification aside, the second part of this phrase is key: don’t fall in love with the solution. You have to be dynamic and flexible. Your solution might look right at first, but then not hold up under scrutiny or testing. If you’re married to that solution, then there’s heartache when you discover it won’t work. But if you’re instead married to solving the problem, you can quickly discard this failure and go back to the solving.

The longer your solution has been working for, the harder it may be to discard it. This is human nature to hang on to it, from some combination of proof points and laziness. Remember the goal: a better future. Do you want this failing solution in place another year from now, or do you want a better solution to be in place?

People problems

Before publishing novels, Andy Weir spent twenty five years as a software engineer. The software engineering industry runs on the Work the Problem mindset. Code is very unforgiving. There is the need for precision. And when problems arise, the only way through is by doing the hard work of debugging.

This background gave Andy a drive to focus on the non-human challenges we face. “In my stories, I tend to like person-versus-nature plots, where there is no bad guy. In The Martian, it’s just all of humanity or a group of ­people working together to try to solve a problem, but there’s no antagonist other than Mars.”⁶

When the environment is the antagonist, then it’s more straightforward to work the problem. But when the problem you’re working is a people problem, added challenges are introduced. The solution there is to make it the least personal that you can. I turn again to Demotivational Posters⁷ for help.

“Dysfunction: The only consistent feature of all of your dissatisfying relationships is you.”

This poster reminds me that if I’m pointing the finger at someone else, there are three fingers pointing back at me. So if I want to blame the person for the problem, then I’m the problem.

Instead, get more precise. The problem is the result of a clash in the perspectives of you two. Identify the relevant differences between you two, and now the two of you can work together to solve the problem, without having to get personal. Chris Voss, professional hostage negotiator, says it best: “The person across the table is never the problem. The unsolved issue is. So focus on the issue.”⁸

Footnotes

1. The Martian, Andy Weir (Goodreads)

2. Project Hail Mary, Andy Weir (Goodreads)

3. Finite Bitching

4. Apollo 13: ‘Houston, We’ve Had a Problem’

5. Unstrung Heroes (IMDb)

6. NAE Website - The Bridge: An Interview with Andy Weir

7. The “Choose your Mantra” section of Timebox Everything, and www.despair.com

8. Never Split the Difference: Negotiating as if Your Life Depended on It by Chris Voss | Goodreads

When a team reorganization gave me a dev manager position in Windows, one of the first problems I spotted was that we didn’t have good clarity on how all the different roles and responsibilities of our team were being handled. If I asked enough individuals, I could eventually figure out each. But there was a lot of hunting involved.

My solution was to add a “Team Chessboard” table to one of my whiteboards. I created seven columns:

• Team Member - Name of the team member.

• Key Strengths - Beyond the standard engineer skills we expected, what does this individual excel at, to the point that they model this skill and could even teach the team how to grow this skill?

• Ambassadorships - What is this individual passionate about? What do they advocate for? This could include aspects of software engineering, things that improve team dynamics, or aspects of team culture.

• Team, Organization, Division, and Company - These represent the four meaningful altitudes in our company. What responsibilities does this individual have at these different altitudes?

With this table on my whiteboard, as I had 1:1s with my 8 leads and skip 1:1s with the 40 developers that reported to those leads, I would ask for their additions to this table. I would create a row for them and we would fill in the columns accordingly. “I organize all of the team’s lunch and learns.” “I am passionate about design.” They were also welcome to call out additions to make to the other rows. “Linda is our Watson contact for the division.”

Along the way, many people asked about why I called this the “Team Chessboard.” I said, “We’re not playing checkers, we’re playing chess. Our team is not a collection of uniform one-dimensional pieces. We are an aggregation of individuals, each with unique abilities. The pieces need to make their value adds known, and the players need to strategically utilize all the pieces for maximum win potential.”

Obviously, talking about people as game pieces can be dehumanizing. When I spotted any negative reactions, I would first say, “Well certainly you’d rather be a chess piece than a checkers piece, right?” That helped some, but my second response was far more empowering. “The players of this game are the leaders on our team. So, if you want to lead¹, our Chessboard presents you with that opportunity.” (At the bottom of this post, I’ll share the evolution of this metaphor that gives team members even more power. But first I want to expand on what our Team Chessboard unlocked for us.)

This table grew over time, with regular “oh yea” additions, as new responsibilities were given to us, and as individual team members came and left. I never thought to do anything more with this until an office move forced my hand. The chessboard had lived entirely on my whiteboard for several months. Now I’d have to take a picture and recreate it in my new office, or … I could seize this opportunity and make an addition to our Team’s External Brain².

I created a “Chessboard” page in our Team’s OneNote and transcribed the content from my whiteboard.

Over time, our published Team Chessboard accrued win after win. Here are the five key wins, in the order we discovered them.

1. Create clarity

2. Encourage contribution

3. Model scope growth

4. Publicize opportunities

5. Turn our Rewards Discussions into team strategy sessions

1) Create clarity

Most directly, this table was meant to create clarity, Microsoft Leadership Principle #1³. Every team has a distribution of roles and responsibilities. And any decent manager is aware of the key strengths of the individuals on their team. But few teams have written it down. This simple move from implicit to explicit⁴ made it straightforward for anyone on the team to readily answer the question of who owns which responsibility.

2) Encourage contribution

Having this table available to the team in a read/write form, alongside all other team knowledge that the team was already contributing to, was an implied invitation to make changes to the table. As a mental list scattered across the brains of the leadership team, this summary was completely inaccessible. In editable table form, anyone could easily spot incorrect or missing information and correct it. This made it easy to keep this chessboard up to date.

3) Model scope growth

Individuals are told that as they move up in level, their scope necessarily broadens⁵. This makes sense intuitively. But what is lacking are good examples of what that scope growth actually looks like. The Team Chessboard gives numerous concrete examples. As we have career discussions with team members, we would guide them on the general trend of:

• Junior level developers (SDE I) are still figuring out the ropes and probably not given any broader responsibilities.

• Staff level developers (SDE II) should have responsibilities at the Team altitude.

• Senior level developers (Senior SDE) should have responsibilities at the Organization altitude.

