“The hardest friend to keep is the one who’s winning.”​
(2-3 minute read)

Hey Reader,

I’m going to admit something that I think a lot of people feel but almost nobody says out loud:

Sometimes your friend wins big… and a tiny part of you hates it.

A few months ago, a close friend of mine landed a massive deal. Career-changing stuff.

And my first reaction was genuine excitement.

My second reaction...maybe half a second later...was:
“Damn. Why not me?”

I didn’t like having that thought. But I also realized it didn’t make me a bad friend. It made me a human being with ambition, insecurity, and a functioning nervous system.

That’s the part nobody really prepares you for.

Friendship can get surprisingly complicated when one person hits a new level.

Not because you stop loving them. Sometimes because you start comparing your life to theirs without even realizing it.

I“I’m happy for my friend… but it also messed with me more than I expected.

And honestly? It happens to the best of 'em.

👥 THE FRIEND: Magic Johnson & Isiah Thomas

In the 1980s, Magic Johnson and Isiah Thomas were incredibly close. They talked constantly. Hugged before games. Kissed each other on the cheek courtside long before male athletes publicly showed affection like that.

Then came Lakers vs. Pistons.

NBA Finals. Championships. Legacy.

And somewhere along the way, the friendship cracked.

Not because either guy was evil. Just pressure, competition, ego, media noise, and the strange emotional math that can happen when two people are chasing the same thing at the absolute highest level. Maybe Magic couldn't accept Isiah leveling up. Maybe Isiah couldn't take that he never reached the level of public adoration that Magic got (Maybe the rumors of Isiah spreading rumors were true!)

Years later, they reconciled publicly. But both have admitted it was never fully the same.

Because comparison changes the temperature of a friendship. Quietly. Slowly. Sometimes without either person noticing until the room already feels different.

🛠️ THE FIX: Don’t Turn Your Friend Into Your Scoreboard

The moment a friend starts winning, it becomes very easy to accidentally start measuring your life against theirs.

That’s when things get weird.

Their promotion starts feeling connected to your lack of one. Their relationship makes you question yours. Their momentum makes you feel stuck.

And if you’re not careful, you slowly stop seeing your friend as a person and start seeing them as a mirror.

That’s the trap.

A healthy friendship should expand your sense of what’s possible, not shrink your sense of self-worth.

Your friend getting the thing you want doesn’t mean there’s less left for you.

It just means somebody close to you proved it can happen.

And honestly? One of the most underrated skills in adult life is learning how to stay genuinely close to people during seasons where they’re thriving in ways you aren’t.

Because if you can do that, without pulling away, keeping score, or making their success about your failure, your friendships get deeper instead of more fragile.

🎬 THE RECO: THE LOGO

The Jerry West doc on Amazon Prime. Talk about a guy who could have turned bitter. One of the all time greats, the LOGO...only one ring some how.
​
What struck me most wasn’t the basketball. It was how clearly you see the emotional cost of ambition and competition...even for people at the absolute top of their field.

This week, if someone in your life is having a winning season, don’t disappear on them.

The friends who survive your best season are the ones worth keeping forever.

Until next Monday,

Matt Ritter

The Friendship Guy

“Friendship is the original life hack.”

🎧 Listen to The Buddy System on Audible​

⏩ Forward this to a friend who’s in a winning season right now. Let them know you see it. They can join the Friendship Challenge here.​