The role luck plays in shaping our careers

Published in the San Diego Union-Tribune, November 13, 2017

As I get older and older, my enthusiasm for trying to do the right thing has increased exponentially. As you know, I consider myself astute at measuring risk, so I am doubling down on the likelihood that there is a God and that if I happen to catch the up escalator, I want to be armed with an improved résumé.

The trick in that sentence is getting people to do “what you so obviously think is the right thing.” Like all of us, I am always puzzled when other folks don’t see it the way I do. Welcome to America.

I just finished reading an article about Robert Redford, 81, and there were two words that he used in talking about his friendship with Paul Newman — incredible generosity and humility. I want to own those two words in my own life. I want to share them and celebrate them and imbue them into the lives of other entrepreneurs — and so far, I have not been as successful as I would have hoped.

One of the areas that appears to increase that disconnect in my compatriots is the inability to acknowledge the power and place that luck plays in your life. Robert H. Frank, author of “Success and Luck: Good Fortune and the Myth of Meritocracy,” argues that people are much less likely to remember external events that may have helped them along the way. He points out that the risk and the unfortunate consequence of seeing ourselves as entirely self-made is that this “perception makes us much less likely to support the public investments that made our own successes possible in the first place.” For further reference on that topic, review the Elizabeth Warren 2012 “you-didn’t-build-that speech.”

But where I am wound up is not about public investments but rather, private investments — investments of time and talent. I want my community to be more generous and more humble. And the community I am calling on is the innovation economy. Why is it so hard to get the big guns to step out of their silos and work on something together? I want to explore how to ignite gratitude in my peers and in the entrepreneurial ecosystem (I wish we could replace that word — maybe with entanglement — which is how it seems at times.)

Recently, I was talking with someone who said, “Our town is not really that generous.” I was puzzled. After all, there are dozens of buildings with philanthropic names on them, and even more organizations that have been extensively supported by our community; I wondered what he meant.

The discussion morphed into the difference between time and money. It seemed to him that asking people for their time was somewhat of a lost cause, but asking for a check was easy, even if the check were smaller than hoped.

Let’s go back to Redford and the word “humility” that he found so powerful and pervasive in Newman. I am deeply aware of the “look-at-me syndrome.” Recently, I again watched the “Seinfeld” episode “The Doorman” (you can find it). The tech-crunch mantra of manure that “you are your own brand” creates a powerful need for recognition that culminates in each of us standing on a street corner twirling an arrow pointing at ourselves. If everyone is the founder or CEO, then who is left to actually do the work?

Surprisingly, when I talk to my young entrepreneur clients, I actually find a deeper sense of humility than I find in my peers. How long do you have to stand on the stage before they give you the hook?

Frank goes on to say that when successful people are “prompted to reflect on how chance events affected their paths to the top” they become much more inclined to pay forward to the next generation. He says, don’t tell me how lucky I have been, ask me to remember how lucky I have been. That resonates. It is always how you frame the question.

We all know the impostor syndrome (high-achieving individuals who have a persistent fear of being exposed as a fraud). My personal sense of late in my little world is that it may not be a syndrome at all — maybe it is just the truth.

Rule No. 537:  Mirror, mirror on the wall.

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