• Principal level developers (Principal SDE) should have responsibilities at the Division altitude.

• Partner level developers (Partner SDE) should have responsibilities at the Company altitude.

If they needed examples of responsibilities at their target altitude, they could use this table. And if they needed more details, they could ask the owner.

4) Publicize opportunities

It is quite common for new responsibilities to arise in an industry as dynamic as ours. The typical way to find a match for an added responsibility would be for the manager to add this to an agenda item for the next leads meeting and ask around the table to see if anyone had a match on their team. But with the Team Chessboard in place, we had a new place to advertise these opportunities. I created an Up for Grabs row at the bottom of the table.

This made leaders more aware of what responsibilities were currently slipping through the cracks. And any engineer hungry for more could look at this row to see if they could take on any of these unclaimed duties.

5) Turn our People Discussions into team strategy sessions

With all four of the above wins now in operation, my leads and I realized a true golden opportunity. We held People Discussions three times a year⁶. In a People Discussion, we discuss every member of the team and assess what has gone well for them and what opportunities for improvement we see. When it came time for leads to bring the summary of these discussions back to the engineers in the form of their performance evaluations, it was common for the engineers to want clearer guidance on how they can better set themselves up for success.

Our solution was to make the Team Chessboard a tool that we would leverage in our People Discussions. When we realized that, say, a senior developer was light on their contributions to the broader Organization, we could turn to the Chessboard and see if anything in Up for Grabs would be a good fit for this engineer. If we didn’t find something there, we could look at the entire Organization column and see if there was a balancing opportunity with another engineer.

Now, when the lead had the conversation with that senior developer, it became much more upbeat. “We identified that you don’t have enough work at the Organization scope in this review period. You can remedy that by taking on our Shell Liaison responsibility. Does that sound like a fit for you?”

Uplevel the game

It was about 10 years ago when I first started building a Team Chessboard. And from how it has evolved, I think it would be better to call the game Three Dimensional Chess. But even that is too limiting. The Team Chessboard is an ever-growing gameboard, with added dimensions of complexity to the board itself, and with added abilities to the game pieces on the board. Rooks that can fly. Knights that have night vision. And even entirely new pieces.

The rules and the play of the game are not static. Each piece brings unique abilities that fundamentally change the parameters of the game. It is exactly as Gordon MacKenzie said, “When you come into an organization, you bring with you an arcane potency, which stems, in part, from your uniqueness. That, in turn, is rooted in a complex mosaic of personal history that is original, unfathomable, inimitable. There has never been anyone quite like you, and there never will be. Consequently, you can contribute something to an endeavor that nobody else can. There is power in your uniqueness -- an inexplicable, unmeasurable power.”⁷

Speaking to the leaders of the team: as a player of the game, you need to be dynamic, and you need to be aware⁸ of everything the game pieces can do. If you’re not paying enough attention, don’t be surprised if you discover game pieces leaving your board … to go play somewhere else.

Speaking to the individuals of the team: as a piece on the game board, you need to be highlighting your capabilities and looking for opportunities to uplevel the game⁹. And if your team hasn’t explicitly created a Team Chessboard yet, then consider this one of your Ambassadorships, and start pushing for it.

Footnotes

1. The “When do you become a leader?” question that starts Play Your Part

2. Your Team’s External Brain

3. Propagate the Signal, Not the Noise

4. “OneNote Or It Didn’t Happen”

5. Earning Trust

6. The “Work: People Discussions” section of Your Team’s External Brain

7. The “Unique Value Proposition” section of You Are a Grand Synthesis

8. Raising Your Own Awareness

9. Self-Promotion

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My father joined the Navy at age 18. He always spoke appreciatively of the Navy for whipping him into shape. Obviously never knowing what my father was like as a kid, all I could witness was the after-Navy man. What I saw was a man with a strong work ethic who had a lot of healthy self-discipline routines and had a very hard time sitting still for any prolonged period of time. A perfect example of how this manifested itself: whenever my parents came out to visit me in Seattle, I needed to have a long enough list of projects so that my dad could have some productive time while he was out.

When it came to behavior, my dad used general, non-scientific terms such as “whipping into shape” and “control yourself.” And those worked fine for me growing up. I didn’t spend all that much time pondering over what came easy for me vs. what was a challenge for me. My peers also talked about my behavior non-scientifically, using words like “spaz” and “random”. I always credited my six brothers and sisters for being harder on me than any of my peers (I say this in the most loving and appreciative way), such that by the time I reached the point of hearing words like this directed at me, I had a pretty thick skin and rarely thought much of it. I knew my family loved me and I was as encouraged to give them a hard time as they were to give me a hard time.

By copying my dad’s behavior, things seemed to work pretty well for me. It wasn’t until well into my Microsoft career that I started to look at my behavior more objectively and scientifically. Why was I so routine-oriented? Why would I have unpredictable surges and lulls in my execution? Around this time, I read Scott Peck’s “The Road Less Traveled.”² Among the many takeaways I got from this book, one that was especially important was how he presented therapy. At that time, there was a huge stigma associated with seeing a therapist. If you were seeing a therapist, it meant you were crazy. Scott countered that, saying that the healthiest individuals are the ones that seek therapy, because they are prioritizing their health, and taking specific steps to understand more about themselves.

Scott’s perspective resonated with me. As a computer geek, I saw therapy as debugging my brain. And given how much I had learned about software through my debugging experiences, I actually became excited about going to therapy. From my earliest therapy, we replaced those general terms from my childhood with more scientific terms: “ADHD” and “addictive behavior.” There was no judgment or labeling associated with the use of these terms. It was all about understanding. As we talked about this science, I could replay my experiences and see how these behaviors were exhibited in my dad and in myself. The genetics behind this made that none too surprising.

Coping skills

After understanding these disorders as being part of my wiring, we started talking about how to handle it. I was clearly not debilitated by these, having a very successful schooling experience and having a strong start professionally. But there were times when I did feel very stalled or stuck. As I replayed my childhood experiences with my therapist, he introduced me to the term “coping skills.” Whether you build these skills with full awareness of what behavior you’re trying to counteract, or you build these skills as part of learning an overall routine, coping skills are the habits that you build that offset the disorders that you have. In my dad’s case, from a time when there was no talk of therapy and disorders, it was as simple as the Navy giving him a rigid routine that he found comfort, ease, and quiet in. He came to value routines to help with his self-control, and modeled that constantly for me to follow.

