Midlife MavericksYour best clients might be sitting in a contact list from 2004.
The Zoom invitation arrived with a name I could barely recognise.
He’d reached out on LinkedIn first. Followed up through channels. Listened to the Odds On Podcast where I’d been a guest. By his account, he devoured it. Then went to some length to get the call on the calendar.
By the time we got on the Zoom, he had a proposal to put in front of me. Specific and real.
Halfway through the conversation, the penny dropped. We’d worked together twenty years ago. He’d been a client in a previous version of my career I’d almost forgotten I had.
Now he was across a screen on a Friday afternoon in April, proposing a partnership.
Quote of the Week
“Friendship is born at that moment when one person says to another, ‘What! You too? I thought I was the only one.'”
- C.S. Lewis, The Four Loves
The Reconnection Economy
In midlife, work stops arriving the way it did in your thirties.
It doesn’t come from cold outreach. It doesn’t come from the algorithm. It comes from people who already know what you do, who’ve watched you over years, and who finally have a reason to pick up the thread.
Call it the reconnection economy. Old clients. Former colleagues. People you shared a trench with fifteen years ago and then drifted away from when life rearranged itself.
They are not dormant. They are stored. And when the moment lines up — their need, your current offer, a bit of context that reminds them you exist — the thread gets picked up again.
Most midlife women I talk to underestimate this. They treat their network like it expired when they changed industries, or had kids, or went quiet on LinkedIn for a few years. It didn’t. It compounded.
Treat a relationship as a long arc instead of a single transaction, and this is what happens. A conversation from 2004 becomes a proposal in 2026.
The Call That Had No Commercial Input
Here’s the part that should reset how you think about this.
I did nothing to cause this call.
I didn’t pitch him. I didn’t nudge him on LinkedIn. I didn’t run a re-engagement sequence. I wasn’t following up on a thread. Twenty-five years had passed since we were in the same room, a networking event where someone introduced us and I followed up afterwards the old-fashioned way. He became a client. Then he wasn’t. Then, apparently, he was listening.
He re-entered the picture because he’d watched something shift. He heard me on a podcast. He connected on LinkedIn. He tracked me down on email. He booked a call.
All of that happened without me doing any of the work usually associated with “pipeline.”
The work I did was twenty years ago. Be good at what I did. Be pleasant to work with. Leave the relationship in a state where picking it back up didn’t feel weird.
That is the asset. Not my current LinkedIn output. Not my content strategy. The residue of having worked well with someone long enough ago that they’d forgotten the specifics but remembered the shape of me.
Why This Is Easier Now
A version of this used to be much harder.
Reaching back out to someone from decades ago once meant a phone call you’d have to psych yourself up for. A secretary gatekeeping. An office you’d have to track down. An awkwardness that scaled with the number of years gone by.
Now it’s different. LinkedIn does the hard part — it shows you what someone has become, where they are, what they’re close to. Substack tells you what they’re thinking. Instagram tells you what their life looks like.
By the time you reach out, you’re not reconnecting cold. You’re stepping back into a relationship that has been quietly updating itself in the background.
The person who booked the Zoom with me didn’t need to summarise twenty years. He knew roughly where I’d been. I knew roughly where he’d been. We could skip to the interesting part.
This is the real shift. Reconnection used to require effort that most midlife women in a busy season couldn’t justify. Now the infrastructure does a lot of that lifting for you.
You just have to be willing to send the message.
OWN IT
Most of us won’t.
Not because we don’t want the work, or the friendship, or the collaboration. Because reaching out to someone from a past version of your life feels like asking for something — and in midlife, most women have been trained to conflate asking with being needy.
It isn’t needy. The person you’re reaching out to is likely sitting on their own version of the same hesitation, wondering whether it’s weird to message you after all this time. Someone has to go first.
This week, pick one person who’s been absent from your life for ten years or more. Not someone you owe an apology to. Not someone you’re hoping will give you work. Just someone you genuinely liked working with, who disappeared because life kept moving.
Open a message. Do not pitch. Do not suggest a call. Write two sentences about what reminded you of them. Ask one question about what they’re up to now. Press send.
Then watch what happens over the next six months.
Reply and tell me who you reached out to, or tell me who you’ve been avoiding and can’t bring yourself to write to. I read all of them.
See you Wednesday,
