Last week, I took a morning off to hike with my nephew. At 15, he’s at that age when everyone is asking him what he hopes to be when he grows up—not in an exploratory Career Day way, but in a college-is-right-around-the-corner way.
I hated this question when I was his age, but admittedly, I’m guilty of asking it myself. For me, and I’m sure for many others, it’s less about needing to know his entire life trajectory and more about being impatient to understand the person he’s becoming. Statistically, his career will change many times—as will mine, as will yours.
And having been a teenager, I also know his answer could be anything or nothing, depending on the day, the hormones, and the desire to sleep off another growth spurt rather than envision a future cubicle.
Where do you hope to be in five or 10 years? is not necessarily his priority.
So, instead, as we hiked, I kept my curiosity mostly to myself, and we talked about other things: his dream from the night before (he was a pancake soldier fighting in a pancake-waffle conflict) and the plot of The Matrix. Whether the terrain around us was real or a simulation.
And during the quiet spells of the ascent, I turned the question on myself instead.
During job interviews, dates, and even conversations with strangers curious about my background, I’ve always answered future-oriented questions honestly: I don’t have a five- or 10-year plan.
I’m an ambitious person. Opinionated, too. Editors have to be. But throughout my career, many of the roles I’ve held and things I’ve built didn’t exist before I got there, so planning has often felt counterproductive.
I don’t live to predict exactly how the world will evolve. I pay attention to my interests and strengths, and I look for places where they’re useful. I adapt.
That answer lands most of the time, because people understand it. They’ve experienced the same uncertainty. Even in our recent poll about new challenges in the workplace, readers described how difficult it is to keep pace with constant change:
“The speed at which change is happening seems to be increasing, and HUMANS need time between changes to get feet back underneath. We no longer get that time. Some people seem to be getting left behind, and my peer executives either are not seeing it, or do not care.”
“The pace has gone absolutely crazy the last few years and leader expectations, especially c-suite, are completely unreasonable here in the U.S. They act like constantly living in fire fight mode (read high stress) is something to be proud of.”
Imagine if I had built my career around a rigid five-year plan in this workforce. In this economy.
Still, my no-plan answer doesn’t always resonate, and that’s important, too. A few memorable times, it has come across as too cavalier—as if I don’t have a vision for the life I want to lead.
That isn’t true at all.
I could tell you the themes that matter to me, both at work and at home: working with smart people who are also very funny and proud of what they do; being a part of communities where belonging feels like a verb rather than a state of being; having the freedom to follow good ideas even when they aren’t technically in my job description; having the flexibility to take a random morning off to hike with my nephew.
That vision has emerged over time, through experiences with great teammates, friends, and unexpected opportunities. It surfaces most often in interview questions, but it’s actually a way of living—a combination of knowing what energizes me, recognizing what matters, and trusting myself to adapt when the details change.
I thought about that as we reached the top of the mountain, our turning point and also our resting place, where we’d planned to picnic while enjoying the view. There, we counted four or five hawks circling the summit.
A few years ago, I spotted six hawks in one day and asked my coworkers in Slack whether they thought it meant anything. Our sales director looked it up: independence, adaptability, vision. Some cultures consider repeated appearances a reminder to pay attention.
I told my nephew about this. As he ate his sandwich, he joked that the hawks were paid actors, there to ensure we got the real hiking experience.
I laughed. That’s exactly the kind of thing someone in my family would say. He’s truly my brother’s child.
There was no dramatic career or life revelation in that, either. It was just a dry one-liner about hawks with jobs. And it wasn’t immediately clear what the hawks were doing there besides, perhaps, catching a vibe. Maybe they were a sign. Maybe they weren’t.
But the comment was so familiar and easy that it lit up another favorite, long-held part of my operating system: the ability to find lightness in uncertainty of all kinds.
Sometimes the things that carry us forward become so natural that we forget they’re doing work at all.
Consider the traits quietly doing work in your own life. Instead of asking “Where do I want to be in five years?” try asking:
- What strengths or instincts do you keep returning to?
- What do you notice yourself doing when you’re at your best?
- What qualities do you consistently look for in teammates, communities, or workplaces?
- When have you surprised yourself with how you handled uncertainty?
- What’s something you’ve carried with you across every job, role, or chapter of your life?
Love what you're reading? From career growth to midday meditations, our email lineup delivers thoughtful insights, relatable data, and space to just be. Add InHerSight to your inbox today. (It's free!)
