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Sitting in Uncertainty
March 17, 2026
He sat at the kitchen table, staring at a course catalog like it held the answers to his future.
My 14-year-old son is planning his freshman year of high school—choosing classes, mapping out a path—and the weight of it landed on him hard. What if he chooses wrong? What if the class is too hard, or it feels like a waste of time?
He spiraled a little. And I recognized every bit of it. Because I’ve been there, more than once.
I told him about all the things I was certain I wanted to be in high school. Then college came, and I was equally certain about that next chapter. Then I sat at my first job, stared at my computer for at least an hour, and thought: ‘Why did they hire me?’ Hello, imposter syndrome. It showed up again a decade later when I was hired as an analyst at Microsoft. Same feeling, different chair.
Becoming a parent was no different. A few months before my son was born, I panicked — all the unknowns just around the corner. And yet, somehow you navigate it. The uncertainty becomes more familiar. Where you end up is often nowhere you imagined, and sometimes, exactly where you needed to be.
That’s what I wanted my son to take away. Not knowing isn’t a sign that something is wrong. It’s part of the cycle.
The Pressure to Have It Together
Here’s the story we tell ourselves: If you know where you’re going and how you’re getting there, you’re on track. If you don’t — you’re failing.
My son isn’t alone in this. I see it everywhere right now. Kids who haven’t taken a single high school class yet are already auditioning for a future self they’ve never met. They’re doubling up on science classes, loading up on AP classes because somewhere along the way, they feel like they need to have it together.
And honestly? We do the same thing as adults.
The inner dialog gets loud fast. What if I make the wrong choice? What if I disappoint people? What if I waste time or close a door that can never reopen? The mind naturally gravitates toward worst-case scenarios. You overthink. You wait for a sign. You try to control what you can’t yet see.
It is exhausting.
Here’s what I’ve come to believe: not knowing what you want isn’t a personal failing. It’s a signal that something no longer fits. And something new hasn’t quite formed yet.
You’re in the in-between. And that space, as uncomfortable as it is, takes courage to sit in without forcing an answer.
When the Ground Feels Unsteady
Certainty, real certainty, rarely shows up on demand. And waiting for it is one of the ways we stay stuck.
One way to get unstuck is to get curious. The great thing about curiosity is that it doesn’t demand answers—it just opens a door for possibilities. When you shift from “I need to figure this out” to “I wonder what this is telling me,” something loosens. The pressure drops, helping you think more clearly. Here are a few questions to get you started:
What is this uncertainty pulling me toward?
What am I passionate about?
What do I want more of in my life?
What am I afraid of?
Uncertainty usually has something driving it, like failure, regret, judgment, or loss of security. When you can name the real fear, it loses a little of its grip and helps you move forward.
Come back to your values. They give you direction without forcing a destination. They don’t tell you what to decide, but they remind you who you are while you’re deciding. At your core, what matters most to you right now?
Living in the In-Between
Curiosity and values can point you in a direction, but sometimes you still have to live in the uncertainty.
What can that space look like?
Start with your own body. When your nervous system is dysregulated — poor sleep, no movement, constant stress — ambiguity feels unbearable. When you’re taking care of your body and keeping some rhythm in your days, uncertainty becomes something you can actually sit with. Consistent sleep. Regular movement. Time to reflect, even 10 minutes. A check-in with someone you trust.
And sometimes, the best thing you can do with uncertainty is stop staring at it. Close the laptop. Take a walk. Pick up something creative—a sketch, a recipe, a project that has nothing to do with the decision at hand. Not as a distraction. As a reset. The mind works on hard things in the background when you give it permission to step away.
The View From the Other Side
Here’s what I know from the other side of every uncertain moment in my life: the path rarely looks the way you thought it would.
Over the years, I’ve made choices that looked wrong from the outside and turned out to be exactly right. None of it was clear in the moment. All of it makes sense in hindsight.
That’s what I want my son to carry with him—not a perfectly mapped out freshman year, but the quiet confidence that he’s going to figure it out. Because uncertainty isn’t a sign you’re lost. It’s part of the path.
Try this: At the end of this week, take 10 minutes and write down 3 things: What got clearer? What gave me energy? What might be next, even if it’s just a hunch? You don’t need answers. You just need to keep the conversation with yourself going.
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