There was one point during this first therapy series when I attempted medication for my ADHD. For me, it was part of debugging and objectivity. I wanted to compare my natural normal with this modified normal. Was it night and day for me, or just a slight change in focus? Did it subdue creativity, or did I still feel inspired? I took the medication for two weeks. My original plan was to take it for a full month, but I had physiological reactions that made for a pretty unpleasant experience after two weeks, so I stopped early. What I did get a glimpse of during those two weeks was a quieter mind. And while there was less chaotic thought which I had often leveraged for my creativity, I could see the value of this quietness during times when I needed less creativity and more raw execution.

From this more informed vantage point, thanks to the reflection and experimentation of my therapy, I turned my attention to intentionally developing my coping skills. It was a very empowering feeling, and was a key pivot point in my personal and professional growth. I knew what my own mental impediments were, and I knew how to avoid them. My dad had given me a solid set of skills to work with the genes I had been dealt, and now it was up to me to take them further.

I’ve shared many of my best coping skills in earlier posts. Let me summarize my top three here. For more detail on any of these, follow the footnotes.

1. Timebox everything³ - When I introduced timebox everything, I called it my #1 coping skill. In its fully developed state, it’s now as simple as telling my brain, “You just need to give me 30 minutes of relative peace and quiet and then you can go back to free firing.” This skill was built over time, with each successful iteration convincing me that it would save me. I measured success for how long of a timebox I could maintain my focus in. I started with 5 minutes. I declared success when I achieved 90 minutes, repeatedly. It has given me on-demand focus.

2. Read with a pen⁴ - Reading was always a struggle for me, because I couldn’t get my brain to focus on the words over the constant distractions in my head. When I found myself re-reading the same paragraph for the third time, I would typically give up. The original motivation behind my “read with a pen” habit was to force my brain to pay more attention to what I was reading.

3. Reflexive capture⁵ - I describe my ADHD brain as a dripping faucet that I can never turn off. The ideas just keep dripping. With each drip, I had a choice: ignore the drip and stay focused on what I was doing, or turn my attention to the drip and derail my focus. Neither option was that ideal, so eventually my level of frustration drove me to discover a third option: capture the idea in real-time so that I don’t lose it, and then get back to what I was doing.

Passing it on

We pass on our genes to our kids. This is a mixed blessing. And after being diagnosed with ADHD, I was focused on the bad I had given my kids. I remembered what was hard for me because of my unfocused energy. And I was watching it play out with my boys. Perhaps Pop felt the same way, but I never heard him apologizing or acting down about it. What I remember from my dad was him modeling the better alternatives, through his own routines. So that’s the approach I took.

I remember when my youngest was in college and he was talking about, “Being behind on some easy things.” I had that same feeling in college, where I was knocking out the hardest problems thrown at me, but couldn’t seem to finish the simple stuff. I pointed him to the post-it note system he had already been using, with notes stuck to his computer to track his work. I suggested he color code the post-its to indicate how long each task would take. Then, when he found himself with a short window of time to get something done, he could grab one of the appropriate colored post-its and knock it out. A week later, Drew sent me a text message with a picture of his updated system, and a “Thanks.”

He and I can talk about genetics, therapy, disorders, and coping skills later. For now, I’m just focused on building up his base, as Pop had done with me.

In Control Your Phone, Or Your Phone Will Control You⁶, I said that the smartphone has created an “attention deficit norm.” So my 10 pro-tips that I shared there are not only to help the genetic-ADHD population, but the naturalized-ADHD population alike.

The upside of ADHD

When you build a strong set of coping skills to offset the negative effects of your disorder, what you’re left with are the positive effects. That turns your disorder into an extraorder … contributing to your extraordinariness. Here are my top three celebrations of ADHD.

1. ADHD turns your brain into a relentless idea factory. Need to come up with a creative idea? Just plant a seed and give it time … and then be ready to capture the ideas when they come. Creativity unlocked.

2. You can handle more simultaneous distractions. Your brain has been building your context switch⁷ muscle from a very early age. I found this to be especially helpful in my management role, where you are more bombarded by the disparate needs of your entire team.

3. You have creative syntheses. While you don’t experience a linear path to the idea, often times you are able to draw from several seemingly unrelated sources to arrive at a unique synthesis. This expands the possibility spectrum of any brainstorming session.

Don’t let the disorder define you. By developing the right coping skills, the disorder can propel you.

Footnotes

1. Randy Pausch’s Last Lecture (YouTube)

2. The Road Less Traveled, M. Scott Peck (Goodreads), also referenced in the “Love is a verb” section of Love It Or Leave It

3. Timebox Everything

4. The “Read with a pen” section of Mining for Gems

5. The “Reflexive capture” section of Harness the Power of “Idea Bombs”

6. Control Your Phone, Or Your Phone Will Control You

7. Clean Context Switching

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Charu and I had a “provide alternatives” rule with our boys. When we were picking which activity we were going to do or which restaurant we were going to go eat at, anyone could throw an idea out, but you could not simply respond, “No.” Instead you had to respond with another suggestion, “Instead of Subway, how about Taco Time?” This rule keeps the conversation going, which generates more ideas for consideration. The generalization of this rule would be: favor conversation expanders over conversation enders.

When someone is asked to do something, a very relatable and understandable response would be, “I don’t have the time.” But that’s not much of a conversation expander. It fails to give important information to the requester, and were the requester to probe any further, it would most likely come across as pushy.

The conversation expands when you ask yourself, “Why don’t I have the time?” Here are seven alternatives, from easiest to most challenging

1. Suspension: “I will get to that in <ETA>.” - You’re telling the person that you are temporarily booked out, but you can schedule this for the given date. If that date works, then you’re all set.

2. Delegation: “You should ask <person>.” You’re telling the person that you’ve delegated this problem space to another person or team. Now they can forward their ask on to that owner.

