Leaving Startup Life
One thing I miss about startups is the feeling that you are going somewhere. There is always a sense of movement, of momentum and of progress. Building a startup is a kind of "fuck you" to the universe as it reminds of us of how small and insignificant we are. We constantly move, move, move, and build, build, build. The energy created is optimistic, satisfying, and contagious.
In the later half of 2014, I traded the motion for introspection. I traded the fulfillment of action with the contentment of stillness. Ok, fine: that was just a fancy way of saying that I started slacking off.
But while slacking off, I started taking care of my body: going to the gym, taking on rock climbing and yoga. The woman teaching yoga at my condo focused on the meditative aspects of yoga as much as the physical, so through her I came to appreciate the physical triggers of happiness. I started taking care of my mind.
Through those little changes, I became a little more physically energetic. Not the get-up-at-5-am-and-run-a-marathon-then-stay-up-all-night-to-code kind of energetic, but noticeable enough to be a welcoming change. My emotions fluctuated a lot less. More importantly, I could notice it better when it did.
I finally started learning how to drive. I started interacting with people socially more often. I started reflecting more. Set small goals for myself. I continued work on a 10+ year secret project that means a lot to me, after years of hiatus.
In terms of vanity-metric-like accomplishments, I got a job this year. (Well, two.) I taught an 8-hour data visualization workshop at Humber College. I took a real vacation with Greg for the first time, travelling by train toward the east coast before giving up and hopping on a plane. I participated in a Kaggle competition. I can sometimes climb a 5.9 too.
Circles vs. Lines
Let me start with this quote from the Unbearable Lightness of Being:
If Karenin had been a person instead of a dog, he would surely have long since said to Tereza, "Look, I'm sick and tired of carrying that roll in my mouth every day. Can't you come up with something different?" And herein lies the whole man's plight. Human time does not turn in a circle: it runs ahead in a straight line. That is why man cannot be happy: happiness is the longing for repetition.
-- Milan Kundera, The Unbearable Lightness of BeingWe desire motion as a way to give our lives meaning, and to make the world a better place. It creates progress and gives us fulfillment. This is the line.
We desire repetition or stillness, because contentment and the feeling of well-being comes from the simpler things in life. Living this way is what we are biologically wired for, so it is logical that repetition gives us more of the in-the-moment feeling of happiness. This is the circle.
Those two desires appear to be in conflicts. We want to be the agent of progress. But we crave the simpler pleasures. How do we reconcile the two? Must the answer be to buy a dairy farm and live the "good old days" to live a happy life?
The dairy man had a Ph. D. in mathematics, and he must have had some training in philosophy. He liked what he was doing and he didn’t want to be somewhere else — one of the very few contented people I met in my whole journey.
-- John Steinbeck, Travels with CharleyI do believe that the contentment of the circle is a surer way to happiness than the fulfillment of the line. But before 2014, I was convinced that the "pursuit of happiness" was moot. There are thing in life that are much more valuable than happiness. Any great, lasting change would be worth more than the transience of personal happiness. Alas I lacked the Herculean level of discipline to turn this belief into action.
The insight is that happiness is as important as physical health. In fact it is a lot like physical health in many ways. It is a state to be maintained so that one can be resilient and productive. At the same time, just as it does not make sense to pursue great health as an end in itself, an excessive focus on happiness is as much a distraction.
Happiness should be a means to an end.
This is why when I read about Stoicism and being content with a tranquil life, I was somewhat uneasy. Happiness, tranquility, contentment, or equanimity are tools I wish I had, but they are not the whole story. They won't teach us what to pursue in life. They are answers to the question of how, not what.
Of course, the how can be as important if not more important than the what. Two people who choose the exact same opportunity will achieve different results, because of how they decide to act upon it. This is really the same concept as how "implementation is more important that the idea" in the startup world.
So that, in my opinion, is the role of happiness, and how to reconcile the circle and the line. Keep one foot in the circle to recharge and to keep happy as much as necessary. Then, once rested, walk the tightrope that is the line.
Regardless of whether you are doing startups in 2015 or not, I wish you a fruitful and happy year. May you do whatever you do, but with more happiness and joy.
 When people ask how I felt about that, it’s a little difficult to give the honest answer. It was a mix of relief and loss, and it's difficult to express those proportionally. I may have emphasized the relief, sounding rather cynical and defensive. Or I may have emphasized the loss, which may have made me seem more troubled than I actually am.
 There are several reasons I don't think happiness does not make sense as an end in itself. The most convincing one is that fails the "dream test" -- we do not value simulated happiness (e.g. through mind-altering substances, or something like the Matrix) as much as "the real thing". This suggests that it is something else that is related to happiness that we are really after.