Incoherent thoughts on exploration


I’ve always been an explorer.

In a world where it’s often a lot easier to join something prefabricated, I’ve consistently taken the harder road towards building something of my own. One summer between my 7th and 8th grade year, I got the bright idea to start a baseball league. Not a team, an entire league.

As you can imagine, I had no idea clue about things like insurance, sponsors or even players. I called the local newspaper and for some reason, they printed my ad for players and for weeks, people from all over Central Jersey started calling my parents house about this baseball league. Whenever someone proposed a new challenge, I’d explore ways to solve it. From . insurance to sponsors, I talked my way into partnerships and alliances from grown adults who did not question my moxie.

As all good things do, the experiment only lasted a few weeks. I didn’t have enough players because who in their right mind lets a thirteen year old organize a baseball league with a straight face? But it was an interesting few weeks nonetheless.

That was only the first experiment.

With this path comes all of the inevitable challenges of trying to make a way out of nothing. What’s more difficult is getting to the point of realizing there’s only so much you can do by yourself. I don’t realize at the time how difficult the road is.

Whether it’s a conference or a shoe brand (both things I’ve done) or thinking about my own work trajectory and the future, I spend a lot of time contemplating what the so-called right way is. I’ve met enough smart people in my life, with life paths I’ve admired to know that there is no prototype to the canvas we paint on. We just start working and fill in the gaps as we go. Sometimes, you start over entirely. Except, there’s no such thing as truly starting from scratch.

It’s so alluring at a certain point to believe that you have to put on the armor of being a know-it-all, because we reward it. At least in America, anyway. You sit in meetings and these days, turn on the TV and watch people talk outside the side of their mouths with the faintest regard for whether anything they are saying really meshes with reality.

It’s frustrating to think that’s the way you’re supposed to get ahead. I’ve always favored a path, especially in recent years, of an earnest recognition of what I do not knowEmbracing the fuzziness makes me feel like I’ll get closer to answers I didn’t imagine, because I concede the things I’d like to learn more about. Probably not a winning strategy for proving you’re the smartest person there ever was, but that’s never been something I’ve wanted anyway.

So much of the challenge of knowing where you fit is assembling the right puzzle pieces for a life that makes you want to get up everyday poised to add more pieces. At least, that’s the formula in my head. As I get older, I keep feeling like it’s supposed to make more sense and the opposite ends up being true.

Much like playing an easy board game, you know where all of the pieces go and how they’re supposed to work. I just find that winning is harder and harder even as I’m better prepared than ever to play.

Perhaps it’s just being sure of the game you’re playing in the first place?