🟢 To never have to work a day in your life
Which is the bigger sacrifice? Solid income, or enjoying your days? Should we hold out for both?
(4.5 min read)
As a kid, what did you want to be when you grew up?
Over the years, here were some of my answers:
🟢 elf for Santa 🎅 (yes, really)
🟢 detective 🕵️♂️
🟢 astronaut 👨🚀
🟢 pilot 👨✈️
🟢 video game design advisor 🎮
🟢 stay-at-home dad 👨👧
Any of those could have been fun, I thought.
In high school, I started to allow the concern for income to creep in.
I figured “Maybe I’ll become a lawyer” since people said I’d be good at it, and since so many older members of my extended family were lawyers.
Luckily, I got bone-chilling advice from one of my uncles (a successful lawyer).
☠️❗ I don’t think he threatened to kill me if I became a lawyer, but I remember that’s how I felt.
He seemed miserable and did not want me to take that path.
Heard.
Later, my favorite courses at Princeton were about bioethics.
Discussions within that topic were engrossing.
I decided I wanted to become a high school bioethics teacher.
Turns out those don’t exist!
I literally got rejected by teacher headhunters. 😮
So it was senior year, and I didn’t have a plan.
Somehow I got recruited and hired by the #1 hedge fund instead.
(Surprisingly, their interviews asked me bioethics questions, not because they relate to investments but because they’re a decent test for logical and creative thinking.)
Funny how that works out.
4 years into working on spreadsheets and slide decks, I admitted to myself:
I’m not passionate about this.
The money is great, I’m surrounded by brilliant coworkers, and I’m glad I’m learning from legendary investors, but…
I always imagined I’d be more jazzed about my day-to-day.
This quote had always been on my mind:
“Find something you love to do, and you’ll never have to work a day in your life.”1
“Maybe I’m not in the right field? This damn sure feels like work.”
And so began the iterative process of trying to find the right fit.
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What I’ve tried:
investment associate
portfolio construction and quality assurance
marketing
client service / strategy
project manager
software engineer
product manager
for our coaching businesses:
coach
internet marketer
online course creator / YouTuber
salesperson
software engineering manager
newsletter writer
But am I being too picky? And how will I find the right fit?
Here’s Paul Graham’s take:
How much are you supposed to like what you do?
Unless you know that, you don’t know when to stop searching.
And if, like most people, you underestimate it, you’ll tend to stop searching too early.
You’ll end up doing something chosen for you by your parents, or the desire to make money, or prestige — or sheer inertia.
[…]
You have to like what you do enough that the concept of “spare time” seems mistaken.
Which is not to say you have to spend all your time working.
You can only work so much before you get tired and start to screw up.
Then you want to do something else — even something mindless.
But you don’t regard this time as the prize and the time you spend working as the pain you endure to earn it.
I put the lower bound there for practical reasons.
If your work is not your favorite thing to do, you’ll have terrible problems with procrastination.
You’ll have to force yourself to work, and when you resort to that the results are distinctly inferior.
To be happy I think you have to be doing something you not only enjoy, but admire.
It’s scary to have such a high standard (since the process of searching is neither fun nor income-producing).
But I keep thinking:
I want to do something that I enjoy so much that:
I would do it even if it were impossible to receive any external validation of any kind for it (including money).
Of all of those past money-earning activities , the only one that I actually still do for fun is code software.
Coding has been fun enough that I do it just for myself.
Similar to how friends of mine like putting together 1,000-piece puzzles. Or knitting.
But the world of coding is fast-changing and bizarre (and the recruiting for it is broken2) and not something I want to go all-in on.
Plus, I try to avoid saying “I AM a software engineer”, the way so many people say that they ARE their careers.
I don’t IDENTIFY my career with the verb “to be”.
I am more than the work that I do.
And the work that I do might keep changing.
As for writing this newsletter, what would be fun?
I suspect it would be fun to hear subscribers raving about how helpful it was.
And it would be fun if they said “Build ____ for us, and we’ll pay you for it.”
But to rely on that kind of reception to the work feels superficial. Is the work itself fun?
Writing this newsletter maybe could become fun, I think.
I still haven’t figured out a flow that feels addictive, cathartic, enlivening, and inspired.
But I think it’s possible.
And this is only issue #8 out of 105 for the year, so we’ll see.
By the way, Universal Basic Income (UBI) will happen in our lifetime.
AI will push out even the most capable people from their jobs.
I’m not against this.
But I’m trying to get ahead of it emotionally.
