Breaking the Long Silence
There’s a particular kind of anxiety that comes with opening an old LinkedIn chat or searching for someone you haven’t spoken to in years.
You hover over the “Message” button and think:
“Is this going to feel like I’m only reaching out because I need something?” “If I cared, why haven’t I stayed in touch all this time?”
That hesitation is real. And for a lot of us, it’s enough to keep us from reaching out at all.
But over the past month of intentionally reconnecting with people I’ve worked with or known in previous chapters of my career, I’ve learned something simple and important:
I’ve crossed paths with a lot of genuinely great people, and it's great to catch up with them.
That sounds obvious, but it runs counter to the story many of us tell ourselves.
The Awkward Fear: “They’ll Think I Want Something”
Most of us don’t want to be that person—the one who only pops up when they’re job hunting, prospecting, or “circling back” for a favor.
So we overcorrect.
We avoid reaching out at all. We wait for a “better time” (which never comes). We decide it will feel fake or opportunistic, so we do nothing. The result is that years go by and people who were genuinely meaningful to us—colleagues, managers, mentors, peers—fade into the background.
The irony is that this outcome is worse than the thing we’re trying to avoid.
We don’t want to appear transactional, so we let good relationships quietly die from neglect.
The Reality: Life Is Busy and Bubbles Shift
The older I get, the more obvious this becomes:
It’s not that we don’t care. It’s that life is full.
Careers pivot. People move. We change companies, industries, and cities. We take on new roles, new responsibilities, families, kids. The “bubble” we live and work in shifts every few years.
It’s almost impossible to maintain deep, ongoing relationships with everyone we’ve respected, enjoyed, or learned from along the way. There’s nothing malicious about that. It’s just math.
Once you accept that, the story changes:
Not staying in touch doesn’t mean you didn’t value someone.
Reconnecting after a long gap doesn’t automatically make it transactional.
A long silence is normal, not an indictment.
The real question isn’t, “Why haven’t I stayed in touch?” It’s, “Do I want to reconnect now—and can I do it in a sincere way?”
What I’ve Learned from a Month of Reaching Out
Over the past month, I’ve made a deliberate effort to reconnect with people I haven’t spoken to in a long time—former colleagues, clients, peers, and others I crossed paths with in earlier roles.
A few things have stood out:
I’ve worked with a lot of good people. When you actually start sending messages and hopping on calls, you remember: “Oh right, I really enjoyed working with this person. They're sharp and thoughtful. I’m glad I know them.”
Most people are on a similar path. Under all the different titles and industries, most of us are trying to do the same basic things: earn a living doing work that we find interesting.
People are more open to reconnecting than you think. If you’ve worked together, solved problems, or just had a positive dynamic in the past, you’re not a stranger. You’re part of their story, just like they’re part of yours.
The best conversations aren’t about “asks.” The calls and messages that have felt the most worthwhile have been where I learned from an old friend where their career has taken them, and some of the challenges they have had to overcome
In other words, it’s not complicated. It’s just two people in motion comparing notes on their careers and lives.
A Simple Rule: Reach Out When the Thought Is Positive
Here’s the practical guideline I’ve landed on:
If you see someone’s name or profile and it triggers a positive memory or feeling, that’s enough reason to reach out.
You don’t need:
A perfectly scripted reason.
A highly strategic angle.
An immediate “ask” or agenda.
You can simply say something like:
“Hey, I saw your name come across my feed and it reminded me of [project/company/time]. I’ve always appreciated [something specific]. How have you been?”
“It’s been a while, but I noticed you’re now doing X. That looks really interesting—how did you land there?”
The key is to make it about them, not you:
Let them tell you what they’re excited about.
Let them share what motivates them right now.
Let them walk you through the journey of their career since you last spoke.
If there’s a natural way for your work or interests to intersect, that will emerge organically. It doesn’t need to be engineered.
Relationships First, Opportunities Second
Does reconnecting sometimes lead to opportunities? Sure.
It might turn into:
A collaboration.
A referral.
An introduction.
Or simply someone in your corner who understands what you do.
But the best starting point is: "I’d like to know what your world looks like now.”
If that’s genuine, it comes through. People can feel the difference between being treated as a contact in a CRM and being treated as a human being you’re actually glad to know.
The Encouragement
If there’s a quiet takeaway here, it’s this:
There is far more goodwill stored in your past relationships than you probably realize.
So if you’re scrolling through LinkedIn or another platform and you see someone you haven’t spoken to in years—but their name brings up a good memory or a sense of respect—that’s your signal.
Reach out. Break the Long Silence
Not to ask for something. Not to pitch. Just to say:
“I remember you.”
“I’m glad our paths crossed.”
“I’d love to hear what you’re up to now.”
Chances are, they’ll be happy you did.