04/23/2015 07:59 am ET Updated Dec 06, 2017

Is 'Respectability' Overrated?

A while ago, I wrote that while most of my business school colleagues spent years amassing their millions, I was out becoming an expert of dating.

This, of course, was an exaggeration -- on both counts. Some of my friends didn't make millions (though plenty did), and I was doing much more than dating, and in fact had many jobs working with many accomplished people in arenas my classmates would consider respectable.
(I suspect that if any of my classmates read my dating columns, they would shake their heads at the very idea that I would write about something so lowbrow instead of emerging markets or trends in high tech.)

Then, recently I guy I know was named president of a prestigious local non-profit arts organization. He's a nice fellow, well-educated, with modest professional accomplishments. In fact, except that he is younger than I, we come from very similar places.

All of this got me to thinking about respectability, specifically, about living or not living a life of conventional respectability, particularly when everyone thinks you should.


The key word, I suppose, is conventional. Respectability takes many forms. When you grow up a certain way, it's expected that you'll travel a certain path: serve on boards, go to cocktail parties, attend important conferences, maybe even give a TED talk if you really have made it (after all, what could possibly be more important?). I grew up on that path, but deviated from it, first because of circumstances, then by choice and temperament.

I served briefly on a couple of minor boards, but would find myself looking outside during endless meetings and wishing I was out there and not stuck in a room posing as respectable while listening to debates about "best practices." Truth be told, I probably should not have gone to business school -- I'm guessing the school would concur -- especially one where the expectation was that you would achieve great things in, well, business. I always felt like an outsider there.


So after the pricey schools and the good (or good-sounding jobs), I found myself longing for something different. And something different found me. Divorce led to raising my kids alone which made reevaluating and reinventing myself a necessity rather than a luxury. That path I had been on was no longer within my reach, and honestly, no longer attractive.

During what should have been prime earning years (whatever that means) I was scrambling to provide for my kids as best I could. Respectability now was measured by doing whatever was necessary to keep the family whole and as happy as possible.

I tell my kids the story of applying for a job driving the cart that picked up golf balls at a local driving range. Our long custody battle had just ended, and my bills had grown from hilly to mountainous. When I interviewed for the job, the guy looked at my resume, then at me, and muttered something not quite flattering.

Apparently I was overqualified. But if I had been offered the job, I would have jumped at it. In 10 years, I had gone from country clubs and premieres and the brink of unlimited possibilities to hoping someone would hire me to pick up golf balls. My intellect was still the same. My energy level was if anything, higher than before. I hadn't fallen into substance abuse (had never been that type anyway, but now I couldn't afford it even if I wanted to!) Once I emerged from that particularly bleak period, I found out something revolutionary. Not only was I good at being resourceful and following a different path. I enjoyed it.

Wearing suits to work, wishing I could be invited to world economic forums, joining a country club (again, like substance abuse, beyond my financial grasp) held no appeal.
Respectability meant something very different at 50 than it had at 30 or 40.


I remember dating a woman for several months who had a place in the Hamptons where we would go every weekend to party with the same people over and over. And over. I would endure this, then slip away from the party and walk along the beach. She thought I was being anti-social. Quite the contrary. I love being with interesting people. It's just that these people were having the same conversation every weekend, which always revolved around who they knew.
A few years ago, I worked for a guy who obsessed about respectability. He boasted about being able to skip the plebeian security lines at airports and being told by friends that he should run for office. That was all fine. It apparently worked for him.

Living a respectable life and living an interesting life are by no means mutually exclusive. I did both for a long time.

I don't miss traditional respectability. I would miss interesting.

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