I trusted 5 strangers

Four refueled my soul, and one scammed me.

Jul 07, 2025

This week, I ran an informal listening tour. In the midst of a summer slowdown in my software mentorship work, I’ve been racking my brain for ways to add more 1:1 conversations to my weeks.

You’ve seen some of the experiments in these pages: Python office hours, my local walk group, line dancing. Yet after all of that, my calendar was still wide open. And without a local pub to walk to, I had space for yet another experiment.

By the time the fireworks were lit, I’d had five real conversations. I felt like I’d found my people one coffee chat at a time, until the last one low-key tried to rip me off.

Here’s what I walked away with.

A shared sense of clarity

The people I chatted with this week didn’t have lives that looked much like mine on paper. But we all had some version of the same pattern: a handful of things we filled our weeks with, and a clear sense of what each one gave us, whether income, social support, or a way to give back.

I found myself part of an invisible tapestry: people operating outside of institutions, yet still stitching together lives that feel deeply connected.

Peer support is real and needed

While I felt incredibly fortunate to widen my sphere this week, a common refrain was how we all wanted to give and receive more peer support. Preferably without needing a license to become a certified therapist.

And we have each created our own little systems to have more conversations like the ones we were having, each with varying success. Let’s be honest, my systems were easily the weakest of this group, but they inspired me to keep going. More on that in a minute.

We all have a term for the life we left

The rat race. The hamster wheel. The treadmill. The default path.

I was struck by how everyone I spoke with had their preferred term to describe the way of living we observed go unquestioned by others. For many of us, it was the way we used to live: not questioning the systems we were shuttled into.

You may be wondering about the fifth person. The interaction that went…less well.

That involves another experiment of mine. I’ve been trying to start a small walking tour for all the same reasons I won’t shut up about: connection, belonging, public life. I want to take a small group of people into my city once a week and give them an hour or two of conversation in a new place.¹

My tour has been bogged down by self-doubt, Airbnb bureaucracy, and confusion over whether I need an NYC tour guide license. (Yes, I do. But I’m not eager to hop into another system which will treat me like a number.)

To continue my research, I signed up for someone else’s walking tour. One that I could see as a model for my own.

The host didn’t show up and then blamed me. Super fun.

Fortunately I got my money back. But they added a blemish to my week of quality conversations.

I hinted at improving my systems for regular 1:1 conversations in my life, so I’m just gonna say it.

I’m lonely.

I have loving friends, family, and a partner. I’m very fortunate! But my weeks do not contain enough interactions, moments where I feel seen or even just noticed. The institutions which once gave me a sense of belonging slowly eroded sometime last decade.

My conversations this week were exactly what I needed, and I want to offer the same for others.

I’ll be holding two hours per week for 1:1 conversations.² They are open to anyone navigating change, isolation, or simply needing to be heard.

Book a time here, if you’d like to talk.

If these conversations meant this much to me, maybe they’ll mean something to someone else too.

An aside for social geometry: if I’m in a group of four, I don’t expect to feel space to speak or expect anyone to ask me anything about myself. But when I lead a group of four, for whatever reason I become interesting to people. I don’t know why social norms say it’s okay to ignore our peers, on a tour or literally anywhere, but that’s been my experience. My goal would be to lightly include everyone. Unless they talk too much, and I may toss them overboard. Did I mention my tour may involve a boat?
And maybe more during The Half Pint Pilgrimage! More on that to come.