Training to Take Risks

This past week I read a very nice blog post from the unique Tim Ferriss, about people’s propensity to overestimate risks and underestimate opportunities.  In a nutshell, his thesis was that evolutionarily science has trained us take what’s safe over what’s possible, and this mindset may hamper us now in modern society.  There was also a very nice contest about submitting the best comment re. the article with cool prizes, including mentor time with Reid Hoffman, but I figured I probably wouldn’t win (at last count there was over 600 comments!).

I believe in this philosophy wholeheartedly, though never had nor tried to verbalize it.  I joined the risky United States Army after a rather safe and sanguine University of Chicago college experience.  And now after my MBA, instead of taking up my investment banking offer, I had decided to take up a tremendously risky career of entrepreneurship. I believed, and still believe, that my payoff from these risky moves have and will pay-off.

But how did I ever learn to take risks?  I believe there’s really three seminal experiences in my life; one was when my mother passed away at 16, and I questioned the very safe world I lived in - thus realigning my new reality.  The other was when I joined the Army, where I risked my life consistently (even jumping out of helicopters!); but what I learned as a process was that risks are always around - it’s just how you manage risks that makes the difference between failure and success; this is repeating the learning that risk is something to be managed, not feared.  The third is a continuous commitment to take risks, in order to remember that risks are ever-present, and how to manage them.  Case in point - I did the Rickshaw Rally two years ago, and the Mongol Rally this past year.  Both rallies had me driving ridiculous distances in piss-poor vehicles and conditions, in environments better suited to Mad Max movies!  If you don’t believe me - see here.  In summary - consistent reinforcement that risk is ok.

Summarizing this process, it was Realignment->Repeat->Reinforcement that got me confident in taking risks.  And hopefully it’s a mental model that will serve me well for the long-term!