40 Things That Helped Me Become the Current Version of Myself

Published Jan 14, 2025 at 17:07

Today I turn 40! I use an exclamation mark there but everyone who taks to me regularly knows I’m not particularly excited about the milestone. I had the same struggle when I turned 30 many years ago, so I guess this is just how I am with the decades.

Anyways, here are 40 things that have had a large impact on my life. (One note, it’s pretty obvious that all humans are influenced and impacted in innumerable ways by the people they are surrouned by. So it goes without saying that I’ve learned a lot from my partner, my kids, my extended family and friends.)

Personal Traits

First, some things about me that may or may not be common, but I have found quite important.

1. Asking Questions

Is there anything more joyful in life than being curious? Can we truly learn without questioning things? What if the desire to have a stable, fully understood world is an irrational belief we lock in at an early age to feel safe? What if there’s more? What if there’s a different way to think about things? What if I can think about things differently? Where would I be if my brain didn’t work this way?

2. An Eternal Commmitment to get better at Failing

I truly do not know when this congealed into a conscious thought, but at some point in my life it did. I hate failing, hate it so much. I hate the embarrassment, the shame, the disappointment. It’s even worse when I fail and it lets others down. I hate it so much, that sometime in my life I decided to stare failure in the face and intentionally get to know it. I realized that failure is a deeply important part of learning, and it can be done accidentally and randomly, with unknown consequences, or it can be done carefully and intentionally, with a limited blast radius. I’ve spent a lot of time since then working to understand how I move more of my failure towards the intentional end of the spectrum. It’s going to happen, but I want to be sure I can learn from it, and minimize harm to myself and others. This is a journey, not a destination.

3. A deep-seated awareness that I might be wrong

Look, I have a lot of anxiety. It took me a long time to name that, even longer to start to map it, and I assume every new year will bring new lessons. Anxiety, I’ve come to believe, is a signal. It’s not always the most accurate signal, but it is a signal. And one of the ways that signal can manifest is self-doubt, an intense fear that everyone else knows more than you, has better information, or is just plain right.

Sometime in my adulthood I began to see that my self-doubt was not always wrong; sometimes I was wrong. Sometimes I was HELLA wrong. However, sometimes I wasn’t. I made an argument, or put the pieces together, or made a plan, and it was the right thing to do. That’s when I realized my fear of being wrong was extremely useful; I could somewhat formalize it into a bunch of questions (see point 1) and check myself, before (see point 2) I decided to wreck myself or not. It’s great! I love this signal now, although it did help to learn to accept that I can be right and I should trust my gut.

4. Bold Hairstyles

I dunno man, sometime in highschool I was like, goofy hair is fun. And then I got older and I never had a career where it mattered, and now it’s just a thing. Boring hair is boring, and life is too short.

5. Bright Glasses

This was a later in life addition, and now it’s a personal signature. I have lots of glasses. Many of them are bright colors, like the neon pink ones I’m wearing right now. As I enter my 40’s, I have a new style icon and may need to level up.

6. Leaving space for serendipity

I have noticed as I’ve grown older a tendency amongst this chaotic world we live in that the tendency at all scales— from individual level to global level— to control things. Remove unpredictability, guarantee outcomes, limit risk, so on and so forth. It’s not that I’m against these things, it’s just, well, I like the unexpected. The word that has begun to mean so much to me is “emergent”. As in “emergent properties”, a concept in complex systems theory. Or Emergent Strategy, adrienne maree brown’s brilliant book. Things that emerge aren’t always predictable, aren’t always what you want, aren’t always pleasant. But their presence means that there’s still room to breathe. The chaos has not been smothered, even if it is somewhat managed.

7. Introspection

Asking and reflecting on my feelings, motives, desires, perspectives and sense of the world has been a continual source of learning and evolution. It’s easy to over-introspect or anxiety spiral, I am quite familiar. But in a healthy state, this practice, of recognizing that something of note happened, and interrogating my internal perception of that thing, it’s good. I’ve done this literally as long as I could remember, and I have no intentions of stopping.

