free(dumb) 55
retirement is bad
Got your attention? Great.
Here’s why I think the concept of retirement is bad.
For starters, it feeds into the idea that happiness is something you defer until you hit a magic age—when you can finally live out your dreams and start ticking off that bucket list.
Because there’s nothing quite like fulfilling your lifelong goal of seeing the Pyramids of Giza… only to get your walker stuck in the sand.
Waiter? Yeah, I’ll take a shot of seasonal depression and the bill, please.
As you might be able to tell - I’m not a big fan of the Freedom 65 thing.
But it’s not because I’m cynical (I promise), it’s because we control our paths in life.
At least more than we think.
By embracing this belief, I’ve been able to:
Travel to nearly 30 countries before the age of 30
Land my ‘dream job’ not once, but three times (spoiler: dreams change)
Build a lifestyle I don’t feel the need to escape from
Here’s the thing—it’s NOT because of any special talent or secret formula. It all comes down to a simple mindset:
You only have one shot at life—why not make every second count?
This perspective is everything for me. Instead of waiting for some future moment to “start living,” I build a life I love now.
Here are a few frameworks that have helped me design a fulfilling, high-performance lifestyle.
imma stoic and i didnt even know it
I know what you’re thinking, “oh wow another white tech dude talking about Stoicism 🙄”
But bear with me for a minute.
To be honest, I’m no expert on Stoicism. I had to look it up after a few people said I was Stoic (and for a second, I thought they meant Sociopath… and, well, I could see their angle).
This makes me perfectly qualified to explain a 1,000+ year philosophy to you in 11 words—here we go:
Stoicism teaches that we control our mindset and actions, not the chaos around us*
*you can’t see me right now but I’m drinking mushroom tea out of a Live, Laugh, Love mug
How powerful is that for entrepreneurial founders?
There’s a famous expression by Marc Andreessen (the famous tech investor whose head looks like an egg):
In a startup, you're essentially building the airplane while it's falling off a cliff.
I like to add to the quote, “In a startup, you're essentially building the airplane while it's falling off a cliff. Meanwhile, birds are flying by and pooping on your head, you’ve never built a plane before, and your co-pilot is also Googling "how to build a plane."
In short, entrepreneurship is chaotic. But life at large is often chaotic, which can make it suck.
But the chaos is what makes life beautiful. Can you imagine a life where you do the exact same thing every single day, you never grow, never try new things, never overcome difficult (what seems like impossible tasks) and just sleep-walk through life until age 65 - get (maybe) 10 years of ‘fun’ achieving your bucket list - and then die?
Oh right, some of you are living that life right now.
I swear I am not cynical.
Why I love Stoicism is that you don’t need to fight chaos, you can embrace it.
It’s focusing on what you can control, then letting go of what you can’t.
Sometimes it’s as simple as saying, “who cares”.
my crazy tattoo
I did a crazy thing a few years ago, I got this tattoo (I was sober):
You know what’s funny? My mom loves it.
And while I’m on a lying streak, I also can bench press 500 pounds.
Truthfully, she didn’t get it at first. So, Mom, if you’re reading this, this blog is for you 😂
I got this tattoo for the reasons I described above. Prior to getting this tattoo a bunch of crazy life (unexpected) shit had happened - including a global Pandemic. The real Pandemic was watching the entire population kill their dreams for the future because of something they couldn’t control.
At a certain point (in the midst of all the chaos) my friends made a joke of ‘who cares’.
As in - we can’t control any of this bullshit - let’s not let it ruin our lives.
Do you know how liberating that saying is?
Your employee left you for a competitor? Who cares.
Your fitness tracker says you had a bad sleep score? Who cares.
Your product gets a bad review? Who cares.
Now, before you think I’m dead inside—I’m not. This is about choosing how you respond to life’s randomness.
Your employee leaves you for a competitor? Who cares. Now you know retention isn’t as strong as you thought. Use this as a wake-up call to check in with your team and make improvements.
Your fitness tracker says you had a bad sleep score? Who cares. Why let an app (that could be making it all up for all we know) dictate how you are going to enjoy the rest of your day?
Your product gets a bad review? Who cares. Negative feedback is a gift. Use it to improve, respond with grace, and build even stronger trust with your customers.
It’s not about ignoring reality. It’s about focusing on what you can control and letting go of the rest.
So that weird tattoo? It’s about building founder fitness.
living a soulful 55
Okay, let’s bring it back to positivity.
I started this rant, ironically, by emulating that of an old man shaking his fist at the sky—retirement is bad!
But here’s the thing: I don’t actually think life is bad. Quite the opposite. Life is incredible—messy, chaotic, soul-crushing, and still incredible. The trick is learning to embrace all of it, not just the easy parts.
Hopefully, you’ll see my perspective: life is wonderful, even when it feels like it’s falling apart. So, how do we make the most of it? How do we live a fulfilling life before retirement and apply these lessons to our businesses?
become a Stoic founder
When you’re a founder, every minute is precious. Stressing over things you can’t control—like a negative review or a competitor’s new product—is a waste of time and energy. The who cares mindset isn’t giving up; it’s focus. It’s choosing to prioritize what moves the needle.
Here’s how it works:
move fast: perfectionism is a creativity killer. So many great ideas are lost in the fear of the fictionalized customer. You know the saying, “if I tree falls down in the woods?”
Well, if a shitty product is never released, does it really suck?
Lesson: Start now, refine later.
nobody is special: it’s easy to obsess over your competition—what they’re building, how they’re marketing, what they’re posting on Twitter/LinkedIn. But here’s the truth: the more time you spend worrying about them, the less time you are putting energy into your business.
Lesson: Don’t stick your head in the sand, but keep your head down.
try to fail: if you’re not afraid there is some chance of failure in a project, workout, business you are undertaking - maybe you’re thinking too small. Remember, failure is how humans learn, iterate, and become better.
Lesson: Fail fast, learn faster.
Your Turn
So here’s my challenge to you: Stop deferring happiness to some mythical future. Stop stressing over things you can’t control. Start building the life you want right now.
What’s one thing you can do today to embrace chaos, focus on what matters, and take a step toward your best life? Write it down, commit to it, and go make it happen.
Every second counts.
Pssst - mystery reader,
If you’re enjoying my writing, you’re going to love my internet mail. It’s this groundbreaking concept where I send you cool stuff to your inbox each week—pretty revolutionary, right?
Curious? You can read it here.
