I remember when I first returned to secondary school teaching in 2023 after three years of working for myself.
I was excited. Like, embarrassingly excited.
Because as fulfilling as those three years had been, I knew it was time to go back to the classroom.
I was moving to the Netherlands at that time, and after weighing up my options, being employed and sponsored — as a single woman at that time, on my own — seemed to be the most straightforward path.
Yes, I had my practical reasons, but I wasn’t going to just take any job so I could live in Europe long-term. I wanted to continue teaching — whether that meant teaching in a traditional classroom setting or mentoring adults.
Plus, I’d always had this “teaching in Europe” dream in the back of my mind, and I was excited to finally get to live it!
So, long story short, I was happy to return to the security of a 9–5 — the kind of decision that might make some perpetual-freedom-seeking entrepreneurs drop their jaws and think:
“Ah oh… another one of us has admitted defeat and returned to the prison of paid employment.”
And then, over the next three years, I would often come across business coaches telling people just how terrible the 9–5 was.
“You’re trapped.”
“Why are you wasting your life making someone else rich?”
“Your job is sucking the soul out of you.”
“You could be working from your laptop by the pool in Bali instead!”
Blah blah blah. The drama of it all.
And then, conveniently, comes the sell: here’s how you escape. Buy my course. Join my programme. Quit your job. You know how it goes.
I understand why the messaging works. If you genuinely hate your job and feel burnt out, the idea of escaping can be very appealing. And I do believe there are people who thrive working for themselves.
There are things I love about having my own business: the autonomy, the creativity, deciding what I work on and who with. But having now sat on both sides of this — self-employed, back in employment, and now building a business again — I’ve become genuinely uncomfortable with the idea that entrepreneurship is the enlightened path and employment is the consolation prize.
Because honestly, not everyone is meant to run a business. And I don’t mean that as an insult — I mean it quite literally.
Business coaches who sell you the dream — the rosy picture of working from your laptop by the pool in Bali — without being upfront about the mental load, uncertainty and responsibility that come with it simply aren’t telling you the full picture.
Not everyone is able, or even wants, to withstand that kind of uncertainty. And that’s not a personal failing. It’s simply a different way of working and living.
Some people like knowing exactly what their responsibilities are. They like having colleagues, being part of a team without having to build one themselves, and having the security of a regular salary, paid leave and a pension. Hey, they might even like their boss.
And a job can hand you structure, the chance to work on something bigger than yourself without also having to think about marketing, invoicing, and whether anyone will actually buy the thing you spent three months working on.
None of this is to say employment is perfect. There are toxic workplaces, bad managers, unfair pay, cultures that ask for loyalty without giving much back. Some people genuinely need to leave.
But “I don’t like my current job” and “I should become an entrepreneur” should not — and are not — the same conclusion.
There are so many exits from an unhappy situation: finding a new company, changing careers, going part-time, negotiating better conditions, taking a sabbatical, retraining, moving countries… the list goes on.
Starting a business is one option among many, not the answer.
I actually had an unpleasant moment during my teaching job in Amsterdam when I realised that I wanted to go part-time because I also needed more space in my life for other things I wanted to build and explore (that’s a story for another time.)
But that experience also made me realise something.
It’s this narrative that many “business coaches” are selling that I find problematic.
“If you don’t have freedom, multiple income streams, a personal brand, and the ability to work from anywhere, you’re thinking too small!”
“And if you return to a 9–5, that means you either didn’t try hard enough or you had the wrong approach.”
*Yawn* 🥱 (Are we done here?)
Because sometimes, choosing a 9–5 isn’t giving up on your dreams. Sometimes, it’s simply choosing what makes sense for your life right now.
The bottom line is, not everyone wants to live in Bali with a laptop by the pool. Not everyone wants the uncertainty and responsibility that come with running their own business.
Because when you work for yourself, the flexibility is real — but so is the mental load. You’re responsible for finding the work, making the money, paying the bills, making the decisions, managing the admin, dealing with the quiet months, and constantly figuring out what comes next. There’s no one else to hand the problem to when something goes wrong.
And for some people, that kind of uncertainty is energising. For others, it’s exhausting. Neither is wrong.
Some people thrive in employment. Some people derive a lot of fulfilment and enjoyment from paid employment — and make very good money doing it.
Some people thrive in self-employment. Some people derive a lot of fulfilment and enjoyment from building something of their own — and make very good money doing that, too.
One isn’t inherently better than the other.
A business can give you freedom and hand you uncertainty in the same breath. A job can give you structure and security, while also coming with limits you didn’t choose.
There is no magical version of working life where you get all the upside and none of the trade-offs.
They simply ask different things of you — and give different things back.
So maybe the better question isn’t: “How do I escape the 9–5?” Maybe it’s:“What kind of life do I actually want my work to support?” And then build from there.
Maybe the answer is a 9–5.
Maybe it’s a business.
Maybe it’s a bit of both.
Maybe the answer changes five years from now.
All of those are okay.
As for me? I’m now off the paid-employment bandwagon again, building my own thing, and enjoying the freedom and the uncertainty that comes with it. Just following what feels right for this season, making room for the things I care about, and seeing what grows.
And perhaps that’s the whole point. Your career is meant to serve your life. Not the other way around.
And I think that’s a much more interesting definition of freedom than simply being able to work from a laptop in Bali.
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