Your Weekend Overthinking Won't Fix Your Life

Make a friend, instead

Welcome to Freedom Focus—your weekly dose of career and work-related rants and insights from a multi-hyphenate young professional obsessed with escaping the 40-year-in-a-cubicle blueprint.

You might’ve come for the remote work tips. You’ll probably stay for the feeling of being seen in your hunger for a freer and more intentional life. Pull up a chair and let’s get you a Spritz.

There’s something that has been occupying my mind a lot since last weekend: the loneliness so many of us in our 20s and 30s have quietly accepted as our default mode, often without even realizing it.

The thought came to me during yet another wide-open Sunday I was blessed with—no preset plans, just hours to fill as I pleased.

Instead of starting the day with joy and making the most of that spacious, exciting freedom, though, I threw one of my worst “5-year-old-in-the-body-of-a-30-year-old-woman” tantrums.

Directed, unfortunately, at the kind presence of my partner.

Now, this took place after what I’d call a pretty lively 48 hours

…a party at our place, friends, wine, followed by a slow morning of coffee and pastries, and then more friends, another party, and more wine.

By the numbers alone, come Sunday, I should have felt fulfilled.

I should’ve been the kind of woman who pops up on your Instagram feed, ready to put on her red light therapy face mask (which, for the record, I don’t own—**donations accepted via Buy Me a Coffee BELOW**) and sink into a peaceful “Sunday wellness routine.”

Or at the very least, I should’ve tackled my long-overdue adult to-do list (read: the meal prep I’ve been promising myself since January 1st, 2025).

But no.

Instead, I woke up in a full-on rut, and the next thing I knew, I was crying over the sponge while washing dishes from the Friday party.

As tears slid down my cheeks in the most unnecessarily dramatic way possible, I gave myself a pep talk:

“CATERINA! You’re the woman who’s moved to multiple countries alone. Who’s traveled solo a thousand times. What is happening to you, girl?? Why so fragile???”

Honestly? I didn’t have an answer.

But I did know something was off.

And thanks to the many hours of meditation collected during my Petty Goals Summer Detox (wrapped successfully on July 31), I was at least able to hear myself clearly.

And what I heard was this:

I wasn’t done socializing. I still needed more connection.

So I did what any millennial living abroad would do:

I scrolled through 30 different platforms, groups, and Instagram pages, trying to find a girls’ event that didn’t come with a $40+ price tag—because yes, this is NYC, where even making friends has been commodified under slogans like “third places!” “girlies’ date!” and “find your village!”.

Eventually, I posted in a “last-minute plans” chat from a women’s Facebook group in Brooklyn.

And guess what?

A girl replied. We went on a two-hour walk through a gloriously sunny Prospect Park.

Needless to say, I came home a normal human again.

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That one walk got me thinking about the difference between city life and small-town life

…and how folks like me in our 20s and 30s might need to radically rethink how we approach our weekends.

I’ve lived in plenty of big cities scattered around the world—Lisbon, Rome, Warsaw, Seoul, now New York.

And although I’ve only ever lived in one small town (my hometown in Italy), I’ve noticed a pattern:

Sundays in a big city are a mousetrap for the overthinker.

They’re the days when we spiral into career rumination, second-guess life choices, and make empty promises to fix the existential void.

So after falling into that trap one too many Sundays, I finally realized:

The problem isn’t my life. Nor my past or future career decisions.

It’s my loneliness.

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Weekends are meant for company

Sunday, in particular, is one of our only two days off—and yet we’ve stopped honoring it the way it deserves.

We’ve capitalistically repurposed it into a prep day for the workweek.

Where are the long Sunday lunches?
The family gatherings or the post-Church chit-chat?
When did we stop honoring real diversion and start giving ourselves a really hard time by staying alone with our thoughts?

I love the concept of low-stakes friendships—the ones that don’t require endless coordination or moving mountains to meet.

As

Rosie Spinks

writes so compellingly in her essay ‘The friendship problem’:

“Add in the pandemic, which I think has accelerated this, and we’ve lost entire categories of social interaction that used to foster friendships, especially low key ones. Our lives are bereft of ways to see people in the low-effort, regular, and repeating ways our brains were designed to connect through.”

As much as I don’t want to join the Substack chorus that romanticizes life across the pond, last Sunday reminded me of something about my lifestyle there:

in Italy, it doesn’t matter if you already saw your friends on Friday night and again on Saturday afternoon and Saturday night. If you're free on Sunday, you’ll still meet them for coffee, a walk along the promenade, or an aperitivo. You’ll probably end up playing with your friends’ kids (who are passed around from lap to lap and teased lovingly by the group). If you’re feeling adventurous, you’ll visit a nearby borgo—a tiny medieval town with a castle perched on a hill.

But here’s the important part:

You won’t talk much about work (at least not in the existential way we do with ourselves when we’re alone).

You won’t be “working on yourself.”

You won’t be strategizing your five-year plan.

You’ll be living. You’ll be laughing. You’ll be regenerating.

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I don’t have a perfectly packaged solution for you

But what my Petty Goals Summer Detox showed me is that the quote “if you worry, you suffer twice” has never been truer.

I’m becoming increasingly allergic to my own complaints and obsessive life troubleshooting.

Because truthfully? I’ve never heard anyone say their endless ruminations helped them solve a real problem.

On the other hand, I’ve met plenty of people who stumbled into their next chapter in life through a random chat with a random person.

So maybe the problem isn’t the decision you made in 2021, or whether its ROI was worth the trouble.

And the solution won’t be found in overthinking it all while biting your nails on the couch.

Maybe the real problem is just that you’re alone with your thoughts on a random Sunday.

So do yourself a favor—don’t spend this weekend alone.

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Thanks for reading Freedom Focus! While I’ve been a bit AWOL lately, I’ve been trying to walk the talk—if not by fully re-creating in NYC those low-effort, Italy-style friendships (which, let’s be honest, might not even be possible in a city of 8 million)—then at least by getting out of my mind and into my life more often. That shift has already led to plenty of spontaneous, inspiring chats—some in person, others online. One of those conversations even landed me in a Guardian article on the digital nomad lifestyle (!).

At the end of the day, it’s all part of this slightly clumsy commitment to being a bit more present, a little less neurotic, more trusting of life’s default uncertainty, and… OK, I’ll stop here before I start drafting a letter to my ideal self.

As always, thank you for being here.

If you’d like to support my writing, you can fuel it with an overpriced—but deeply appreciated—Brooklyn cappuccino, a subscription, or by booking an office hour to chat about whatever’s troubling you in your life or career right now.

Until next time!

Yours,
Caterina