Start-ups and Emotional Debt (2014)

I can say with some confidence, in the twilight of my twenties, that it is inherent nature that has guided my decisions, not the story I tell myself at any given moment.

Like my parents and extended family, I fall into intensive training and skill-building when I feel like it, not for the pragmatic reasons I was told to believe. I'm not enterprising; although I've done some business, I am not a founder, certainly not in the SV sense of the term. I am content with a simple life with many friends, find little pleasure in making deals or drawing attention to myself, and at the end of the day, would like to focus on building the world through the esoteric, not the popular.

Valuable things for me are not something I can weigh or measure like assets and work hours; neither are they idyllic stories and images, or carnal pleasures. They're weird stuff, and nobody particularly cares about weird stuff except other weird people. And so the startup narratives ultimately fail to work for me; I don't want to allocate that level of commitment into the marketplace. It feels like a distraction, because the market values the popular and the practical, at any level. Everything else slips through the cracks, and I like slipping through the cracks. The way to hook me on a get rich quick scheme is to tell me that I'm slipping through the cracks and need only make one small change.

I didn't come to this conclusion without lots of attempts over the last decade, though. If I had genuinely wanted to pursue a popular, practical approach, I had many chances to do so. I convinced myself, like many a confused young person, that I did want this, and I took some of them, and the experience was worthwhile, but not enough to stick around for. Successes tended to feel empty; failures felt delusional. The biggest satisfactions usually came when I walked away after getting bored with the idea - yes, bored. Not after a definite, final, concrete answer, but after simply being unwilling to take the next step forward and drifting off. I know that some of those things I walked away from could work, could still work now. I don't care.

This is a step that my parents stop short of acknowledging. They still live with the burden of "being successful" as a universal, and their struggle as one measured against that universal, tearing themselves apart a day at a time as their behavior mismatches their expectations.

What do I actually do? Today I met someone I've only known for an hour or two outside of the internet. We had coffee, and I met some of their relatives. They were on vacation. We had no business together. We just sat and talked, with luxurious pauses and lulls in the conversation. For three hours. It was fine, and now I have a closer friend.

And that is me, that is the type of thing I do and like doing. But it's not rational thought. I felt and did, and rationalized after. As such the way forward for me is to fuck off with planning my professional career in any more than a broad "make a little, save a lot" conservative generality. If I do anything more risky or ambitious, it'll happen suddenly, because it always has, but in most respects I value inner life more.

And that is not you, dear reader. Maybe you're similar to me. Maybe you're more like a founder. Maybe take some personality tests(that are not Myers-Briggs).

It applies to the types of personalities that decide that their life is defined by what they do to pay their mortgage and put food on the table. At the end of the day a startup is still just a job.

(5) in the list, over and over and over again. Started up nine years ago when I was 22, and my 20's are a meaty blur of distressing situations, all of which fundamentally stem from trying to fulfil the often conflicting needs of staff, investors, clients, and all the rest. I care about people being happy, far, far too much. Many telephones died brutal deaths to bring you this message.

The outcome is that I have nil joie de vivre, and have become a dour old fuck at the ripe young age of 31. I've gone from boundless enthusiasm and optimism when we started, even though we are now finally coming into our own and running the business less like asshats, to viewing the world through crap-stained glasses.

It's cost me friendships, relationships, my health, my sanity, and pretty much everything else that's actually worthwhile in life.

I suppose I do at least still have enough introspection and perspective to realise that it's not as bad as my wounded instincts lead me to believe, but it's a never-ending struggle to consciously adjust my perceptions.

If there's any moral to this story, it's to learn to not give two craps about other peoples' happiness as early as you can, and to learn to clamber over people and stamp on their faces to achieve your goals. Unfortunately, I can't get behind that ethic, so am doomed to forever feel that I'm letting people down - thanks, negativity bias, you sod.

Point #6 puts the entire article into doubt in my eyes. Getting "good" at "startups" is a skill in and of itself. The ability to start and manage a small organization is an immensely valuable skill set and one that I would rather learn in my 20s, than in my 40s after having a corporate job 'prepare' me for such management.

Indeed, I've been managing my startup for 3 years and in the process have learned to hire, fire, sell software, test software, manage investors, and more. These are all skills I'd rather be getting now than later.

Different people are built for different organizations -- some do well in small groups, others are great in large, hierarchical structures. Both are important skillsets and knowing where you fit and will succeed is important.

I'd encourage people to read "Managing Oneself" by Peter Drucker to help decide if a startup or small company is, or is not, for you.