The Peculiar Loneliness of the Entrepreneur

Last updated on: December 6, 2015 at 2:01 pm by Mission:Work

The Peculiar Loneliness of the Entrepreneur 2015-11-24T16:31:42-05:00 Mission:Work

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By Timothy Askew; reprinted from Inc. with the kind permission of Timothy Askew.

Lonely.

God, that word sounds pathetic. It’s not the first thing that comes to mind when pondering the entrepreneur. In fact, I don’t believe I’ve read any articles specifically about loneliness and the entrepreneur, yet I believe it’s a reality that exists ubiquitously. I know it certainly exists for me.

Most folks think of owners and CEOs as hard driving, autonomous, tough and energetic. Kind of mini-masters of the universe. And most of my successful business peers are that, in their very different ways. However, I believe there is a closeted yearning in most of us to connect communally, safely, discretely. Vulnerably.

Friendships, for entrepreneurs, are hard. We’re busy. Most of us have primary commitments to our families and homes in our little free time and we can’t even keep up current friendships. Most of our human contact is within our own firms and it is simply not practicable to have real, open, intimate friendships with employees, even your top executives. Being a boss requires a certain distance.

One of my all-time favorite TV series was HBO’s The Sopranos. Tony Soprano is a kind of an entrepreneur when you think about it. I remember an early episode where Tony is worried about being yessed to death by his gang. He asks his wife Carmela what she thinks. She replies, “[Your subordinates] go around complimenting you on your new shoes, telling you you’re not going bald, not getting fat. Do you think they really care? You’re the boss! They’re scared of you. They have to kiss your ass and laugh at your stupid jokes.” Unfortunately Carmela is utterly right.

Furthermore, you often cannot really talk honestly about your business even to your wife, lover, or significant other. They truly cannot understand the unique frisson of terror that many of us wake to every day as we rise to try to methodically slay our individual business dragons. And even if they could understand, is it really fair to burden them with our existential anxiety? Each of us faces the prospect of possibly failing every day, but most of the time it would cause useless anxiety to share that with our familial intimates.

In his excellent book The Middle Class Millionaire, Lewis Schiff’s research shows that middle-class millionaires (net worth between one and ten million dollars, according to Schiff) choose to let friendship to be crowded out of their lives by their maxed-out work and home commitments. Yet there remains a need for a place of safety to discuss and share specific personal business conundrums, as well as triumphs.

I have personally found some solace from business loneliness for six years through my affiliation with the Inc. Business Owners Council, which is a membership community of Inc. 5000 company owners. I almost didn’t join for reasons of time, but it has been well worth the commitment. For me the reward has been a growing concatenation of peer friendship, humor, and allayed loneliness. I know there are other organizations, like EO and Vistage among others, that attempt to fill this business dearth. I have found a safe business intimacy with my peers healthful and whole-making.

An easeful peer community of shared assumptions and base experience is increasingly rare in our balkanized society. Yet the soulful amelioration of business aloneness is not a need that any owner should repress or shove aside lightly. It shouldn’t be ignored.

To quote Mother Teresa, “The most terrible poverty is loneliness.” Thank you, Mother Teresa.

Tim Askew is the owner of sales firm Corporate Rain International and a member of the Inc. Business Owners Council. He has several advanced degrees, and has been a tennis pro, actor, opera singer, Broadway producer, dishwasher, bartender, minister, and college assistant dean. Askew is the author of the new book The Poetry of Small Business (available on Amazon). @TimothyAskew

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