8. Anger

There was a period in my life when I was angry all the time in an incredibly unhelpful way. It was a result of an unhealthy relationship and living situation that I felt very little control over. I hated anger for awhile after that; it felt toxic and harmful. I learned a lot when I came out of that period, and one of the things I learned over the ensuing years (after lots of introspection, natch) is that I can hold anger in healthy ways, and it’s not a toxic emotion by default, if you can express it in cathartic and expressive ways.

That lesson has proven true time and again, because fucking hell, there is so much to be angry about. The world is fucked up in so many dimensions, and the people with power like to pretend they are helpless to change things. Well, that’s been true, but, next week the US gets a new administration filled with people who aren’t afraid to use any and all power they find at their disposal.

I have a feeling the anger will burn brightly for years, and I will be constantly on the hunt for comrades who are livid that any of this is happening and furious to do more. Witness us.

Feeling

I am a human with big feelings. These were not fully drilled out of me as a child (as many other AMAB people have experienced), but I was never really given any guidance on how to accept and navigate my big feelings; it’s been a long journey to pick up some skills and tools to help. Here’s some things that helped.

9. Live Music

My parents took me to my first concert at some point, I’ve no idea what age, and that was my first taste of the sublime, I like to imagine. This is an entirely apocryphal self-myth, but it registers truthy for me. I’ve been hooked on live music ever since. I’ve moshed, I’ve screamed along, I’ve sat in silence, I’ve wept, I’ve even taken an infant (my oldest) to a Josh Ritter show. Live music gave me space to sit in my feelings and let them be big, as big as they needed to be. Music played live feels like magic to me.

10. Sufjan Stevens

“Will anyone ever love me”, Sufjan asked on his most recent heart-wrenching album filled with grief, and once again I found myself listening to songs that somehow splayed my soul out on an operating table, as if one could autopsy the innermost knowledge one has of oneself. My friend Drew introduced me to Sufjan around the time that his Illinoise! album dropped, and I’ve been sobbing along with him ever since. Whether it was Casimir Pulaski Day creating a space for me to ask about my still quite stifled queerness, or Pittsfield, validating that small courages matter, or I Want to Be Well with its cathartic ending cries of “I’m not fucking around!” which I sang way too many times in the car, or the entire fucking album Carrie and Lowell which to this day is the album I put on before I even realize how sad I am, or the entire Javelin album, where he lays out how hard it is to love truly, but how wondrous and beautiful it is, in all its horror, fuck, I’m crying while typing this. Sufjan, if you ever read this, thank you so much.

11. Frightened Rabbit

I’m already crying so let me just point you to this post from a few months ago about the impact Scott Hutchison and company had on my life. I’m eternally grateful.

12. The Postal Service (band)

In 2023 the Postal Service did a 20 year reunion tour and I got to go back to my adopted home city of Philly to see them live with my partner. Very few moments in my life have generated such full-bodied joy. The Postal Service’s 2003 album Give Up has been a constant companion for 20 years, I turn to it when I’m happy, when I’m sad, when I’m bored, when I need something familiar, and particularly when I want to dance.

13. Alone time

One of the things that has helped me sustain my ongoing love of people and extroversion is, obviously, spend a lot of time by myself. It’s very hard for me to step out of the rhythms of daily life and settle into that beautiful space of contentment unless I’m alone, and that space is so deeply meaningful to experience regularly.

14. Soft Pants

Look this post is not all high-minded. For goddamn years I deprived myself of comfort and coziness because it was very hard for me to find things that actually felt comfortable and cozy. Then my kids came along and had a bunch of sensory issues and it turns out I also have had sensory issues for my entire life, and I had a whole host of adaptations to deal with them. That was great, and then I found Vuori’s Dreamknit line of clothing, which is truly the softest thing I’ve ever put on my body, and now I live in their active pants (which do not have annoying cuffs at the ankles like all joggers). Comfort is good, actually.

