We’re all different – some of us are circles, triangles or squares. Yet we are all forced to fit through the same square hole.
If there’s anything I learned during my pre-school years it’s that circles fit in circular holes, squares in square holes, and triangles in triangular holes. If you try and force a triangle through a square hole, it’s not going to come out looking great.
The same thing happens with people and work. Some people really aren’t meant to do certain kinds of work.
I remember working at my last 9-5 job, learning about starting an online business. I literally felt no connection with my engineering career and, while I could’ve had a worse job, it wasn’t what I was meant to do.
I just knew it.

I’d try to get my work done as quickly as possible so that I could leave on time to do my favourite thing: listening to entrepreneurship podcasts on my drive home!
I had two favourites: Pat Flynn’s The Smart Passive Income Podcast and Chris Ducker’s Youpreneur Podcast.
Listening to those and working on my business when I got home were the only points in the day when I felt happy – like I was giving the best of me.
Related: What It Takes to Start a Business While Working Full-Time
Looking back, I definitely suffered from Repressed Entrepreneur Syndrome. If you feel some of the 5 symptoms below, you might have an inner entrepreneur, waiting to be unleashed!
The 5 Symptoms of Repressed Entrepreneur Syndrome
1. You don’t like being told what to do
Sometimes in a job, you’re ordered to do something. You may have a nice boss who’s pleasant with his/ her requests or quite the opposite.
I’ve had experiences with both kinds of bosses and, while I understood that they were paying me to do what they said, something just didn’t feel right.
Entrepreneurs work best when they are in charge.
They have the vision and the determination to get to where they want to get. For natural-born entrepreneurs, being told what to do feels like wearing a pair of heavy metal shackles.
2. You feel that your creativity isn’t being nurtured
If you’re a creative person, it’s quite likely that you’d thrive as an entrepreneur. Some claim that creativity is a better indicator of success in life than intelligence!
Think of it as a muscle: if you exercise your creativity, you’ll get better at it. Ideas will flow more easily and you’ll find creative solutions for any problem in your life.
On the other hand, working a 9-5 job where you’re sitting in an office all day long is killing your creativity muscle. You’re forced to follow the rules and you’re often limited by your job description.
Having been an entrepreneur for the last 9 months or so, I love how much I’m able to use my creativity. I get to write from the bottom of my heart and to play around in Photoshop to create my blog images and other graphics for the site!
I also get to find creative solutions to grow my business and to keep trying new things without anyone’s prior approval. I love it!
3. Imagining yourself still working in the same career in 10 year’s time makes you dizzy
In every 9-5 job I’ve worked in, there have always been much older people who were at the same level as me. They were even doing the same job I was doing – with an added 20+ years of experience.
It was easy to imagine them, decades earlier, still doing the same things are doing now. Not growing or changing – just getting by.
I must admit that it was easy to see myself following the same career path they did and keep doing the same job for decades.
It was horrible!
I could always tell the ones who genuinely enjoyed their jobs from the ones who didn’t. The latter seemed to enter some sort of trance that would help them to get through the working day and go home to actually start living their lives.
If this sounds familiar, maybe you have an inner entrepreneur waiting to get out and take you down the path you were always meant to follow.
4. You spend a lot of time thinking about escaping your 9-5 job
Life is short, people. Spending most of it doing something you don’t like isn’t a good way to spend it.
In my article about getting over procrastination and starting your thing, I showed you a picture of how many months there are in a 90-year life. It’s a scary view, and it really puts things into perspective!
If you don’t like your job and you dream of doing something else that will bring you joy – like starting a business around one of your passions – then you definitely suffer from Repressed Entrepreneur Syndrome.

5. The concept of the 9-5 doesn’t sit right with you
A 9-5 job forces you to wake up at a certain time, endure a horrible commute, and sit in an office for 8+ hours a day. After a sleeping break (AKA. going home after work) you get to do it all over again! Yay!
I find the 9-5 concept to be bonkers. It’s evolved to become something that a lot of people really should not be doing.
Worst of all, it’s the norm. If you don’t do it, you’re the weird one.
You’ll know you’re meant to be an entrepreneur because you prefer other ways of working that just feel better.
Ever since I left my 9-5 job and started working on my business full-time, I’ve been able to find out the best working arrangements for me.
I still wake up at around the same time I used to, but I don’t have to be stuck in traffic and do things when everyone else is doing them. I go to the gym in the morning when it’s empty, shop for food without having to wait in queues and try not to drive during rush hour.
Best of all, I don’t have to follow any of the silly office rituals and customs. I don’t have to wear clothes that don’t feel comfortable, I don’t have to pretend to like anyone just because they’re above me in the hierarchy, and, best of all, I don’t have to pretend to be working!
I don’t have to wear clothes that don’t feel comfortable, I don’t have to pretend to like anyone just because they’re above me in the hierarchy, and, best of all, I don’t have to pretend to be working when I’m not!
If I’m not feeling productive at a certain time I can always go do something else and come back to it later. Thet’s the beauty of being your own boss!
Not everyone can be an entrepreneur – but a lot of people should
The 9-5 lifestyle certainly suits some people. Most of the people I know would not make great entrepreneurs – they’d rather be told what to do and get a regular paycheck.
That’s absolutely fine, and our society is certainly built on people who are good at being employees.
However, I think a shockingly high number of people try to force their way through a conventional career when they should embrace the fact they’re natural-born entrepreneurs and start their own business!
A great way to start is by reading my guide on quitting your 9-5 job and starting your own business. This is what I did and my life has never been better! 🙂
I think the big one is feeling that you were born to be better. I was born in a middle class family, but always felt that I deserved more. I thought that I was born for an above average life. That’s why by starting my own business I aim to be avbillionaire one day (lofty goals, but attainable).