Being Strategic vs Being Opportunistic

When approaching a problem or a challenge there are two main approaches you can take: being strategic and being opportunistic.

Being strategic means thinking through all sides of the problem. Looking at what people have tried, what’s worked, what hasn’t. Considering the context of the problem and how this context evolves over time. Mapping out a plan, executing on it and taking the time to measure your progress against metrics you’ve established. Strategic is Billy Beane and the Oakland A’s.

Being opportunistic means taking things as they come. Looking at what makes sense right here, right now. Jumping right into the thick of things and figuring it out as you go along. Exploring interesting connections, poking your nose into strange places and smashing stuff together to see what happens, always angling toward a particular, but vaguely defined, direction. Opportunistic is the story of Todd, Ben Folds Five and Improv Everywhere.

Each approach has it’s trade-offs:

  • Thoroughness vs Speed.
  • Protected downside vs Unlimited upside
  • Steady progress vs Rollercoaster ride.

There’s no right or wrong approach. But you ought to recognize that there’s a difference and try to make the decision a deliberate one.

How do YOU approach your problems? Are you strategic or opportunistic? Tell me in the comments!

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Jason Shen

Jason is a tech entrepreneur and talent expert. He is CEO of a performance hiring platform called Headlight, a Fast Company contributor, and an advocate for Asian American men. Follow him on Twitter at @jasonshen and subscribe to his private newsletter.

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