If you don’t know where you are going, any road will get you there

People are lousy at risk assessment.

There are whole industries based on this. (Gambling, sure. But also insurance, time shares, several categories of banks…)

And in a moment of self pity, I realized that taking too few risks has probably held me back in my career.

Let’s review:

  • In 1997, I worked for a small subsidiary of a large company.
  • I had turned down opportunities to jump to several (then-)startups, committing to go to b-school.
  • Most of my co-workers at this small subsidiary left to start their own companies, or to join startups.
  • After b-school, I tried my hand at entrepreneurship. I didn’t succeed.
  • I rejoined a large company, and have managed my career conservatively. Once my son was born, I prioritized secure income over risk.
  • Those co-workers that went to startups? Not all succeeded on the first go-round. But all succeeded, eventually.
  • I’m the exception to that group, in that I’m not an executive or retired.
  • On the other hand, I’m one of the few that has a pension lined up.

But lately, I’ve been thinking—it’s easy to choose a risk profile at one end of the chart, as I did. But most folks don’t realize where they actually are, trading of risk/reward.

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