Have you ever noticed that learning to swim feels a lot like drowning? At least at first. How can we tell when all that flailing around is actually exactly what we’re supposed to do on our way to mastery? Founders have to start from scratch a lot. When you’re hiring someone new to lead a function, for instance, you have to master enough of the material to assess someone else’s ability to actually take action in that domain. Design, marketing, or engineering—how do you know when you’ve learned enough?
If you’ve worked at a startup, whether as a founder or employee, you’re definitely familiar with the joys and challenges of learning on the job. In my twenties, I co-founded three companies. At my first two companies, I had to learn everything from operations (accounting, compliance, legal), sales (how to sell a thing, how to hire salespeople, how to hire sales leadership, how to be a sales leader, sales strategy), customer success, recruiting, hiring, firing, layoffs, and much more. The only way I could manage this was to remind myself that if it felt like drowning, swimming was around the corner.
Just over three years ago, I decided to leave the second company, Mattermark. A week or so after I had left, unemployed for the first time since college, I stood at a bar with one of my former colleagues, now my best friend. As someone who knew me better than anyone else, I asked him what I should work on getting better at as I began exploring what I would do next. He told me I got in over my head too easily, assuming I had learned more than I had, trying to plow forward too soon. Poor results and poorer credibility were all I was going to get by not giving enough respect to what I didn’t know.
That’s really what it’s all about. If you’re learning to swim, and you don’t respect the water, you actually are going to drown. If you’re learning to swim, talk to the best swimmers you can find. But also talk to people who just learned to swim themselves, and even other people who are learning, too. These days, I use Tim Urban’s 1–10 scale of knowledge (I call it, brilliantly, “the Urban Scale”) to accurately judge how far along I am in mastering something new—or at least becoming as familiar with it as I need to be to not massively fuck things up. I try to make sure that I know enough to be able to tell if someone else is struggling in that domain, if they’re “not waving but drowning.” I might not be able to bring them back to shore by myself, but I’ll know the signs, and be able to call the right people for help.
