Going out on your own: Should you take the leap?

If you’re sitting on the edge wondering whether it’s worth it to take the leap into entrepreneurship, here are the pros and cons of starting your own business from someone who has.

Starting your own business isn’t easy. I remember the first few months of going into business for myself – when I started SBO I was working 70+ hours a week and not paying myself a cent. It was terrifying, but it was also exciting to finally be doing what I wanted.

However, an interesting discussion on Quora recently got me thinking: Is society conditioning us to think that we have to be employed, as opposed to being in business for yourself?

Since starting my own business, I’ve had multiple conversations with different friends who each expressed how unhappy they were with their jobs. These were all well-paid, stable corporate jobs – not overly demanding, but boring and unfulfilling. These conversations aren’t unique, and I seem to have them each week with a different person.

My usual response is: “Well, quit! Start your own business.”

What follows is always something along the lines of: “But it’s too risky – what if it fails?”

I would argue that this deep-rooted way of thinking is just as, if not more, dangerous than trying to go out on your own, leading to an unhappy and unfulfilled life.

So, are you in this position?

If you’re sitting on the edge wondering whether it’s worth it to take the leap into entrepreneurship, here are my two cents on the pros and cons of starting your own business (and I’ve done it).

The pros of starting your own business

Fulfilment and happiness

It’s extremely liberating being in charge of your own endeavour. You are free to be truly creative, make your own decisions and bear the fruits of your efforts. There’s also the added benefit of not having a boss. Make your own decisions – but deal with the consequences if you get them wrong. Personally, I’m much happier when I make mistakes and answer to myself.

Take the risk, reap the reward

Yes, you’re putting in the hard yards – but for good reason. When you work for someone else,  your upside is capped, but the downside? Getting fired and having no job. When you work for yourself, your upside is unlimited and you have the same financial downside as being an employee (but much higher personal satisfaction). Seems like a no-brainer to me.

Being able to challenge yourself and always learn

One of the things I love most about being in business is the constant learning. Every week I’m meeting people who are smarter, more successful and more interesting than myself – and I learn from all of them. How does that sound compared to sitting in the staff room talking about The Bachelor?

The cons of starting your own business


Going out on your own is not easy. To build a truly successful business you’ll have to work really hard – but wouldn’t you rather put your energy into something you’re passionate about? At the end of the day, you will be putting time into building your own future, not someone else’s. That’s time well spent.

Resentment from others

I happen to work better at night, so I tend to sleep in more now than when I was a wage slave. When people stumble across this fact, I often hear “You’re so lucky!” with a bitter tone, like I had some unfair gift bestowed upon me. They don’t really hate you – they’re just jealous. (Don’t be one of those people.)

Fear of failure

Despite your worst thoughts, it’s unlikely you’ll end up on JobSeeker. I think people overestimate the risk of quitting their job. If you’re reading this, you most likely have a job now, so you can get another one. Chances are that you won’t have to – if you’re putting time and energy into something you’ll love, you’ll figure out a way to make it work.

Of course, all of this must be balanced out by saying that I do know plenty of people who are satisfied with their jobs who are constantly learning, being challenged and achieving a sense of fulfillment – but there are just as many unhappy people who have no excuses. 

Weighing up the above, I think you’ll find the “riskier option” is to stay and work for someone else while wasting your talent away.

It goes without saying that starting a business isn’t easy. Not only will you need to go above and beyond in the short-term, you need to have a solid financial plan and budget in place to truly understand how much personal runway you can afford before you pull the pin.

But in the end, for me, it’s worth it. 

Are you a business owner that took the jump? What was going through your mind when you did it? Let me know.

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This article was updated on 17 May 2024.  It’s not…