How to Know if You’re Climbing the Wrong Ladder
I see it all the time: smart, driven, accomplished professionals - people who have climbed rung after rung on the corporate ladder - finally pause long enough to look around and think, Do I even like this view?
You’ve been confused on the next promotion, the next big project, the next credential. But, when you’re at (or near) the top, what’s it all for? Is this ladder even leaning against the right wall? Have your priorities shifted without you noticing?
I work with high-achieving professionals at every stage from early career to the C-suite, and the question I hear most often is, “Now what?”
Sometimes they can articulate it:
“I know something’s wrong, but I don’t know what, or how to fix it.”
Other times, it’s more of a vague unease, like they’ve outgrown the life they built but can’t quite see what comes next. Or maybe they’re just going through the motions, without any particular sense of purpose or motivation.
Here are a few patterns I’ve seen:
The Almost-Manager: On track for a promotion, they’ve worked toward for years, but the lifestyle no longer feels sustainable. They like the work, but something about it doesn’t fit anymore. The question becomes: quit, or adjust?
The Burned-Out Leader: Thriving in their role on paper, but living with no boundaries between work and home. They love their job but need a way to keep doing it without sacrificing themselves in the process.
The Newly Promoted Manager: Worked hard for the role, but now they hate it. The people problems they didn’t anticipate are draining the joy they once had, and they’re questioning if this is really what they wanted all along.
Lately, I’m seeing more “micro-retirements,” extended leaves of absence, and “sabbaticals”. Not just as a response to burnout, but as an intentional pause to reset, rethink and realign.
Here’s the thing…
It’s easy to blame your job when something feels off. It’s visible, it's time-consuming, it's the most obvious target. But in my experience, the job itself is rarely the real problem. Usually, it’s a catalyst pointing to a deeper misalignment between the life you’re living and the life you actually want.
I’ve seen it happen to:
An early-career go-getter who suddenly hates the hustle they once loved.
A senior leader who wants to make Partner but struggles to maintain any sort of stable leadership.
A parent balancing caregiving and deadlines, struggling to meet expectations at home and at work.
Someone who finally reaches the career summit, only to find the view is underwhelming.
Your Priorities Change. Your Work Should Too.
At the start of your career, the why might be stability, proving yourself or building financial freedom. Over time, it might shift to freedom, flexibility, purpose or legacy. If you don’t stop to check in, you can end up sprinting toward a destination you no longer care about.
When clients are in this space, we slow down and work through four powerful steps:
Pause - Create space to see clearly. Where are you right now? How did you get here? What’s actually causing the disconnect?
Unpack - Look beneath the surface. What values are no longer being honored? What assumptions are you carrying about success?
Redefine - Get clear on what success and alignment look like for you, not just your company or industry.
Rebuild - Make intentional, sustainable changes that fit the life you want now, not the one you wanted five or ten years ago.
Your career and your life will keep evolving. The key is to keep asking: Why am I doing this? Is it still leading me somewhere I want to go?
If your job feels “off” right now, that’s your sign to dig deeper. It’s not about chasing the next title or salary bump, it's about designing a work life that actually fits who you are today.
You don’t have to figure it out alone. Head over to our contact page to start the conversation.
