Or: Confessions of a Reformed Solopreneur Who Learned the Hard Way
Let me tell you a dirty little secret that nobody talks about in those glossy "quit your job and follow your dreams" articles: being self-employed might actually make you unemployable.
Yes, you heard that right. While LinkedIn influencers are busy humble-bragging about their "entrepreneurial journey" and productivity gurus are selling you courses on "escaping the 9-to-5," there's a darker truth lurking beneath all that #hustle culture nonsense.
The Great Self-Employment Experiment (Spoiler: It's Complicated)
Last year, I took the plunge. Full independence. Complete freedom. The whole solopreneur fantasy package. And you know what? It was everything I dreamed of, and absolutely nothing like I expected.
Sure, I had freedom. The freedom to work at 2 AM if I wanted. The freedom to stress about money every single day. The freedom to realise that "work-life balance" is just a cruel joke when your bedroom doubles as your boardroom and your anxiety never clocks out.
The constant mental chatter was relentless: Am I charging enough? Is this client going to pay on time? Should I take that project I hate just to keep the lights on? What if I never find another client? What if this is all a massive mistake?
Turns out, being "always on" doesn't make you more productive - it makes you a caffeinated zombie who's physically present but mentally calculating profit margins during date-nights.
The Crete Reality Check
This summer, I had my hand forced: to go work remotely while figuring things out back home. Crete, to be specific. Sun, sea, and presumably, serenity.
Plot twist: working alone on a Greek island while the rest of the world is living their best vacation life is about as isolating as it sounds. The heat doesn't inspire productivity - it liquefies your brain. The stunning sunsets lose their charm when you're the only one watching them through your laptop screen.
The romantic notion of being a "digital nomad" quickly devolved into being a digital hermit with really good Wi-Fi and a vitamin D overdose.
The Harsh Truth About Going Back
So here I am, trying to crawl back into the "real world" of employment and trying toreturn to a life I hope is still there. And guess what? It's not going well.
Turns out, hiring managers have some... interesting... assumptions about people like me:
"You'll just leave again." Because apparently, once you've tasted the sweet nectar of entrepreneurial freedom, you're forever tainted by wanderlust and an inability to commit to anything longer than a quarterly review.
"You can't work with others." Yes, clearly my ability to manage clients, build software, negotiate contracts, accounting, customer service, and run every other aspect of a business screams "doesn't play well with others."
"You're overqualified/unemployable." Schrodinger's candidate: simultaneously too skilled and completely useless for any normal job.
"Why would you want to work for someone else?" As if the only acceptable reason to seek employment is complete professional failure rather than, you know, wanting health insurance and the radical luxury of not lying awake calculating if you can afford groceries this month.
The Skills You Didn't Know You Were Losing
Here's what nobody tells you about extended self-employment: you start developing some habits that don't translate well to corporate life.
You get used to making every decision instantly. No committees, no approval processes, no "let me run this by my manager." In the corporate world, this reads as "doesn't respect hierarchy" rather than "decisive leader."
You forget how to play office politics. When your biggest interpersonal challenge is negotiating with your cat for desk space, you lose touch with the subtle art of corporate diplomacy.
You develop an intolerance for inefficiency that borders on the pathological. Suddenly, 30-minute meetings that could have been emails feel like small personal attacks on your sanity.
The Irony of Independence
The biggest irony? Self-employment is supposed to make you more marketable. You're running a business! You're wearing all the hats! You're a one-person Swiss Army knife of professional competence!
But apparently, Swiss Army knives don't fit neatly into job descriptions that require you to be specifically a screwdriver.
The skills that make you successful as a solopreneur - resourcefulness, adaptability, comfort with uncertainty - somehow become red flags in the hiring process. You're not a team player; you're a wild card. You don't follow processes; you're a loose cannon.
The Way Forward (Or: How to Reintegrate Into Society)
So, can being too self-employed ruin your chances of landing a "real" job?
Yes, absolutely. But also no, not permanently.
The trick is learning to translate your experience without sounding like you're slumming it or planning your next great escape. You need to convince employers that you want to be there, not that you're settling for being there.
Start networking like your mental health depends on it (because it does). Remind yourself how to have conversations that aren't about conversion rates or client acquisition.
Practice talking about collaboration without sounding like you're reading from a corporate buzzword dictionary. Remember what it's like to be part of something bigger than your own anxiety-driven empire.
And maybe, just maybe, admit that there's something to be said for predictable income, actual weekends, and the simple pleasure of problems that aren't entirely your fault.
The Real Talk
Here's the thing: neither path is perfect. Employment has its soul-crushing moments, and self-employment has its bank-account-crushing realities. The grass isn't greener on either side, it's just a different shade of complicated.
The real question isn't whether you can go back. It's whether you can figure out what you actually want from work and life, rather than what you think you're supposed to want.
And if you're reading this while contemplating your own great escape from corporate life, maybe ask yourself: are you running toward something, or just running away?
Because trust me, geography and job titles are terrible therapists.
Currently writing this from Crete, where the sunset is gorgeous and my career prospects are... pending