10 Years Self-Employed. + VAT.

On leaving a job I loved, a tax bill I wasn't ready for, and why nobody has it figured out.

I was supposed to write this post 2 years ago. I didn't get around to it, clearly. Which is, come to think of it, a pretty neat summary of self-employment.

June 2014. I handed in my notice at The Print Box in Finnieston, where I'd spent years as a graphic designer and manager working with people who are close friends to this day. It was never my plan to leave. I loved that job. What happened was that photography - which had always been a hobby, something I did for fun alongside everything else - started bringing in money, the commissions started getting more interesting, and I found myself unable to say no to them. For about two years I worked seven days a week trying to do both. Then the nosebleeds started.

It's not the heroic origin story. There was no burning ambition, no grand vision, no moment of clarity where I knew I was meant to do this. There was just a hobby that quietly became a job, and a body that eventually sent me fairly unambiguous signals that the current arrangement wasn't sustainable.

A week after leaving, I was on a plane to Milan to photograph a contestant on The Voice of Italy. I thought I'd made it.

Then things went back to normal.

Nausicaa Magarini shoot. Milan, June 2014

I've had a few moments like that over the years - a high profile project, a significant commission, something that feels like a turning point - followed fairly swiftly by monitoring my bank balance and wondering where the next job is coming from. The highs are real. So is everything that comes after them.

Nobody tells you about the tax bill. Or maybe they do but you just don’t wanna hear it. I certainly didn’t - I’ve always been much better at spending money than managing savings. I was completely unprepared for the first tax bill and it was not a pleasant experience. Put away 20% of every invoice paid. And really put that money away instead of convincing yourself, like yours truly here, that a new lens is a much better use for it. So put money away and do it from the start. Do it before you feel like you can afford to. Do it especially when you feel like you can't afford to. This is the single most practical piece of advice I can offer and I'm giving it to you for free because I wish someone had given it to me.

Something I did right, early on, was set up a weekly accountability meeting with a friend who had also recently gone solo. We checked in, compared notes, kept each other honest. It helped more than I expected. We eventually got too busy to keep it up and didn't feel the need for it anymore, which is probably the best possible outcome for that kind of arrangement.

I also started having coffee with various self-employed creatives - photographers, designers, writers - to pick their brains. What became clear very quickly is that nobody has it figured out. Everyone is blagging their way through it to some degree. I found real freedom in realising that. The people who look most like they know what they're doing are often just better at not showing the parts where they don't.

I've been lucky in many ways. I don't have children, which removes a category of financial pressure that shapes a lot of decisions for a lot of people. I have a partner who has championed me throughout - providing the kind of quiet reassurance that means you're not entirely alone if things go tits up. That safety net, even when you never have to use it, changes how you operate. I think it's worth saying because self-employment success stories often tend to be presented as solo achievements and they rarely are.

The hardest part, twelve years in, is still the quiet weeks.

It doesn't matter how long you've been doing this or how well things are going overall - a few slow weeks and the doubts arrive on schedule. You start questioning your talent, your prices, your choices. You wonder if the work has dried up permanently this time. You read your client testimonials to remind yourself that you're not completely shit at this. Then work picks up, confidence returns, and you feel fine until the next quiet patch.

I don't have a solution for this. I'm not sure there is one. What I can tell you is that it happens to everyone, it passes, and reading your testimonials is genuinely useful and not as pathetic as it sounds (okay, perhaps a little pathetic :-)).

Is it worth it? For me, yes. But it's not for the faint-hearted and anyone who tells you otherwise is selling something. Yes, the freedom is real. So is the uncertainty. You have to be able to hold both at the same time, more or less indefinitely, without it breaking you.

I wouldn't change a thing. Except maybe staying on top of that tax bill. I’m still not great at that.