Learning

Look I’m curious and enjoy learning. Here’s some things that have fostered that, or milestone books that I keep returning to.

15. Books

Yeah first I just have to give a shout out to books. I’ve always loved them; as a child we would go to the library and I’d check out the maximum amount of books (2 or 3 dozen, if I remember correctly) and I’d get home, sit down, and read them as fast as I could. Then I would read the stack my sister checked out (shout out to American Girl and Babysitter Club books, I loved ’em). Ever since then books have been my happy place. Also bookstores. And libraries. And little free libraries. And book sales. And friends houses with books. I love it.

16. Science Fiction & Fantasy

Here is where I admit I fell for the trap. I listened to the assholes who said that genre fiction wasn’t serious, that only non fiction and literary fiction was worth reading, for way too long. But friends introduced me to SFF sometime in the past decade and I’m better now. Talk to me about N.K. Jemisen, or Ann Leckie, or Becky Chambers, or Ursula K. Le Guin, or Tamsyn Muir, or or or or. Literary fiction is all “ooooh what if boring ass people did boring ass things and we called it sublime” meanwhile SFF writers regularly are like “what if shit was different?” and they FOLLOW THOSE THOUGHTS THROUGH. I love it. I’m sorry for my snobbery.

17. The Real World of Technology

This book came to me via Mandy Brown a long fucking time ago, and it is the gift that keeps on giving. First delivered as part of Canada’s annual Massey Lectures series, then published in 1989(!!) and later expanded, this book by Ursula Franklin is one of the most tightly argued, cogent theories for how technology works. Period. It’s fucking brilliant, and I find it meets me anew every time I reread it; always relevant and still prescient.

18. From the Mixed Up Files of Mrs Basil E. Frankweiler

Fuck yeah I have to credit my favorite book of all time. A few years ago in Philly I wondered if I had fallen prey to the hyperbole of memory; what if this book doesn’t hold up? So I walked up the street to my neighborhood bookstore, grabbed a copy (thank you Head House Books in Queen Village!) and walked home. Within 2 hours I finished it, sobbing with joy, because not only had I not overblow the memory, I had forgotten just how exquisite it is. Two siblings run away from home to the Metropolitan Museum of Art in NYC, and while they evade security guards and methodically explore the museum to learn, they also end up solving an art mystery that no adults could put together. Talk about empowering! Claudia, you are my hero, and E.L. Konisburg, you changed my life for the better with your novel.

19. Wishbone

If I’m going to write about how much I love books, is it any surprise I’m going to sing the praises of the dog who loved to read and inhabited the stories as the main character? Of course not. Wishbone is one of the greatest tv shows of all time, fight me.

20. Thinking in Systems

Donella Meadows is the one who introduced me to the field of complex systems, and talk about a revolutionary concept. I read this first in 2016 or so, and I expect the rest of my life I’ll be trying to make sense of systems and how to map/understand them. I might go so far as to describe this book as the thing that pulled me out of Plato’s cave, into the light. Suddenly I had a vocabulary for things that I had noticed since childhood, and the delight to know that many people had been thinking and theorizing and exploring the concept for many decades. The best kind of late to the party.

21. Against Purity

  • Cover for Against Purity

    Against Purity

    by Alexis Shotwell

    Copyright 2016, Minnesota Press

    Disability Theory, Cultural Analysis

Admittedly, this is a niche book and I’ll be surprised if many ever picked it up to read, but I found it brilliant. Alexis Shotwell wants us to tell better stories, or, to steal from Donna Haraway, she wants us to have better stories to tell stories with. In this book she looks at a few examples in biology and ecology and interrogates how, if we default to the standard set of lenses and frames that western civilization uses, we close down the interpretations and emergent ideas the examples otherwise lead us to. She questions our desire for purity in numerous realms, and challenges readers to think better. The embrace of nuance and complexity in this book was a personal delight.

