In my 20s, I spent my working hours at different gigs—running my editorial studio Wonder Shuttle, doing Prologue, writing at Medium, and a bunch of other cool projects. I had found or created a lot of opportunities, and I gave in to my ambition to pursue all of them. I was running on excitement and hype. In my low moments, though, it felt like I had bitten off a lot more than I could chew and I was just trying to process all of it. Some projects worked out, others did not.

Ev Williams is the co-founder of Medium. When he reflects on building it, he says, “I wanted to build everything new, and that may or may not have been possible, but I tried to do it all at once, which was, I think, the mistake.”

The mistake we both made was the timing: all at once.

The lesson I learned the hard way, which I’ve written about this before, is how every CEO’s job is to prioritize. You can do something—anything!—but you can’t do everything. And you can’t do it all at once.

Which comes first? Which comes later? Which must be done, and which can you risk leaving out? How much space have you made to get lucky? The path matters. 

You can nurture a couple of options, for sure, but it costs you resources. If you overextend yourself for too long, reality is going to catch up.

Last year, I made “restraint” my word for the year. While I’ve made progress, it’s still my word for this year because I found myself still needing to practice it.

It feels painful to give up things that you like, especially when it feels like nobody is forcing you to. But that’s the job. A writing adage applies here, “Kill your darlings.” You’ll know you’re doing it right when it hurts.