City Club is no longer the best kept secret in town. When potential new members ask me to describe City Club, and the profile of the ideal member, I tell them “City Club is a Securus Locus where black sheep can feel comfortable being who they are.” Black, white, rich, poor, old, young, gay, straight, Republicans and Democrats alike feel safe here.

Imagine this scenario: There you are, dressed to the T, as you and your spouse attend an elegant social gathering, spending most of the night talking with two very different invited guests.

The first is an almost too good looking guest who proceeds to tell you how great life is, that he graduated Harvard law, made a small fortune at Goldman Sachs, and then, having started a tech company in his four-car garage, exited that venture with a nine-figure package, all on his way to an anticipated net worth of a billion dollars by age 50. He, with his wife, have a real estate portfolio including six houses, from Main to Hawaii, each worth over $10M. He adds that they vacation at Martha’s Vineyard every summer with their golden retriever and their 2.2 kids.

Then you run into a distant acquaintance and ask him “how are you doing?” After a few moments of silence and slight hesitation, he responds, “To be honest, not so well. My wife recently moved out and filed for divorce, so I am in the middle of trying to figure out how to balance work and child care, all the while dealing with an overwhelming sense of loneliness. This whole thing came totally out of the blue and is affecting both my health and work performance. Looking back, I see myself as having been the cause of this situation, but now I feel totally stuck with no idea how to recover. In short, life right now really sucks!” 

On the drive home, your partner asks, “Who were those guys you were talking to all evening?” How might you respond to her question? Are you going to tell her about the hotshot who made you feel small and inadequate, making you hear echoes of your parents’ voice whispering how you are falling short? Or, are you going to tell her about the other guy’s deeply affecting story, share the reasons for his misfortune, along with what you learned from his experience?

Many City Club members are black sheep who have experienced misfortunes and failures. Taking the road less traveled, our members push the envelope again and again, sometimes failing, learning from their mistakes, to then get up, dust themselves off, try other things, perhaps make new mistakes from which they learn yet another lesson. 

So, the next time a member asks who you are and why you joined the club, be open to sharing something about your life challenges, even failures, and what you might have learned from them.

— Sina.