My Unhealthy Relationship With Work

I have a confession — I am in a very unhealthy relationship... with my work.

Here's the thing — I absolutely love my job. I get to sit around and bullshit with Founders all day. This is my dream job, by design. We're normally conditioned to believe that our jobs are some sort of liability that we should try to escape from whenever possible. We want to retire so we don't have to work anymore. I think of not doing my job as Michael Jordan would have thought about no longer playing basketball — it's not how I'm built.

But over time this obsession has created some brutally bad habits that have become a massive liability later in life. Fortunately, I know there are many other Founders dealing with the same issues (because I talk to them all the time!) so I figured it'd help to have a bit of an open dialogue about how I got so upside down.

More Work or More Guilt

I learned long ago that what's driving my obsession isn't the actual work — it's guilt. When I was just starting my career, all of my focus was on "not being poor anymore." It lurked like a constant menacing shadow behind me that I had to keep sprinting to get away from. So long as I was working all the time, that shadow would never catch me.

Then at some point early in my career, I had some success, no doubt from working every waking hour. But what surprised me was this — the shadow never disappeared — it kept growing in fact. My early success turned into a high water mark that became very hard to maintain. So I worked even harder, trying to sustain that pace, those outcomes, and essentially the fear of losing them.

I quickly developed a painful habit that meant I was either working all the time or feeling guilty that I wasn't working. I could take as much time off as I needed to. I could just get up and go hang out with friends in the middle of the day if I wanted to. But I didn't. I subconsciously assigned all of those things that normal people do in their day as me falling off the wagon. So there I stood, free of guilt, but shackled to my work.

We Set the Pace — or Else

I was also completely convinced that if I didn't set the pace at whatever company I was working at, then everyone else would slow down too. For a long time, this was due to the fact that we were all so visible in our offices. I would show up at 6 a.m. to the office — always the first car — and then leave well into the night - always the last car. For about 20 years it didn't occur to me that people drove to and from work in daylight.

But then some life happened. I had kids and a family and I couldn't stay at work all night anymore. We started working remotely and I simply wasn't in the office anymore. I was stripped of my ability to be "super office guy" by being an "hours hero" like I had been trained so diligently to be.

So did the whole company implode into an apocalyptic anarchy? Nope. Nothing changed. My ability to "set the pace" in a very physical manner was lost to me. No one cared. Now we're 200 people that are all remote. No one has any idea if I'm working all day or bingeing on Netflix. And yet miraculously, everyone gets their job done. This would have been really useful information 30 years ago by the way.

I Need to Breakup With Work

After 3 hard-fought decades of building startups as my life's work — I need a breakup. That doesn't mean I need to quit my job — quite the opposite. I need to be able to do that job that I love without the soul-crushing guilt and broken routines that I worked so hard to create. Much like our primate bodies, these are instincts and muscles that served me well when I needed them to survive but are now simply drowning me like an albatross.

I write this to say I'm guessing I'm not the only one. I've met countless Founders who have a very similar relationship with their work — and it's not OK. While it's fun to tell stories of how hard I worked to get where I am, the epilogue to this story, where I couldn't slow myself down, is a much harder tale to tell. Bad habits can lead to great outcomes, but there's a reason they are bad habits.

If you're a Founder early in your career and some of this is starting to sound really familiar, my only hope is that you read this and something here starts to drive you in a different direction. I hope it justifies some of the time you spend with your loved ones, or even just enjoying life a bit more. If you're further in your career and this just sounds entirely like your life, I'm here to tell you it doesn't have to be. I'm writing this as I'm about to take a month off to relax and reset. It's possible, if only we allow it to be.

In Case You Missed It

Fat, Sick, and Nearly Startup (podcast). Join Wil and Ryan as they break down the ways Founders can learn to deal with personal hardships that are often a result of our own Startups — while we're still running them.

Optimizing for Happiness. We do something in our planning at Startups.com that is relatively unheard of in the startup business: we optimize for happiness. Here’s how we do it.

How I Harness My Insane Startup Anxiety. There are two types of Founders: those that admit they are wracked with anxiety, and those that are lying about it. We’re all going to deal with it for the rest of our lives — so why not use it as a superpower, instead of reacting like it’s kryptonite?