I’m often asked why I decided to leave my old life to pursue my current adventures. The answer to that question is obviously complicated. But a few ideas and principles played a significant role in helping me break through the inertia that chained me to my career.

High on that list is the idea that I needed to expose myself to opportunities for real success.

Although I’m pretty sure it didn’t start this way (I’ll skip why to keep this post short), life for me as a career lawyer evolved into a way of avoiding failure. It provided certainty about the lower bound of my life by limiting the risk of significant downside. Through consistent paychecks, a high standard of living, and relative job security, I had assurance that my worst case scenario was still pretty enviable.

As I came realize, that life also removed any possibility of real success (of the kind I’ve previously discussed here). Looking at the best possible outcome, I would have spent the next thirty years confined to an office 250 days a years, focusing in great depth on a very narrow field, while experiencing significant stress and hoping against hope that I would be healthy enough when I reached retirement to then do the things that I really wanted to do.

In short, I was buying security. To pay for it, I wasted my time and energy on things not truly my own that could not get me where I wanted to go. It was years before I could admit how bad that bargain was.

This where I can hear certain people saying that I could have made the work my own. I know that know now, I knew it then, and I struggled with that decision for years. I chewed on that fork in the road – with one path leading toward a “normal” life in a safe and secure profession, and the other leading … somewhere else – until my teeth wore out.

But, not to get all Robert Frost-y, I knew deep down that I could not take that first path. It led with certainty to stress, depression, an over-muscled sports car, and alimony payments. You know, a normal life.

Clearly, this discussion is personal. Some people out there are excellent lawyers and professionals, enjoy the life the that such an occupation provides, and can find true success in that way. I know many of them and truly respect their skills and abilities (which far exceed mine).

I am not one of these people. For me, each successive year spent in a “career” marked a personal failure because I was not challenging myself in the ways that I longed to be challenged. I wasn’t growing enough and I needed to grow more to become the person I wanted to be.

It is only by exposing myself to the uncertainty of the unknown that I could possibly hope to achieve what I wanted to. If doing so means bearing the risk of failure, then so be it. I can always go back to being a lawyer.


For a more eloquent discussion of some of the ideas in this post, I highly recommend Naseem Nicolas Taleb’s The Black Swan. Don’t worry, it’s not that “The Black Swan.”

"Why would you do that? That's crazy!"
How I Discovered That Success Doesn't Mean What It Used To