Lessons from my 36th year

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Lessons from my 36th year

This past year brought a significant amount of change to my and my family’s lives. And, per my lessons from my 35th year, I feel I have stewarded that change with grace and care.

I’ve just completed my rigorous Annual Review process, and the tail end of that flow includes rereading last year’s lessons. I continue to resonate with each lesson and have made substantial progress in improving and integrating most of last year’s lessons. For structural reasons, I still traveled too much to focus on daily and weekly routines (including my music practice), but with my move to Southern Oregon, that will change dramatically in 2024.

Across the broad and diverse experiences of my perfect square year, here is what I learned:

Clean air, water, and food are critical to Thriving

It sounds so simple as to be trivially obvious. Only in my 36th year did I prioritize moving to a place that is resource-resilient with clean air, water, and food.

And the difference I feel is shockingly dramatic.

I feel calmer, stronger, and healthier. I feel more resourced to sense broader and deeper. I feel empowered and inspired to refine my path of Thriving. And to offer more simple clarity for how others may walk their path to Thrive.

In three short months, I sense a substantial shift in my psyche and body. And I know that it will only positively compound over time.

I could never imagine the world of difference, and now that I know, I cannot imagine living anywhere with compromised base needs again.

When the lights go out, my professional skills are toast

In May, I attended a permaculture workshop that had a profound impact on me. The workshop was focused on how to understand and manage natural waterways for potable water and food systems irrigation.

I learned a lot about water, but my most extreme realization was that, when the electricity goes out, my professional skills are largely irrelevant. No one needs a data analyst, project manager, go to market expert, or much of the other skills I’ve spent the last two decades honing if there is no electricity or internet.

Beyond my career and earning money, I conclusively don’t know how to build shelter, collect water, or feed my family. Sure, I can help organize other people who do have those skills, but if they don’t want or need my skills, then I’m relegated to entry-level day laborer status.

That is very sobering.

Even if I didn’t follow the data of blunt conclusions of degrading US infrastructure or the climate change-inspired climate disasters, the random possibility of a Carrington Event level solar flare leaves me wanting to be prepared, just in case.

I don’t expect to earn these skills in a single year, but I’m often reminded of my favorite Chinese proverb:

When is the best time to plant a tree? 40 years ago. When is the second best time to plant a tree? Today.

While I still have time, I’m going to start focusing on learning critical skills to support those who matter to me most, just in case.

Less screen time, more outside time

I’m bluntly aware that my current way of digital life cannot persist. My work is on a screen. My writing is on a screen. My AI projects and many personal pursuits are on a screen. Consuming content (writing, podcasts, videos, movies) is on a screen.

Of my ~16 waking hours, it’s not uncommon for me to spend 12-15 hours at a screen. When I’m at a screen, I’m not moving. All the screen time negatively impacts my body and my eyes.

As I consider Thriving into my sunset years, it’s absurdly clear that 12-15 hours of screen time a day simply does not serve for the long run. Or medium run. Or … short run.

Coupled with the “lights out” lesson above, I’m very clear that I want to spend more time outside, moving, planting, and building. It will take time to gain the skills, but the benefits of movement and outside time are imminently accessible today.

I have much to learn from the Dao of Clowns

One of my favorite annual traditions is the Oregon Country Fair. This past year, I had a shocking and profound experience where I stumbled into channeling Gustafv, a provocateur clown-like entity. Gustafv took over my body for ~6 hours, and it was an exhilarating and existential ride.

That experience prompted me to buy a number of books on clowning and sign up for a clowning workshop with world-renowned expert Christopher Bayes. I’ve already learned a lot about the nature of reality, and I’ve only scratched the surface.

I’m excited to deepen my study into the Dao of Clowns. And I’m hopeful that Gustafv is stoked to come play at OCF this year.

It’s healthy to challenge deeply held identities

I’ve read studies suggesting that the most resilient individuals are those who have multiple and loosely held identities. It makes sense - when we become too attached to any one identity, the loss of that identity can be cataclysmic.

I hold most of my identities with an open palm. Moving to Oregon has highlighted a number of identities that I was unexpectedly holding too tightly.

A simple example is that “I’m a night owl”. For most of my life, I’ve gone to bed later than most of the people I know. I used to say that my most productive time was from 10 pm to 3 am because that’s when the world was quiet, energy was still, and I felt like I could truly focus.

In Oregon, I found myself unexpectedly becoming tired at sunset and feeling totally drained by 10 pm. I argued and cursed for a few weeks and pushed myself into old patterns with caffeine and sheer force of will. But … why? Perhaps I’m entering a new phase of life that offers new identities to explore and internalize.