22. Legacy

A few years back I was able to visit Birchbark Books in Minneapolis and treat myself to a shopping spree of sorts. I had saved up and could justify spending a good bit on books, so I just built a stack, regardless of price. It was wonderful. When I got home with all the books, I started working through the stack, and early in it read this book, by Suzanne Methot. In it, she uses her life experiences as an indigenous woman as a lens to tell the story of how Complex PTSD (CPTSD) works, and to apply that frame to all indigenous people in the US. This description does not do justice to how insightful, powerful, and wonderful this book is. It was the first time I read about CPTSD, which led me to seeking out a great deal more education on trauma. It’s also one of the first books I’ve read relaying the history of indigenous North Americans from an indigenous lens. Learning that history has become a lifelong project, and I mark this book as one of the first steps down that journey.

23. Mushroom at the End of the World

The last book I want to call out (and I had to cull a lot of options) is Anna Lowenhaupt Tsing’s incredible work of ethnography and sociological theory. I’m due for a reread of this book, to be honest. In it, Tsing uses the matsutake mushroom as a frame for asking questions about the end of capitalism, among so many things. The subtitle captures it well: “On the possibility of life in the capitalist ruins.” Readers meet mushroom hunters in the pacific northwest, follow the mushrooms to their final destinations, but also learn quite a bit about the conditions that lead to the matsutake thriving, and the histories that turned these fungi into valuable cultural items. There is honestly so much more, it’s a struggle to summarize well. Having the stories and theories in this book to think with has been so very generative for me.

Exploring, generally

When I started making this list and then organizing it, I realized that uh, I had a lot of exploration things, and some of them were conceptual and some of them were very specific. So here’s the bigger things.

24. The Open Road

For my 18th birthday and highschool graduation in 2003, my dad bought me a 1996 Nissan Pathfinder. In that vehicle, I fell in love with the quintessential American myth: the lure of the open road. In the ensuing 22 years, I’ve driven across the country numerous times and taken so many other road trips (including an 18 month road trip that was very helpful in ending my first marriage, indirectly). I am tired of cars now, I’d like to be a person who gets by with just public transit and long bicycle rides (see next point), but there’s no doubt in my mind that the many hours in the car gave me space to think, places to scream along to songs and feel my big feelings, and generally see this beautiful country.

25. Bicycles

Bicycles are joy machines, I know no other way to put it. When I get on a bike and start moving, the dopamine hits and my smile is intense.

26. Mountains

Nothing improves my morale like staring at big fucking rocks and realizing how old they are and how insignificant I am. I love them, looking at them, climbing them, walking around them, whatever. Mountains are great.

27. Long Walks

When I was in a very shitty living situation during my divorce, I used to plug headphones in and wander Philly. That was the safest way I could be alone with my thoughts and work through all the shit. Later, when the living situation improved, long walks became one of my favorite ways to think and explore. I’ve walked so many of Philly’s streets in all types of weather, because it felt so good. Before I left Philly, a woman I was seeing and I decided to go on an “urban hike”—we did 12 miles in a day and it was lovely. In the past few years, here in Chattanooga, my partner and I would go on long evening walks to converse and unwind from the day. Walking, even on very familiar terrain, changes things in such a good way.

Exploring, specifically

In all my exploring, some places have mattered the most.

28. Philadelphia

There is a classic billboard that said “Philadelphia is not as bad as Philadelphians say it is.” and let me tell you, accurate. Philadelphia is my personal nominee for best city in America. It sucks so much, but god it’s great. I lived there for 4 years and during that time completely put my life back together after divorce. Philly will always be the place I most felt at home, and even though I don’t expect to live there again, I will always love it.

