How to Avoid the Sad Sixty


"Friendship is the only part of your life that doesn’t automatically restart in September."
(2-minute read)

Hey Reader,

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September resets almost everything.

Kids get new classrooms. Work picks up. Calendars refill. The loose rhythm of summer gives way to carpools, meetings and standing obligations.

But one important part of life doesn’t restart unless you restart it.

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👥 THE FRIEND: The Fall Friend Fade

Think about the friends you saw all summer.

At the barbecue. By the pool. On vacation. At the party where everyone promised, “We need to do this more often.”

Now look at your calendar between today and Thanksgiving.

How many of those people are actually on it?

Fall is when friendship quietly gets pushed out by everything more organized than friendship.

Your kids have a syllabus. Your job has deadlines, budgets and a fourth quarter. Even football knows exactly where it will be every Sunday.

Your friendships get a group text that says, “October is crazy, but maybe November?”

Nothing is officially canceled. It simply never gets built.

Friendship is the only part of your life that doesn’t automatically restart in September.

🛠️ THE FIX: Build Your Own Restart

On our Audible Original "the Buddy System", we call this stretch The Sad Sixty: the dead zone after Labor Day when summer plans disappear and the holidays haven’t arrived to force everyone back together.

It’s sneaky because your life doesn’t feel empty. It feels extremely full.

You’re busy. Your friends are busy. Everyone assumes they’ll reconnect once things calm down...which is code word for never.

The problem isn’t that you stopped caring about your friends. It’s that every other part of life arrived in September with a plan.

Friendship didn’t.

So don’t wait for the perfect weekend or attempt to reunite eight adults whose calendars now resemble air-traffic-control screens.

Pick one friend. Pick one activity. Put one date on the calendar.

Dinner. A game. A hike. A Sunday morning coffee. Anything concrete enough to survive the sentence, “Let’s definitely figure something out.”

If you don’t plan your fall friendships, fall will plan them out of your life.

📅 THE RECO: Take a One-Day Vacation

My move for the Sad Sixty is to go slightly bigger. A day trip. My go-to is Los Olivos, a small wine-country town about two hours up the coast from Los Angeles.

It’s far enough away to feel like we escaped, but can get back by dinner. If you ever go, you must stop at Cold Spring Tavern, an old stage coach stop, turned bar located just a short drive from Los Olivos on the San Marcos Pass. Best tri-tip sandwich you'll ever have. Plus they have live music.

If you really want to feel like you've escaped the Sad Sixty, it's important to calendar something you're excited about. Find your version: a town, trail, beach or restaurant just beyond the edges of your normal life.

A weekend away sounds awesome and dies in committee.

A one-day vacation might actually happen.

The Sad Sixty has already begun, whether you know it or not.

Don’t let Thanksgiving be the next time you see your friends.

Until next Monday,

Matt Ritter
The Friendship Guy

“Friendship is the original life hack.”

🎧 Listen to The Buddy System on Audible

P.S. Forward this to the person you want to see this fall...and make them pick the date. As always they can join the Friendship Challenge here.

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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