It takes a lot of guts to quit a secure job to become self-employed.

It takes even more guts to do it after you have already tried and failed. You have more reasons to doubt yourself, and it feels you’ve got more riding on it.

Here’s what helped me get across the line the second time.

Change the context

First time: I hit a wall with the work I was doing inside organisations and wanted a way out. I’d run my business as a side hustle for a few years, and decided now was the time to go all in.

This was Jan 2020 – little did I know that less than a month in we’d be going into the first of 6 lockdowns.

Dear reader, I cannot stress how ill-prepared I was for building a business in the early throws of a pandemic.

Second time: Late 2020 I made a strategic retreat back to in-house work. I chose a year long contract, and used that year to lick my wounds, hone my skills, and gird my loins. I knew when the contract would end, and when my return to my own work would begin.

Sit with the discomfort

First time: Sole traders need to be a jack of all trades. I arrived with a fairly diverse toolkit, but there were some gaps.

I hated self-promotion. I felt like an inconvenience every time I posted about anything to do with my business. I felt unworthy and afraid that people would hate what I’m doing, so I made myself small and made as little noise as possible.

Second time: I recognised that my fear and discomfort was holding me back. I spent the last 6 months of year contract changing the way I thought about marketing, and practicing the skills I needed to help my audience find me so I could provide them value.

By starting again, I haven’t failed – I’ve learned from my earlier attempt and am stronger for it.