Crossroads in Life

There’s an interesting NY Times article this morning on an entrepreneur and his mid-life crisis. He sounds like a quirky and interesting person, and he is trying to simplify his life.

His $100MM net worth obviously enables him to have options regarding what kind of crisis he can have. Call it “crisis optionality,” I suppose. He can choose his crisis, whereby most people cannot.

I think the word “crisis” isn’t the right one to use for most mid-life folks I know. Certainly, some people go through a dramatic turn of events, such as leaving a marriage, engaging in super-risky behavior in their personal life (yes, let your imagination run wild), and becoming a very different person, at least for a while.

But, IMO, a better word is this one: crossroads.

Life is full of crossroads. After high school, you can choose to go to college or not. After college, you can choose to get work in academia, the public sector, or the private sector. When you date, you can choose to pursue some relationships or end them.

As an adult, you continue to face crossroads. Do you marry, and, if so, whom? Do you go to graduate school, or do you keep plugging away at a job? Do you move to a new city?

For me, in my mid-30s, my crossroads was this: do I keep working for someone the rest of my life? My decision was “no”; hence, Kepha Partners was born. I wanted to do something new, to break free and forge my own path, to create a culture and a firm that would embody my personal values.

I am so glad it all worked out.

During my recent college and b-school reunions, I think there was a new vibe for those of us in our late-40s and early-50s: acceptance. People seemed much less anxious and more accepting of life. There was no talk about work, for example.

To me, there also didn’t seem to be any social ranking process. You may recognize this when you go to a cocktail party and meet strangers who ask: What do you do? Where do you live? Where’d you go to school? I think that’s a clear attempt to hear more about you, but they’re pretty pointed questions to try to figure out where you fit in the social hierarchy.

These days, when I’m asked these questions I answer them in a few ways:

“I just got out of prison. I’m looking forward to a fresh start.”

“I just retired as a fashion model. I quit because I didn’t get any gigs. I learned they only wanted good-looking guys.”

“I’m in-between jobs right now. But, my probation officer thinks I’m doing much better.”

These days, I’m pretty choosy about which social events I attend on the weekends. I used to accept nearly all social invitations: this dinner party, that charity event, that group play-date for kids. I used to feel obligated to go to all the events and host many dinner parties.

Now, I don’t.

My crossroads question in my mid-40s is now this: does that event energize me or take away energy? Being a good spouse, father, and VC takes a great deal of effort. I now care very little about the social hierarchy.

Like the entrepreneur mentioned above, I too am trying to simplify my life.

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4 thoughts on “Crossroads in Life

  1. The reverse of your crossroads to leave working for an employer and be your own employer, I am actively interviewing to leave self-employment and find the right fit at the right organization. It’s surreal how each of us searches for simplicity in our own ways.

  2. That’s quite interesting as what you are experiencing sounds like you are going through a life evolution, similar to Maslow’s hierarchy of needs .

    For those who have been successful in their career life, the question begins to loom what next? and Maslow purports that leading a life of significance is what people look for next.

    Significance can be found in many things, but most popular is charity and recognition in one shape or form. Giving back to the community either individually or as part of a group.

    Which is why many people in their later years join foundations, or Rotary Clubs (guilty) as a way to express this. My cousin once told me that the need to be charitable creeps up on a person in their mid to late 40s.

    What is your experience ?

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