I hadn't spoken to my former mentor in eleven months. Not because anything happened. We just stopped connecting. Work got busy. Weeks turned into months. By the time I noticed, the silence felt too heavy to break. I needed a reason to reach out, and I didn't have one.
This is how relationships drift—not with drama, but with neglect. The good news: you can rebuild the habit of reaching out without turning it into another overwhelming task. Here's what actually works.
Start by listing the people you want to keep in your world. Not everyone you've ever met—just the relationships that matter to you now.
Grab a notebook or open a simple document. Write down names in three groups: close friends and family you want to talk to regularly, professional contacts you want to maintain, and people you've let drift but want to reconnect with. Don't worry about the number. Some people have fifteen names. Others have fifty. The right number is whatever feels meaningful to you.
For each person, note one detail: the last time you connected. Not to guilt yourself, but to see patterns. You'll probably notice clusters of people you haven't reached out to in months. That's normal. It's just data.
Not every relationship needs the same rhythm. Your best friend might hear from you weekly. A former colleague might be fine with quarterly check-ins. The key is matching frequency to reality.
Look at your list and assign a simple cadence to each name: weekly, monthly, quarterly, or yearly. Be honest about what you can sustain. A quarterly text you actually send beats a weekly reminder you ignore every time.
For close relationships, aim for something that feels natural—not forced. Maybe that's a fifteen-minute call every other Sunday. For professional contacts, a brief email every few months keeps you on their radar without demanding constant attention.
The frequencies can change. You'll adjust as you go. The goal isn't perfection; it's a system that works for your actual life.
Your brain isn't designed to remember who to contact and when. Offload that work to a system.
You have options. A paper calendar works. Digital reminders on your phone work. A spreadsheet with conditional formatting works. The tool matters less than the consistency.
Some people use dedicated tools for this. Extndly, for example, lets you set personalized rhythms for each contact and sends gentle reminders when it's time to reach out. But you can start simpler: set recurring calendar events with names in the title. "Text Maria" every Tuesday. "Email David" on the first of each month.
The reminders should feel like helpful nudges, not obligations. If you're dreading them, the frequency is too high or the relationships are wrong. Adjust until it feels sustainable.
Staring at a blank message box kills momentum. One option to keep contact frictionless is to have templates ready.
Not corporate-sounding scripts—just simple starting points you can personalize. For friends: "Hey, thinking about you. How's life?" For professional contacts: "Saw something that reminded me of our conversation about X. Hope you're well." For reconnecting after drift: "I realized it's been way too long since we caught up. No reason for the radio silence—just life. Would love to hear what you're up to these days."
The magic isn't in the words. It's in lowering the friction. When a reminder pops up, you shouldn't need to craft a perfect message from scratch. Grab a template, add one personal detail, and send.
For some people, it helps to keep a note on your phone with five or six go-to openers. Update them when you find something that works better. For others, they find improvising in the flow of life is easier, and it's best to make it up as you go. Find what works for you.
Logging every interaction can become busywork. Track just enough to know where you left off.
For each person, note the date you last reached out and one detail about the conversation. "October 15—she's starting a new job in December." "November 3—he mentioned his daughter's soccer tournament."
This isn't for data analysis. It's for making your next outreach easier. When you reach out in a month, you have a natural opening: "How's the new job going?" or "Did the soccer tournament happen?"
You can do this in a simple notes app, a spreadsheet, or a tool that organizes it for you like Extndly. The method doesn't matter. What matters is having context so your outreach feels personal, not generic.
Don't try to contact everyone on your list this week. Pick three people.
Send one text today. Make one call tomorrow. Write one email this weekend. That's it. Small wins build momentum better than ambitious plans that collapse under their own weight.
After two weeks, add two more people. Then two more. Build gradually until you're maintaining the rhythm you want. If you feel overwhelmed, you're adding too many people too fast.
The habit forms faster when you celebrate tiny successes. Sent that text? Good. That's the win. Don't worry about the perfect follow-up conversation. Just send the message.
Sometimes you stop reaching out for months. Maybe you were dealing with a crisis. Maybe you just fell out of the habit. The silence feels awkward now. Here's how to break it.
Start with the people where the connection was strongest. These are easier to rebuild. Send a simple message: "I realize it's been months since we talked. No excuse—just dropped the ball. I'd love to catch up if you're open to it." Most people respond positively to honesty.
For professional contacts where the drift feels more fragile, reference something specific: "I was thinking about the project we worked on last year and realized I never followed up on how it went. Would love to hear about it if you have time for a quick call."
The key is not over-explaining. Don't write a novel about why you disappeared. Acknowledge the gap briefly, then pivot forward. "I know it's been a while. I'd love to reconnect." That's enough.
Expect some people not to respond. That's okay. The silence might mean they're overwhelmed too, or the relationship has run its course. Focus on the connections that feel mutual.
After you send a few of these recovery messages, you'll realize something: most people are relieved you reached out. They're often in the same boat, feeling guilty about not connecting. Your message gives them permission to respond without judgment.
Here's a simple weekly routine that works for many people:
Monday morning: Review your reminders over coffee. Pick three people to contact this week. Tuesday evening: Send one text. Thursday lunch: Write one email. Sunday afternoon: Make one call. Total time investment: maybe thirty minutes spread across the week.
At the end of the month, you'll have reached out to twelve people. In three months, that's thirty-six connections you might not have made otherwise. Some will lead to long conversations. Some will be brief check-ins. All of them keep relationships alive.
The system works because it's light. You're not managing a complex database or spending hours each day. You're just sending a few more thoughtful messages than you were before.
You don't need to become a super-connector. You just need to stop letting silence become the default. Pick one step from this list. Try it for a week. That's how habits start—not with a massive overhaul, but with one small thing you actually do.
Your future self, looking at a calendar full of actual connections instead of good intentions, will thank you.
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