One year of freelance

A year after making the decision to go freelance, here’s a report from the field

So, we made it a year. It feels worth pausing to acknowledge, take stock of what I’ve learned and how I feel about it, even if that part’s still settling. Here’s a few lessons and thoughts from the year.

This one-man band isn’t a one-man band

It might look like I’m working solo, but I’ve got a whole team behind me.

There’s my partner - doing the billing, the proofreading, being a sounding board, and keeping me sane. An accountant for the tax things. A couple of trusted collaborators I’ve shared projects with. Friends and family who’ve stepped in with childcare, dog care, and general life support.

I couldn’t do this alone, and I won’t pretend I do. So I owe some thank-yous.

To the aforementioned, and: if I’ve ever asked you for for advice or a catch-up, if you’ve tagged me in a LinkedIn post or sent a referral my way, if you’re one of the small-but-elite group of people who read my blog, and finally — if you’re a client*:

Thank you.

I’m getting used to rejection

I used to fear rejection. Turns out I’d just never experienced the right kind.

This year I’ve written a lot of proposals. Most of them were rejected, and it was fine. There’s always another proposal to write, another relationship to build.

Proposal writing deserves its own post*, but I’ve tried to stick to one guiding principle: be honest and clear. If I’m not the right fit, then we’re probably not the right fit.

Work is still work

Freelancing brought a rush of novelty and freedom at first, but that quickly faded into something familiar - the daily rhythm of just doing the work.

I even managed a few months of weeknotes before it felt like I was writing the same thing over and over*.

I love my profession and the work I do — helping people, solving problems, making things better — but it’s still work. And I won’t pretend I wouldn’t sometimes rather be doing fun things with the people I love.

Money is different now

Money used to just arrive. Every month, roughly the same amount, without me having to ask.

Now, if I want money, I have to ask for it - send invoices, track time, submit proof that I’ve earned it. The amount varies directly with how much work I’ve done, and that’s taken some getting used to.

I’ve never been brilliant with money. I’m getting better, mostly because I’m married to someone who is - who occasionally grabs me by the head and makes me stare down the barrel of the bank balance.

So I’m trying to think about money differently. I tried to use income as a success measure, but found the payoff lacking. When I hit my target for year one, I felt relief more than anything. My target for year two is the same, but I’ll be finding my dopamine hits elsewhere.

I worked too much this year

I took Christmas week off. I worked half-days on a family holiday to Malta. I eased up a bit for the school holidays in August. That’s about it.

Fear was a big motivator - the fear that if I stopped, the work might disappear. So while the work was there, I kept working. I don’t regret it, but looking back, I could have taken my foot off the pedal a bit more. I’d imagined a natural lull would come — that things would quieten down and I’d get some time off. That never happened.

Nice problem to have, but still a problem. Lesson learned.

I didn’t make the most of the freedom

I worked from the local co-working space now and then. I did a few mornings from a hotel in Malta. But mostly, I worked at the same desk, in the same room, like always.

Next year, I want to make better use of the flexibility, find some new spaces, meet different people, spend more time out there.

And conferences! I went to just one*. I’ve worked in places where the conference budget was tight and I hated that. Now I’ve got an unlimited conference budget, and somehow forgot to use it.

Martin from one year ago: you aren’t destitute, there’s food on the table, clothes on your children, things are going well. Spend year two enjoying yourself.

Year one, done

So that’s year one: a mix of freedom and fear, support and solitude, success and second-guessing.

Mostly, though, it’s been a reminder that work - even when it’s your own - is still just work. The trick is remembering why you chose it, and giving yourself the space to enjoy everything else too.

I keep using this phrase when people ask how it’s going: “I’ll ride it till the wheels fall off.”

That’s still the plan. The wheels are still on, and if they’re still on this time next year, I’ll see you again — for more lessons, and definitely more thank-you’s.

*I have those now.

*It would focus on how writing a proposal for work that you’ll actually have to deliver yourself is so different from the traditional agency experience. It’s wild.

*There’s only so many ways to talk about drawing rectangles. Could you tell? I felt like people must have been able to tell.

*Product for the People, highly recommended!