A good intermediate lesson in chess is that even a bad plan is better than no plan at all. Having no plan is chaotic. And yet people default to no plan. When I taught at the law school last year, I’d ask law students what they wanted to do with their life. Most had no idea. Few wanted to become law firm partners. Even fewer thought that they would actually become partner if they tried. Most were going to go work at law firms for a few years and “figure it out.”
That’s basically chaos. You should either like what you’re doing, believe it’s a direct plan to something else, or believe it’s an indirect plan to something else. Just adding a resume lines every two years thinking it will buy you options is bad. If you’re climbing a hill, you should take a step back and look at the hill every once in awhile. If you just keep marching and never evaluating, you may get old and finally realize that it was a really low hill.
One reason people may default to not thinking about the future is that they’re uncomfortable being different. It is unfashionable to plan things out and to believe that you have an edge you can use to make things happen.
Over my career, I’ve done the exact thing described above. Every few years, I try to think what I want things to look like in my life in four years. As someone else put it, what does your resume look like if you wrote it in four years?
For example, after I decided that I didn’t want to be an engineer around 1994, I thought hard about what I wanted to do. I knew that I didn’t want to be an entrepreneur. But I wanted to be the guy who helped or advised the entrepreneur. I did that with my Dad and his business and found that rewarding.
But there was no formal job of “advisor to an entrepreneur.” There was no linear path like becoming a doctor or lawyer. I decided that business school or law school was the fastest - or most leveraged way - to get there. For reasons that I won’t go into, I decided to go to law school. I spent six years as a lawyer - six years more than I intended. But I always felt like I was getting closer to that vision of “advisor to entrepreneurs.” It was an “indirect plan” that Peter describes above. Being a lawyer helped prepare me in ways that’s hard to get from other professions - mainly, what it’s really like to work in a services industry.
I struck gold when I landed in my current role. It was like winning a lottery ticket that I didn’t even buy. It was a tremendous, unrepeatable stroke of luck. To say that this was my plan all along would be bullshit. But I do believe that even if I weren’t working with a Ron Conway, I’d be doing something along the lines of my current job.
Tiger Woods says that when he’s putting, he tries to “putt to the picture.” His father taught him at an early age that he should envision what he was about to do and what the putt would look like before he even hit the ball. I have tried to use that technique when thinking of my life. But mine is more impressionistic. It’s not as clear or precise. It’s never as direct as putting a golf ball.