unexpected

When I was a kid, I always knew exactly where my Christmas presents were hidden. I had every opportunity to sneak into that closet undetected a thousand times a day, and yet, I never so much as peeked in. I wanted the surprise more than I wanted to know, so I let the mystery sit there for weeks, sometimes months, saving myself for the delightful moment I got to unwrap my gifts.

I don’t know when that appreciation for the unknown started to diminish, only that it did, and that a heart once open to life’s uncertainties slowly gave way to something more brittle: the need for predictability, and a grip on control over every aspect of my future. I recall a catalyst for that shift in my sophomore year of college, when a routine dental procedure led to an infection in my throat and lungs that nearly killed me. There is nothing like a brush with death to reorganize a nervous system around one objective: survive. I came out of that year more disciplined than I went in, more terrified of failure than I’d ever been, counting calories, moderating every emotion, and managing every interaction like a variable I could control if I just tried hard enough. It was exhausting, and I didn’t comprehend the toll it would eventually take on me.

We are primal creatures underneath all our sophistication, wired to scan for threat, even when that threat is hardly existential. As a result, we seek the certainty — the known entity. Tony Robbins has spent decades teaching that certainty and its apparent opposite, the craving for surprise, variety, and change, are both core human needs, often battling inside the same person. Certainty says: if I know what’s coming, I can prepare, and at least minimize the damage. Antithetically, uncertainty implies that a life fully mapped in advance, with no surprises and nothing left to discover, would be unbearable. We vacillate between the two all the time, and we spend most of our lives trying to reconcile a largely unconscious contradiction.

The most unexpected thing I’ve done, astonishing even myself, was leave a stable corporate career for an entrepreneurial path. The version of me five years ago would never have believed it if you’d told her she would give up the apparent “security” and professional identity of “success” for a career where the only certainty is that the odds are stacked against you. I still don’t have the predictability I spent decades trying to manufacture, particularly after my illness. And to be honest, I still don’t know what next month’s income will look like, yet somewhere inside that ongoing uncertainty, I have never felt more alive and like myself.

Somewhere in the leap, I started trusting that the parachute would open, not because I’d calculated the odds, but because I’d finally let go of needing to.

Since then, the best parts of my business have taken shape through people and opportunities I couldn’t have foreseen. I was on a train in New York, a city neither of us lives in, reading (not ironically) The Courage to Be Disliked on my way to visit my college roommate, when I met someone who is now a dear friend and business collaborator. It was an encounter we both now call a serendipitous Universe Collision. A separate opportunity, coaching and facilitating a founders group, came from a woman I met at Hoffman, which, if you are unfamiliar, is essentially an anonymous healing experience that can only be described as ten years of therapy in one intensive week. Neither one came from crafting social media content, a pitch deck, or a strategic plan. I was simply being myself, unguarded, out in the world, following my joy and doing things I love (and yes, I even love the therapy).

The same thing happened recently in my personal life, after many years of singledom and cycling on and off the obligatory dating apps that mostly left me depleted and uninspired. A couple of months ago, on my regular morning walk, a man stepped into my path and asked me out. I would never have clocked him as a potential partner, but I was impressed by his courage, so I said yes, never expecting it to evolve beyond a first date. In the short time since, he has changed the shape of my days, even though very little of this relationship resembles what I thought I was looking for.

None of this is an argument against a clear vision and goals. A direction still matters. Certainty is useful when you need driving directions. But it is uncertainty, the unexpected, that makes the actual trip worth taking. It’s the wrong turn that becomes the better route; the sliding door moment when you meet the person who alters the trajectory of your life.

Margaret Mitchell wrote, “Life’s under no obligation to give us what we expect.” I’ve come to think the unexpected is closer to the point than we give it credit for, that it might be the actual doorway to our most vital lives.

I believe wonder to be the most underrated emotion we have access to. We throw the word ‘wonderful’ around so casually that we’ve lost the felt sense of what it’s actually describing: the state of being genuinely in awe of your own experience. If you’ve spent years optimizing, gripping, trying to engineer every outcome so that nothing catches you off guard, I understand the impulse. I lived inside it for a long time. But I wonder what possibilities would unfold if we all opened our palms instead of tightening our fists? That kid in front of the closet already knew something it took me a lifetime to relearn: that not knowing what’s behind the door was the best gift of them all.