Leslie Rohonczy, IMC, PCC, Executive Coach & Author
The first few years of my adult life were the striving years. Striving to make ends meet, striving to get noticed in my career, among a sea of other young professionals who always seemed to be better at standing out from the crowd than I was; striving for a promotion to the next level, without ever really asking myself why a title was my end game; striving to feel my own worth, when I didn’t feel at all worthy.
And when I finally got that hard-fought promotion, and found myself in that shitty little clapboard office in the middle of the advertising department at our local newspaper, I had a sphincter-shifting moment of clarity: “Was THIS what I had been working so long and hard for? This office with no window and no purpose? How could all of my striving, motivation, blood, sweat, and tears really have been about THIS?!”
That experience, and that question, changed my career. The promotion was exactly what I'd wanted, which was precisely the problem. I'd spent years chasing a destination chosen by a version of me who no longer existed.
At the time, I couldn't have explained what was happening. I just knew something felt profoundly off. Looking back now, I realize it was the first time I'd noticed that somewhere between the striving and the arriving, it was me that had changed, not the destination.
That experience isn't unique to me. I've heard versions of this experience in many of my executive coaching conversations. The offices are usually much nicer than mine was, and the titles on the business card are more impressive, but eventually the same uncomfortable question appears: Now what? Or sometimes: Is this really all there is?
Life reshapes us while we are busy building our careers. The destination we chose at twenty-eight no longer fits the person we've become at forty-eight, but we may not see it if we don't pause long enough to notice the mismatch.
A few weeks ago, I found myself watching a YouTube video of a single sculler crossing a perfectly calm lake. There was something mesmerizing about how the boat cut through the glassy water. Every stroke looked powerful yet effortless, as it glided across the water with absolute purpose.
I find rowing kind of a strange way to travel. The boat moves confidently forward while the rower faces the opposite direction. Rowers can clearly see where they've been. They can study the wake they've left behind, and can appreciate every kilometer they've already travelled. The one thing they can't actually see is where they're going.
Hey, that also describes many leadership careers! Early in our careers we choose a direction that makes complete sense at the time. We pursue promotions, bigger teams with more span of control, financial security, influence, recognition, and the opportunity to prove ourselves. We want to make our parents proud, build something meaningful, provide for our families, or finally settle that relentless inner voice insisting we're still not enough.
There is nothing wrong with any of those motivations. In fact, they often provide exactly the fuel we need during those demanding early years. But life has a habit of changing us while we're busy rowing.
Successes often turn out to be less satisfying than we imagined. We experience illness, burnout, unexpected opportunities, disappointments, and moments of clarity we never saw coming. And over time, our definition of success begins to evolve. Status starts giving way to significance. Recognition becomes less important than contribution. Freedom matters more than prestige.
The person holding the oars today isn't the same person who first climbed into the boat and set the direction. Yet many of us continue rowing toward the same destination simply because that's where we pointed the boat years ago.
One of my favourite coaching questions catches people completely off guard: How old is the person currently steering your career?
Sometimes it's the twenty-five-year-old you who's desperate to prove she belongs. Or the young father determined to build financial security for his new family. Sometimes it's the ambitious new executive convinced that one more promotion will finally deliver the satisfaction they've been chasing.
That younger version of ourselves deserves enormous respect. They worked hard, took risks, made sacrifices, and created opportunities that today's version of us benefits from every single day. But they couldn't possibly have known who we would become. They didn't know which experiences would shape us, what losses we would endure, what relationships would change us, or how dramatically our understanding of a meaningful life would evolve.
So why are they still deciding where we're headed?
I think this is where many can get stuck. It might feel like lost ambition after decades of investment and building up our expertise, relationships, credibility, and identity. Changing direction can begin to feel like admitting those investments were mistakes. They weren't. They just brought us to the place where we're finally experienced enough to ask a better question.
Instead of asking, “Can I get there?” the question becomes, “Do I still want 'there'?”
That may be one of the hardest career questions we'll ever ask ourselves because the answer often asks us to loosen our grip on a destination we've carried for years; one that feels like our encoded mission, because we've been chasing it so long.
One of the greatest gifts coaching has ever given me is permission to pause before pushing forward. We're conditioned to believe that success comes from rowing harder. Sometimes it does. But sometimes, the wisest thing a rower can do is lift the oars from the water, let the boat glide, and take some time to turn around and really study their trajectory.
Only then can you answer the question, "does this destination still belong to the person I am today?" I encourage leaders to ask themselves uncomfortable questions as part of the process. Questions like, "If you were choosing your career today, would you choose the same destination?" "Which ambitions genuinely belong to you, and which belong to a younger version of yourself?" "What are you continuing simply because you've already invested so much?" "What gives you energy today that barely mattered ten years ago?" "If nobody else's expectations mattered, where would you point the boat?"
Sometimes the answers are deeply reassuring. You discover you're exactly where you're meant to be, and you begin rowing again with conviction because your destination has been consciously chosen by the person you are today, and not inherited from someone you used to be.
Other times the answers lead somewhere entirely different: a new awareness, a different role, a revised definition of success, a shift in priorities, or a career that finally reflects the person you've become instead of the person you once were.
Neither outcome means your younger self got it wrong. That version of you did exactly what they were supposed to do: they got you this far. But at some point, every leader deserves to ask a simple question: Who is this person holding the oars now?
The younger version of you chose a destination with the wisdom they had at the time. You don't owe them blind obedience. You owe them gratitude.
Now it's your turn to decide where the boat goes next.
YOUR COACHING CHALLENGE
This week, spend ten uninterrupted minutes with a blank sheet of paper. Across the top, write this question: How old is the person currently steering my career?
Don't answer it too quickly. Think about the ambitions you're pursuing right now, the goals you're sacrificing for, the opportunities you're saying yes to, and the ones you're turning down.
Then ask yourself: If I were starting my career today, with everything I've learned about myself over the past twenty years, would I still choose this destination?
If the answer is yes, you've just reaffirmed that you're rowing with purpose. If the answer is no, don't panic. You don't have to change direction tomorrow. You simply need to acknowledge that the person holding the oars today deserves a voice in deciding where your boat goes next.