I hear people like Bill Gates worry about his impending identity crisis when a Super AI tells him to step aside and go play pickleball instead of eradicating malaria (since the AI will do it better).
I want to go ahead and have my identity crisis now. 😆
We all should be asking ourselves where we find our fulfillment and meaning.
In a sense, I feel fortunate that I’m able to seriously consider this question as soon as I am.
🕙 What we learned in recent posts:
🟢 The power of slow, power of long, and power of 3 little lines
🟢 How writers hit 500k subs and make posts succeed
👀 Caught my eye this week:
Veritasium - What The Longest-Running Study on Happiness Reveals
Pretty wild that this study included a US President (JFK) and multiple Nobel Prize winners too.
I remember the 2010 Nobel Prize-wining research by Daniel Kahneman, Ph.D. about the magic number “annual household income of $75,000” ($104k in 2024 after inflation) as it relates to happiness, so I was interested to learn that a 2022 study adjusted the findings:
If you separate people into quintiles of happiness, it (still) seems that the bottom quintile (unhappiest people) do not get happier even if their income increases beyond $100k.
But:
For the happiest 30% of people in the various income categories, happiness rises with log(income) at an accelerated rate beyond $100k.3
In other words:
Money can keep buying happiness for already happy people, but among the most unhappy, the money helps stave off unhappiness only to a point.4
I’m no social scientist, and I know that it’s difficult if not impossible to prove causation rather than mere correlation, but summaries of these various studies seem to recommend:
🟢 Take care of your physical health (exercise, eat healthy foods, etc)
🟢 Prioritize your relationships
You might think “Isn’t that obvious?”
But consider that studies have NOT seemed to recommend:
Obsess about money
Strive for fame
Be a people-pleaser
Live like a monk
Move into a city (or out of one)
Surround yourself with people (or be alone)
etc etc
Tim Ferriss / Noah Kagan interview
Jump to 1:26:56 and watch a couple mins where Ferriss explains slowing down and zooming out:
I think part of what you’re reading in me in terms of less chasing is that I feel like (and I suspect many people feel like) the dog that catches the car… or the greyhound that catches the mechanical rabbit, and you’re like, “THIS is what I was chasing?! FUCK. That’s funny.”
That’s kind of like tragic-comic.
Jump to 1:36:55 and watch a couple mins where Ferriss says :
We haven't even seen a glimpse of some of the mental health challenges that are on the horizon.
and
[The people I respect and admire most realize that they] don’t need to rush.
So if I find myself feeling compelled to rush, either it’s a false signal I should ignore, or I’m about to do something that a lot of other people could do [and so I wouldn’t stand out], and that for me is a cue to really chill the fuck out and be like:
‘Wait a second, let me go back [and zoom out and remind myself about what is important].’
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Thanks! 😁
❤️ Special thanks to:
Sabrina Bonini of Diary of a Modern Solopreneur and Ibrahim SowunmI of
. I appreciate your support!💬 Question for you:
What did you want to be when you grew up?
And if you could focus more of your week on anything right now without worrying about income, what would you like to do more of?
Reply or leave a comment!
I’ll be so excited to write back to you.
And if you've got a moment, I'd love to hear what you thought of this email.
Send me a quick message — I reply to every email ❤️
Apparently this quote comes not from Mark Twain or Confucius but an acquaintance of a Princeton professor.
See my rant in a previous issue: 7 days into my new life and I’m freaking out
Aww! Thanks for the mention, Ryan! I'm really enjoying our mutual support. Your newsletter is getting better and better.
To answer your question about what I wanted to be when I grew up, I thought of being an astronaut too, as well as a firefighter, a veterinarian, a racing driver, and probably many other things I can't recall now. I didn't become any of those things, but I enjoy most of them in different ways.
Something that resonated with me was the famous phrase: “Find something you love to do, and you’ll never have to work a day in your life.” I have always been on the lookout for that something, but have struggled because I often found that my love for an activity changed once it turned into "a job". Typically, what I love is a hobby, and doing that hobby on a daily basis and as a job can alter my perspective of it. Sometimes experiencing that hobby in a professional setting takes all the fun from it. However, as I read that line in your newsletter today, it suddenly felt different. I think I have found something I love that doesn't feel like work, even though I do it every day, and used to consider it a hobby. This is doing my own thing, trying new things and finding ways to potentially monetize them. Essentially, I get to do what I want to do without any pressure, and pursue things that I love while making them my "work". Does this make sense? I'm feeling a bit sluggish today (I walked 13km uphill yesterday, and I'm still recovering like the old lady I am).