My first day as a freelancer was incredibly scary

The reality isn’t always how we imagine it will be

Jo Driscoll
2 min readSep 1, 2021


I’ve written about my freelance journey multiple times, and I’ve so far managed to muddle through but it has been very up and down.

I was working as a web developer and redundancy was looming. Despite applying for jobs, I didn’t get anywhere so I had to revert to plan B — go freelance.

So, with no savings, some debt, a mortgage, no clients, and only a small amount of redundancy pay, I took that leap. Well, not so much of a leap as falling off a cliff and hanging on by my fingertips.

With my salaried employment over, this was it. I was now my own boss. And what did I do on my first day? I actually don’t remember to be honest but I probably worked on my website as that was something I knew how to do. Working out how to run a business had to come later.

I think I spent the next few weeks trying to get into a new routine while also destressing from work — I could feel the work stress melting away. Sounds great, but that stress was replaced with the new stress of how was I going to pay the bills and keep a roof over my head? Christmas was also fast approaching and I barely had the money to pay the bills let alone buy presents.

Things did eventually fall into place and I did pick up enough work to keep going. Plus I came into some money which gave me some much-needed breathing space. But that was not before scraping the very rock bottom with not knowing how I was going to keep a roof over my head. Losing my house was a very real possibility and I never want to go through that experience again.

I survived. I made it through and I’m still freelancing today though as a writer, not a web developer. I’m stubbornly sticking to the freelance life as it gives me the flexibility to care for my horse. Thanks to the switch in career, I’ve had to start from the beginning and build up the income again so money is still an issue but I’ll get there. I’m still surviving.

To anyone thinking of going freelance, please go into it with your eyes wide open. Forewarned is forearmed as they say. Have a big stash of cash you can dip into to tide you over. Don’t let all the stories on Medium about other people making bundles of money in their first month of freelancing cloud your thinking. Of course, it’s possible but you may just find the reality doesn’t quite live up to your expectations.



Jo Driscoll

Writer. Reader. Thinker. UK-based freelance writer.