5 / 25 / 150

Last week, I caught up with a former boss I hadn’t spoken to in nearly a year.

We worked closely together five years ago and have kept in touch here and there. Nothing forced. Just the occasional check-in when there’s something worth sharing or celebrating.

In recent weeks, we've both been navigating our own career shifts. I had updates on Laid Off Launchpad and they had recently decided to pursue a new career path. Reaching out felt timely and relevant, but also familiar... like picking up where we left off.

That conversation reminded me of something most people overlook in a job search:

>We put so much effort into making new connections…While overlooking the ones we’ve already built.

If you’re mid-career, you’ve likely worked with hundreds (if not thousands) of professionals. These people know what you’re capable of from projects. They’ve seen your work as partners. And many would be happy to help you if given the opportunity.

Here’s the thing... It's hard to advocate for you if they haven’t heard from you.

Maybe we see their updates on LinkedIn, but years pass quickly. And as more time passes, it feels more awkward to reconnect. Unfortunately we lose touch of our biggest advocates — our former coworkers, managers, and peers.

And yet, every stat reinforces this truth: most jobs are landed through relationships.

So how do you consistently stay connected in a meaningful, non-transactional way?

The better way

He called it 5 / 25 / 150.

The 5: Call them your 'inner circle'. People you talk to weekly. You help them, they help you. These are your brain trust.
The 25: Trusted peers, mentors, colleagues, connectors—people who think highly of you and could advocate for you, but aren’t in your weekly orbit.
The 150: Former teammates, friendly acquaintances, light-touch contacts who’d gladly refer you if you were top of mind.

Each group has its own cadence. For the 5, it’s weekly check-ins. For the 25, monthly contact. For the 150, quarterly messages.

Yes, it sounds like a lot.

Yes, it takes work.

But this increases your surface area for opportunity.

When people know what you’re working on, what you’re looking for, and how they can help, they often will. But this only works if your outreach is generous. If you want the relationship to be authentic, give.

Great relationship builders reach out to just keep in touch. They stay curious about others. They share relevant opportunities. They make introductions. They offer encouragement or a resource because they can.

Over time, these small moments of generosity stack up. And when the timing is right, people will be eager to reciprocate.

That’s why the 5/25/150 system works. It forces you to think about others first which requires empathy on top of the effort.

This is one of those things... it's simple, but not easy.

How to Get Started This Week:

Audit your LinkedIn connections. Scroll slowly. Look for former colleagues, great managers, past collaborators, mentors, mentees.
Sort into your 5 / 25 / 150. Start a spreadsheet, or download a free copy of the one I created, and track who’s in which group, when you last reached out, and what matters to them. This is about relationship stewardship.
Start your outreach. It doesn’t have to be big. A thoughtful check-in, a quick email, or a note of encouragement.

Need help with what to say? Try this:

> “Hey, I’ve been reflecting on past teams I loved working with, and you came to mind. I’d love to catch up and hear how things are going for you.” That’s it.

It's about deepening relationships.

Networking is often thought of as meeting new people. But I think it's better to ask: How well do you know the people you already know?

Because those are the people most likely to advocate for you. To refer you. To help you.

And here's a simple reminder:

LinkedIn is great at creating connections. But it’s terrible at building relationships.

That’s on you.