The Ladder I Was Told to Climb

I have spent close to twenty years in HR. I've designed executive pay structures, built people functions from nothing, sat in rooms where careers were decided, and helped hundreds of people navigate the hardest moments of their working lives. For most of that time, I knew exactly where I was going. I was going to be a Chief Human Resources Officer (CHRO).

Lately, I've been sitting with a question I never expected to ask: why?

The Script We Were Handed

If you're somewhere in your late thirties or forties, you probably know the script. Get a good education. Get a good job. Climb as fast as you can. Every promotion was proof you were doing life correctly, and the next title was always the one that would finally make it feel worth it.

We followed that script through a remarkable run of events. Many of us were starting out when 2008 hit. We built careers through years of economic uncertainty, then lived through a pandemic, then inflation, then constant instability in the world around us. Each one was described as once in a lifetime. They just kept coming.

In the last few weeks, I've had several conversations with people in my cohort who all said some version of the same thing: I'm done. Not done with work entirely, but done with running a race they're no longer sure they signed up for.

I recognized myself in every one of those conversations.

My Own Question

When I picture the next fifteen years of my career, I don't feel ambition. I feel tired. And that has forced me to look honestly at what the CHRO goal was really about.

Was it the influence? The money? The prestige of the title? The approval of the people who raised me to aim high? Probably some mix of all of them. What I can't find, when I look closely, is a clear picture of a life at the top that I actually want to live.

I don't think I'm alone in this, and I don't think it's a failure. Psychologists talk about the “arrival fallacy,” the belief that reaching the next milestone will bring lasting satisfaction. Many of us arrived at milestones and found the satisfaction didn't last. The natural next question is whether the destination was ever ours to begin with.

Burnout or Reevaluation?

Burnout is real. The World Health Organization describes it as the result of chronic workplace stress that hasn't been managed, and it shows up as exhaustion, cynicism about work, and a sense that you're no longer effective. If that's where you are, it deserves real attention.

But I'd suggest that much of what our generation is feeling is also something else: a long-overdue reevaluation. We were taught one definition of success, and we're now old enough, experienced enough, and worn down enough to question it. That questioning can feel like a crisis. It can also be the beginning of building a career on your own terms.

Questions Worth Sitting With

If any of this sounds familiar, here are the questions I've been asking myself. They're harder than they look.

• When you imagine your next promotion, what specifically do you feel: excitement, relief, or obligation?
• Whose voice do you hear when you think about “falling behind” — yours, a parent's, or your peers'?
• If the title and pay stayed exactly as they are, what would you change about your work tomorrow?
• Is it the work itself that drains you, or the organization, the role, or the pace?
• What would success look like if nobody else ever saw it?

The answers don't have to lead to a dramatic exit. For some people, they point to a different organization. For others, a lateral move, a reduced scope, a sabbatical, a portfolio career, or simply renegotiating what they give to work. Sometimes the answer is to stay and climb, but this time by choice rather than momentum.

Where Humanly Fits

I started Humanly because I kept seeing talented people make huge career decisions alone, often at their most exhausted, without anyone on their side who understood how organizations really work.

Humanly isn't therapy, and it doesn't replace it. If you're struggling to function day to day, not sleeping, or feeling hopeless, please speak to a doctor or mental health professional first. That support matters.

What Humanly offers is the career side of the conversation. Together we can separate what you want from what you were told to want, look honestly at whether the problem is your role, your employer, or the path itself, map realistic options you may not have considered, and plan how to act on your decision in a way that protects your finances, your reputation, and your energy.

If you're asking yourself whether to leave or stay, start with the free Resign or Stay Framework. It's a structured way to get your thinking out of your head and onto the page. And if you want someone to think it through with you, book a consultation.

I'm still working through my own answer. But I've stopped believing that questioning the ladder means I've failed at climbing it. It might just mean I'm finally ready to decide where I want to go.