Why I'm Either Working or Feeling Guilty

I have two modes — working all the time and feeling guilty about not working all the time. There's no third mode.

I'd love to say this is a new phenomenon or that I've got some monopoly on this curse, but having spoken to countless Founders just like me, it appears I'm certainly not alone.

Now, part of that might just be self-selection. Perhaps the people who tend to work tirelessly often want to do it for themselves, or at the very least, have more motivation than the people they left back in their cubicle farm. I can't think of anyone who works harder than a Founder without anyone telling them to do it!

How Did This All Start?

Everyone's origin story comes from somewhere else, so I can't pretend to triangulate the genesis of this affliction from one single source. Mine happened to that be I grew up a ridiculously poor kid whose parents abandoned him and had to do whatever he could to escape that. Hopefully, yours was much less painful, but it probably wasn't.

So as a kid, I would quickly tie working hard and hustling to "safety and survival". I didn't have lunch money, so I would have to go run a little candy sales ring in 7th grade to come up with the funds. I didn't have a way to pay for college, so I would have to work two 40-hour jobs per week and go to school full-time on the weekend.

Everything was always solved with a single option — work more. But that work gave me the fundamental safety I needed to survive. If I'm being honest, it was awesome! I never minded working harder, and to me there's nothing more genuine than earning your keep. It's definitely what made being a Founder so appealing to me.

It Went Great... for a While

When I was 19, I started my first company, and all of a sudden, my work-all-the-time mantra was given a proper outlet. As Founders, working all the time is kind of the job, but for a guy like me who loved working, it was heaven. The years from 19 to 25 were mostly a blur. I don't remember anything about being in college, only that I worked the whole time. Most people have college memories of their first keg parties. My memories were the first enterprise deal I closed.

My work ethic and ambition were rewarded handsomely. The company grew by leaps and bounds, and the more I worked, the more I achieved. It was glorious, and for the first time in my life, I was being rewarded not just with enough to pay for food but enough to build a savings account. From that point on, I could easily attach "more safety" to "more work."

When you're rewarded for behavior, you're naturally encouraged to do more of it. The problem with a reward cycle is that there is rarely ever any indication that the cycle has been broken.

And Then it Became a Curse

So what happens when all the work gets you the things you want? You stop, right? Do you sit back and enjoy it? Nope. Not even close. You get to a point where you are so hard-wired over such a long period of time to associate "work" with "safety" that the idea of not working feels terrifying.

I get up at 4 a.m. (I don't recommend it) and start working. I will keep working, sitting at my computer non-stop, sometimes without breaks, until my wife literally pulls me out of my office. When I take breaks — I feel guilty. When I take a vacation — I feel guilty. The only time I'm not guilty is when I'm working, which obviously sounds awful because it is.

I share this little cautionary tale not as a personal cry for help (I'm good, mostly) but as a reflection for my fellow Founders. Whether you're just starting your career and you haven't yet realized what this extreme mindset can become, or you're well into this affliction and you're reading this saying, "Wow, this is a problem."

The work is important, but it's also a means to an end, not an end itself. Unless we find a way to enjoy the fruits of our labor, then, well, it's just labor. And that doesn't sound like any kind of fun at all.

In Case You Missed It

Why No One Tells Founders "It's over, move on." (podcast) No one ever actually tells Founders it’s okay to quit. No one except other Founders, of course.

How Do I Design My Startup Around My Life? There’s very little preventing us from designing our startups around our life goals. It starts with us being very clear about what we want to achieve and then taking clear, small steps toward those outcomes.

The Curse of the 37-Year-Old Founder Let's talk about the dues Founders pay for neglecting their health. Pushing yourself too much, putting your body through so much pressure, and then ignoring the warning signs as they come, you’re unconsciously trading your life for the success of your company.