The Text I Almost Never Sent

This essay first appeared in The Stir, our every-other-week newsletter, on August 4, 2026. You can join at simmer.social/stir.

There is one thing almost everyone gets wrong about staying in touch. I know because I got it wrong too, with less excuse than most.

For years I ran a software consultancy, where the network was the business: finding help, making introductions, knowing who to call. Staying connected was the job.

A few months after I graduated business school, my partner, Portia, asked me a simple question: had Julio taken the leap yet? Had he finally started his own thing?

And I just sat there.

I had no idea. I hadn't talked to Julio since graduation. Not a call, not a text, nothing.

And here is the part that took me a while to admit. Nothing had happened between us. There was no falling out. I wasn't avoiding him. It simply never occurred to me, because there was no occasion for it to occur. School had been the occasion, and school was over.

I want to be honest about why that question stung the way it did.

I went back to school on purpose. I wanted the structured study, and I wanted a deeper understanding of the kinds of cross-functional problems where I thought I could make an impact. But if I'm honest, the thing I wanted most was the people.

A big boost to a high-impact network is one of the main things a program like Kellogg sells, and it is a little uncomfortable to say that part out loud, because it sounds transactional. It didn't feel transactional from the inside.

The program is designed to build strong bonds within a cohort, and it works. Two years of deadlines and late nights turns classmates into people who know you at your best and your most stretched. The friendships were the point. Somewhere along the way, they became the whole point.

Which is why the months before graduation felt so strange. Everyone around me was celebrating, and I was feeling something closer to dread. I could see it coming: the calendar that put us in the same rooms was about to disappear, and all of these people were about to stop being part of my daily routine.

I told myself I would build a new system for keeping them close. I build systems for a living. That is literally what I do.

I didn't find one.

So when the question about Julio landed at my kitchen table, it landed on all of that at once.

Julio might have been out there taking the biggest swing of his life, and if he could have used an assist, an intro, a sanity check, or just somebody in his corner, I would never have known.

I am the kind of person who would move the earth to help someone I know. Not knowing when someone could use that help is a special kind of pain.

I had regretted losing touch with people before. Sitting there, I realized I was doing it again, this time with people I had just spent two years telling myself I would keep.

So I did the obvious thing. I sent the text.

I wish I could tell you it was dramatic. It wasn't. He wrote back, and we picked up like no time had passed. No awkwardness, no apologies needed. We just talked.

The friendship had been sitting there, intact, the entire time. Nothing about it was broken.

The only thing missing was an occasion.

We treat losing touch like a failure of caring, and it almost never is. Relationships survive. Occasions die.

The program ends, the job changes, the city changes, and every time, the structure that did the scheduling goes with it.

I had tried to fix this before, back in my consulting days: spreadsheets, CRMs, at one point an honest-to-goodness graph database.

They all failed the same two ways. Nothing held me accountable to reach out, and none of them helped me stay familiar with what was happening in people's lives between conversations.

That night at the kitchen table, Portia and I started pulling on the thread. We are both entrepreneurs. We have moved, changed jobs, gone back to school, and scattered friends across the world between us, so we had felt this problem from every side.

A few months later we could describe the idea end to end. We prototyped it right away, and we were our own first testers. I have been running some version of Simmer ever since.

I'm not going to list features here. This essay is for something else.

The Stir is a newsletter about staying close to the people who matter, and every issue will try to be useful in that direction. But the more honest description is that this newsletter is me practicing the habit in public. It is us, reaching out.

Be there.