3. Negotiation: “I can help with <part of ask>.” - This is a “meet me half way” response. You’re telling the person you can help with part of their need, but then they’ll either have to take on the rest themselves or find another owner for that part.

4. Prioritization: “I’m not prioritizing that.” - You’re telling the person where it ranks in your relative prioritization. This will get you into the discussion of importance, and perhaps uncover other motivations or benefits that move this ask up your priority list.

5. Optimization: “Let me figure out how to fit this in.” - You’re telling the person that you’re the right owner for this, but need to do some tuning to figure out how to work this into your sustainable rhythm.

6. Confession (Short-Term): “I’m behind on what I’m supposed to be doing, so I can’t even entertain an additional ask.” - You’re making it clear that you’re currently underwater, and focused right now on finding stability. This opens the door to a deeper conversation with the asker.

7. Confession (Long-Term): “I don’t think I have time. But, in all honesty, it’s not something that I know. Time is elusive to me.”

Or “I don’t regulate my time and therefore I don’t know what amount of time I would have.” - This is a conversation ender because most people wouldn’t know what to do with this response. But it’s captured here for completeness, and as the setup for the deeper dive below on confessions.

The first three of these are pretty straightforward in terms of the follow-up conversations they generate. Now I want to expand on the last four.

Prioritization

The prioritization response will spark the most elaborate and enlightening discussions. It is very common for two people to be operating on different relative prioritizations. The discussion that follows the “I’m not prioritizing that” statement is two people trying to understand each other’s priorities and, where possible, align. Teams have a collection of priorities that come from several sources (e.g. project planning, repo roadmaps, and team missions). And individuals have their own priorities that come from their career goals, personal agenda, and their team commitments.

With all of these inputs, it’s not surprising that the individualized priority ranking differs between people. Conversations on priority are some of the best at learning about different ways to rank importance and the benefit of being clear with yourself on the priority order you’re assigning to things.²

Optimization

The optimization response will initiate an internal dialogue. That dialogue can include reevaluating the first four alternative phrases. “Do I have an opening in my rhythm in the future where this work could be done?” “Do I need to delegate this work, or delegate some other work to take this on instead?” “Can I potentially own part of the solution?” “Should I revisit my priorities?”

After those alternatives have been explored, then it’s time to get creative, in the literal sense. You need to create the space. It’s not about taking time. It’s about making time. How can you tune your rhythm to allow for more space. Where and how can you up your efficiency? As Lord Chesterfield advised, “Take care of the minutes and the hours will take care of themselves.” There is always room for more tuning.

We’re all busy. We all have finite hours in our day. So we need to collectively be intentional and economical with our time. For most people I’ve worked with facing optimization challenges, optimizing their Triage Shield³ has given the biggest payoff.

Confession

Let me clear, I don’t expect that alternatives #6 and #7 are likely to be ones that you would ever verbalize. #6 maybe, but #7 would be highly unlikely. But if you internally think about either of these responses when the request is made, it’s worth a little more self-exploration. And if you haven’t thought of these responses, having them here as options is a way of checking your own self-awareness⁴. We’ve got really good defense mechanisms that can keep such thoughts out of our consciousness. Invite them in. Spark the internal dialogue.

“I’m behind on what I’m supposed to be doing, so I can’t even entertain an additional ask.”

This communicates stress to the requester. They realize that you are understandably in more of a survival mode given the feeling of being buried by your work. At the very least, they will back off of this ask. But, more importantly, this response creates an opening for them to extend help for some of your behind work. Requestor: “Oh, I didn’t realize that. Well, given how important this ask is for me, is there something in your current workload that I could take off your plate to free you up for this?”

Actually admitting that you’re behind can feel embarrassing to you. If it does, most likely that’s because you think you’re the only one who’s behind, or has ever been behind. Trust me, we’ve all been there. Professional work is all about individuals and teams pushing the envelope. Overstacking the work is a natural side effect of high ambition.

Rather than seeing your admission as a moment of shame, think of it as an invitation for empathy.

“I don’t think I have time. But, in all honesty, it’s not something that I know. Time is elusive to me.”

This is a much stronger confession, making it far less likely that you would ever actually say this out loud to someone else. It’s value is more as a potential statement to try out with yourself to see how it fits.

This is the last option on the list for a reason. This is the “none of the above” trailing option. If you’ve made it through responses #1 - #6 and still haven’t found a fit, then this response may be your reality. It may take a bit to be convinced, so try this out. Keep a tally over a month or so of how many times you’ve gone through this “alternatives” exercise, and what your response has been. Is there a trend a landing on this #7 “none of the above” response? Face that fact, and then take action.

If your time isn’t managed, then start with these two questions: (1) Do you believe your time is manageable? (2) Do you think time management will help you? You have to first believe it’s possible, and that it will be beneficial. If you answered “No” to either question, then you can stop here. The only path out of a defeated mindset is through belief that it’s in your power to change the situation for the better.

Try this out. Open excel and create a new spreadsheet List out all of your responsibilities big and small. Then next to each responsibility, write the number of hours you’d like to devote to that commitment each week. Don’t forget to create a sum cell at the bottom to make sure that everything is fitting in your target number of work hours. If you prefer, you can do all of this as percentages of the week’s time, and then build a formula to compute the hours for each item that the percentage translates to.

Share the resulting breakdown with your manager or mentor. Do they see any items to add or remove, or have any suggestions about the distribution? Once you’ve reached agreement, you’re ready to print this out and put it on your desk to make sure it gets the attention it needs from you as you work to adhere to it.

Then try my exercises in Timebox Everything⁵ and Finite Time⁶.

Michael Altshuler said it perfectly: “The bad news is time flies. The good news is you’re the pilot.” You are in the driver’s seat.⁷

Footnotes

1. That, detective, is the right question - I, Robot

2. The “In order to say ‘yes to this, what must you say ‘no’ to?” section of Fear of Overcommitment and the “Top-Down Meets Bottom-Up” section of Manage Project Tasks Responsibly

3. Triage Shield

4. Raising Your Own Awareness

5. Timebox Everything

6. Finite Time

7. “Serenity Now!”

