100 conversations

Adventures in connection that doesn’t feel icky

This Substack is where I put all the bits of me in one place, so yes, it’s usually neurodivergent family life, and today it’s neurodivergent work life. Same brain, different corner of it.

A big part of being a freelancer is all this networking, outreachy stuff that just makes me feel a bit gross.

I’m a digital business manager. I work in Notion, I love the brain-untangling stuff, the brainstorming, planning, techy bits, community building, all of that.

But the “putting yourself out there” part has, for weeks, made me want to go and lie down in a dark room. I build it into this whole grim transactional thing in my head and then do everything I can to avoid it.😬

The thing is, I actually LOVE connecting with people on a deeper level. A conversation with no agenda, just genuine curiosity, past the small talk, sparking off into fun ideas.

Really listening to the other person, what’s going on for them, soaking it all up. That’s my favourite. It’s where most of my good ideas have come from too. For ADHD brains especially, it’s a bit of magic.

So two things nudged me in a new direction on this whole thing recently…

First, Carly Valancy wrote about reaching out to one person a day for 100 days and feeling like a different person by the end. The outreach framing wasn’t quite me, but the 100 stuck. I loved what she said about how the showing up, and the boldly taking action.

Thennnnnn I watched Nicholas Epley’s TED talk on connection. How we consistently underestimate how much the other person is craving it too, how much they enjoy real depth. His closing line is: when in doubt, reach out. I’m trying to actually embody that.

So here’s what I came out with, mashing all these brain dots together

100 conversations.

Slower than Carly’s sprint. Or maybe faster. But without the timeline or the need to be consistent, which can be a tricky one for ADHD brains.

Still within that 100 container though, because something about the number sticks. It gives you something to hold onto. Makes it more of a practice, a ritual.

And conversations, not outreach. New people. People I’ve lost touch with. People I keep meaning to message. People I’m a bit scared to reach out to but really relate to. No pitch, no agenda, none of that. Let’s just have a conversation.

It can even be the reason itself. “I’m doing this 100 conversations thing, fancy a chat?” is a perfectly good way to talk to more people without some agenda hiding behind it. Could be fun. Who knows.

There aren’t any rules here. We build it as we go and figure it out together. No perfect version waiting at the end, just the fun of the process.

But if you want a steer on what counts: anything that goes past the small talk. Standing in line for coffee and taking the “how are you, fine thanks, you” a bit further. A DM. A voice note. A phone call. A coffee catch-up. Whatever feels good.

You’re the judge, and I’m figuring it out as I go too.

So that’s it.

I’ll share mine here as I go, and I’ve opened up a Substack chat so there’s somewhere to join in if you fancy your own 100.