A few weeks ago, I found an Apple gift card at the bottom of my desk drawer.
I had no idea how long it had been there. And no clue if it was still valid.
I almost tossed it. But I thought, Why not? Let’s check.
Sure enough, it worked.
$100 Apple gift card just sitting there, waiting to be used.

It reminded me of something:
Old relationships are just like that gift card.
We forget they exist.
We assume they’ve expired.
We tell ourselves it’s too late to reach out.
But when you take the chance?
There’s often still value there.
The Problem
We think relationships “expire” if we haven’t nurtured them in years.
That professor who inspired you in college. The boss who taught you everything at your first job. The colleague you loved working with five years ago.
You think: “It’s been too long. They probably don’t remember me. It would be weird to reach out now.”
So you don’t.
And the connection just sits there untouched — like that gift card in my drawer.
The Big Small Thing
Reach out to someone you haven’t talked to in 13 years.
(Or 10 years. Or 5 years. You get the idea.)
Maybe you reach out to…
- A former boss who taught you something important
- A colleague from a previous job who you respected
- A professor whose class changed your thinking
- A mentor you lost touch with
- Someone whose career path you’ve always admired
That relationship hasn’t expired. It’s just dormant.
Here’s a script to send:
Hi [Name],
I was thinking about [specific memory/lesson/project you worked on together] and wanted to say hi.
Your [advice/leadership/perspective] during [time period] really shaped how I approach [relevant skill/area].
I’d love to catch up and hear what you’re working on these days.
Would you be up for a quick coffee or call sometime in the next few weeks?
Best,
[Your name]
Why this works:
- You lead with gratitude, not a request
- You’re specific about the impact they had
- You’re genuinely curious about their current work
Let me share a personal example:
I did this recently with my former boss and Harvard Business School professor, Michael Wheeler.
I hadn’t spoken to him in 19 years.
So I sent him an email telling him how much our negotiations research had shaped my approach to business.
When he replied, he even mentioned coming to see me perform in “A Chorus Line” during the time we worked together.
Here I thought he might not even remember me. Instead, he had this vivid, special memory of supporting me outside the classroom.
We reconnected. He helped promote my book, Wild Courage.
What started as a simple “thank you” email turned into a meaningful professional relationship again.
How This Helps You Get What You Want
Old connections often become your best opportunities.
They know your work. They’ve seen your potential. And they’re usually delighted to hear from you.
That “expired” relationship might be exactly what you need for your next career move.
Just like that gift card, it probably still works.
You just have to test it.