Work Less, Work More

If I ever start another company, one of the main things I’ll do differently is that I’ll “work” a lot less.

I put “work” in quotes because I’m actually referring only to a specific subset of work—it’s just that it’s a subset often confused with the entire thing. I’m talking about the things that look like work, the things you’d spend your day doing in a typical job: the completion of individual tasks, or the direct management of others doing the same.

If I did it all again, I’d spend a lot less time on that stuff, and a lot more time thinking about the larger, more strategic issues: whether we were operating in the right market, whether we were building the right things, whether we had the right team. Thinking about that stuff often doesn’t look like work. It often doesn’t even feel like work to you when you’re doing it. It might involve taking a long walk, or doodling for hours, or even just sitting and thinking deeply. Or it might involve taking an intentional break from any kind of thinking about work altogether and letting your subconscious mind do its thing, as the proper solutions to most complicated problems tend to resist active thought.

I say all this because when I look back on my former startup days, one of the things that stands out the most is how little most of what I did actually mattered.

Every day brought dozens of tasks and decisions that felt important at the time, and I stressed myself out—and worked myself to the bone—over all of them. But in reality, the company’s ultimate fate was almost entirely determined by a few key decisions, many of them made very early on. On a typical day, almost none of what I did made any real difference. You can’t win a race by running in the wrong direction, no matter how fast you go.

Of course, much of the work that “doesn’t matter” still has to get done—every endeavor is built on a base of so-called “unimportant” work without which the entire thing would collapse. And even for work that was truly unnecessary, it wasn’t always obvious which was which at the time. As the department store mogul John Wanamaker famously said, “Half the money I spent on advertising is wasted, I just don’t know which half.” But some real chunk of it was, in retrospect, nothing but busywork I was creating for myself.

On some level I probably knew this even back then. But it’s one of those things that’s easy to understand intellectually, harder to process emotionally. Some of that resistance comes from imposter syndrome. In the early days, I was devastatingly insecure about not being a “real” founder, and the stereotype of “real founders” is that they work all the time, so it followed that the more work I did, the more real I became. Unsure how to tell if I was doing a good job, I turned to hours worked as the nearest proxy.

But there was something else going on too. Sometimes we work because we have to work; other times we work to distract ourselves from existential dread. As a founder, so much of your fate is out of your hands, and “working” all the time—even on stuff that doesn’t really matter—is a way to at least give yourself the illusion of control. If I were to have stepped away from the computer and just thought really deeply about the biggest questions affecting our business, I would have had to sit with a lot of difficult emotions and confront a lot of possibilities I didn’t want to confront. Easier, most of the time, to just bang out another twenty emails and tell myself I was working as hard as I could.

There’s a lens through which this whole concept is depressing. But there’s also a lens through which it’s relieving, especially when extrapolated out to apply to the whole of our lives. The success of one’s life, too—however you define “success”—is mostly determined by a few key choices. In the long run, most of what we do day-to-day doesn’t really matter. Most of it we won’t even remember. There have been so many times I’ve reread an old journal entry in which I’m deeply upset about something and don’t even bother to explain what it is, so certain that my future self will always know exactly what I was referring to. But of course, looking back, I almost never have any idea.

There’s a freedom in that forgetting. It’s like that old joke in the Talmud where that guy asks a rabbi to explain the whole Torah while standing on one foot. “What is hateful to you, do not do to your neighbor,” the rabbi says. “The rest is commentary.”

So it is with startups, with other projects, and with life. Get a few big things right, and the rest is commentary.

Yours in admitting that the only other story I know from the Talmud is the one about that rabbi who had laser eyes,

Max