The Connection Challenge: 10 People to Reconnect With Today (Your Soul Will Thank You!)

Who do I need to drop everything and reconnect with today? Not to ask for a favor, not to angle for advice, and certainly not to climb the proverbial career ladder—just to reconnect for the sake of it. And voilà, this top-10 list was born.

Fun, colorful animated image of people making connections
Connections, Connections Everywhere

A week ago, I started working on an article about building more meaningful professional relationships, including through LinkedIn. To kick things off, I posted a poll with this question: How often do you actively engage with connections on LinkedIn (not just read posts/profiles)—through likes, comments, DMs, tags, etc.?

I have to admit, the results surprised me (unscientific though they were). Turns out, many of you don’t engage on LinkedIn all that often. Sure, the platform isn’t perfect, and there are plenty of other ways to stay professionally connected, but it got me thinking:

  • How well am I staying connected?
  • Are there people I’ve lost touch with?
  • Is there someone I really meant to contact recently and didn’t?

Well, spoiler alert: I didn’t have great answers to any of those questions. And this from a guy literally writing an article about building better professional relationships. As. We. Speak.

Sigh.

So, I decided to issue myself a challenge: Who do I need to drop everything and reconnect with today? Not to ask for a favor, not to angle for advice, and certainly not to climb the proverbial career ladder—just to reconnect for the sake of it. And voilà, this top-10 list was born.

So, if you’re reading this, consider it your challenge, too. Nope, nope...too late...you already read this. Gauntlet thrown down!


10 People in Your Professional Network You Should Totally Reach Out to Today (I Am!)

1. The Boss Who “Got” You

The one who appreciated your quirks and brilliance. They championed your work once, and they might just offer some fresh wisdom or career tips again.

2. Your First Job Buddy

Remember fumbling through the office together trying to find the right printer or figure out how to use the coffee machine? A nostalgic “Remember when…?” message could spark a long-overdue conversation.

3. The Mentor Who Changed Your Life

No hyperbole. This person changed your life in some way. Reach out to them and let them know that what they taught you, the advice they imparted, the way they coached you to become better at your job…did not go unappreciated. In fact, without them, your life would be different. Bonus: they might drop some new wisdom your way.

4. The Rockstar You Quietly Idolize

You’ve been admiring their career from afar. Time to channel your bold side—send that message! Who knows? They might even become a mentor or ally…or maybe even consider you a bit of a rockstar too!

5. The Insider at Your Dream Company

That friend-of-a-friend who works at your ideal company. Drop a casual “What’s it like there?” message—it could lead to insights or inspiration (or, heck, maybe a job down the road).

6. The Classmate You Always Meant to Stay in Touch With

You promised to stay connected after graduation but…life happened. Now’s the perfect time to reconnect. Bonus points if they’re thriving in a field you’re curious about. Demerits if it’s an ex-girlfriend or ex-boyfriend. We’re keeping this professional, folks.

7. The Team Member You Rooted For

Maybe you led them, or they led you. Either way, you knew they were destined for greatness. Reach out to celebrate their success and swap stories about your journeys.

8. The Wildcard Who Knows Everyone

The ultimate networker, this person is a goldmine of connections. Drop them a line and you might unlock a whole new circle of opportunities…or just cool connections.

9. The Conference Connection

You met them at an event or training, clicked instantly, and vowed to follow up—but never really did. Now’s your chance to pick up where you left off. (Pro tip: you might need to remind them where you met.)

10. The Trailblazer Who Just Made a Big Move

They’ve landed a new role, launched a startup, or made a bold life change. Congratulate them! Everyone loves a little acknowledgment, and it’s the perfect excuse to reconnect.


Reconnect Your Way

However you do it, make a conscious effort to reconnect with people in your network this month. Send a quick note, a DM, or even suggest meeting up in person (whaaa!). Just, for the love of all that is good and holy, please don’t send a boring “Hi, hope you’re well” message. Add some personality, for gracious sakes (as my grandmother used to say). One of my messages is sure to read something like: “Hey joker, remember when you fell asleep at your desk after pulling that proposal all-nighter? You still snoozing on the job?” Make it fun and personal so they can’t resist replying.


Your Turn: The Connection Challenge

Who’s on your list? Your boss-turned-mentor? The classmate you always meant to email? The ex (nope, nope...that's to make sure you're still paying attention)? Take the Connection Challenge and reconnect with 10 people this week. Your soul—and maybe even your career—will thank you. Oh, and keep an eye out for my upcoming article on building more meaningful professional connections…because if you do this challenge, that article might just hit home.

P.S. Please go call your mom first. This list is just about professional connections and staying in touch with them. Not friends and family. Seriously, call your mother!

Coming Soon