Midlife MavericksMy friend sent me a voice note last week.
She said: “Claudia, I have a lot to say about your voice. I think you can do lots of things. You can write an abstract just as it is. Maybe a little book. You can write an article for a magazine. You can do a small documentary or a small cartoon. You’ve narrated it and you’ve told, in three minutes, four very powerful and relevant stories.”
Then she said something that stuck:
“You are a risk-loving woman. So am I. I think both of us have something in common. We are independent and we don’t care what people think. We care maybe 10%, but we do what we think is right.”
I laughed because yes. That’s me.
And I suspect that’s half of you reading this. The women who can run a £50m program at work but overthink a single LinkedIn post like it’s a nuclear launch code.
Then she asked the question I can’t stop thinking about:
“How were you raised that you loved risk? How was I raised that not only I love risk, but it was rewarded? Being yourself was rewarded in my house.”
Quote of the Week
“Only those who will risk going too far can possibly find out how far one can go.”
T.S. Eliot
The house you grew up in
In my house, what got rewarded was: try something new. It’s okay to fail. Just try your best.
My dad used to say something I’ve never forgotten: “Some people say if they had to do it over, they’d do everything the same. Not me. I’d try completely different mistakes. Why bother doing the same ones?”
My mom raised me as if I were a boy. She told me I was more trouble than had I been a boy. I broke every body part available. I did physically stupid stuff. I loved to dismantle toys and put them back together.
When I failed at something, she’d shrug and say: “It’s human capital. An experience you’ve learned.”
I didn’t think of any of this as courage. I still don’t. When someone asks me a question or puts something in front of me, I don’t think “Should I take this risk?” I think “Let me figure out how this works.”
I believe everything in life is figureoutable.
And I’m extremely stubborn. Tell me I can’t do something? That’s the fastest way to get me to do it.
But not every house worked like that.
A meta-analysis on autonomy-supportive parenting—36 studies—found that when parents trust kids to make choices, those kids grow up with better perceived competence and psychological health.
When you grow up getting trusted, you learn to trust yourself.
When being yourself was rewarded, you practice being yourself.
When it wasn’t? You learn a different skill: reading the room. Staying small. Not making waves.
That skill kept you safe. Now it keeps you stuck.
The Global Preference Survey studied 80,000 people across 76 countries and found risk preferences vary systematically by age, gender, and background. You’re conditioned, not broken.
So if you weren’t raised in that house, we build the skill now.
What risk actually looks like
Most corporate women I work with call themselves “risk-averse.”
But when I look closer, they’re not risk-averse. They’re risk-untrained.
They confuse risk with recklessness.
Reckless is quitting on a random Tuesday because your boss annoyed you on Zoom.
Smart risk is capping downside while increasing upside, and doing it in a way your nervous system can survive.
I separate two things most people conflate: financial risk and ego risk.
For most high-achieving women, the scary part isn’t money. It’s “people will see me try.”
Ego risk. Once you name it, you can manage it.
I cap downside in writing. Time, money, energy, reputation. Example: “I will spend 5 hours per week, no more.” Or “I won’t post daily. I’ll do one proof-based post weekly.”
One boundary can save you weeks of panic.
I run pilots, not life decisions. One offer. One buyer. One problem. One clear outcome. A pilot is the entrepreneurial version of “let’s not marry this person after one date.”
And I collect proof like a lawyer. Every call booked. Every yes. Every message that says “I needed this.” When you have evidence, it’s harder to talk yourself out of it.
Picture this: It’s 9:30 p.m. The kettle is boiling. You send one message:
“Hey—quick one. I’m offering a paid diagnostic to help [X] fix [Y]. If you know someone this would help, I’d love an intro.”
A step, not a leap.
A client once told me, “I thought I needed a brand. I needed one brave conversation.”
The 10% that matters
If you’re a woman who “doesn’t care what people think” but still cares 10%? Good.
That 10% keeps you from doing stupid things on the internet.
I care what people think. I do get bogged down by it, for a moment. But I’m too curious to let that stop me.
What they think of me? That’s their problem, not mine.
Do it anyway.
The problem is when that 10% controls everything you do.
You’re not choosing between safe and risky. You’re choosing between controlled risk—small experiments, capped downside, proof-building—and uncontrolled risk: another year of resentment, health cost, and shrinking options.
The midlife women I admire most aren’t louder. They’re more self-trusting. They do the thing before they have permission. Not recklessly. Methodically.
I’m too curious not to try. If I fail, I’m going down trying.
There’s one risk I didn’t take. After I moved to the UK, I had opportunities to work in other parts of the world. I didn’t take them. My husband didn’t want to move. Maybe I wish I’d explored that.
But opportunities came from staying, too.
Risk isn’t who you are. It’s what you practice. And sometimes the practice includes knowing when to stay.
Hit reply. What house did you grow up in? I read every response.
Yes, I’m writing this at 6 a.m. with my third coffee. No, I don’t want to hear about your cortisol levels.
See you Wednesday.
