Starting from the day my 4th grade class dove into the Hobbit, I voraciously read fantasy books. They were an escape into wondrous worlds where I could live a thousand lives. This not only fostered my love of independence, creativity and vision - it also left me with a deep sense that one should live by a code of higher ideals that guides right action in the face of challenge.

As I progressed from the naivete of youth through the complex nuances and conflicts of the real world, I found that having a consistent set of operating principles is more, not less, important. 

Life throws an endless stream of choices at us. Without grounded reasoning, it's easy to get swept into short term or localized decision-making at the cost of what more sober contemplation would reveal. A coherent set of principles grounds our choices and actions in our ideals and values.

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Many people seem to believe that decency is a luxury, like polite language - nice to have, but not relevant when it's time to fight for what we believe in.  I think that's backwards, and the distinction is a core reason why our politics and online debate are so often toxic and unproductive.

Decency is, in fact, a necessary protocol for a properly functioning system.

Fundamentally, decency encompasses a commitment to honesty, fairness, and consistency in how we treat people and how we handle truth—especially under dislike or disagreement.  It is about epistemic and moral integrity.

This is not the same as politeness or propriety, which are more oriented towards social norms and can be co-opted to shut down speech. It is also not the same as kindness, which can be weaponized to demand comfort at the expense of truth. 

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Starting in 2023, I shifted my consumption of information towards a deliberately sparse diet so I could focus my attention on cultivating the inner creative who had been underexpressed through my many years of academic achievement, career advancement and building startups.  I shut down all the newsletters, podcasts and scrolling that had previously generated a constant hum of mental background noise and I cloaked myself in the resulting silence with glee. 

It was a delicious window for self growth which brought me on a necessary journey of love, grief, connection and catharsis about which I'll write more at some point. 

Last summer, though, I felt the readiness inside of me to reawaken the part of my spirit which had been napping.  

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These are some of the most important lessons I have learned in the 33 years of my life, which started as a pretty informal checklist and expanded to become the full notes below after a 3-hour sit-down with several of my younger relatives. I sent them the following afterwards:

I know that it's easy to read things like this, nod studiously to yourself, and then promptly walk away and ignore it all.  I hope you'll treat this a bit differently… really *think* about each item here, how I might have learned it and how you might actually apply it to your hypothetical life.  Because this is exactly what I would have taught myself when I was 12, 15, 18, or even 25 years old to save myself *years* of difficult learning along the way.  

I've learned many of these myself but had lots of help too.  This includes reading hundreds of books and blog posts along the way and, most significantly, I've talked to other people.  Some lessons come from people who have made tens of millions or hundreds of millions of dollars in business and others from people who have managed to achieve the difficult task of having healthy, stable relationships with other people.  They are all valuable to me and I think a complete person is built from such lessons regardless of where they come from.

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I'm always amazed that people seem shocked when something they've trusted is usurped for commercial gain. Somehow, in a world that's incredibly dynamic and built on Darwinian evolutions at all levels from single cell organisms up to commercial entities, we still hold onto this naive view that our trust in systems is somehow static.

This is probably because we build our relationship with trust based on our relationships with close friends and family. In most (healthy) cases, this one-to-one trust grows slowly or remains constant over time. A fairly static model for trust is reasonable in this microscopic system.

Unfortunately, we tend to implicitly model the trust we place in third parties and macroscopic communities along similar lines and that simply doesn't reflect reality.

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"Inch towards daylight" is one of my favorite mantras from a book I read recently. It also accurately describes how to develop the oft-discussed but seldom mastered skill of Grit.

Grit is generally defined as perseverance in the face of obstacles and/or lack of positive reinforcement. It's the ability to do hard things regardless of whether the environment is supportive, and it's the ability to maintain determination and motivation for long term goals through all the shit work between now and then.

Grit is often and inaccurately presented as an innate characteristic. That gives those who lack it far too convenient an excuse to stop trying or to justify their deficits. In reality, Grit is a muscle that needs to be trained.

