What Drives Entrepreneurs to Overwork?

A huge reason we entrepreneurs drive ourselves to overwork is because we get lost in abstract ideas. If we keep it concrete, however, we have a much easier time - and almost certainly accomplish more of what matters with less effort.

Let me explain.

If we learn anything from the existentialists it’s that our existence is characterized by three concrete facts: we’re embodied, in a shared world with others, moving ever closer toward death.

Is there anything more fundamental?

Taking these as our starting point, we’re much better positioned to live, work, and love in a way that’s aligned with our essential nature. We’re able to organize a life that viscerally feels good, that expresses who we are, and that is linked to a greater sense of meaning.

Doing so brings us closer to the life that only we can live, one that’s true to who we are.

As a result we increase the odds that our everyday activities result in more pleasure, purpose, and profit. After all, aren’t you more inclined to give your best to games that you actually want to win?

Each of these three existentials deserves many, many posts, but for now I’ll focus on the “deathbed filter.” I find that a lot of the difficulty that brings entrepreneurs to work with me finds its roots in the fact that their activity is at odds with what they actually want.

Let’s say that one of your top values is spending time with your kids while they’re young, being the kind of dad that you wish you’d had growing up. If it turns out that your work habits prevent you from spending time with the kids (and leave you exhausted when you actually do spend time with them), then your activity is counter to your stated aims.

At this point you have a choice.

You can either adjust your behavior so that it’s more in alignment with what you value, or you can be honest with yourself that — for now, at least — it actually is more important for you to work than to spend time with your kids.

Either way is fine so long as it’s what you genuinely want to be doing.

A lot of us end up in repeat cycles of overworking, exhausting ourselves, pushing hard to catch up because we’re not all that clear on our personal priorities. We end up taking on a lot of projects that seem valuable (and may in fact be) but put us in conflict with where we want to end up long term.

One client, for instance, had the opportunity to emcee one of the world’s largest educational events which brought a lot of prestige. However, it was also an insane workload and resulted in two years’ worth of burnout and lost time with his family. It wrecked his health, nearly cost him his marriage, and took a huge toll on his business because he was too exhausted to think straight.

In hindsight, it just wasn’t worth it for him. Everything that genuinely mattered to him was threatened as a result of his involvement with this event.

This is what makes the deathbed filter so useful. It puts our decisions in perspective of the concrete stakes against which we’ll someday measure them. It takes us out of the (all-too-often) reactive thinking of the present and connects us to awareness of the long term consequences of our actions.

We can look ahead with honesty to the fact that we will someday die. And we can ask ourselves two questions in relation to that fact:

- What do I want out of life?

- What does life want out of me?

It’s at the intersection of these two that our lives become most pleasurable and purposeful. The thing is, there’s no “right” answer to these questions in the abstract. There’s only what is concrete and real within your experience.

Only you know what you want out of life, and only you can have an intuition of what life wants out of you. And once you have answers to these questions (however tentative they may be at the outset), you have clear filters for how you organize your existence.

It becomes so much easier to avoid overwork when you remind yourself what — at the end of it all — you’re really working for in the first place.

If what you really want is to spend time on the land with your horses but your work glues you to the computer on Zoom calls all day, then it’s no wonder work feels depleting. Likewise, if what you want most is to become a mother and start a family, but the high stress of your work is impinging on your efforts to conceive, then your experience of exhaustion is telling you something important.

Your deathbed filter sets the priorities for your life.

The only job then is to remain true to yourself in the face of social pressures. That, of course, can be a challenge, but whose life are you here to live?

For whatever it's worth, I'm rooting for the life that only you can live.