What Nobody Tells You About the Climb: Frontline to VP in 10 Years

There's endless advice on how to lead. There's much less honesty about what the climb actually costs — the identity shifts, the things you have to grieve, the moments when the rules quietly change depending on who's in the room.

I write about this because I wish someone had written it for me. What I learned wasn't just about strategy or skill. It was about identity, control and what you have to let go of at every level to grow into the next one.

Here's my version of that journey.

Ten years. Five roles. One company.

When I look back, the path seems clean: individual contributor to supervisor to manager to director to vice president. But living it was anything but linear. Every step came with something I had to learn — and something I had to let go of. And those two things were rarely what I expected.

The First Promotion: The One That Felt Inevitable

I became a supervisor one year into my first role. I was good at my job — an overachiever, hitting big targets and delivering big wins. The promotion felt natural. Almost inevitable.

What came next was one of the two hardest moments of my career.

Creating success yourself and guiding others to create it are completely different skills. That gap is why so many people struggle in their first management role. It's why, without the right support, so many fail.

I was lucky. I had good people around me. That period taught me the fundamentals: how to recruit well, how to support people who were struggling, how to open doors for people who were already shining and get out of their way, and — the hardest one — how to let go of people who weren't performing.

I also had to learn to manage my own insecurities. When you stop being the person doing the work, your identity shifts. That takes time to absorb. Nobody warns you about that part.

Manager: The Season I Thought I Had It All

This is the chapter I didn't expect to be the warmest one to write.

I got pregnant. And instead of pulling back, playing it safe or looking for stability, I did the opposite. I took on a bigger role. I came back from maternity leave directly into it. I did some of my interviews while my baby slept.

Giving birth was the hardest thing I had ever done. Everything else felt possible after that.

I was confident. I was happy. So what should have been a hard transition felt almost easy.

And then COVID-19 hit.

Travel collapsed overnight. Every plan I had built during maternity leave became irrelevant the moment I walked back in. For someone who had always controlled her way through things, suddenly nothing was controllable. Not the business. Not the market. Not the timeline.

What I could control was how I showed up. That turned out to be enough, and it became one of the most important lessons I've carried with me since.

The letting go at this stage wasn't just professional. It was personal. Work stopped being everything. And that made me better at it.

Director: The Part I Loved — and What It Required

The real challenge at this level became strategic: regional planning, macroeconomics, competitive positioning and value proposition. This part I genuinely loved. It came easily.

What was harder was the distance. Client relationships I had built over years were no longer mine to hold. I had to hand them over and trust my team to carry them.

This was also the moment something else shifted — one I hadn't anticipated.

Travel and hospitality skew female on the front lines. It's where women are the norm, not the exception. Up until this point, being a woman had, if anything, worked in my favor. But the pyramid narrows as you climb. And somewhere around this level, I started to feel that shift.

I started getting side-eye in client rooms that my male counterparts didn't get. An opportunity was redirected because a specific market was deemed to need a man in an authority role. I had to prove myself before walking into rooms where others were simply welcomed.

It didn't stop me. But I'd be dishonest if I said it didn't cost me energy. And the higher I've climbed, the more I've noticed how often I'm expected to justify what got me here while others simply aren't.

Director to Vice President: The Second Hardest Moment

Remember I said there were two? This is the other one — and the step that surprised me most.

Many of the skills that had served me well became less relevant. I'm far less involved in day-to-day people management. My team is made up of experienced leaders who don't need me in that space. Data, analysis and execution? Handled. Most of what used to fill my day has been delegated.

The physical act of doing the work is now a small fraction of my time.

What replaced it is harder to describe.

Three things define the role: decisions, questions and story.

You can't make good decisions without the truth. But the truth rarely surfaces on its own. You have to ask the question beneath the question — the one that gets past the comfortable answer to the real one.

Then comes the harder part: helping people move with the decision. That's where storytelling matters — not as spin, but as the clarity that helps others understand what you see and why it matters.

The real weight of the role is that the decisions never stop. They get bigger, the information gets less complete and the stakes get higher. Every choice carries an opportunity cost. Every "yes" is also a "no" to something else.

Your brain is always running — pressure-testing, anticipating what's around the corner and carrying the consequences of the decisions you've already made while preparing for the next ones.

Decision fatigue is the part of this role I was least prepared for. It's one of the things I'll explore more deeply in the posts that follow.

What I'd Tell Someone Earlier in the Journey

• The skills that get you promoted are not always the skills that make you effective at the next level. Sometimes they actively get in the way.
• Every transition asks you to grieve something — a way of working, a relationship, a version of yourself that felt safe and competent. That's not weakness. That's growth.
• If you're a woman moving up, the dynamics shift. Be prepared, not surprised. Find your people. And don't mistake having to prove yourself for not belonging.

One last thing — the honest part.

Writing this made me feel more exposed than anything I've published. I went back and forth for weeks before posting it. But I hope it makes a difference to someone, somewhere.

None of us are perfect. Whatever you see on social media is never the full picture.

Ten years. Five roles. One company. More lessons than I can fit into one article.

This is the first in a series on leadership transitions. Future posts will go deeper on decision fatigue, executive presence, what to unlearn at every level and navigating the climb as a woman.

What's the transition that surprised you most? The level where the rules changed in ways you didn't expect? I'd love to hear about it in the comments.

Originally published on LinkedIn by Danielle Von Weyhrother and shared with permission.