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A few years ago in this very publication I read a piece by Amity Shlaes (who was writing about the dour nature of her family) called Family Affair that stopped me in my tracks. She said:

[My father] gave the best career advice I’ve ever heard: There will come a moment when you are bored with an area of study and will want to try something new. But that boredom is the signal you’ve achieved mastery. You’ll be quitting at the moment when it’s most costly to do so. Only a mastered trade can be properly monetized.

This insight, so deceptively simple and elegant, helped me to find a voice for a nagging feeling that I had long felt. I’m not happy unless I’m experiencing new things, learning new skills and living on the outer fringes of my competency. Amity’s quote helped me to see that the moment I master something, I get bored with it, and with boredom comes the itch to try something new.

I don’t know if it’s the endorphin rush of not really being sure of what one is doing, or the testosterone high of mowing down obstacles in one’s path, but my focus intensifies when this level of danger is present. I’ve come to believe that this trait is characteristic of many entrepreneurs since now that I’ve identified it, I’m seeing this quality present in many places. Is it conceivable that to experience flow, you have to be hanging out over the edge?

The best way to motivate me is to tell me that something can’t be done. Early in my career I was part of a team at IBM that created a groundbreaking cooperation agreement with a Big Eight accounting firm (Arthur Andersen & Co.). We had a framed letter from an IBM director who said something to the effect of, “Don’t waste your time. It can’t be done.” That became our rallying cry.

I’ll never forget my first meeting with the scientists at Argonne National Laboratory who invented a new method for turning greenhouse gases into diamond. Prior to that meeting, I knew nothing about diamond except for what I recalled (which wasn’t much) from a materials science class I took in college some 15 years earlier. Despite this apparent drawback, I became the founding CEO of the company we formed and my lack of background and industry experience in diamond never was a limitation. I had co-founders who were technical experts, and I relished climbing the learning curve to become competent in the domain.

Once I master something, it ceases to interest me unless there’s a way to leverage that knowledge in pursuit of the next dragon. That may explain why I’m on my fifth career and may be one of the reasons why leading a startup is so intoxicating. There’s always another mountain just ahead. No matter what is in your rear view mirror, the next day brings new challenges. When I left the synthetic diamond company the relevance of my hard-won industry expertise slowly declined. What I took away (to leverage again) was an understanding of how to build and lead a company.

In a startup there’s never a moment of comfort. A former business partner of mine called this “perpetually skiing beyond the tips of your skis”. Or driving beyond your headlights. Steven Wright described this perpetual feeling of instability, “You know when you’re sitting on a chair and you lean back so you’re just on two legs then you lean too far and you almost fall over but at the last second you catch yourself? I feel like that all the time.” Saul Kaplan, in his post Innovation Lessons From Tarzan, uses the metaphor of Tarzan swinging from vine to vine to explain the same phenomenon.

Absent the endorphin cocktail that comes from living on the edge, what’s a guy to do? How do you glide into a career where you can take advantage of your experience yet still feel challenged—and not be susceptible to entry-level wages? How do you find meaning and motivation in doing something that you’ve already done? Part of the answer is to do something that’s hard.

Had I been of age in 1962 when John F. Kennedy threw down this challenge to the nation, I probably would have dropped everything I was doing:

We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard….

I think this is a characteristic trait of entrepreneurs and I didn’t understand it until I benefited from Amity’s father’s wisdom.

I’m left with a question: How do you stay challenged and motivated in a field that you’ve mastered? -Neil Kane

~Preston Byrd