The Genius Guide to Keeping In Touch
How to stay connected to the people who matter without it feeling like a full-time job. Read time: 7 minutes.
1. Here’s the thing you want:
You want to be the person who stays in touch.
The friend who checks in. The colleague people remember fondly. The one who doesn’t let relationships die from neglect.
Right now? Keeping in touch feels exhausting… not because you don’t care. You do. You want to be thoughtful. Present. Available.
Buttttt…. you’re also running a business, managing your own chaos, trying not to drown in your inbox. And every time you think “I should text that person,” you feel guilty because you haven’t in three months.
So you don’t text them and now it feels weird and the longer you wait, the weirder it gets.
You’ve probably seen those people who just… seem to know everyone. Who run into friends everywhere. Who have this effortless web of relationships that looks like ✨magic✨.
My co-founder Brian is one of those people.
We can’t go anywhere without him running into someone he knows and who genuinely loves him. I’m not joking when I say I’ve brought him to events where we walk in and he knows the host from something they worked on 10 years ago…He’s the best connector I’ve ever met. It’s not an accident. It’s a skill he’s built over years.
When we launched our business together, his ability to keep in touch with people brought in our first paying clients. Not through sleazy networking, just through genuine, consistent connection.
So one day last year I asked him: how do you do this without burning out?
What he told me changed how I think about relationships entirely.
Below is his system…adapted and in my words, but the philosophy is all his:
2. Here’s how to do it:
Step 1: Accept that you can’t keep in touch with everyone (and stop trying)
Brian’s first rule: you can’t maintain meaningful relationships with 500 people.
Your brain wasn’t built for it. Your schedule doesn’t allow it. And trying to will just burn you out.
There’s this concept in anthropology called “Dunbar’s number”—the cognitive limit to stable social relationships is around 150. But for close relationships? The number drops to 5-15 people.
So stop pretending you can give equal energy to everyone.
Brian’s approach: Make a list. Be ruthless. 30-50 people max.
His list includes:
Immediate family (partner and parents)
Close friends he actually wants to stay close to
Colleagues he’s building with or learning from
People he’s intentionally investing in (even if he barely knows them… yet)
Anyone in his personal growth orbit (like his recovery community)
This is the real network. Everyone else? They’re fine. They don’t need weekly check-ins.
Brian reviews his list twice a year. People drift. Priorities shift. That’s okay.
The point isn’t to be cold. It’s to be intentional and know that when you spread yourself too thin, nobody gets the real version of you.
Step 2: Eliminate decision fatigue (pre-decide who you’re reaching out to)
Brian’s insight: the worst time to figure out who to text is when you finally have 10 free minutes.
You’ll freeze. You’ll overthink it. You’ll scroll through your contacts and feel overwhelmed. Then you’ll end up on Instagram instead.
His solution: pre-decide.
He keeps his list in a simple note. Names, birthdays, last contact dates, and a reminder for who he wants to check in with this month.
When he has time, he doesn’t think “who should I text?” He just opens the note and picks someone.
Zero thinking required. Zero decision fatigue.
Research on willpower shows we have finite decision-making energy each day. Every choice—even small ones like “who should I reach out to?”—depletes that reserve.
Pre-deciding removes the friction. You’re not deciding whether to reach out or who to reach out to. You’re just doing it.
Step 3: Stop keeping score (one-way is fine)
This is the part Brian hammered into me: keeping in touch isn’t a transaction.
Texting someone doesn’t hinge on whether they replied last time.
Some messages are gifts. You send them because you thought of the person… Not because you need something back.
“Thought of you today. That random memory made me laugh. Hope you’re good.”
That’s it. No pressure. No expectation. Just care.
The people who matter will respond when they can. The ones who don’t? That’s information too.
Brian told me he used to get in his head about this. If someone didn’t reply, he’d assume they didn’t want to hear from him so he’d stop reaching out.
Now he realizes: most people are just busy. Or they saw the text and forgot to respond. Or they meant to but life got in the way.
It’s not personal. And even if it is… fine. He still sent the message because he wanted to, not because he needed validation.
Step 4: Ask better questions (and actually care about the answer)
Brian’s pet peeve: most “how are you?” texts are autopilot garbage.
You’re not really asking. They’re not really answering. It’s just filler.
His approach: ask questions that give people permission to be real.
Instead of:
“How’s it going?”
“What’s new?”
“What are you up to?”
He asks:
“What’s one thing that’s going well right now?”
“What are you actually excited about lately?”
“What’s been harder than you expected this month?”
These questions invite actual conversation. Not small talk.
And here’s the key he emphasized: ask because you’re genuinely curious. Not because you’re waiting for your turn to talk.
If you’re using someone else’s answer as a prompt to talk about yourself, they’ll feel it. And they won’t open up next time.
Step 5: Make it a ritual, not a routine
Brian’s philosophy: keeping in touch is a mental health practice.
Loneliness kills more dreams than failure and the people you think are “too busy” to hear from you are often hoping someone checks in.
If you wait until you “feel like it,” you never will.
His system: schedule it. Put it on your calendar like a workout or a meeting.
He blocks 20 minutes every week. Sends 3-5 “thinking of you” messages. Sometimes more. Sometimes just one.
It doesn’t need to be deep, it just needs to be consistent.
Research on habit formation shows that behaviors tied to specific times and contexts are more likely to stick. “Sunday mornings = reaching out” becomes automatic. You stop debating whether to do it. You just do it.
Here’s what Brian told me surprised him: the more he did it, the easier it got. Not because he got better at writing texts but because he stopped overthinking them.
3. Here’s why it works:
You stop carrying guilt about who you “should” have texted.
When you have a system, you know you’re already doing what you can. You’re not ignoring people. You’re just being realistic about your capacity.
You actually stay in touch (instead of just feeling bad about not staying in touch).
Consistency beats intensity. Five people you check in with regularly matters more than 50 people you think about texting but never do.
You build real relationships, not shallow networks.
When people know you’ll actually reach out not just when you need something they trust you more. They open up and most of the time, they show up when you need them too.
You stop absorbing other people’s flakiness.
When you stop expecting everyone to reciprocate, you stop feeling hurt when they don’t.
You reach out because you want to. If they respond, great. If not, that’s okay too.
4. Now go:
This week, try this:
Make your list. 30-50 people. Write it down.
Then schedule 20 minutes this weekend to reach out to 3 people on that list. Wish them a happy holiday, tell them you hope their well.
Not because you need something… literally just because you thought of them and see how it feels.
Start here if you only have 10 minutes:
Text one person right now. Someone you’ve been meaning to reach out to but haven’t. Don’t overthink it. Just say: “Hey, thinking about you. Hope you’re doing well.”
Hit send.
This weeks prompt: What’s been the best part of your week?
P.S. I’ve been using Brian’s system for a few months now. Some people reply immediately. Some don’t reply at all. Some send me voice memos about random shit happening in their lives.
All three of those outcomes are fine because I’m not texting them for a response. I’m texting them because I care.
If this resonated, hit reply and tell me who you’re going to reach out to this week. I read every response.
Writing from Austin, staying connected,
Alex