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Start the year informed. Not overwhelmed.

It seems like every quarter I have a viral LinkedIn post like the one below.

A lot of people don’t know this, but the origin story for Habits stems from my own experience.

This past Sunday didn’t start with a plan. It started with a text.

I was in Houston. Buried in what was easily one of the most intense weeks of work I’ve had in a while. We’d just launched an invite-only pilot that was finally showing signs of life. Hiring conversations everywhere. Fundraising threads open. Product things breaking and being fixed at the same time. Content deadlines. Ideas flying. One of those weeks where you look up and realize seventy hours somehow disappeared before Saturday even showed up.

Then a friend I’ve known since childhood texted me. He said he could get us 100-level tickets behind the Rams bench for the Bears playoff game. Pennies on the dollar. He just needed an answer fast.

I don’t remember typing yes. I just remember scrambling to pack on Saturday morning.

By that afternoon I was landing in Chicago, stepping into a beautiful ten-degree welcome, dragging my bags onto the Blue Line, and crashing with one of my closest friends from elementary school and his wife. They’d just gotten married and I hadn’t seen them since the wedding. That night, a group of us bounced around Division. Old stories. New arguments about books, shoes, nothing, everything. No filters. No posturing. Just people who’ve known each other long enough to not pretend.

At one bar, the bartender tossed us a few shots of whiskey on the house because he liked our energy. One of the many dumb takes that night was that people who do Dry January might actually need Dry Social Media more. Less scrolling. More showing up. That kind of thing.

We ended the night watching the Bastogne episode of Band of Brothers, mostly as mental prep for the weather we knew was coming. Not a comparison. Just inspiration to survive Soldier Field.

Some of the best weekends begin when you stop trying to optimize them.

Sunday morning was slower.

Coffee with my buddy and his wife. The real update. Talking about buying a home. Kids. Travel. The stuff that only comes up when no one is rushing anywhere. After that, I rode the train to a diner off Fullerton in Logan Square. Cozy Corner. Absolutely fire.

Decked out in Bears gear, I sat alone with a breakfast burrito, orange juice, and a stack of pancakes. The breakfast of champions.

One of my resolutions for ‘26 includes trying to spend less time on social media (I recognize the irony), but because I wasn’t glued to my phone, I ended up talking to the couple next to me. Late twenties. Just moved to Chicago. Lions fans, unfortunately, but rooting for the Bears that night. We swapped recommendations. They asked about neighborhoods. We laughed about how hard it is to meet people without an excuse these days.

After breakfast, I grabbed my luggage and headed to my brother’s place nearby. New apartment. Beautiful. We caught up on everything since the holidays. He and his girlfriend loaded me up with extra hand warmers, a better hat, and some toe warmers that ended up being completely useless.

Then I went to Omri’s. He moved to my hometown junior year of high school and immediately became the tenth member of our friend group. The kind of friendships built on shared embarrassment, not taking each other too seriously, and knowing exactly when to show up if something actually matters.

A drink or two. Then the train south to meet up with some college friends tailgating in Waldron Lot. Our pilgrimage included a 30min ride on the Red Line and then a healthy 30min walk (because Soldier Field is the most inconvenient place to get to in the entire city). Upon our arrival, I bumped into fraternity brothers and friends from my alma mater who I haven’t seen in years. We took turns reminding one another of stories from the past. Nothing scandalous. Mostly dumb. Mostly funny. Mostly proof that time doesn’t erase shared history.

Connection doesn’t require novelty, it requires presence.

Then we walked into the stadium.

Section 112. Row 8. Snow falling like a snow globe. Lights on. Skyline fading into black. We turned strangers into friends in about fifteen minutes. I grabbed a polish sausage with everything on it, a Miller Lite that turned into a slushy almost immediately, and settled in.

By the second quarter, my feet were gone. Cinder blocks. Painful to walk. Every bathroom run felt like a religious experience because it was warm. The score was tied at ten at half, which if you’ve watched the Bears this year, felt like a miracle.

Then came the fourth quarter.

Caleb Williams threw one of the most insane playoff passes I’ve ever seen. In a fraction of a second, I was hugging strangers, beers flying, Omri and I screaming into each other’s faces. It was pure chaos. The good kind.

But alas…overtime didn’t go our way. And losing sucks.

The walk out was brutal. Minus ten with wind chill. Soldier Field doing Soldier Field things. Eventually we made it home, took hot showers, recapped the night, and passed out.

Lying there, feeling my toes slowly come back to life, responding to a few texts, I realized something that surprised me.

I hadn’t once thought about how much the weekend cost. Not the flight. Not the ticket. Not the food. Not the drinks. I wasn’t worried about my slate of meetings beginning at 8am CT (the curse of ET). I wasn’t stressed about explaining my hoarse voice to customers or why my face looked like it lost a fight with the weather.

Money never entered the mental equation.

And that’s the point.

Sometimes the best use of money is when it disappears entirely from the experience. When it stops being something you manage and becomes something that quietly enables a memory you’ll carry forever.

If you never forget what something cost, it probably wasn’t the point.

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