All entrepreneurs want to quit. (unless they’re lying)

Updated to Business on May 3, 2023.

The first time I was self-employed I couldn’t even spell ‘entrepreneur’ – I just knew I wanted it.

I’d worked night-shift, feeding paper rolls from cash registers into temperamental computer readers, washed dishes in a hospital kitchen, built fences and even tried my hand at writing software.

It was time to start on my own.

But, here’s the deal about self-employment: most people won’t survive.

Any certainty that comes with being employed is quickly replaced with the insecurity of no set work hours, no deadlines and hundreds of decisions (and all look critical) screaming for your attention.

And then there are success stories.

If you harbor any doubts about your fledging new venture, turn to an issue of Success, Inc, Entrepreneur, Forbes or Wired, or listen to one of the hundreds of ‘success story’ podcasts.

Success seems to be growing on virtual trees. Kids still living in their parent’s basement are driving Porsches to the bank with new-found riches.

Success stories are like dessert: they’re usually on the menu, but not always good for your health.

Here’s what those articles rarely share: the real cost of reaching success.

The real cost of success

Glory articles won’t talk about this and you’re unlikely to hear it on your favorite business podcast. I’m talking about wanting to quit.

You know…get a J.O.B.

We’re all victims to self-doubt. And then – GREAT NEWS – even if you work hard and are lucky enough to enjoy a modicum of success, then you get to enjoy that pant-soaking feeling psychologists dress up with the name ‘imposter syndrome’ (feeling like a fake).


When I started BlogWorks it was just a side hustle – a way to help other speakers get more traffic to their blog. I didn’t take it seriously.

And then more people asked for it and BlogWorks started to grow. My baby side hustle was looked like it wanted to grow up to be a business. And then came more hours, more work, more worry and paying more bills.

And as the opportunity grew so did the self-doubt “I must be crazy – everyone is better/more experienced/better connected than me!”

And then there were the thoughts of quitting. For your reading pleasure, I included a chart showing the frequency of my thoughts of quitting (not to scale).

Ask any entrepreneur and (if they’re being honest) they’ve wanted to quit. After all, who would know? Who would even remember?

“Hey, didn’t you used to have a business that….?”

“Oh that? Yeah, it just didn’t work out…but, let me tell you what I’m working on now.”

Want to start a side hustle or jump in with a full-time venture. You’ve been forewarned.

You will want to quit.

Advice you don’t need

And now here comes the advice you don’t need.

If you’ve read this far you’re either thinking about starting your own business, are already down that path or are extremely bored. Either way, you already know what I’m going to suggest.


No business book, podcast, or TED talk compares to what happens when you hang up your shingle and declare you’re in business. It’s a defining moment and there’s no turning back on the lessons coming your way.

Think of it this way:

You have a product or skill that people want (even need) and your puny, whiney, snivelling self-doubt is the only thing between helping people and walking away.

And you are going to want to quit.

It will be too hard, confusing and frustrating and many times feel like a Greek tragedy involving a very large boulder being pushed uphill.

And then are there are the glory moments when you receive a wonderful, self-affirming compliment or someone just put $9 in your PayPal account.

Be prepared: both the tragedy and glory are mixed in the entrepreneurial salad.

Success guru’s won’t talk about it, but their success came as a result of weathering through those moments of self-doubt and wanting to quit.

I don’t think it can be any other way. And maybe it shouldn’t be.

Do it anyways and enjoy the journey. Most would have never even started.