What Are You Leaving Behind?


“A new year isn’t only a chance to decide what comes next. It’s a chance to decide what doesn’t come with you.”

(2-minute read)

Hey Reader,

I'd love for you also follow me on Instagram, if you're not already. Lots of fun stuff there.

Longtime readers know I consider fall the real New Year. I made that case last year and again last week, and I stand by it.

But this week, it’s also literally the New Year for me. (sidenote - I ended up in a deep rabbit hole on what year it really is, according the Hebrew calendar it's 5787, if you want to see the debate on how they came up with that number, this is a fascinating read here)

I’m Jewish, and one of my favorite Rosh Hashanah traditions is Tashlich: you stand beside moving water and symbolically cast away the mistakes of the past year. I probably didn't crumble enough breadcrumbs if I'm being honest ;)

Most New Year’s traditions ask what you’re going to add to your life. I love that this one asks what you’re finally ready to stop carrying.

A quick word from our sponsor: Superhuman AI. Sometimes I wonder if I'm too old to bother, and then I realize I'm smart and capable, and it's actually not all that complicated if you have the right resources. This is the best newsletter I've found to help luddites like me level up.


👥 THE FRIEND: The Weight We Carry

Friendships accumulate baggage.

The invitation that never came. The apology you still owe. The friendship you’re keeping alive entirely through nostalgia. The disappointment you’ve replayed so many times that you can now perform both sides of the argument.

We carry these things because carrying them feels easier than deciding what to do about them.

But eventually, the grievance becomes part of the friendship. Sometimes it becomes bigger than the friendship itself.

🛠️ THE FIX: Make a Leave-Behind List

Instead of writing another list of goals, write down three things you don’t want following you into the next year.

Then decide what each requires:

Repair it. Release it. Or stop pretending it isn’t there.

This isn’t about forgiving everybody or pretending legitimate hurt never happened.

It’s deciding which parts of the past still deserve a place in your future.

🔥 THE RECO: Throw Away Your Dirty Shoes

I did something this week that I almost never do: I bought shoes. Two pairs, actually.

Shopping therapy has never been my thing, probably because we didn’t have enough money growing up for shopping to qualify as an activity.

I still remember one of my first stand-up jokes. Every year at the shoe store, my mom would ask which basketball players I liked.

“Michael Jordan.”

“Who else do you like?”

That’s how I ended up wearing Dikembe Mutombo sneakers.

But this week, I finally decided to stop walking around in dirty, beaten-up shoes. I bought two new pairs so I could rotate them and give myself a little more runway before inevitably ruining both.

My recommendation: throw away one pair of shoes you should have gotten rid of a year ago.

Then consider what else you’re holding onto simply because you haven’t decided to let it go.

Until next Monday,

Matt Ritter
The Friendship Guy

“Friendship is the original life hack.”

🎧 Listen to The Buddy System on Audible

P.S. What’s one thing you’re leaving behind this year? Reply and tell me.

The Friendship Habit

Helping 20,000+ busy adults build better friendships — one small move at a time. From Matt Ritter, co-host of Man of the Year, the #1 podcast on adult friendship and and author of The Buddy System on Audible. Start the seven day challenge today— and make connection a habit.

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