This example is relatively trivial, and many more follow. I look forward to re-meeting myself in all the seasons of my life.

Patience needn’t be passive

A few years ago, when I drafted my core values, I specifically noted that “patience was an anti-pattern” because patience implied tolerance for inefficiency and the status quo. In other words, patience bleeds urgency to change that which does not serve.

I maintain that worldview for myself - I never want to be patient with my own limitations or inadequacies. Note: not judging myself or not engaging in negative self-talk is distinctly different from patience.

Although that sense of urgency to change is meaningful to me, I’m learning that for others, the felt sense of patience (from me, especially) can be a powerfully positive force for connection and Thriving.

I’ve been exploring formats of patience that do not bleed urgency and proactive approaches to change. When I find a format of patience that isn’t passive, I can better balance offering that felt sense without compromising my reach for efficiency.

Curious indeed, and worthy of deeper meditation.

Managing energy is an art & practice

This past year, I’ve felt long stretches of what felt like infinite energy and capacity. I’ve also felt stretches where, even with plenty of sleep and good nutrition, I’m just … tired. Exhausted really.

It’s a valuable skill to be able to sprint. It’s equally valuable to master the rest and recovery phase after a sprint. I’ve lived most of my life in this cycle of boom and bust, binge and purge, and I’m proud of my progress in both domains.

A new skill I’m cultivating is the ability to hit a sustainable hum of consistent creative capacity that doesn’t burn me out (or those around me). Managing my energy is a surprisingly complex undertaking, and I’m up for the challenge.

What got me here won’t get me there

I learned this phrase, made popular by Marshall Goldsmith’s book of the same title, in business school. And I’ve been noticing that pattern in myself tremendously this past year.

Most of what I’ve accomplished in my life has been self-taught and achieved through many late nights and long weeks. I’ve often felt like a lone wolf archetype who cultivated a few very deep relationships and eschewed loose ties. I’ve focused on 1:1 or 1:few mechanics of communication and stepped away from social media and the 1:many or 1:very many formats.

All of these are valuable tools that I have in my belt. This year, I acutely felt that I’ve reached the peak of what I can achieve if I continue to use this limited toolkit.

There are a number of new skills and capacities that I’ll be cultivating in the coming year(s) to focus on expanding my toolset. To get “there” personally and professionally, I am opening myself to what new capacities I need to cultivate.

Sense-making is more valuable than truth

This year I hear a lot about “truth”. I heard, “we each have our own truth” and “there is no truth”. On a political level, each side has its own “truth” and can’t even agree on the basic facts by which we measure progress. I’ve thought a lot about objective and subjective truths, especially as they are impacted by cultural, religious, and other frames of reference.

Overall, I’ve concluded that debating the nature of “truth” is largely unproductive. I’m becoming much more interested in understanding skills for sense-making - the process by which people give meaning to their collective experiences. This is related to truth but removes the pressure to make it absolute and gives a lot more room to explore your experience, my experience, and our collective experience while sidestepping judgment or disregard.

Sense-making leaves more room for value-based orientations, whereas truth prompts more position-based orientations.

This coming year I’m going to focus more on how to make sense than the pursuit of truth.

Do less, more

In my annual review, I noticed a recurring pattern for the first time. For the last three years, I’ve taken on ~100 projects, and over the course of the year, I’ve deprioritized 30-40% of my initial aspirations. Some of that is related to legitimately changing priorities, but most of those nixed projects are because I simply did not have the personal resources (time, money, energy, inspiration) to get them done.

Knowing that, why do I keep putting so much on my plate?

This year, I capped myself to 50 projects to try to force myself to get tight and stay focused. I want to do fewer things and do them more consistently and at a higher level. Enough said.

Aspirational community is crucial

Part of the reason I moved to Oregon is to integrate with a community of high-level individuals. So far so great.

I’m now surrounded by a wide array of humans who have cultivated philosophies and skills that I’ve never studied. More importantly, I witness how they parent, live, work, and love and see qualities that I aspire to cultivate in myself.

In nearly every structure of annual review, there is a line of questioning that looks something like, “Who can support / guide / inspire / coach / model for you what you seek to achieve?” For the last few years, I’ve felt like I had to reach for thought leaders or examples in books, blogs, and online formats. Now, I feel very excited and inspired by the people I call neighbors and community members.


My year of the perfect square was fantastic in many ways. I learned a lot, and look forward to living those lessons into my year of peak prime.

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