37 Life Lessons I’ve Learned In 37 Years

Every year around my birthday — October 3, Mean Girls Day — I try to sum up key takeaways from the year that was in a tidy little listicle, with links to where I’d previously disclosed them in past pieces. Well, we’re back, and we’re about to turn 37. As proof: you can read 35 hereand 36 here. Enjoy.


  1. Your health will fail you. Everyone you meet will leave you. Time will run out on you.
  2. I’m not 100% sure who I am at baseline. I’m complex, contradictory, blank, bland and eccentric. I’m a collection of paradoxes and idiosyncrasies, and my value is either worthless or priceless. More to the point: I’m not sure I’m anything at all.
  3. Changing the world requires just three things: A great idea, a transcendent skill, and other people’s belief in you.
  4. People want just one thing out of a romantic partner: dependability. Someone they perceive to be less fucked up than they are. (If they can also be mildly thrilling, that’s icing.) I fail miserably at this, and still do, in a myriad of ways that haunt me to this day.
  5. If everything is meaningless, then nothing is. We could probably stand to laugh more, learn more, feel more, do more good than harm. And maybe enjoy the ride a little more, since it could end at any time.
  6. I think the key to gaining greater satisfaction out of life is to keep expectations reasonable, and place less weight on them.
  7. Words don’t matter nearly as much as we think they do, and certainly not as much as the way we wield them.
  8. If you’d like to be the most compelling communicator in the room: be an excellent listener. This is, also, the secret to being great at sex.
  9. I’m mostly dumb and full of shit. I know next to nothing outside of my own lived-in experience, and books I’ve read, and things I’ve seen. I write pretty words, and that helps, but — honestly — I’m not woke, not a sage, not a poet, not an oracle. I’m just a fucking quotable white guy with a large audience on a website. I’m figuring shit out … same as you.
  10. Burning down your neighbor’s house doesn’t make yours look any better. Be an architect, not an arsonist.
  11. Getting shot up with high doses of psychedelics was, by far, the most effective treatment for depression and anxiety I’ve ever tried. Sadly, it wears off after a few months, and I failed to incorporate enough consistent and consistently healthy coping mechanisms to prevent a relapse.
  12. The point of all human existence is to belong, and to cultivate belonging.
  13. I toggle back and forth as to whether or not I’m a real writer. At times, I think it’s total bullshit I’m not more recognized for my work, at others, I think it’s positively ridiculous that anyone would read me at all. Perhaps that’s insecurity talking. Of course it is.
  14. Humans were not meant to be this productive, nor this connected. I hope to god I can find a time in my life where I can slow down to a crawl, unplug from the vast cosmos of technology and humanity, and simply be. I thought it’d be this summer … it wasn’t. Maybe next week. Maybe.
  15. Happiness is weather. Joy is climate. Happiness comes from without. Joy comes from within. Seek joy. Change the climate … not the weather.
  16. BBQ’ing people on the Internet is something I’m truly transcendent at, yet, they’re rooted in a deep-rooted desire to seem like I’m more rogue and bad-ass than I actually am, mixed with an anxious energy that comes from being hungover from last night’s booze bender.
  17. The greatest relationship I ever had was my first relationship. I regretted leaving it every single day, until my last relationship, which was the first one that both equaled and surpassed it.
  18. Naturally, that one ended too soon, because sometimes you’re just not what someone needs at that given time.
  19. Health. Joy. Peace. Purpose. Communion. Wisdom. Freedom. These are the seven noble pursuits of humanity — the measures of our success in life.
  20. Trading time for money is almost always a losing deal.
  21. All relationships are promises we make to others. Contracts between parties. I fundamentally seeing myself as a serial promise-breaker, and this is the root of almost all my pathological behavior.
  22. Life is data. Reality is an operating system (OS). Our perception is the User Interface. Our emotions are the User Experience (UX). Boiled to its most elemental, our only occupation as humans — at home, at work, at play, in public, in solitude, or abroad — is to create the best UX possible for ourselves and for others. It is our only moral, professional, and personal obligation.
  23. Emptiness is not a lack of things. Emptiness is a lack of space for things we actually want.
  24. Along those same lines, learning how to say no to things I want, but really don’t have room for, would be a nice skill to cultivate in year 38.
  25. Speaking of cultivation: Boundaries are the most important things we can cultivate for the sake of our mental, physical and social well-being — and most of how we view crafting boundaries is fundamentally backwards. We don’t create boundaries by saying “no” to more. We build them by saying “yes” to ourselves.
  26. I hated who I was. So I wrote a better me into existence. I read me over and over until I memorized my lines. Now I hate myself (a little) less.
  27. My root pathology is that I’m a validation-seeking missile. I crave validation and acceptance because I don’t appropriately provide those for myself. Without them, boundaries are impossible.
  28. Best dating advice I can give fellas? Get really good at giving orgasms, and give them freely, with enthusiastic consent, without expectation of reciprocation.
  29. Good fucking lord, Twitter is a tire-fire. Then again, so is everything.
  30. The pinnacle of human existence is “flawless self-expression.” It’s the purest distillation of liberation itself. It is the soul, unflinching and unencumbered, communicating with its surroundings in the warm infinity of positive reinforcing feedback. It is your heart on fire. It is love. It is a current that connects and strengthens us. It is the tuning fork of the spirit, vibrating at the frequency perfectly pitched with where we find ourselves in the vast expanse of the cosmos. It is concentric congruence between your image, character, communication, reputation, dreams, deeds and inner light.
  31. Achievements are side-effects of the life you live, and the side-effects are not the cure — the treatment is. Thought, emotion, intention and action are that treatment. They’re the cure for what ails you — the antidote to what ails us all.
  32. Who we were, who we are, and who we will be never really exist outside of our own memory or ego. I suppose what’s why I write so candidly and transparently about my life … to convince myself of my own very existence.
  33. Last year, I took a trip to New York, Paris, Marseille, Barcelona, Tangier, Lisbon, Porto, Madrid and London. It lasted 21 days, and I was drunk for every one of those 21 nights. Within two weeks of returning home, glitching and enveloped in dystopia, I tried to off myself. Depression doesn’t care how great your life is going. It doesn’t care how good you look on “paper.” It just shows up and blows you off the mountain.
  34. Evidently, I did not learn that life lesson. My last day at my job was September 6. Since then, I’ve been to Washington, New Orleans, Austin, Atlanta, Austin, St Louis, Memphis, and Nashville, and I’ve been drunk nearly every one of the past 26 nights. This year’s trip is on track to end equally poorly, and I haven’t even left the country.
  35. I’m not saying going sober will cure all of what ails you (or, more accurately, me), but it certainly helps lift the fog cover so you can figure out what the fuck’s not going so well.
  36. Previously unpublished: If I could change one thing about myself in the year to come, it would be this: I want to care more, and more deeply, about other people.
  37. The one thing to work on in the year to come: I’ll be attempting to further break the validation-seeking missile habit.

