Midlife MavericksLast Tuesday I did a Substack Live with John Brewton. Forty-five minutes with no script, comparing notes on how we got here. I closed my laptop at the end and thought about half a dozen of you.
John runs Operating by John Brewton. Consulting practice underneath, content business on top. Portfolio career, same shape as mine. We didn’t know each other before that call. By the end we’d swapped enough about the actual mechanics that I sat down on Wednesday morning and decided this week’s issue should be a tour through three things he said that I think you specifically need to hear.
If you want the whole conversation, the live is here: listen to the full thing. 45 minutes. You don’t need to be on Substack to play it.
Quote of the Week
“Better to write for yourself and have no public, than to write for the public and have no self.”
Cyril Connolly
I wrote anonymously for 6 months
This is the bit I tell people privately and almost never write down.
I started on Threads under a name nobody could trace to me. The hedge fund world is conservative in a way that’s hard to explain to anyone who hasn’t sat in those rooms. For 50 days straight I wrote a long-form post every single day. Nobody who knew me knew it was me. One of those posts hit 12 million views. Six months in, after a podcast appearance brought enough inbound that the cover was no longer the point, I went back to my real name.
That arc, anonymous to real, twelve million views to clients quoting my work back to me on intro calls, is what John and I went deepest on. I’m telling you in this issue because the version of you who can’t put your name on anything yet is earlier in a path more women have walked than will admit it. The full breakdown of how the six months actually worked is in the live.
Voice-forward, not face-forward
About 20 minutes in, a woman who works in government consulting joined the audience and asked the question I get in DMs every week. She said: I’m not social media native, I’m not putting my face on camera, where do I even start.
John’s answer was the one I wish someone had told me at 35. Start with a long-form piece on Substack. Break it into three to five LinkedIn posts. Be voice-forward, not face-forward. Your expertise carries you. The face thing is optional, almost always for longer than people think.
If you’ve been telling yourself you’ll start when you’re ready to film, you’re holding yourself hostage to a constraint that doesn’t exist. The full version of John’s answer, including what he tells the hedge fund managers who are even more allergic to camera than you are, is around the 22-minute mark of the live.
AI is the reason a one-woman shop is now viable
Three years ago, the business I run today would have needed a team of four. A fractional editor, a VA who did social, someone for the Notion mess, a copywriter who never quite got the voice right.
John and I are both running operations that look like a 6-person company from the outside and a single person plus AI on the inside. Newsletters, social repurposing, CRM, client work. The control stays with us. The output is bigger than what some teams I worked with at UBS produced in a quarter.
This is the part that’s most underpriced in the conversation right now. Everyone is panicking about AI taking jobs. Almost nobody is talking about what it means for the woman in her 40s who wants to leave but never wanted to run a 20-person business. That woman just got handed the keys. John has a much better way of explaining this than I do, and his version is in the second half of the live.
I didn’t start by writing about my job
The other thing worth saying out loud, because it might be the part you actually need: when I started writing, I didn’t write about hedge funds. I wrote about being a woman in midlife. About leaving the corporate version of myself behind. Not a word about the competence I’d built a 20-year career on. The work-adjacent stuff felt too exposed. I was afraid to put my expertise on the page.
Two things happened in that gap.
Writing turned out to be the clearest thinking exercise I’d ever done. The kind that doesn’t get published, the drafts you delete before anyone sees them. The act itself sorts something in your head that nothing else gets near.
And before writing gave me an audience, it gave me a mirror. Into myself, into who I was now that the corporate job wasn’t there to answer the question for me. A kind of confidence I don’t think anything else could have given me.
Then, this year, I finally had the balls to launch a hedge fund newsletter. The Emerging Manager, fortnightly, written under my own name about my own field. The thing I’d been most afraid of writing for fifteen years.
The reception has been a little ridiculous. 51% open rate. The men in finance I was so worried about are subscribed. One LinkedIn post last week pulled 250 connection requests and an inbox I’m still digging out of.
So if you take one thing from this issue, take this: write. The topic doesn’t matter. Write under your name or under a fake one. There’s someone out there who wants to read what you have to say. The act of writing it will change you before any of them ever find you.
What I want you to hear
The pattern I see in DMs and in coaching calls is the same one. You want to write the thing. You have the expertise. The block is that you cannot afford for the wrong person to see it.
Your boss. The senior partner. The MD whose bonus pool you sit inside. Your mother-in-law. The friend who’ll roll her eyes. The ex who’ll screenshot it. Whatever your specific version is.
What the John conversation crystallised for me is this. The stealth start is the strategy itself. You write under a name they can’t trace. You build the muscle and earn the receipts before the spotlight finds you. Then, when the moment comes, when one piece hits or one MD calls asking if you’ve got time for a side project, you step out from behind the curtain with proof in hand.
Most of the women I admire who left their corporate jobs in the last five years did some version of this. Almost none of them write about it openly, because it’s still considered slightly embarrassing to admit you wrote under a pseudonym first. I don’t think it should be.
Your Move This Week
Give this question ten minutes. On paper or in your notes app.
If you didn’t have to put your name on it yet. If none of the people whose reaction you’re afraid of could ever find out. If I could wave a magic wand and make sure none of them could see it, so all the fear goes away. What would you write about this week?
Reply to this email and tell me. I read every one.
Listen to the live
The whole conversation with John is here: listen on Substack. 45 minutes. Best 45 minutes of background audio you can put on this week if any of this hit a nerve.
See you Wednesday
