I woke up this morning knowing just what I wanted to write about today, but I couldn’t remember if I’d already covered it here, so I scrolled through old posts, hoping to jog my memory.  It wasn’t long before I gave up—it turns out my titles are all pretty obscure.

David Sedaris once shared that his editor called the title of his collection of essays, Let’s Explore Diabetes with Owls, “willfully obtuse.”

I wonder if there may be something about holding one’s cards close to the vest that feels a little bit good, or maybe a little bit useful?

Back in our twenties, Paul and I stumbled on this groovy wooden easel left behind in the basement of a Yale building that was under renovation. It had serious1950s-boardroom-vibes and instantly crowned us the King and Queen of Pictionary parties.

The only catch? No one wanted to be on a team with Paul.

Instead of letting teammates shout guesses while he sketched, he’d hover over his drawing until he was done, then step back for the big reveal—often with just seconds left on the clock. Everyone wanted to kill him, but he insisted his record spoke for itself.

In my thirties, I was at some seminar about goal setting and was told to shout your goals from the rooftops. Tell everyone. Commit to them publicly. Announce a date to hold yourself accountable.

It works (sometimes).

In my forties, I got the opposite advice: keep goals to yourself. Write little notes and stash them in your wallet, notebook, or pocket, but don’t share. The thinking is, if you talk too much about what you want, you’ll scratch the itch of having it and lose motivation to actually make it happen.

I’ve seen that one work too.

So, what makes for the best titles—or Pictionary tactics—or goal strategy? Do we invite people in, or do we play our hand close? When there’s not one clear answer, how do we figure out what’s best?

Your head will tell you to rely on your experience. But the truth is, that’s a trap.

Your experience, while valuable, only tells you one thing: what happened in the past. This is super useful in situations where there’s really only one possible outcome, like driving all the way back to college on less than a quarter tank of gas. 

But most things we’ve experienced are far more complex than that. Like the examples above, any number of variables could affect a favorable or unfavorable outcome.

Rely on experience alone in those cases, and you’ll find the past begins to create future.

It doesn’t have to.

In the business world they call it contextual intelligence, I find it easier to just call it wisdom. Rather than leaning on solely on what you believe your experience has taught you, wisdom requires that you also look around you to assess present circumstances and then ahead at what you’re hoping to create or avoid. 

In short if you’re hoping to forge a future that’s different than the past, you’ll need to let go of what you think you know for sure in order to make room for what may be possible.