Discover more from Stew's Letter
Many experiences, few stories
The virtues of turning your experiences into stories. Also: the extremely-abbreviated story of my career (Stew's Letter #105)
Howdy, happy Wednesday.
At the beginning of this year, over 50 of you volunteered to keep me accountable to write more – and it worked!
I published six Stew’s Letters and 12 Twitter threads before the end of March. Mission accomplished.
The bad news is that I haven’t written a single thread or newsletter since. Classic. I have no good excuses other than I’m lazy and also I got married (it was a spectacular weekend and I’ll share more once we get the pics back).
But, alas, I’m back with a few things to share.
To all the new readers, welcome. Haters, smash unsubscribe.
Let’s get to it!
Many experiences, few stories
A while back, I read a quote that said something to the effect of “all of us have experiences, but very few of us have stories.”
The author’s point was that we’ve all lived rich and varied lives, but very few of us have spent the time turning our essential experiences into stories we can share with others. A single, well-articulated story about ourselves can tell other people a whole lot of what they need to know about us.
For example, my friend Juvoni once shared a story about how his dad gave him $20 in cash as a gift when he was a kid. Instead of keeping it, he spent it on ice cream for all of the other kids in his neighborhood. If you only ever knew that story about Juvoni, you’d have a pretty good understanding of his essence. Also, you’d probably want to hang out with him.
Most of us have defining experiences like this, but we’ve either overlooked them or failed to wrap them in a clean story we can share with others.
If somebody asks what we do outside of work, it feels more natural to say “I like fishing” and leave it at that. But how much more memorable would it be if you also shared a short story on why? “Growing up, my parents taught me to only eat what you catch and so I….”
This can be super hard to do, of course. The experiences that illustrate who we are might feel obvious or trivial. And talking about ourselves can be fraught, especially if we feel like we’re hand-crafting an image to present to others.
But that doesn’t change the fact that other people do want to know about us and we should do them a favor by giving them the goods.
When we share our essential experiences with others, we open a door to connection. Other people can see us more clearly. We’re more memorable and interesting. Our humanity radiates outwards.
My story in 12 bullet points
I wrote the tidbit above because I historically suck at sharing my stories. I share my thoughts pretty often, but rarely my stories.
As it turns out, we invited Foster members to revamp their “about me” pages a few weeks ago. These pages tend to be pretty career-oriented, but they provide a powerful excuse to uncover and polish certain stories that define us.
This exercise was way harder than I expected and I failed to find an overarching narrative arc to my life so, instead, I wrote a new about me page with 12 bullet points that felt telling.
I thought I’d share the relevant excerpt here so that you can know more about yours truly. Here’s my story in 12 bullet points:
Born on the coast of Virginia. Grew up surfing and cleaning out old ladies’ attics for money.
Taught myself how to write code after a scammer posing as a for-hire software engineer stole my life savings.
Co-founded and led engineering at one of the first publicly-traded tech companies in the cannabis industry.
Burned out and quit.
Started journaling to figure out what to do next. Fell back in love with writing. Started this blog.
Launched a satirical newsletter called TechLoaf (think: The Onion for the tech industry). For a moment, I thought it might be a good business. It wasn’t.
Once WellSaid was off the ground, a friend recruited me to join his startup Banzai as their CTO. I led engineering there through a $7M Series A.
Burned out again. Quit.
Decided to merge my personal passions with my business pursuits. Otherwise, I’d burn out again. The jury is still out on this one.
Co-founded Foster to help hobbyist and indie writers like me (and maybe you?) write better stuff.
So, there. Hopefully, we feel more connected now.
Cheat codes to life
I recently asked Twitter, “what are some cheat codes to life?”
I wanted a bunch of life hacks like how to get into Amex lounges without an Amex card or how to get free donuts at Dunkin Donuts.
But Twitter saved me from myself. Most people shared sage-like wisdom on how to live well, not tips on how to get free Chipotle (damn).
Of the 300+ answers I got, these were the most popular “cheat codes” to living:
Don’t take things personally
Don’t compare yourself to others
Default to assuming positive intent
Turn off all phone notifications
Don’t do things you don’t want to do
Get a dog
Curate your environment (it shapes who you are)
Make connections between people who should know each other
Spend more time outside
Quite a few people replied with my favorite trifecta:
And I did get one true life hack tip. Max Nussenbaum snuck in with this:
“Use your car's seat warmers to keep takeout warm when you're driving it home.”
Not surprisingly, I got a bunch of smart-ass comments along the lines of “there are no cheat codes to life.”
Really? There are no cheat codes? An unhinged reality TV star became president of the free world. This guy has 10 full-time remote jobs and is on track to make $1.5M this year (LOL, WTF). A friend of mine got like $4k in free Doordash meals via an elaborate backdoor he found in a promotion.
There are cheat codes, people.
🗞 Newsletters I love
Over the past two years, I’ve subscribed to over 100 newsletters.
My wish for you is that you never subject yourself to such torture. Instead, I’ll spotlight the best of what I find.
This week, I wanted to highlight three favs (each link goes to their signup page):
Playing Favorites. I am in a high-risk group for becoming a Twitter threadboi. I want people to read my stuff. I am occasionally willing to be shameless. I want to be a star, damn it. But thankfully people like my friend Jay Acunzo keep me on track. Jay is a masterful writer & storyteller who gives a shit about doing work that matters. Every one of Jay’s emails contains a profound lesson on storytelling or resonance. I use his writing as a compass.
Every. Alright, I’ll stop plugging them soon I promise. But there’s no way around it: I am an Every fanboy. Every reliably produces some of the most thoughtful explainers & analyses on productivity, strategy, Web3, the creator economy, and even writing – in other words, nearly all of my professional passions.
The Rubesletter. A while back, I wrote about the Comedy Cellar and got a reply from an NYC comedian who’s a regular there (the Internet is cool like that). It turns out he’s a hell of a writer who shares insightful takes on comedy, tech, and culture, amongst other things. Good writing is contagious and I find myself inspired by just how easy Matt Ruby makes the job look.
🔥 Fire TikTok
*takes bong rip*
I won’t pretend to understand the sequence of events that led to The Scientific Revolution and modern-day technology, but I feel confident in saying this:
One of the key differences between us and our ancestors is how we think. Our explanations of physical reality are different.
These new ways of thinking about physical reality have enabled our new God-like powers, for better or worse.
With that, enjoy this extremely pithy TikTok.
🧠 Big brain corner
I thoroughly enjoyed this conversation my friend Tori Dunlap hosted with Justin Baldoni. They dig into and re-imagine two topics that I live in every day: masculinity and money. I found myself confronting some ingrained beliefs in this chat and coming out feeling lighter (read: my favorite type of conversation).
Until next time,