In 2017, I ran an Ironman triathlon and sold a challenging service business that I'd bootstrapped through 4 arduous years. I live with a group of highly motivated high achievers who span the world of entrepreneurial and life success -- the collection of their acquisitions, press articles, TED talks and general awesomeness gives me constant awe -- yet they constantly express amazement at the kind of will I'm able to deploy to the fulfillment of a particular goal. Why?

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I'm a huge fan of any models that find applicability beyond their intended domains and there are few quite as versatile and useful as The Hedgehog Model.

In his seminal book "Good to Great", Jim Collins examines 1,435 businesses over a period of 40 years in order to answer the question "what separates the good companies from those which make the leap and become great companies?" Over the course of his analysis, he uncovers a variety of factors that drive this distinction but one of the most fundamental concepts he explains is "the Hedgehog".

This idea is based on a fragment attributed to the ancient Greek poet Archilochus which says "a fox knows many things, but a hedgehog one important thing." Both these animals have survived successfully by deploying greatly different strategies. The fox is clever -- she knows a great many things and tends to rely on her intelligence to hunt and survive. The hedgehog is a far simpler creature -- when she is threatened, the hedgehog simply curls up into a ball and points her spines outwards.

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The proper way to start a conversation in San Francisco during the past couple of weeks has been to ask "how are you holding up?" A palpable sense of pain, disbelief and fear has captured the city since the recent and historic upset in the presidential election. To those outside the city this may seem like an excessive comparison, but I honestly haven't felt a sense of shared loss and mourning like this in the 15 years since the national tragedy of 9/11.

I knew this outcome was a possibility, especially given the trends of the previous few weeks and the dangers of voting between such deeply unfavorable candidates. On the trading floor, you have to develop a healthy appreciation for clear signals that "the market" is trending away from what you consider to be "the fundamentals". In this election, it felt like sentiment was divorcing aggressively from fact but, until the very end, it still seemed like the results would be forgotten as just a painful close call.

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A common saying holds that you are the sum of the five people you spend the most time with. More simply, the people you surround yourself with matter. They are the sounding boards for your ideas and the key forces which shape your growth.

Growth is achieved only when you are challenged. It isn't a single-track process but occurs across four dimensions (which are simply the four dimensions of self):

1. Physical
2. Intellectual
3. Emotional
4. Spiritual

Most of the challenges you will receive across these dimensions are laid extrinsically by others because it's basically impossible to change a system without some form of external stimulus. People can challenge you via three modalities:

1. Inspiration: They inspire you by exhibiting a behavior you aspire to enable in yourself.
2. Collaboration: They offer to work with you towards a shared goal.
3. Direct Challenge: They lay a gauntlet at your feet and say "show me".

Inspiration is the wind at your back and it's maximized by putting yourself in an environment where you are constantly inspired by the people around you. Moving to San Francisco and choosing to live in a co-op based around the goal of "mutually assured non-complacency" were two big steps towards my doing this and I'm endlessly curious to find people who inspire me, whether they are intellectuals, artists, entrepreneurs, or pretty much anyone living their life fully engaged.

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TLDR: I actually expected to get depressed, it still surprised me when it finally happened and I'm rather suspicious of its apparent resolution.

A few weeks ago, I couldn't focus, get stuff done, or even remember simple things. Work felt purposeless. Relationships seemed shallow and fleeting. I couldn't get more than nominally excited about things I'd normally jump to do. I felt like a ship drifting without an anchor, unable to latch onto anything for stability despite the supposed familiarity of the surrounding landmarks. All the usual ways I might find comfort -- leaning on community, taking pleasure in the challenge of work, experiencing the wonder of the outdoors -- were bereft of their power.

It sucked and it had been building for months.

For the last couple of years, I've kept a wary eye on my mental health. You probably know that I'm an incessantly optimistic ball of energy, particularly when you're still groggy from lack of coffee in the morning. I have a high natural frequency and, for the last several years, I've chased the high-energy thrill of starting a business with reckless abandon. At the same time, I've also been keenly aware of the phenomenon of "Startup Depression". I've seen a number of friends spiral, sometimes for many months, through deep bouts of depression that seem to counterbalance their otherwise ebullient energy.

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