A Bite of the Worst Kind of Pie

I was feeling unproductive and blue when I left San Francisco, and I thought new scenery with new faces might wake me up from my stagnation. I started with two months in Thailand in an attempt to give the #digitalnomad life a shot. I quickly realized that $5 Thai massages and lack of cultural angst to succeed in spite of one’s own happiness was a surefire way of getting nothing done. I’m blessed/cursed to have an almost constant nagging itch to do something of note. I still wanted some solitude to explore new ways of living and thinking, so rather than return to SF, I chose to move to it’s redneck sister city. 

I started 2019 in Austin, Texas, but found myself back in San Francisco by the year’s end. I vaguely wrote about my brief time in Austin already, so I’ll save myself from getting into it again. But I will say that Austin is dope. If you love food, heat and not paying too much for rent, move there. But I got a sick deal on an apartment in SF and I realized this place would likely be better for my long-term career prospects. So back to the city I so love to hate. 

I learned a lot this year. I also learned (again) how little I really know. I’m getting the sense that this is a lesson that might take years to drill into this egotistical brain of mine. Somewhere along this path I’ve embraced a vision of myself as being better than most people in most disciplines despite having put in less work. It’s an ideal that I’ve always admired growing up. I hated the kids who worked hard in school, and I prided myself on being able to squeeze out an A- without really giving a shit. But I did give a shit. I gave a shit about being perceived as not giving a shit. But learning how to game standardized tests and essays has close to no relevance in the real world where hard and smart work is a requirement for success.

So began a period of busting my ass to achieve. I saw some data suggesting that CEOs that rate high on a scale of work/life balance show poorer results, so I sold my digital piano, stopped working out and basically stopped going outside. I thought, if I work hard now, I can meditate and do all that living-a-healthy-life bullshit later. But then my business’ sales dropped. And a few projects took longer than expected. And I made mistakes on a few key decisions. Before when I wasn’t working hard, I had an excuse. And now? 

It turned out, I wasn’t quite the hot-shit that I thought I was. Eating this humble pie sucked. Realizing too that I thought so highly and unrealistically about myself was tough to swallow. I was playing status games. I wanted people to think I was high-achieving despite being dealt some shitty cards. I still want that if I’m being entirely honest. Maybe some part of me will always crave adoration from others. But striving for the sake of admiration is a loser’s game. It’s a thirst that can never be quenched. While I don’t think striving should be thrown out entirely, I’m starting to think that the real goal in life (or at least one of them) is to work towards giving less and less fucks about what others think of you. We simply cannot control the opinions of others, so why bother trying? Bill Gates has haters. The man founded one of the world’s most valuable companies and he’s donated more money to effective causes than anyone in human history. And a lot of people hate his guts. So my aim going into the new decade is to learn to do important work at a sustainable pace while giving zero fucks about what others think about me. So fuck you and Merry Christmas.


P.S. In an effort to train myself to give less fucks and (hopefully) get less awful at writing, I’ll be committing to posting here once a week in 2020. Most of it will be shit. A lot of it will be weird, experimental and embarrassingly transparent. But maybe. Just maybe. Some of it will be alright. Or at least make you chuckle. Or maybe it will be like a horrible car crash with bodies and blood that you simply cannot take your eyes off. Either way, tune in if you’d like. Subscribe with your email and I’ll send you something to your inbox every Friday. 



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