Wisdom

As a kid, I can remember times when the adults in my life would stare at me wistfully, usually after I had made some daft decision, and say, “If only I had known then what I know now.” I wasn’t quite sure if they were insulting me or merely pining over their lost youth—or both—but I did implicitly understand that they believed the young lacked a certain type of wisdom.

We are obsessed with acquiring knowledge. The idea being if, and when, we acquire enough of it, we will finally figure out how to live our best lives. There is more information at our fingertips than at any other time in history, but I am not sure that translates into more wisdom.

The famed investor Charlie Munger once quipped, “All I want to know is where I’m going to die so I’ll never go there.” Munger, known for his no-nonsense wisdom, captures the irony of our situation: we have a lot of knowledge, but that knowledge doesn’t necessarily yield wisdom.

I recently went on a walk with a new acquaintance. We spent our time recounting our biographies, as often happens when you’re getting to know someone. It was fascinating to notice what each of us emphasized and what we left out. As we spoke, it became clear that we had both arrived at this moment almost in spite of all our planning and efforts.

Details such as where we went to school, our GPAs, family circumstances, and even our successes were strangely irrelevant. What stood out were the unplanned, unexpected moments that led us down paths we could never have anticipated. This idea is hardly new. Countless books, TV shows, and films have explored it. I call it the Sliding Doors effect, after the 1998 film: those moments that shift the direction of our lives without warning.

And yet, despite knowing this pattern, most of us spend hours worrying, planning, fretting, and accumulating more knowledge in an attempt to answer, “How should we live?” I am certainly guilty of this impulse. In my own life, I confront my fear of the unknown with obsessive planning, anticipation, and strategy—my incessant activity providing me with the illusion of control. It is only recently that I realized most of the truly meaningful moments in my life were not planned, anticipated, or strategized. They simply happened.

“Letting go” has become a cliché, and that is unfortunate. Most of us know people who live their lives with an enviable freedom. I often resent the ease with which they seemingly sail through life, and I have come to recognize that my resentment stems from the realization that their lives are, in fact, enviable. Much of the beauty of life lies in its unplanned unfolding: those rare, surprising moments that take our breath away. And unlike me, these individuals don’t miss those moments because they are too wrapped up in their heads.

Rick Rubin, in The Creative Act, meditates brilliantly on the importance of letting go a bit more. In one place he says, “Most variables are completely out of our control. The only ones we can control are doing our best work, sharing it, starting the next, and not looking back.” It is this balance that I am trying to cultivate: to lean into what I can control—my effort, time management, daily habits, and even my ability to recognize opportunities—while creating more space for the unexpected.

So, am I saying that we should all throw out our plans and let life unfold entirely on its own? For some, that might be a healthy corrective at least for a time. However, for most of us, the lesson is more subtle: to loosen the reins slightly and notice what arises when we actually “let go.”

As I practice this approach in my own life, I have noticed real benefits. I wake up more rested. The perpetual tension in my shoulders has nearly disappeared. I have more time for the people in my life. I am more attuned to what is happening around me. Unsurprisingly, as I have reduced the time spent in my head, I have found space. But what has been surprising is how that space has yielded more clarity, calm, productivity, and an effortless sense of flow.

Maybe this is the wisdom the adults from my youth were lamenting: the ability to pause the endless quest for more knowledge and observe life as it unfolds. To stop worrying about what lies outside our control. And to see beauty in the unfolding. Then again, maybe they were insulting me.

In any case, it might be an enlightening exercise to consider how much of your own trajectory was unplanned or unexpected. And then, as you consider the future, rather than bracing, loosen your grip, if only a bit. Not irresponsibly, but with awareness and humility. You never know where it might lead.