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The only family home I remember is on Teddington Drive in Richmond, Virginia. I was four years old when we moved into this house. I have no memory of the house on Covey Street where we had lived before. The closest memory I have is walking out the door to the Covey house and getting in our station wagon … on the day we were moving.

Mom had a piece of wall art that she hung above the kitchen sink the day we moved in. And it stayed there until the day she moved out, 40 years later.

Mom loved this prayer. Mom lived this prayer. When we cleaned out our family home before selling it, my sister Ann claimed this art and it is now hanging in her kitchen. I don’t have a physical reminder. But given how much I saw Mom demonstrating it, I didn’t need it. This prayer is etched into my brain, and onto my heart.

Prayer of Serenity
God grant me the Serenity to accept the things I cannot change,
Courage to change the things I can,
and the Wisdom to know the difference.

The Prayer of Serenity has been adopted by Alcoholics Anonymous, as it perfectly captures the struggle we face in life to control what we can control and to let go of the rest. My family’s genes gave us a proclivity to addiction (accept). My father’s biggest addiction was alcohol. Mine is video games. Pop overcame his drinking (courage). I’m doing alright managing my video games (courage in progress).

Your overall effectiveness as an individual comes down to how well you can recognize what things you can change and what things you can’t change, and then how well you can direct all of your energy to what you can change. This is Stephen Covey’s first habit in “The 7 Habits of Highly Effective People”². Habit #1 is called “Be Proactive”, where Covey introduces the two circles: the Circle of Concern and the Circle of Influence.

Your Circle of Concern contains everything that you think about. Embedded inside this circle is the smaller Circle of Influence that captures everything that you can influence. The weather and the stock market are inside your Circle of Concern but outside your Circle of Influence. Building your habits and helping your neighbor clean their yard are within your Circle of Influence.

Covey uses the arrows to highlight that, by focusing your efforts on the inner Circle of Influence, you grow that circle. And while you will never get to the point of being able to control the weather, through these expanding efforts, you will discover that you have more influence than you realize.

This concept was a light bulb moment for me, and has done wonders for focusing me ever since. When I dwell on things outside my Circle of Influence, I am powerless -- the victim. When I focus on things inside my Circle of Influence, I am empowered -- the change agent. Covey’s 7 habits book remains at the top of my list because of the level of change it instigated in me, beginning with habit #1.

Action-oriented

Mom’s Prayer of Serenity and Covey’s circles have come together in my brain as one blended image. The three actions (accept, change, know) of the Prayer of Serenity replace Covey’s terms.

The Accept ring

For the things outside of your control, your action is to accept them. Let go. Don’t worry. Move on.

A precursor to the Prayer of Serenity appeared in the Christian Gleaner and Domestic Magazine in 1827³.

How to go smoothly through a crooked world
For every ailment under the sun
There is a remedy, or there is none;
If there be one, try to find it;
If there be none, never mind it.

Acceptance is the punchline of this rhyme. Try to fix it. If you can’t, let it go.

The Change circle

The Change circle is what you should call home. This is where you get to work. This is where you make a difference. The courage that you demonstrate in the Change circle is what grows your Change circle. Change yourself (private victory) or your environment (public victory) for the better, and you will discover ways that you can further improve.

Minimize the time spent in the Accept ring so that you can maximize the time spent in the Change circle. You’re revving your Energy Flywheel⁴ when you’re in the Change circle.

The Discern dividing line

Wisdom is the punchline of the Prayer of Serenity. The key to this whole system working is you being able to discern what is actionable vs. what you have to just accept. This dividing line is a muscle you will build. Much like with the Triage Shield⁵ work, the secret is practice. Practice makes faster. Intentionally decide, for each concern, do you need to Change or Accept. Here’s a good exercise to do to help raise your awareness⁶.

1. Pull out a piece of paper, or open a notebook page on your computer screen.

2. Write out everything that was on your mind throughout the course of the day.

3. Do a pass over that list, and for each item, mark it either as Change or Accept.

4. If you are “on the fence” on any item, try to break that concern down into all of its relevant sub-concerns. Keep breaking it down until each sub-item (or sub-sub-item) can be identified.

Let’s use the standard “money management” concern as a good example of #4. This concern is usually a dark looming cloud. But when you repeatedly apply your discern muscle, it becomes more manageable. Money management is a mix of Accept and Change, so break it down …

• Investing - still a mix …

  • Portfolio Strategy - Change - what’s the winning long-term strategy?

  • Market Volatility - Accept - we have no control over the market

• Earning - still a mix …

  • New Job - Change - Is my current job a good return on investment? Should I find a better job?

    • Job Market - Accept - I have to accept the reality of any restlessness in the job market

  • Promote - Change (grow circle) - I don’t directly control the amount of money I’m paid. But through increased performance, I can be promoted, which does give me more money.

• Spending - I have a family, and we’ve made decisions for that family. But we can revisit periodically as our needs change. Breaking it down …

  • Housing - Accept - we’ve already had the discussion about moving and, comparing options, we love where we’re at.

  • Cars - Change - we had a set of cars designed around raising two boys. They’re grown up now. So what cars do we need now?

  • Food - still a mix …

    • Groceries - Accept - grocery prices are going up, but we’ve got a good diet and have been in good health because of it.

    • Eating Out - Change - we don’t really have a plan around when we eat out, and we should just so that we can better plan.

This list would now narrow my focus to the things I can do something about. The dark cloud becomes smaller. Name it to tame it.

You may notice a couple of “Accepts” in my money example above that I am, in fact, able to control (e.g. Housing and Groceries). If you can willingly move an item out of your Change circle, that’s an example of proactively Choosing Your Battles⁷. The key to maintaining your sanity is by being selective. In “The Inner Game of Tennis”⁸, Timothy Gallwey concludes, “Stability grows as I learn to accept what I cannot control and take control of what I can.” The Prayer of Serenity, aka The Prayer of Sanity, aka The Prayer of Stability.

