This week, Claude said something to me that stopped me in my tracks.
"You've just blown up your career to build a startup."
It's not entirely wrong.
Life recently handed me an unexpected window. I'd spent decades building a corporate career — one that paid well, gave me opportunities around the world, and taught me more than I could ever fit into a LinkedIn profile. When the window opened, I jumped through it.
And now I'm spending my days building a software company from scratch.
The funny thing is, I don't actually feel brave. Not because there isn't risk involved. There is. Not because I know this will work. I don't. And certainly not because I have some grand master plan. Anyone who has followed this journey for more than five minutes knows that isn't true.
Here's a number I keep coming back to.
A study of 2.7 million startup founders found that the average age of a founder at the most successful tech companies is 45. Not 22. Forty-five. And a 50-year-old entrepreneur is nearly twice as likely to build a runaway success as a 30-year-old. A 60-year-old is three times as likely as a 30-year-old to found a company in the top 0.1% of all startups.
The Zuckerberg myth is a lottery winner being used as an average.
Here's what that data doesn't say.
It doesn't say why midlife founders outperform. The researchers point to experience, execution, networks. All true. But I think there's something else.
By midlife, you've accumulated enough evidence about yourself to actually use it.
What I realised this week is that I think I've been telling myself the wrong story.
I've spent a lot of time over the past few years trying to figure out what came next. Eventually that journey became the Midrising framework. At the time, I thought I was creating a framework to help other women navigate major transitions.
What I'm slowly realising is that I wasn't creating it at all. I was documenting the path I'd already walked. Because when I look at the woman building Cherry today, I keep hearing people talk about courage. Bravery. Taking a chance. Backing myself.
The truth is, I've been backing myself my entire adult life.
At 24, I walked away from permanent employment to become an IT contractor. At the time, that wasn't a common career move. The contract market was full of middle-aged men. I was young, female and apparently optimistic enough to believe I'd be fine. Everyone thought I was taking a huge risk. Maybe I was. What happened next was eighteen years of contracting across Australia, the UK and Ireland.
Eighteen years of finding work. Eighteen years of proving my value. Eighteen years of landing on my feet.
Not once did I spend a day without a contract. I didn't know exactly how things would work out. I just trusted that they would. Somewhere along the way, I forgot that. Or perhaps not forgot. Maybe I buried it under decades of responsibility.
Careers. Children. Mortgages. School lunches. Leadership roles. Budgets. Performance reviews.
The practical realities of being a grown-up.
Then came midlife.
And like so many women, I found myself asking bigger questions.
Who am I now? What do I want? What's next?
The answer wasn't sitting in another book. Or another podcast. Or another round of overthinking. The answer was hidden in my own history.
And that's what eventually brought me here. To Cherry. An idea I've suspected for years was somewhere inside me. The sort that keeps showing up when you're in the shower, driving the car, walking the dog or trying to fall asleep.
Maybe Cherry is that idea. Maybe it isn't. Ask me again in five years.
What I do know is that after decades of helping other people build things, I've finally decided to build one of my own.
Recklessly? A little. Selfishly? Probably. Blindly? At times.
But then again, every worthwhile thing I've ever done, started before I had all the answers.
That's not a new pattern. That is the pattern.
I think this is what we get wrong about midlife and courage. We talk about it as if bravery is something you have to find. A quality that arrives when you're finally ready.
What I'm finding is that it isn't new at all. It's prior evidence you forgot to count.
Before you decide you're not brave enough, ambitious enough or capable enough for whatever comes next, it's worth looking at the evidence.
Chances are you've already done harder things. You just haven't given yourself credit for them lately.
So here's what I'm wondering this Friday.
What have you already done in your life that would make your younger self think you're brave?
Not what you're planning to do. Not the goal you're chasing. The evidence that's already there.
Because maybe the answer to what's next isn't hidden somewhere in the future.
Maybe it's buried in your own history.
Start steady. Then decide.
— Gill
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