The Certainty Trap - Alyssa

Alyssa

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The Certainty Trap<br>Why the life you're looking for can't be planned from the sidelines.

Alyssa<br>Jul 10, 2026

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I started working weekly with a therapist after what felt like a panic attack in a supermarket.<br>Several weeks after I broke my arm, I found myself standing in the freezer aisle with the door open, trying to cool my face. I was suddenly so overwhelmed by the people around me and the pain signals my body was sending that I abandoned my shopping cart, which I was pushing with one hand, and went home. I had reached my pain limit.<br>After that, these episodes would happen at least once a month. The pain management clinic called them flare-ups, but they rarely looked the same. Because of my back injury, sometimes parts of my body would go numb. Other times it felt like my leg was on fire. Nerve pain is strange that way.<br>Because the pain was so unpredictable, my brain, which had made it through West Point and five years as an Army officer, began reacting in ways it never had before. I became consumed with anxiety.<br>My back injury and recovering from my broken arm made it difficult to drive, to sit or stand comfortably in public for more than thirty minutes, or even to make plans with confidence. As someone who had always been fiercely independent, I began to feel like I couldn’t trust my own body.<br>Therapy helped me understand what was happening. My therapist didn’t promise certainty, because how could she? Instead, she did something better: she helped me rebuild my sense of agency.<br>What could I do if I was driving and a flare-up started? What could I do if I was in a meeting and the pain became so overwhelming that I couldn’t process what anyone was saying? What could I do if I suddenly needed to lie down?<br>Over the next four years, we worked on boundaries, patient advocacy, information seeking, perspective shifting, and learning to ask for help. Looking back, I realize we were doing something much bigger than managing chronic pain. We were teaching my brain that uncertainty didn’t have to mean danger.<br>That lesson has stayed with me long after my recovery because I’ve realized it applies to far more than chronic pain.<br>Most of us aren’t navigating chronic pain, but all of us are navigating uncertainty. We wait until we’re certain we’ve chosen the right career, found the right partner, or determined it’s the right time to have children. We wait until we’re certain it’s the right business to start, the right city to move to, or the right opportunity to leave.<br>We tell ourselves that once we’re certain, we’ll act. But is certainty really what we’re looking for? Or are we looking for reassurance that we’ll be okay if things don’t go according to plan?<br>At some point, we started believing that uncertainty meant we were making the wrong decision. In reality, uncertainty is often just the price of doing something you’ve never done before. And I don’t know about you, but I can’t imagine a life where I stop doing things for the first time.<br>There’s a difference between being informed and being certain. You should gather information. You should ask questions. You should seek advice from people you trust. But at some point, you run out of information before you run out of decisions. There comes a point when the only way to find out is to participate.<br>Participation creates information. Otherwise, you could learn whether you’ll enjoy running a business by reading about entrepreneurship. You could discover whether you’ll love a city by studying a map. You don’t learn whether writing is for you by outlining your first book. You don’t learn whether you’ll enjoy being a parent by reading parenting books.<br>You don’t learn whether a path is right by standing at the trailhead. You have to walk it. Or maybe the phrase is, you get to.<br>Some of the big decisions I’ve made looked uncertain at the time. Going to West Point. Leaving the Army. Moving to Vietnam. Going to law school. Starting this newsletter. None of them felt like a sure thing.<br>The only reason I know what those experiences meant to me is because I participated long enough for the answer to reveal itself.<br>Clarity is often the result of action. The world reveals itself to participants.<br>My therapist, who helped me navigate unemployment, the GMAT, school applications, law exams, my pituitary disorder, business school, and the bar exam, wasn’t trying to teach me how to eliminate uncertainty. She was teaching me that I could handle it.<br>That’s what agency really is. Trusting that you’ll be able to respond when something out of your control occurs.<br>We dedicate a lot of energy trying to build the “perfect” life; we forget the point is to simply live a life. The people who seem to have clarity are the ones who participated long enough for clarity to emerge. They got out there and collected a lot of data points, some really good and some really bad, which made the decision-making process easier.<br>Fortunately, you can't solve...