“Am I Wasting My Life?” Entrepreneurs Ask This Question too!

Could I be wasting my life?

With the rate I’m going, I’ll end up spending most of my life starting and running businesses. Should I be doing some other kind of work?

I spent the past year or so thinking about this. My entrepreneur friends warned me that all this ruminating is dangerous. They appear to be right. I had a little crisis of meaning for several months, affecting my productivity and the quality of my work.

Thankfully, I have emerged from that dark night of the soul, and I’m back to that beautiful state of momentum, with fast-moving days, hitting goals and powering through problems like Godzilla in some unfortunate coastal city.

Here is the lesson I brought back from that journey: Your measure of excellence as an entrepreneur is the amount of value you create for your customers and the personal and financial growth you create for your team.

Why is creating value and growth for people meaningful? Like a blind man about to fall over, I grasped at whatever was within my reach, and turned to the worldviews that I grew up with. I discuss three of these below. Then I share some ways to survive a crisis of meaning.

1. Aristotle

The number one thing I learned from Aristotle is that the key to happiness is growth in virtue. And virtues are simply good habits. One gains these habits the way athletes hone their skills: through relentless practice.

For me, entrepreneurship has been like an Olympic training camp for virtues. Sales, for example, has been the hardest thing I had to learn in business. It has also been my greatest teacher. Nothing has taught me humility, empathy and emotional self-mastery quite like sales.

2. Humanism

My humanist teachers taught me that anything that contributes to the progress of humanity is meaningful.

I’m just some guy in some emerging third world city. Yet I have more access to knowledge than King Solomon, I have travelled farther than Genghis Khan, and I can live a life healthier than the most pampered aristocrat of renaissance Europe.

I am privileged but not extraordinary. The world has countless of problems, but we live in a time of unprecedented access to information and opportunity for the most number of people. This is a heritage from the work of countless men and women in the past, including many who worked within the context of business.

My gratitude to our predecessors, most of whom have been forgotten by history, also gives me hope that my unsexy business also lays a brick or two in the building of civilization.

3. An Epic Life

The great works of literature allow us to walk in the shoes of medieval heroes, space criminals, and young Victorian women deftly executing matrimonial strategies. If reading such works brings enlightenment, how much more if you are to live one?

Since I started this entrepreneurial journey, my days have been filled with impossible quests, the camaraderie of warriors, failures that bring me to my knees, and hard-won victories. Entrepreneurship lets me live what artists try to express and what the human race seeks in art.

Surviving a Crisis of Meaning

Let me share how I continued to be productive despite a slump in motivation. It might be useful to you or someone you know.

First of all, make sure the crisis is not because of physical or mental tiredness from the long grind of entrepreneurship. Here’s my personal checklist to prevent burnouts:

I was living these things yet I still fell into that crisis of meaning. I had responsibilities to my customers and my teammates, so I could not simply drop everything, travel the world and go on a quest for meaning. I needed crutches to keep me productive while I nursed that injury in my motivation. These two were effective:

1. Weekly meeting with a peer group. The shorthand for this is “Mastermind.” We follow a set agenda designed produce the following:

2. Timeboxing. An Italian programmer branded and popularized this as the Pomodoro Technique. It consists of 25 minute work sprints with 5 minute breaks, or a similar variant. The ability to count and track the number of Pomodoros I do every day activates the competition maniac in me. I use Trello + Pomello.

I’m even better off now than before the slump. I’m back to 100%, plus I increased my capacity by continuing with the Mastermind and the Pomodoro technique.

This is just based on my own one-time experience of recovery, so I’d love to hear your own experience. I imagine different techniques work for different personality types. I’d also love to hear your perspective on the meaning of work.

I look forward to having a conversation here in Founder’s Guide. In the meantime, I better get back to work. This meaning thing only works if I’m actually creating value.

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