Damn, I should have left sooner.

Taking ‘the big leap’ into independent work is bloody hard. It’s one of the biggest decisions you’ll make about your career and what lies beyond will directly impact your happiness, financial stability, and the opportunities you encounter.

I did it, but I did it five years too late. I’d like to help you avoid that mistake.

Why does this matter?

In truth, it doesn’t, really. Since I left my job, I’ve been happier and more successful than I ever thought possible. Sure, it’s been tough at times, but every time I’ve hit a bump in the road, I’ve been able to navigate it without someone else dictating how I navigate it.

I’ve never looked back.

Until someone asks what my biggest regret is.

I should have left my regular job five years before I did. And the reason for that is simple: it would have given me more time.

As you’ll discover when you enter the world of freelance work, time is everything. It’s directly related to how much you’re paid and dictates how much stuff you can get done in a day. More importantly, the more time you have, the quicker you’ll grow and learn as a small business owner.

If I’d left my old job sooner, I’d have gained more time to learn the intricacies of accounting (a huge weak point of mine), worked more solidly on my future plans and refined my services more.

I’m doing these things now. Five years in, my services look very different from what I’d originally conceived, and I’m gradually getting my head around the numbers. But, occasionally, it feels like I’m chasing my tail a little.

How to know when to jump

When it feels right – do it.

Looking back, I know exactly when that moment was. And I bottled it.


‘Regret’ is a big word. In fact, it’s a horrible word, and it’s one I barely use.

When it comes to my business, though, I do have this one regret. But it isn’t a sad, forlorn regret. It’s one that keeps me on my toes and allows me to advise others to avoid the same mistake.

What about you? Are you ready to make the leap, or, like me, did you wait a little too long to make the leap?