37 was, by far, the most successful and rewarding lap around the sun in my history. (36 and 33 take the silver and bronze, respectively.) Yet, if this past untethered month’s taught me anything, it’s I still have deprogramming to do. I want health, joy, peace, communion, purpose, wisdom and freedom. Right? Validation-seeking flies in the face of all these things.

To do this, I will be attempting to break entirely from booze, Xanax, casual sex, unwarranted flirting, purposeless travel, porn, Facebook, over-commitment, America, writing and working for free.

I want to love. I want less. I want to unplug, unwind, and unlearn the bad programming that’s led me to back to the hell I first tried to leave a year ago. I spent 11 months climbing a mountain only to reach the top and get blown right off all over again. I feel flawed and fraudulent, restless and listless, immoral and immaterial. And there’s no sense in doing everything I did this year, learning everything I learned, if I can’t find joy or solace in them.

Maybe that’s the greatest lesson I learned this past year … that the 7 Noble Pursuits are just that — pursuits — and this struggle will be lifelong, non-linear, and a series of hells mere steps from heaven. I hope I make it through them. I hope I make it.

Here’s to 37, and all that it entailed. Let’s be great in 38.

This piece was brought to you by P.S. I Love You. Relationships Now.

About the author
John Gorman is a writer and washout living in Austin, TX. Follow him on Medium here. Follow John on Instagram or read more articles from John on Thought Catalog.

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