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Archive for the “Loneliness” Category


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 ever read an article about loneliness and the entrepreneur. Yet I know it’s a reality that exists. 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 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.

I remember sixteen years ago when I started my executive sales outsourcing firm, Corporate Rain International, a man named Fred Klein, a very successful lawyer, serial investor, and entrepreneur, invited me to join his group Gotham City Networking. I attended for about a year. Fred was quite kind in introducing me to his colleagues and friends. Though I got too busy to attend, I was deeply grateful from the time I was a member. (It also helped me feel less like a fraud as a parvenu businessman.) Fred was a generous nurturer and his group reflected this.

I started thinking about this again last fall when I reluctantly joined Lewis Schiff’s Inc. Small Business Council. While Lewis’ seminars sounded very useful (and were) I was quite reluctant to join. Mostly for time reasons. But I did. The reward I gleaned from this has been very different from what I expected. That reward has been a growing concatenation of real friendships and allayed loneliness. An easing of a hunger I was not even aware of.

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. It is simply not practicable to have real open friendships with your employees, even your top executives. Being a boss requires a certain distance.

One of my all-time favorite TV series is 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 complementing 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.

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 an owner should repress or shove aside lightly.

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

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