“You Did See That Coming. Why Are You So Surprised?”

Let’s call it out: Running like a maniac in the corporate hamster wheel does, from the inside of the wheel, look a lot like climbing the corporate ladder. I came across this quote on LinkedIn last week. It resonates with many of my clients and even more so with my own corporate story.

I meet seasoned leaders every week who realize, often too late, that they’ve overstayed. They knew it. They felt it. And yet, they stayed. Promotions, bonuses, prestige… all the external rewards that once felt like purpose. Until one day, the ladder they were climbing turned out to be a loop. And the exit? Five quarters ago.

When clients come to me at this moment for Reverse Headhunting or Executive Coaching, I say straight:

“You did see that coming. Why are you so surprised?”

No judgment, just truth. I can say it because I’ve been there. Twenty-three years of loyalty, performance, and impact… only to discover that going from “indispensable” to “invisible” can take exactly one meeting.

This article is for every leader who waited too long to leap. And for those still running hard, mistaking motion for momentum, let’s dig in.

The Psychology of Staying Too Long

Why do visionary, capable executives miss the signs that it’s time to go?

Because the system is built to keep you in. Promotions, merit increases, retention bonuses, stock plans, and other incentives are powerful psychological anchors. They’re not just rewards; they’re validation. And we require validation, especially when the job gets hard.

We also face the “sunk cost fallacy", convincing ourselves that since we’ve invested so much, it’s worth making one more effort. Thus, we craft narratives for ourselves:

·       “I’ll leave after the next bonus cycle.”

·       “I owe it to the team to stay through the transformation.”

·       “It’s not that bad.”

·       “I already sacrificed so much for this role; I might as well ride it out.”

·       “If I just stay a little longer, maybe it’ll finally pay off.”

·       “…”

Meanwhile, the signals we easily spot in our teams, such as constant criticism of leadership and their decisions, reduced creativity, and loss of motivation, are often ignored in ourselves. This is because we are not trained to recognize our own burnout; instead, we are conditioned to override it.

Three Signs You’ve Outstayed Your Role

Are you unsure whether the wheel is still moving forward or just spinning in place?

These are the red flags that matter:

🚩 You’re Criticizing Everyone “above” You: If your inner dialogue sounds like “He/She has no idea, I could do it better,” you have entered “immediate jump” mode. The target is now on you. Do you feel the heat of the red laser dot on your chest?

🚩 You’re Defending Instead of Creating: When your energy goes into justifying why you’re still the right person for the role, instead of building what’s next, you’ve shifted from leading to surviving.

🚩 You’ve Stopped Challenging and Started Coasting: If you’re no longer provoking ideas, stretching talent, or questioning the status quo, you’re likely stagnating. And stagnation, at the top, is contagious.

One Note on Tenure: I truly believe leadership has a halftime.

We don’t talk enough about this: leadership roles have a shelf life.

It’s not failure to move on; for me today, it is about evolution. Staying too long can dilute your legacy and block your team’s next chapter. The best leaders know when it’s time to hand over the reins. This is not because they’ve failed, but because they’ve succeeded. Their next challenge isn’t waiting for a sign. It’s waiting for a decision.

Reinvention Without Regret

Reinvention isn’t about erasing the past; it’s about using it as fuel for what’s next. These three strategies for leaders who have stayed too long will help you shift from feeling stuck to moving forward, without wasting time on regret.

1. Own It Without Beating Yourself Up: Yes, you stayed too long. So what? Recognizing it is power. Skip the shame and focus on the lesson. There’s no reinvention without truth.
2. Rebuild Your Identity Beyond the Org Chart: You’re not your title. You’re the sum of your experiences, scars, and values. Start articulating your leadership story beyond your last role. What did you stand for, not just what did you do?
3. Move Fast with Intention: Once you’ve seen it, act. This is not the time for another round of analysis. Treat your next step with the same urgency you’d bring to a crisis. Reinvention favors the bold and the prepared.

To My Dear Leadership Peers Out There in Their Hamster Wheels:

If you’re reading this with a lump in your throat or a knot in your gut, good. That’s your signal. The cost of waiting too long isn’t just missed opportunities. It’s the slow erosion of your sense of urgency.

Your next chapter isn’t going to write itself. But it’s waiting! It’s going to need everything you’ve learned on the wheel, and everything you’re ready to leave behind.

“YOU’RE Not Too Late. YOU Just Need to Leap Now.”