29. Tattooed Mom’s

In Philly there is a famous street: South St. It’s where all the Jersey people go on Friday and Saturday nights to walk up and down and drink citywides at shitty bars. In between 5th St and 4th St, though, there is one bar that was effectively my home for a couple years. I lived 4 or 5 blocks from Tattooed Mom’s, and 3-5 days a week you could find me at the bar, drinking happy hour beers and reading a book. Sometimes I talked to neighbors, sometimes I just stuck to reading. TMom’s was the first bar where I was a regular; I’ll never forget a barback coming up and introducing themselves because they were like “I see you here all the time, figured I should know your name!” Bartenders would comp me beers and I’d pay for it in tips. I can’t say this period was healthy for my liver; I definitely relied on alcohol for handling anxiety rather than better options I later learned (see below). But for a couple years, TMom’s was my safe space, where I slowly learned how to reconnect with all the things I love about myself.

30. The General Jackson Riverboat

Look this is a funny one, but I worked on this (super-racistly named) tourist attraction when I first moved to Nashville. It was my only foray into service work, and I will always appreciate the experience. I’ll never ever step foot on the boat again, but I also will never tip less than 20% and I’ll always give service workers the benefit of the doubt because of this dumbass boat.

31. The heyday of Twitter and Google Reader

Look, they were good, and they introduced me to a lot of cool people and helpful ideas. I miss this version of the internet, even though I don’t think it was all that good in hindsight.

All the rest

32. Mycorrizhal Networks

Trees talk to each other! They have networks of mutual aid, built on symbiosis! That’s fucking cool.

33. Email application to Editorially

Sometime in 2014 I sent an email applying for an internship with the coolest startup I knew of, Editorially, and somehow, for still unknown reasons to me, I got the internship. It was paid, not much, and not enough for me to get by, but I met some of the greatest people I’ve ever worked with, and those connections opened nearly every door career-wise that’s led to my current life. One email, and now I have this life.

34. Good Notebooks

I could rhapsodize about notebooks but this post is so goddamn long. Leuchtturm1917 are the best general purpose notebooks, if you’re curious, but there are so many great notebook makers. If ever you need to give me a gift, a good notebook is a guaranteed winner.

35. Bourbon & Beer

The Tattooed Mom’s period is when I finished my lifetime quota of bourbon; I don’t drink it at all anymore (or any hard liquor). Maybe I’m not supposed to praise these things or look back on my reliance on them with any positivity, but I don’t care. I had a real shitty life for a bit, and one of the ways I survived that period was drinking. I don’t wish that on anyone, but sometimes that’s the way life goes.

36. Speech and Debate

In highschool I did competitive forensics, and I did it because it was fun to perform and argue about shit. Now, I have to do impromptu presentations in front of execs and customers who are paying my company millions a year, and thanks to those highschool shenanigans, it’s no sweat at all.

37. Architecture

My dad is an architect, and because of him I learned to pay attention to the built world, to appreciate quality design, and to treat the entirety of the human world as constructed. That’s a wildly important lesson—it’s so easy to think of things as fixed and unchangeable. But every single wall was built, and that means it can be unbuilt.

38. Craftiness

My mother is one of the most creative people I’ve ever met; she’s never met a project she couldn’t tackle. She taught me a lot, but this is the thing I feel like shaped me so much. Where dad taught me about the built world at building scales, mom taught me about the built world at smaller scales. Her ability to turn ideas into reality was something she passed on, and I use those skills daily.

39. Yoga

In the past few years my partner introduced me to yoga and we shared a daily practice for a period. While that daily practice has evolved, the impacts linger. Yoga helped me release trauma, learn to listen to myself, it even made me about 2" taller by unfucking my back and hips so that my posture naturally straightened out. I don’t know how I lived so long in my body without this practice.

40. Mystery

Last of all, is mystery. In my youth, I was interested in mystery for religious reasons, but even though religion no longer is in my life, mystery is ever present. I love the small mysteries (why does that hurt?) and the large mysteries (what does life mean) and all the mysteries in between. Thankfully, I also like asking questions, so mysteries sometimes unravel themselves for me.

I don’t know why you read this entire post but if you did, thanks? I’m on bluesky and would love to hear your thoughts.

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hey i'm winston. i read a lot for fun and to help me better understand and interrogate our world. this web-blog is where i chronicle some of my learning. i work as a product manager for Honeycomb.