Footnotes

1. Scalable Collecting, Suffering = Pain x Resistance, and I Have a Dog-shaped Hole in My Heart

2. The 7 Habits of Highly Effective People, Stephen Covey (Goodreads)

3. Christian Gleaner and Domestic Magazine (Google Books)

4. Revving Your Energy Flywheel

5. Triage Shield

6. Raising Your Own Awareness

7. The “Choose Your Battles” section of Play Your Part

8. The Inner Game of Tennis, W. Timothy Gallwey (Goodreads)

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I met Karl Stock on June 3, 1991, my first day on the job. Karl was my first skip manager at Microsoft¹. I learned a ton about people management from Karl over the four years that I worked with him. But more than that, I have had a terrific longstanding friendship with Karl. We’ve hiked and biked all over the place. And in recent years, on multiple occasions, I’ve visited Karl and his family down in Arizona².

There are countless treasured conversations I have had with Karl over the years, including one piano story. When Karl’s kids had grown and moved out, Karl and Martha decided to move to a smaller place on Bainbridge Island. Karl is a people person, and while he had collected many things in his house over the years, he hadn’t thought much about those things. In their downsizing move, he was surprised to find out that he was having a hard time letting go of certain things … because of the memories that they held.

He had a beautiful grand piano. Both of his kids had learned to play on that piano. Just looking at the piano reminded him of sitting with them at the piano or hearing them from the other room as they played. It made no sense to keep this piano, and yet he couldn’t imagine parting with it. I asked, “What if you just take one piano key with you? Would that be enough to remind you of all of these wonderful memories?”

I didn’t think much about this conversation at the time, but a few years later it was my turn to practice what I was preaching, when me and my siblings got together to clean our childhood home out before we sold it³. Forty years of memory accumulation. I was glad we had seven of us to work through this. It was an incredible experience to have all of us together again under the roof, one last time.

As the cleaning process went on, each of us began building our own separate save pile. These were the things that each of us was going to take with us. The rest went into the huge dumpster that had been dropped off in our driveway the morning we got there.

My save pile was too big. Unlike all my brothers and sisters who had driven to the house, I would be flying home. So I needed to be much pickier with what I took. That’s when the piano key question came to me. With the “a piece is enough to remind me of the whole” mindset, I did a second pass and my save pile fit in my carry-on. And then when I got back to my home in Bellevue, I decided to do a little spring cleaning of some of my other save piles. I turned the resulting collection of piano keys into a memory wall hanging in my shop.

To anyone else, it looks like a bunch of nothing. But to me, it’s a flood of warm fuzzies. The bed post from the bunk bed that I slept on the entire time I lived in Richmond. The first hammer of my dad’s (his small tack hammer) that I ever used. The railroad spike from the train tracks in my parents’ hometown of Shamokin, PA. etc. etc. All presented on shelves that were converted grape crates that I made for college, from the trash I found in the back of the Ukrop’s supermarket I used to work at.

And then I brought my piano key mindset into the office. The result was an office full of memories that’s packable in less than an hour. My office stayed that way right up until the end, when Charu and Luke and I packed it all in an hour and drove off into the sunset.

The Mindset

In Anne Morrow Lindbergh’s “Gift from the Sea”⁴, she has a chapter named “A Few Shells”. That chapter perfectly captures the value of being selective about the things that you collect.

“One cannot collect all the beautiful shells on the beach. One can collect only a few, and they are more beautiful if they are few.” The more selective you are, the more powerful your selections become. Choose wisely!

“One sets it apart by itself, ringed around by space ... For it is only framed in space that beauty blooms. Only in space are events and objects and people unique and significant.” I love Anne’s point about the significance of space. When it’s cluttered, all you’re seeing is a pile of things. But when you separate things out, you can appreciate each thing, individually, fully.

Totems are small objects that are full of significance. In earlier posts, I had called out two other totems I selected, my Angst Mug⁵ and Hobbes’ Bear⁶. There are two more significant totems I want to share with you: the totems representing my Mom and my Pop. I’ll cover Dad’s totem in this post, and then get to Mom’s in my next post.

The Electrician’s Light

When our family got together in September of 2002 at our childhood home in Richmond, Virginia, it was to bid our Pop a farewell. His cancer had taken a final hold, and a man that we had all remembered as active, jovial, and loud lay silently in front of us. When he passed a day later, we all started sharing stories of our full-of-life dad. We congregated out in the garage, which was Pop’s shop. There was no better way to feel close to Pop than to sit in his shop, surrounded by so many of his tools, his collectibles, and his creations. Thirty years of memories.

We all began scanning his shop for souvenirs to remind us of Pop … to take home with each of us. I began searching for my totem, the one object that would trigger the fullest recall of Pop. I looked around the shop at such memorable items as a desk that I remember watching him build when I was eight, a blacksmith’s vice that Pop had gotten from his Pop’s workshop in Pennsylvania perhaps as many years ago as I am old, and a plethora of tools that I can recall him showing me how to use. I looked and I looked, but couldn’t find my totem. And in the week that followed, as my brother John and I began the process of cleaning out Pop’s shop and storage area, I continued the hunt. No luck.

A couple of weeks passed, and I was in our home in Seattle cleaning out some boxes when I came across an old lamp. As I sat looking at this lamp, a growing stream of childhood memories began to flow. This was a lamp that Pop built for my brother John when he was probably five years old. This lamp had, at some point, made it to my desk. And it followed me to college and out to Seattle. Now, as I looked at it, amidst the swirl of memories it triggered, I realized why it was the perfect totem. This lamp symbolized Pop.

Pop was a craftsman and an electrician. This lamp captures both of those skills. The lamp’s design is unique, yet simple, much like its builder. The lamp is durable, having survived three boys who weren’t the gentlest of lamp-keepers. Pop was as solid as a rock (after all, he had to survive those aforementioned three boys and four more children), a dependable spouse, father, friend, and worker.

This lamp is fed its life-giving current through an electrical circulatory system. And anyone who ever spent time with Pop saw how much he was part of the circulatory system of life. A human’s circulatory system is behind the scenes, but you can see it if you look hard enough. But despite its lack of exposure, it is a vital network for the body. Pop’s life was one of significant, yet discrete, effort. The lamp is significant, but is rarely recognized as being significant.

