How A Little Tough Love Helped Me Achieve Freelance Success

When I first decided to go full-time freelance, my husband gave me the huge gift of a little tough love.

I was scared to make this leap, and so I was soft-pedaling the decision: “Maybe I’ll give it a try,” I was saying. “I’ll just see how it goes.”

When you’re in the jar you can’t read the label, and from the depths of my fear about this new venture I couldn’t see that I was setting myself up for failure.

And from his perspective as the person who would be providing the steady paycheck and health insurance while I launched my freelance business, he had an incentive to make sure I didn’t go down the path of self-sabotage.

He said: “I am more than happy to be the one providing financial stability while you do this, but if I see you half-assing it, I am going to be upset when you inevitably fail. I’ll feel like you took advantage of me. If I see you giving it your all, then I’ll be proud of you for trying whether you make it work or not.”

This was the kick in the butt I needed. I knew he was serious, and I snapped out of my tentative mindset.

That very day I reserved the URL for my new freelance website, set up Web hosting, and ordered business cards. In the days that followed I attacked the project of getting freelance gigs with total determination. I knew I might fail – and probably would at some things – but I was either going to succeed over time or go down swinging.

The approach worked better than I ever dreamed: Within three months of that conversation I made nearly $10,000 in a single super-productive month; within two years I was making a modest, stable living as a freelancer; and within three years I was publishing a book with a Big 5 publisher.

This experience taught me an important lesson: One of the biggest hindrances to success in running your own freelance business is fear of failure.

Fear of failure leads to self-sabotage.

One of the biggest hindrances to success in running your own freelance business is fear of failure.

The only way to get over fear of failure and prevent self-sabotage is to realize you’ll probably fail at some point in some way. You may Fail with a capital F and be forced to go back to an alternate career you hated, but chances are greater you’ll just have many lowercase-F failures as you feel your way along your new path. Somehow, some way, you are going to mess up if you do this long enough.

That may seem disheartening, but like me, you may feel liberated to know that as a freelancer, you’ll definitely feel like a failure and look like an idiot at some point or other. Once you can embrace that, you can get over your fear and move on to taking action.

Each of those failures will teach you a valuable lesson that you can use to succeed over the long run.

My success has certainly been bolstered by an ongoing string of mistakes. Like the time I got in trouble by quoting government officials I had interviewed for one publication in a story for another publication without asking them. Or the time I got pranked and wrote a blog post based on a deliberately false press release that was created to prove how easy it is to disseminate fake news. I’ve had to write humbling apology emails, and I even lost $700 once for screwing up a gig.

But each time I picked myself back up, learned a lesson, and carried on.

Failure is what success is made of. Use it as fuel to keep your business running. If you approach your work with that mindset, you’ll establish the conditions to grow a great long-term freelance career.