I Didn’t Expect AI (Or Menopause) to Change My Leadership
Why experience may be the most underrated advantage in the age of AI
When I started my career in accounting, I could never have expected AI to become part of my leadership story.
We were mostly talking about how to survive tax season without losing our sanity. The biggest technology debate (for what felt like forever) was about whether firms should move their bookkeeping software off desktop computers and into the cloud.
AI wasn’t on the radar. And honestly, neither was aging. What young professional is ever thinking that much about menopause?
The idea that one day, your experience might make you feel out of place in a fast-moving industry simply doesn’t cross your mind until you’re my age.
I didn’t expect AI to become part of my leadership story, and I definitely didn’t expect menopause to be a part of it. But somehow, both of these forces — one technological, one deeply human — ended up reshaping how I think about leadership, experience and the strange moment we’re living through in the industry right now.
The Career Pivot I Didn’t See Coming
A few years ago, I sold the accounting firm I had spent decades building. Like most founders who finally reach that moment, I assumed it meant I had closed an important chapter of my career. I thought I would take what I had learned and step into something new with a little more control and a little less chaos.
Instead, I walked straight into the most disruptive leadership transition of my life.
I joined two high-velocity tech startups, led by founders young enough to be my kids and operating inside a culture that moves fast.
Suddenly, the rules were completely different. Speed was everything, hustle was currency and wisdom was negotiable.
The Part No One Talks About
At the same time all of this was happening professionally, my body was going through its own transformation. My role was changing, my industry was changing, my energy was changing. And sometimes, usually late at night, I wondered if I was becoming irrelevant.
Which when you think about it, is kind of ironic. I can probably hustle harder now than I ever could before. My kids are grown. My network is expansive. After decades of building businesses, making mistakes, recovering and building again, I have a level of clarity I never could’ve had when I was younger.
I know exactly what not to waste time on. That kind of clarity is its own form of speed, but the startup world doesn’t always see it that way.
A Conversation with AI
Then, one night, something unexpected happened.
I found myself talking ChatGPT, not asking questions so much as thinking out loud, trying to make sense of the patterns I was seeing and the tension I was feeling between experience and speed.
And something clicked.
The thing I had quietly worried might make me obsolete was actually the most valuable thing I had. Because in an AI-driven world, the real advantage isn’t speed. Machines already win that game.
The real advantage is judgement.
It’s pattern recognition built over decades. It’s knowing when something looks innovative but is actually the same problem wearing new clothes. It’s understanding when technology might be accelerating the wrong decision simply because it can.
That realization changed how I think about leadership.
It’s also why I care so deeply about the work we’re doing with Navi. AI doesn’t just need engineers. It needs leaders who understand context, consequence and human decision-making. Leaders who have seen cycles repeat and know that the fastest answer isn’t always the right one.
Experience is the Real Advantage
It’s National Women’s Month, and the theme this year is “Leading the Change: Women Shaping a Sustainable Future.”
But real change doesn’t always come from moving the fastest. Sometimes it comes from the leader who can pause and say, “I’ve seen this before.”
Because in an AI-driven world, experience isn’t outdated. It’s a strategic advantage.