I thought I had known this about Pop all along, but I never realized how deep and wide the network that he wired ran. Not until, on his passing, those that his life had touched came forward to recognize him. We didn’t even know the lady who helped us at the funeral home, but she greeted us by saying, “Your Joe was such a terrific man … you probably don’t know this, but he did some work on our house quite a few years back.” Upon returning to Seattle, we found a bouquet of flowers sent in sympathy by my son’s Montessori school. Their card read, “We are reminded every day of Joe … when we use the multi-purpose room and office.” Pop had done electrical work for their school during one of his visits to Seattle. At Pop’s funeral service, Father Shrieve compared Pop to Joseph the carpenter, and there was warm laughter from the congregation as Shrieve detailed his analogy, showing just how many people Pop had touched with his efforts.

There is a poem by George Webster Douglas that my sister Beth had framed for Pop. It reads:

A father is neither an anchor to hold us back,
Nor a sail to take us there.
But always a guiding light whose love shows us the way.

This is, for me, the key to why this lamp is my perfect totem for Pop, my small reminder of this giant of a person.

Today, this lamp sits next to my monitor. I have kept it turned on 24/7 for the last 24 years. Burning in tribute to a man whose light still shines in all those that he touched. And burning as Pop’s “guiding light”, reminding those that he touched to carry his torch further, and touch others.

Footnotes

1. The “My favorite morale ‘projects’” section of Morale Matters

2. Let Me Tell You ‘bout a Friend (Facebook)

3. The “5) Share a Love Story” section of Lead with Love

4. Gift from the Sea, Anne Morrow Lindbergh (Goodreads)

5. Suffering = Pain x Resistance

6. I Have a Dog-shaped Hole in My Heart

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Look at that photo! Not staged. Not doctored. Not photoshopped. Not AI-generated. 100% natural Hobbes. This is 2-year-old Hobbes with his favorite toy. That bear is the “totem” I’ve chosen to remember Hobbes by. It is now sitting in my office.

I was the last kid my parents had to ship off to college. I was ready for the college experience, but I wasn’t ready to say goodbye to my parents. I was always very attached to my parents … strike 1. I am also a somewhat emotional person … strike 2. And then there was the fact that I was last in line … Mom and Pop’s final farewell … strike 3.

Friday night we loaded up the van. Saturday morning, the three of us set out on the four hour drive from Richmond to Blacksburg. We chatted the whole time about school and the different friends of mine that would also be at Virginia Tech. This dialogue was all part of their plan to get me more ready for being without them. They had a plan for this whole day. And not filling me in on their plan was actually part of the plan (foreshadowing).

We unpacked the van and they helped me get all settled in to 609 Lee Hall. Then we drove off campus to get lunch. Over pizza, our conversation continued, but now there was a sadness entering the conversation. We knew that soon enough Mom and Pop would have to hit the road for the four hour return trip. I started doing the mental arithmetic and figured in another hour they’d be gone. I was getting quiet.

After lunch, we climbed back in the van and started heading back to Lee Hall. As we approached my part of campus, Pop said, “This move-in traffic is way worse now. Son, I don’t think we’re gonna be able to park by your dorm. Heck, I don’t even think we can get back down that road.” There was a pause. I was at immediate attention … and alarm. Pop looked at Mom and said, “Cookie, we’re gonna have to say our goodbyes here.” Then they both looked back at me.

I stumbled. I stalled. “Uhhh … uhhhhhhh.” Mom gestured me forward. There was room enough in the van for me to basically kneel right between them. I gave Pop a hug. I started crying. I gave Mom a hug. I started balling. We exchanged our “love you”s. Then I stepped out of the van onto the sidewalk, shut the door behind me, and watched as the van drove away. I kept my head down as I walked back to Lee Hall, keeping the tears to myself.

When I saw them again a few months later, I commented on the need for us to do better at goodbyes than my unceremonious college drop off. That’s when Mom and Pop explained how intentional that was. Pop told me that on move-in day, when I got up to use the bathroom at lunch, he told Mom, “There’s no way that actually leaving Jeff is going to be easy. He’s already showing us that. We have to have a clean break or we’ll never get out of here.” Mom concurred, and the executed their plan to perfection. It sucked in the moment, but there was no way for that moment to not suck. So the point was, don’t prolong the suck.

Today, as I reflect on the abruptness of Hobbes’ exit, I’m remembering my college move-in experience and wondering if my parents had shared their pro-tip with Hobbes.

Just after midnight on Monday, Hobbes had his first seizure. 84 hours later, Hobbes left us. Hobbes never gave us any medical drama. For 13 years, he’d been a healthy dog. So when the four of us left the vet on Thursday morning and sent the news out to our family and friends, there was widespread shock. “What happened?” “That came out of nowhere.” “He was fine last week.”

There is tremendous sadness at the loss of Hobbes. But I’m thankful that the suck happened quickly. We only had to see our doggie struggle for a couple of days. When it comes to dying, fast beats slow.

Ten Hobbes Lessons

I am inexpressibly appreciative of all that Hobbes brought into our lives. Hobbes taught us how to be better humans. Here are the ten Hobbes lessons I valued most, in no particular order, other than saving the best for last.

1) Don’t just help one person … help everyone you meet

Our original motivation for getting a dog was to be a buddy and grounding force for our younger son, Drew. Drew’s blend of Bogdan and Kalyan energy gave him some unique challenges growing up. His written response to a prompt in 4th grade captures it best. Prompt: “What does ‘ready to learn’ mean to you?” Drew: “I think ‘ready to learn’ means to not talk but listen, not to be wild but calm, not be loud but silent. BUT you might be so silent that you burst up in flames at recess.”

As parents of energetic boys, we already had a full plate just with their activities. But we accepted the challenge of adding a dog into the mix because we saw the opportunities for helping our kids. We continued to be surprised, every day, that Hobbes wasn’t just there for Drew, he was there for Luke … and Charu and I … and our extended family … and our friends.

Hobbes was there for everybody. There was no shortage of cuddles, tail wags, licks, and grabs.

