The entrepreneur’s dilemma

I think about entrepreneurship in broad terms — as more a life idea than a business one. Jim Collins has said that people who lead entrepreneurial lives — in my book I call them “life entrepreneurs” — reject the paint-by-numbers approach, take out their own blank white canvas, and try to paint a masterpiece. He says, “Try to create a life so idiosyncratically you that it fits you like a glove.”

Chris Guillbeau, on his excellent blog The Art of Non-Conventional Living, casts entrepreneurship in a similar light. He defines “non-conformity” as “a lack of orthodoxy in thoughts or beliefs” or “the refusal to accept established customs, attitudes, or ideas.” Tim Ferriss is another champion of rejecting the 9-to-5 grind and finding work that is fun, meaningful and maximizes freedom to travel and accumulate new experiences.

These philosophies have much to recommend it, even beyond the obvious. For example, as I’ve written, one way to reduce jealousness of other people — one way to stave off the kind of envy that can consume high achievers — is to create a life so unique to you that it destroys reasonable comparisons. Conventional life paths are crowded with others, and there will always be someone of equal age or background walking ahead of you. Walk alone on your own path, and direct comparisons become harder. Envy goes down, genuine happiness for others’ achievements goes up, and success and progress becomes more about achieving individually defined goals and less about keeping up with the Joneses.

But for all the rah-rah-rah, there are serious, under-discussed challenges with an idiosyncratic, comparison-destroying life. The first has to do with motivation. If the will to advance your situation comes only from the guy who’s a few inches in front of you, you’re screwed, since there will be fewer obvious peers who can directly push you to be all you can be. (Anyone in law or medical school, by contrast, has a million peers with whom he can relate and feel challenged.) So you gotta be a self-starter or otherwise intrinsically driven.

The second more serious challenge relates to emotional relationships. Walking on your own path means…you are walking alone. It’s hard to become close to people, primarily because shared experiences are the lifeblood of relationships, and if you’re leading a non-conventional, non 9-5 life you’re probably accumulating unique experiences. Fewer people can understand why you do the things you do. You feel misunderstood, which is problematic because as social creatures we seem to spend most of our time trying to be understood — trying to express what’s inside our head. Many late night ice-cream binge sessions start with the feeling that nobody “gets us.” You feel lonely.

In his book Loneliness: Human Nature and the Need for Social Connection, John Cacioppo says, “Loneliness reflects how you feel about your relationships. Depression reflects how you feel, period.” People living entrepreneurial, high-achieving lives struggle to find common ground with others and so struggle with intimate personal relationships and so struggle with loneliness more than most.

I am not a lonely person. But I do have my moments. Everyone does. Regardless of the conventionality of one’s life or strength of relationships, occasional bouts of loneliness might fit under the David Foster Wallace header of “What It’s Like to Be a Fucking Human Being.” Which is to say, it’s universal. Perhaps even timely. Record numbers of Americans say they have no confidante, and record numbers are living alone.

So no shame in talking about it. Here’s how I think about the loneliness challenge at a “strategic” level.

First, in my relationships, I emphasize strong ties over weak ones. There’s not a question in my mind that people with three intimate friends are less lonely than people with eight medium-strength friends. Of course, being young and uncertain, I’m still meeting plenty of new people, planting new seeds, maintaining an infinite-number of (surprisingly rewarding and useful) email-only relationships, and letting some strong-ties fade to make room for new relationships better suited to my evolving self.

Second, I work on becoming a better communicator so I can express myself and what I’m feeling to others, so as to help the process of feeling understood.

Third, just as loneliness and depression differ, so does loneliness and solitude. There is a difference between being alone and feeling alone. I love batches of solitude. I hate loneliness. But I need to remember that much as I love being alone, too much solitude — too much away time from my relationships — can induce loneliness. As A.C. Grayling put it, “Life is all about relationships. By all means sit cross-legged on top of a mountain occasionally. But don’t do it for very long.”

There are also some useful “tactics.” Most basically, I try to stay in touch with people I know. Simple, but without it your relationships will go nowhere. I also talk about the topic with other people to hear how they think about it. Seth Roberts, for example, has a tip he calls “faces in the morning, voices in the afternoon.” When you wake up, try to look at human faces (in-person, on TV, on the computer, or even yourself in the mirror). In the afternoon, listen to the radio or podcasts of humans talking. Listen to voices.

Bottom Line: Unconventional, entrepreneurial lives are not all peaches and cream. Accumulating lots of unique experiences necessarily means you’ll have less overlap with others, making it harder to form intimate bonds, making the challenge of loneliness more acute.