What happened when I just did the thing

Working in rather than on my business

Illustration: Léo Hamelin

A much-loved business catchphrase is “work on, rather than in, your business”. The idea is that if we don’t make time to look at the bigger picture, we’ll find ourselves endless spinning on the hamster wheel.

In my book, You’re The Business, I wrote about the creative coach Jen Carrington’s CEO Days, a monthly (or even better, fortnightly) check-in and strategy session. It’s good advice. Especially for freelancers, who are prone, as we are, to avoiding any non-billable work.

It’s such good advice in fact, that I recently realised that I’ve been taking it too far. I love a spreadsheet almost as much as I love a strategy. I’ll very happily spend an afternoon faffing over quarterly earnings and coming up with various ways in which I can improve my business. It’s my professional Achilles heel. I tie myself in knots over which order to do things, creating systems and processes so convoluted that I don’t get round to the doing itself.

Take this newsletter. I’ve been in a bit of a pickle with it for months now, unsure of which direction to take it in after more than four years of writing it. My instinct was to MAKE A STRATEGY!! and so now I’ve got Google docs coming out the wazoo about it but I’m not really the wiser about how to actually proceed. It’s a form of analysis paralysis, something the questioner in me has a tendency towards.

Recently, I started writing more features and essays. I’d stopped partly because I was writing my book but also because I didn’t have enough time in my schedule due to all my strategizing over the newsletter.

And then the stars aligned. I’d had a flurry of ideas at the same time that a couple of editors reached out to see if I’d want to write for them. Rather than agonise over the most ~strategic~ way to execute my ideas, I just... pitched them without a second thought.

It’s been invigorating to write more. It reminded me that I love the thrill of a deadline and the mental workout of formulating an argument. I also like being edited. The freedom to post my unfiltered thoughts here in this newsletter is something I’ll always cherish, but I do think the best way to grow as a writer is by working with an editor. It also reminded me of the less fun (read: awful) parts of writing on the internet, like late payments and Twitter trolls.

Sure, I might have been able to work all of that out from a strategy, but it wouldn’t have sat in my bones the way it does now that I’ve actually gone through it. There are things you can only know from doing. So for the time being, I’m just doing the damn thing.