2) Stop and sit

As we were driving home from the vet, I asked the family, “What is the biggest thing that Hobbes taught you?” No one answered that question at the time. It wasn’t a time for much talking. But later that evening we came back to the question. Charu, Luke, and I all had the same answer. Hobbes taught us to stop. If you were at your desk for too long, Hobbes would let you know that enough was enough. He’d walk over to you, stop, and look up at you. Then he’d wait.

It was a brilliant tactic. His cuteness won most of the time. You could reach down and pet him a little bit, or you could use that as an excuse to get some quality cuddle time with Hobbes and either sit on the floor with him or move over to a couch or chair that he would then join you on.

When I was working at Microsoft, my morning routine was rock solid¹. I was up at 6am and out the door at 6:20am. At 6:30, I was sitting in my writing chair at work doing my daily writing block². And for the first year after Microsoft, I kept a very similar morning routine. I just replaced the office with the treehouse³. Then, last year, I decided to move my office from the treehouse to the actual house.

For years I had had complete control over my morning. I decided when I was going to have my first interaction of the day. Now, with my office being inside my home, that was something I no longer controlled. Now, about midway into my 60min writing session, I would hear the clicking of Hobbes’ nails on the hardwood as he pranced towards my office. Hobbes was the second one awake in the house, and he was in search of the first one … me.

Initially, I was bothered by this. I was so dependent on my isolated ritual of 10min stretch, then 20min workout, then 60min writing, that I felt thrown off by Hobbes’ intrusion. Over time, though, I realized this was his first greeting of the day … and mine … and it should be savored. That’s when this intrusion turned into a beautiful ritual:

As soon as I hear his prance, I step to the side of my desk so he could see me. I kneel down and open my arms and say, “Good morning Hobbesey.” He walks up to me just far enough for my hands to reach him. When my hands reach the back of his head, he sits down so that he can pull his head back against my fingers as I massage the back of his head and his neck. When I stop, that’s his cue to get up and walk straight into me. Then I lean over him and pet him from head to toe, massaging his sides and telling him that he’s such a good boy. And as I’m doing this, he’s nuzzling into my legs and rubbing the sides of his head on me. His taile is helicoptering at 1,000rpms for this entire exchange.

This morning when I woke up, I experienced for the first time, an uninterrupted morning routine. I didn’t like it one bit. And now I’m getting ready for a full day without any of Hobbes’ welcome interruptions, such as him joining me for my morning coffee and read.

Thank you, Hobbes, for reminding me of the importance of being in the present tense.

3) Be gentle

Drew’s answer to my “biggest thing that Hobbes taught you” question was, “Be more gentle.” Drew is our “bull in a china shop” son, and we all kid him about it to this day. When we first got Hobbes, Drew had to learn very quickly how to be gentle with this weeks-old puppy. The more time Drew spent with Hobbes, the more instruction he was getting, in the form of immediate feedback from Hobbes. Hobbes was a loving dog, but he wasn’t afraid to let you know when you were annoying him. Drew learned that signal earliest.

Drew and Hobbes had their share of on periods and off periods. Their bond wasn’t immediate. It grew steadily over time. Where they ended up is what matters: they ended up true brothers.

4) Be aware of when others need care

Hobbes knew when you weren’t doing well. Bodily injuries are obvious, but Hobbes was equally aware of the internal aches. If your belly was upset, or if you were having an especially blue day, Hobbes was first on the scene. He’d hop on the couch next to you and lean against you. You could pet him as much as you wanted. He wasn’t going anywhere!

We got to return this favor in Hobbes’ final hours, when he was the one that needed care. The only way Hobbes could sleep on his final night was by being held. Good thing there were four of us to do the rotation. Here’s my 4am cuddle … one of my last good cuddles with Hobbes.

Thank you Hobbes for showing us how to take care of you.

5) You’re never too old to learn

Drew taught Hobbes how to “shake” at age 10.

Charu taught Hobbes how to “fetch” at age 11.

Never stop learning⁴.

6) Stay active

There was no stopping Hobbes. In his final hour, he had enough energy for one last family walk.

7) Stay vigilant

Even when he’s tucked into his favorite spot on the bed, Hobbes remains on the lookout.

8) Travel together

As the African proverb goes, “If you want to go fast, go alone. If you want to go far, go together.”

Hobbes didn’t always enjoy the travel part, but if it meant being together, he was all in.

He was also smart about making sure he was included in trips. His favorite tactic was to block the exit.

9) Kill them with kindness

If Hobbes liked a food, he learned the sound that the container for that food made when it was picked up, when it was put down, when it was opened, and when it was dispensed. He wasn’t a bully about it. He would simply show up and stand in your field of vision. You knew what to do after that. After all, he had trained you well.

10) Be the Hobbes you want to feel in the house

And now for the best that I saved for last. Thank you Hobbes for teaching us how to properly greet each other!

It has been said many ways, because it is universally true. Dogs are the best greeters. Regardless of the day you’ve had, or any household drama that has unfolded in previous days or weeks, when you walk in the door, you are guaranteed one thing … your dog will greet you and love you.

At dinner last night, I said to the family, “To keep Hobbes’ spirit alive in our family, we now all have to be each other’s Hobbes. When anyone comes in the house, give them a Hobbes-worthy greeting.” Charu said, “Well, I won’t lick your face, but I can do the rest.” It will be impossible to hit this consistently. But whenever we do, Hobbes will be smiling … and so will our family. I gave Charu a big hug when she woke up this morning. And I gave Luke a big hug when I saw him this afternoon. So I’m off to a good start!

This was Hobbes’ favorite perch in the house. From this couch back, he could see the front door. He was at the ready for his next greeting. It didn’t matter if you were family, friend, or a stranger, Hobbes’ one rule was, “If you are coming in the house, then you are getting a greeting.” If you made him wait too long, the whining would start. But he wasn’t whining for him. He was whining for you. “Come here and get some of this. You know you need it.”

Among the thoughts shared by our many friends and family, this was my favorite. “Please let me be the person my dog thinks I am.” I’m better for having known Hobbes, and now it’s my duty to live up to the bar he set.

Footnotes 🐾

1. Habit-Propelled

2. Play the Pause

3. Divided Space for Undivided Attention

4. Lifelong Student-Teacher

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