The 500 Hats of a Startup Founder

Or, Balancing the Voices in Your Head

As a child, I read Dr. Seuss’ The 500 Hats of Bartholomew Cubbins— the story of a boy who, no matter how many hats he removes, always finds another underneath. Founding a startup is a little like that. You knew you’d be wearing multiple hats — playing multiple roles — but their sheer number, and the difficulty of juggling them all, catches you by surprise.

I got a taste of this back in the mid-2000s, working as a freelance interaction designer. Clients initially hired me to do their UX, but the role expanded once I got in the door. Often, they needed help with visual design, so I picked that up along the way. Sometimes, their knowledge of HTML/CSS was limited, so I wrote their front-end (or even back-end) code. At times, I found myself digging into product strategy, or even brand.

That diversification was fun, and worthwhile too: today, people seem to value me not merely for my UX & Product expertise but also for my multifaceted background. It’s especially valuable in leadership situations, where hands-on knowledge of the constraints affecting multiple team members can help resolve disagreements.

But those disagreements underlie a real challenge. Your designer is supposed to disagree with your developer to hash out trade-offs between usability, aesthetics, and development time. And when you’re the visual designer, and the interaction designer, and the developer…well, you spend a lot of time arguing with yourself. That’s risky: you don’t get to be the wholehearted champion of one perspective, so it’s easy to inadvertently let one side win. Maybe the visual designer wins, because that animation is just so damned cool that you can’t part with it. Maybe the developer wins, preferring a solution that’s less usable but cleaner to implement. It’s hard to play product manager to the voices in your head.

As I moved into management roles, I found they worked similarly. You have project-centric goals, team-centric goals, and employee-centric goals. You want to release the best product possible, to make your team as efficient as possible, and also to coach each of your employees to be their best, happiest professional selves. On a good day, you can further all these goals in concert; but often, you have to prioritize. The very thing that makes management so rewarding also makes it hard: your choices, good or bad, directly affect the lives of people you see every day.

Founding a company has been another level entirely. I’ve lost track of the number of hats I wear. Design, UX, product strategy, business strategy, investor relations, marketing, recruiting, team management, product management, project management, HR, office cleaning crew, webmaster, space planning…and the list goes on. As with freelancing, these roles don’t coexist peacefully in my head. I’m naturally inclined to do the things that are easiest for me — tweak a design detail here, do a wireframe there — and to let other things slide because they’re hard, or I don’t know how to tackle them. But often, the stuff I want to ignore is far, far more important than the stuff I gravitate toward. And since I don’t have a boss to tell me what to do, I can get to the end of an apparently productive day with no idea whether I spent it on the right things, and no one to blame but myself. That level of unknown can be terrifying.

It’s tempting, faced with such a bewildering array of hats, to respond by working harder, putting in more hours. That’s a mistake. To begin with, it’s bad for your health. There’s an common, damaging notion out there that to run a startup properly you should be working 24/7 — it almost certainly contributes to the depression, and periodic suicides, we hear about in founders.

Interestingly, the startup stereotype also includes crazy office parties, jam sessions, and ping-pong, all of which are ways of blowing off steam and setting work aside. Founders in their thirties have built more ties outside the office, so it’s natural that dinner with friends or time with the kids might replace ping-pong tournaments. But any way you slice it, down time and sleep are critical to productivity.

And some of the most critical hats — the ones that deal in long-term business and product strategy, the ones equipped to answer questions like, “Are we still on the right path?” or, “Did I spend my day on the right things?” —don’t fit when we’re tired, or cranking on a tough coding problem. These are the hats we wear when we step away from our desks, when we talk about the business over coffee or a beer, when we step out for a walk.

Sounds easy and delightful, right? Hah. We don’t start companies because we’re looking for a way to kick back and relax. We expect to work hard, and we dive in because we’re driven. Stepping away from your desk is hard when the app is crashing. Coaching a discouraged employee is hard when an icon is stretched all out funny. Getting a good night’s sleep is hard when your to-do list is your teddy bear. Paying attention on a date is hard when you’ve spent the afternoon trying to come up with a tagline and failing. All the trees make it really tough to get a good look at the forest.

As we’ve built Emu over the past year and a half, I’ve tried a number of things, with varying degrees of success. Deep breathing and simple meditation. Therapy. Blocking off “Forest Time” on my calendar, where I go for a bike ride or a walk and think strategic thoughts. Scheduling lunch with former colleagues, coffee with advisors. Making time to read the news, both tech and (perhaps more importantly) non-tech. It’s probably helpful that my commute is tied to a train schedule, since it creates natural barriers between work-time and non-work time when I choose to accept them. I won’t claim I’ve been great with any of these, but I will say they’ve helped, and I continue to improve.

I continue to learn, and to make mistakes, and then to learn some more. And if there’s one thing worth remembering under all these hats, it’s that it’s both expected and OK to make mistakes. If you’re like me, you accepted that a long time ago when it comes to traditional work product (mockups, code, whatever), but it’s harder to remember with respect to people-based work (yourself or your team). Make those mistakes. Learn from them. It’s OK. And don’t forget, from time to time, to take off all the hats.