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The ‘Two Buckets Theory’ of Creative Work
If you’re self employed, ask yourself these two questions before taking on your next project

I’ve always felt most comfortable working for myself. I decide when I work, what’s worth it and what’s not, and I don’t have to pretend to be loyal to the amorphous concept of “company culture”—a phrase which has always made me feel slightly nauseous.
However, having recently returned to self employment after some time away, I’m rethinking how I approach working for myself. Specifically, which work I say yes to, and which work I decline.
When I first started working as a self employed writer more than ten years ago, I was very much in the “say yes to everything” camp. That made sense at the time. I needed every penny I could earn, and I had little experience to warrant declining opportunities. But as time progressed, I struggled to let that go. I said yes to things that were underpaid because I thought they might lead to something else down the line: connections, exposure, a stroke of kismet that would lead to my inevitable Big Break. It was only a matter of time, right?
I also said yes to plenty of things that — while perhaps paid okay at first glance — involved working with difficult, unreliable people or arcane workflow processes. This often meant that by time I’d answered all the emails, taken all the calls, done all the edits, filled out all the tax forms and contracts, and chased the invoice several times to get paid, I felt I deserved another check just for the administrative portion of the exercise. Once I saved for taxes on that check, the cost benefit analysis came into stark relief: I definitely should have said no.
Some of this is just implied in the machinations of working for yourself. It definitely has downsides, there is no doubt. But there’s also something else at play, something I’m trying to rectify now: I was neglecting to ask how the work in question was serving me, rather than the other way around. I was falling into the mushy middle of self employment.
The mushy middle is a place where nothing is quite what you want it to be. You’re not being paid enough money to warrant the headache or scope of the task at hand. And you’re not really thrilled or…