How Tolstoy Prepared Me For Running a Startup
By: Burgess Powell
Tags: Literature, Entrepreneurship, Business, Startup, Russia

Count Lev Nikolayevich Tolstoy, 1897.

There are lots of things that everyone, informed and otherwise, is anxious to tell you about running your startup. Many, especially those furthest removed from the entrepreneurial lifestyle, are in awe. Their feelings are largely based on mainstream success stories. Those who know a little something about running a business may share a disquieting statistic. Did you know that your odds of “success” are lower than if you play Roulette?

But the world of startups is an internal one. I often joke that the biggest challenges I face — and revelations that I discover — occur in the confines of my skull. One of the lessons I’ve learned in the past ten months is that, like any extreme state — playing a sport professionally, becoming wealthy or famous — the focal point and, to a concerning degree, your company’s success, revolves around individual strength. In other words, your internal life takes center stage professionally as well as personally.

As a recovering English major, the world as I see it is framed by literary references. In Russian literature, the classic juxtaposition critics make is between Fyodor Dostoevsky, the father of extreme psychological states, and Lev Tolstoy, the master of intricate life portraits.

For one reason or another, I thought that pushing someone to “the brink,” as Dostoevsky does with heightened despair and intellectual/spiritual epiphanies, was more interesting both on the page and in real life. Thrill-seeking is part of the reason why many people start their own company, which promises “high highs” and “low lows.” We all hope that it will ultimately end in the high high of an exit. This Dostoevskian path is often depicted in the form of the graph of a startup founder’s emotions (see the trough of sorrow). For people like me, it combines a naive belief in our ability to succeed and a masochistic desire to indulge in deep despair.

But this Dostoevskian narrative is fiction, as Dostoevsky always intended. We love to indulge in extremes via literature (Catcher in the Rye, Crime and Punishment, The Hunger Games…) and media (Project Runway, Survivor, Lost, The Handmaid’s Tale, celebrity breakdowns, overnight stardom…) because extremes promise to show us who we really are. For a startup founder, the desire for this feeling is so strong that you go off and run a small, struggling company.

But the startup journey reminds me more of Tolstoy’s work. It is long — much longer and slower than you could ever have anticipated. For months or years, you may feel like a nobleman (Konstantin Levin) plowing his fields, forcing himself to do something mundane and taxing that he doesn’t actually have to do (Did someone force you to run your own company?). Or rather, you feel like someone reading that long, boring passage about him plowing the fields because, unlike Levin or Tolstoy, you haven’t reached the spiritual enlightenment required to enjoy very boring things.

All this to say, mundane challenges represent the real obstacle of startup life. Waking up and deciding how to work on your startup, how to create a schedule for yourself and hold yourself accountable for it, how to prioritize tasks like DMing influencers and fixing backlinks and watching your money trickle into Facebook AB testing. All this, with the occasional Dostoevskian pitch competition, makes me feel like a Tolstoy character.

Just as the daily grind is your real challenge, so should you learn to love it. Tolstoy remains popular because he painted us as we are. He understood that the mundane obstacles we face are the real ones, and most of these are internal. He made everyday experiences beautiful.

We, the thrill-seeking startup people, don’t all make it, like some of Tolstoy’s characters. But those who do have learned to content themselves with the slog and appreciate the beauty in small victories. Konstantin Levin, a literary representation of Tolstoy himself, reaches epiphany during his child’s birth. The number of fathers who precede and follow him does not diminish this moment’s significance. Levin’s epiphany soon fades, as will any fleeting contentment or success in running your business.

One of my favorite quotes from Anna Karenina occurs at the beginning of the novel when Anna is on the train right after having met Vronsky. Tolstoy writes, “Anna Arkadyevna read and understood, but it was distasteful to her to read, that is, to follow the reflection of other people’s lives. She had too great a desire to live herself.” As an entrepreneur, you must enjoy reading as much as living, or risk feeling like Anna.