How to Turn a Small Opportunity Into a Big One: The Parlay

 

My career so far has all been a gamble.

More accurately, it’s been a parlay — taking the winnings from one bet and wagering them on another bet, and so on, until your small initial stake compounds into something much greater.

The scary thing about a parlay is that you can’t see a clear path from start to finish. It’s a series of opportunistic, escalating bets over time.

When I left a safe, corporate job to join a startup, I was often asked two questions:

  1. What will you do if it doesn’t work out?
  2. What will you do if it does work out? What’s your career plan after that?

My answer to both questions was the same: I don’t know.

What I was betting on was that if it turned out well, I’d have a set of skills and experiences, combined with the money and personal network I’d need to do something. And being in an entrepreneurial environment, meeting interesting people doing interesting things, an opportunity was bound to come along sooner or later, and I’d be in a position to capitalise on it. The perfect parlay.


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