Burnout sucks. I'm not talking about that "I can't wait for the weekend" feeling or even the glazed-eye look you gave your parents when returning home from finals week during college. When I refer to burnout, I mean the structural depletion of energy which makes it nearly impossible to raise your head and get real work done. It's a poison that seeps into and sucks the life out of every working minute.

In startup culture, we glorify working ourselves to death in a way which is completely absurd and totally self-imposed. Along my own 5 year rollercoaster building Viking Education, I became intimately familiar with the feeling of burnout. I distinctly remember the numb progression through checklists of tasks that had become divorced of any meaning and putting on a smiling facade which overlaid an inner me who had long since stopped bothering to panic at his lack of excitement for work.

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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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At 7:41:10pm On July 29th, 2017 I slowed to a halt, put up my hands and wept. I could barely breathe after the deceleration but didn't care because I'd stepped into the moment I'd visualized 10,000 times and it was every bit as sweet as I'd hoped.

This was a moment to culminate the most difficult challenge I've ever undertaken in the course of my life -- and ever hope to. The Ironman triathlon, commonly known as the most challenging single day sporting event in the world, is something so stupidly crazy that it prompts concerned looks and a whole lot of "why?". No one questions any more if you decide to train for a marathon but this mother of all triathlons is that and more -- a 2.4 mile swim followed by a 112 mile bicycle ride followed by a full 26.2 mile marathon.

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A respected friend and academic was speaking about something personal. I wish I could recall what it was but the only thing I can remember about the conversation is how incredibly often she used -- clearly without noticing -- the word "like". It was placeholder, punctuation, and security blanket in one. When this person wrote, I knew, it was clear, eloquent and incisive. When she spoke, she undermined every phrase with disqualifiers, fuzzy words and, of course, "like".

I couldn't help myself... I started counting. She used "like" 13 times in one single sentence. Hearing that broke something in my ability to flow with normal conversation and I began noticing similar things that I never had before. It quickly became apparent how important subtle (and not-so-subtle) communication patterns are in determining a speaker's credibility and impact. A few of these stand out more than the rest.

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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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I woke up nervous about what would happen during tonight's debate between Hillary Clinton and Donald Trump. There were no specific details on which my dread hung but it was instead an undefined sense of foreboding driven by the knowledge that the risk profiles of the two candidates were asymmetric. Specifically, it felt like Clinton had very little to gain and everything to lose from going toe-to-toe with the unpredictable Trump. I left the debate feeling relieved on one level but also tugged by a nagging anxiety.

There is a lot at stake in this election and this was the biggest debate matchup in history. Frankly, I think it went about as well as could be expected for each candidate without a major screw-up from the other. Contrary to potential worst-case scenarios, Clinton didn't get overrun and Trump didn't completely melt down. They each played their parts well.

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