Midlife MavericksNever meet your heroes, they say. I think that’s crap, and I’ve never been one for following the crowd anyway. Last Thursday I got on a flight to Lisbon to have dinner with a stranger from the internet.
Not quite a stranger. Justin Welsh writes the newsletter I drop everything for on a Saturday. He runs a paid community I’m part of, and one of the perks was a small dinner with him in cities he and his wife Jennifer were passing through. Lisbon was one of them. Seven seats. I grabbed mine before I’d finished reading the email.
A few years ago, the idea of flying to another country to eat dinner with someone I’d only met through a screen would have sounded insane to me. It turned out to be one of the best things I’ve ever done, for reasons that had almost nothing to do with Justin.
Quote of the Week
“I’ve got something he can never have. The knowledge that I’ve got enough.”
Joseph Heller, recounted by Kurt Vonnegut
The man is exactly what he writes
Let me tell you how much I rate his work. It makes me look like an idiot and I’m telling you anyway.
Last year I went away with my husband. Two nights, the only two nights we managed all year. Justin’s newsletter lands Saturdays at 1pm, and I’m one of those people gripping my phone waiting for it. So there I am, on a rare weekend away, and 1pm comes and goes and nothing arrives. I go to the community, hundreds of people in there, and I post: “Justin, is everything okay? The newsletter didn’t come out.” He replies, horrified, “Oh my gosh, it didn’t! What went wrong?” And then someone else writes: it’s not Saturday. It’s Friday.
Bank holiday. I’d lost a day. I’d publicly told a man his automation was broken when really I just didn’t know what day it was, in front of a very large room of people. You tell a friend when they’ve got spinach in their teeth, don’t you. That’s how much I love his writing.
So I went to Lisbon half-expecting the in-person version to disappoint. He didn’t. The calm, the feet planted firmly on the ground, it’s all real. Smart, obviously. But smart on its own doesn’t cut the mustard. He and Jennifer were warm and grounded. More relief than surprise.
He cut the things that were working
This is the bit that stayed with me.
Justin has made fifteen million dollars online as a solo operator. This year he cut a chunk of it. Offers that were making money. Communities that were making money. They hadn’t failed. He’d looked at the life he actually wanted, writing a few hours a day, walking, coffee with his wife, his health, and decided the extra revenue wasn’t worth what it cost him to earn it.
He knows what enough is. That’s rarer than any amount of money. Most of us never define it, so we keep chasing a number that moves every time we get near it.
I needed to see that more than I’d admitted. To free up Thursday and Friday I’d worked sixteen-hour days on the Tuesday and Wednesday. I arrived in Lisbon completely shattered. I used to take a day a month for myself, no plans. I haven’t done that once this year. So the unstructured hours, wandering streets with nowhere to be, an exhibition with my mum the next day, were exactly what I’d been starving myself of. The Portuguese national football squad were at the airport on my way home. You couldn’t script it. Twenty-four hours, and it reset something.
Two rooms, two different versions of me
The night before I flew, I went to hedge fund drinks in London. A few hours after my last newsletter went out I was sitting in a café nearby, killing time, anxious. Anxious about what I was wearing. About the size of the room, and who’d be there from my previous life. I like people. But a big crowd of the wrong kind sometimes makes me want to bolt.
The next night, Lisbon. A table of people I’d never met. Apart from one, Patrice, I didn’t know who’d be there. And I felt no anxiety at all. None. We talked past midnight, long after Justin left, and the thing that kept landing was how completely we understood each other. The struggles one of us named weren’t received as struggles, because everyone at that table had lived them. Nobody had to explain themselves. No translating. They got me.
Same person, two nights apart. One room shrank me. The other let me breathe. The only difference was who was in it.
What I’m changing
I took a couple of slow days after I got back. Barely any plans. And in that quiet, something I’d been turning over for a year finally clicked. I write this on a Monday morning knowing exactly where I want to take the business. That clarity came from stopping.
So I want to be in more of those rooms. Full of people from outside my world, who solve problems in ways I’d never think of. The growth was never in the rooms full of people exactly like me.
Own it
You know the room that shrinks you. The alumni drinks. The reunion of your old corporate life, where you stand rehearsing what to wear and what to say before you’ve even left the house.
You don’t owe that room your evenings. The version of you that walks in braced and anxious is just in the wrong room. Go and find the one where you don’t have to translate yourself, where your struggles land as recognition instead of judgement. Those rooms exist. Some of them are a short flight away, full of strangers who’ll get you faster than people who’ve known you for twenty years.
Your move this week
Find one room outside your industry and put yourself in it this month. A dinner, a small workshop, a paid community with real humans in it, a meet-up that has nothing to do with your day job. A webinar you half-watch with the camera off doesn’t count. Book it before Friday, while you can still feel why this matters.
Then do one thing for me. Hit reply and finish these two lines:
The last room where I didn’t have to explain myself was…
What made it feel that way was…
That’s the whole email. I read every single reply myself, and I write back.
See you Wednesday,
C
