Recently, I was struck by how two esteem leaders in technology have both remarked on how you cannot connect the dots looking forward but only backwards. 

Sheryl Sandberg, the COO of Facebook, was recently profiled in The New Yorker:

Asked what she can imagine doing next, she responds, “I’m actually quite happy with Mark and the company. I always tell people if you try to connect the dots of your career, if you mess it up you’re going to wind up on a very limited path. If I decided what I was going to do in college—when there was no Internet, no Google, no Facebook … I don’t want to make that mistake. The reason I don’t have a plan is because if I have a plan I’m limited to today’s options.”

Steve Jobs gave a great commencement speech at Stanford:

You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever.

This advice goes against all notions of “career management” or “career ladders,” which imply some steady progression that can be controlled. The world just doesn’t work this way because there is always so much changing. The rules, norms, and conditions are never constant.

Can you imagine President Obama as a kid making plans to be the leader of the free world? The options of his day would be quite limiting to plan a life around. He certainly didn’t follow the normal education track or career trajectory, but he made it work out in the end. This idea doesn’t mean you should limit your ambition or goals but making such long term plans is almost a futile exercise since you and the world will inevitable change along the way. 

Whenever people ask me what I plan to do in the long run (hi mom!), my answer is I don’t have a plan. I just want to do interesting and challenging things, which will never be predictable by their very nature. Technology as a sector almost by definition fits these criteria since it’s in the business of new breakthroughs.

I trust the dots will all make sense backwards.