This week I feel like I’ve been taught a lesson about entrepreneurial happiness.
i.e. being an entrepreneur and knowing how to enjoy it.
See, the happiest entrepreneurs aren’t the ones with the most money or the most freedom.
The happiest entrepreneurs are the ones who wake up knowing their work is actually moving them forward.
Let me explain…
You’ve probably seen that line on my website: “I run a $10m business working 6 days a month.”
People lose their minds over this.
They think that’s the goal. Work less. Make millions. Sip cocktails on a beach somewhere.
And for a while, it was my goal too.
About 10 years into StoryLearning, I’d done it. Seven figures of profit annually. Worked myself completely out of the business. 4-6 days a month, max.
By every measure, I’d won.
Sounds brilliant, doesn’t it?
Turns out it was a disaster.
Having nothing to do whilst making loads of money might sound like the dream, but what this misses is that most serious humans actually want to do stuff.
We don’t want to sit around doing nothing.
(Even the cocktails got boring in the end, so much so that I quit drinking altogether. Thanks Robin!)
We want to use our skills and talents to do good things.
A bored mind is a dangerous place.
But there’s a catch:
You’ve got to feel like you have agency in your work.
The trouble for a lot of entrepreneurs with established businesses is that they’re stuck.
The exciting early years of rapid growth turn slowly into a form of stagnation, where you’re working harder than ever before, just to maintain things where they are.
Feels like treading water.
And then life starts to feel as predictable as a Netflix romcom.
That’s no fun.
(And for me, that’s when the cocktails started. Escapism, innit?)
This really crystallised for me this week when I was talking to two entrepreneurs I mentor 1-to-1. (Both have been with me for about 6 months.)
The first guy had been stuck with a bad business partnership …
They weren’t aligned. Unequal contribution to the business. Trust issues.
And although the business was doing great, the relationship was dragging everything down.
Every time the business did better, the business parter would take more liberties. Progress in the business was making the situation worse.
(Weird how that happens.)
The key thing:
The entrepreneur couldn’t get excited about any version of the future, because the business partner was going to be there.
Long story short, he ended up kicking the business partner out entirely.
When we spoke the other day he told me the situation:
“I’m busier than ever, taking on all my business partner’s work. But it finally feels like I’m in control. Every day moves me forward instead of just keeping me afloat. I can get excited about the future.”
He’s working just as hard.
But now he has agency.
That changed everything.
The second guy was equally revealing…
Huge YouTube channel. Industry name. Making money from all directions.
But spinning his wheels.
Every month looked the same as the last. Same revenue. Same problems. Same feeling of running to stand still.
He was successful by any measure, but felt like he was slowly drowning.
Over the last six months, we’ve shifted the business model into something entirely different.
Something repeatable and scaleable — given the business a clear direction to grow.
It’s taken 6 months to validate this new model, and it’ll take 2 years to fully build it out.
Make no mistake — this guy is going to be working hard.
When we talked this week, he said:
“It’s funny. I know exactly how the next two years will pan out. It’s going to be a sh*tload of work, but it feels amazing to know that I’m building something, not spinning my wheels. ”
Think about that…
He’s about to work harder than ever. But he’s excited because he can see where it leads.
Both these guys looked like totally different people compared to 6 motnhs ago — I could literally see it in their smiles.
Unrecognisable.
And here’s what’s fascinating…
Neither of them is working less. They’re working more.
But they’re energised because their work has direction. Momentum. A compound effect.
They’re not just maintaining. They’re building.
This is the paradox that most entrepreneurs miss…
We think happiness comes from passive income. From working less. From that “6 days a month” lifestyle.
But actually?
Happiness comes from having the freedom to choose – and then choosing to work hard on something that’s actually going somewhere.
The difference between digging a hole and digging a foundation.
On my side, I’m working harder than ever.
You probably don’t see that from the outside, but you will soon.
- I’ve got a big new rebrand coming
- New website is almost ready
- I’m taking 25 entrepreneurs through a beta group of my new mentorship programme (more on this soon)
- I’m working out a book deal
I’m busy AF, but man does it feel energising.
So here’s my question for you…
Is your hard work actually taking you somewhere?
Or are you just running faster to stay in the same place?
Because if it’s the latter, I highly recommend doing what it takes to figure out a different path forward.
That’s when entrepreneurship becomes intoxicating.
Namaste,
Olly
