Freelancing: the good, the bad and the ugly

Tuesday morning coffee with Grandad vs. constant uncertainty

Mar 26, 2025

∙ Paid

It’s Tuesday afternoon and I’ve just got back from taking my Grandad out for a coffee and a bacon roll. He’s 89 and, having been fiercely independent throughout his whole life, he’s recently had to give up his car. I can’t really imagine how that must feel - knowing that you might never leave the house again without somebody else taking you. It was nice to hang out, even if I’m sure a trip to the farm shop with me didn’t quite match up to driving himself to the allotment for an afternoon of digging.

Growing up, I spent a lot of time with both sets of grandparents. I know that I’m lucky to be in my thirties and still have three of them left, and I equally know that opportunities to take them out are only going to become fewer and further between. It’s Grandma’s turn on Thursday afternoon. She’s requested a visit to a local antiques shop. Being able to do things like this is always when I feel most grateful to be self-employed. The freedom to skive off for a midweek outing, with nobody to answer to, is such a luxury. Actually, I might have my Dad to answer to - the general consensus is that they have a few too many antiques already and shouldn’t be buying more - but nobody professionally-speaking.

I’ve been freelancing for four and a half years now, ever since I got made redundant from my last full-time role back in September 2020 and decided to see how long I could go without getting another ‘proper’ job. That makes this my longest-held position by far. Without a doubt, the thing I love most is the feeling of having more time - no counting days of annual leave! - and that’s what I’d really struggle to give up again.

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Sometimes I wonder if this feeling of having extra time is more of an illusion than a reality. My experience of ‘being my own boss’ is that it’s very all or nothing - I might have several months of back-to-back in-person events, and maybe they clash with a big book deadline and some content being due, and then there’s everything else to keep ticking over (admin, invoicing, social media, responding to leads, plans for upcoming gigs, etc) - and the result is an intense block of early mornings and late nights and feeling constantly behind everything.

But then, always, comes the lull. That’s the phase I’m in now. A few events and some things to get done, but nothing very pressing. Time at home, time to lay the foundations for future projects, time to mull over some ideas, time to have Tuesday morning bacon rolls with Grandad, time to immediately down tools at the merest hint of a good weather forecast.

I wonder, if I added up the hours I work over a year, how they’d compare to my old nine to fives. I’m certain that over the course of a year I average less than a standard 40-hour week now but perhaps not by as significant a margin as it feels. I don’t mind that though. While the reality is that, for the vast majority of us, we have to work and earn money in order to not starve (inconveniently), something I’ve never been able to get on board with is the concept of having this one precious life and spending five days out of every seven working. It might just be an illusion that I work substantially less now, a shadow puppet cast by the fluctuating nature of freelancing, but I’ll happily take this placebo effect if it makes me feel better about the whole thing.

But the price you pay for freedom and time is uncertainty. Although things generally seem to work out in the end, there’s always a lot of waiting around. Waiting for somebody to respond to a pitch, waiting for feedback, waiting for a talk to get confirmed, waiting for the budget to be finalised. It can make it hard to enjoy the quiet periods. Whereas I used to love having a fully booked social calendar, I’m often reluctant to make plans too far in advance now just in case. I might be free on paper but you never know if something is going to come up, and I hate having to cancel. So while I feel freer than I did as a salaried employee, I’m still largely beholden to other people’s decisions.

The uncertainty takes its toll sometimes. When the omnipresent background anxiety steps too much into the foreground - that’s when you’ll find me scrolling on LinkedIn Jobs and Indeed, wondering if the grass might be greener. Then, inevitably, something exciting will come to fruition, or I get paid to do something that doesn’t feel like work at all, or I go for a long run in the sunshine on a midweek morning and I think, okay, let’s just keep at it for a little while longer…