Unexpected highlights from the Final Four

Read time: 4 minutes

Welcome to The Ascend Archives, a 2x/month newsletter where I share a story about a transformation, revelation, or change in thinking that has improved an aspect of my life.

Starting when I was 10 years old, my mom used to let me play hookie on the first Friday of the NCAA Men's basketball tournament every year so I could watch the games.

This was 2006 and there was no button you could click on an ESPN app to "auto generate" your bracket.

This was the real deal.

I would print out a blank bracket from the CBS website and handwrite my selections. Then I would get set up on the sofa in the living room. There was no YouTube TV back then with the split screen for four games, so I made my own the old fashioned way…I brought a TV up from the basement and had a third game running on my dad's laptop.

With a pen and a highlighter in hand I was ready. As soon as each game ended I would highlight the wins and cross out the losses.

I loved March Madness.

Twenty years later that love hasn't faded. With Michigan coming off a 3-loss season and securing a number one seed, I was stoked for this year's tourney.

It wasn't until after we won the Sweet 16 that I texted my friend Cam: "you thinking about Indy?"

He gave me a maybe.

Then once we beat Tennessee and secured our spot in the Final Four, I checked in with a few group chat of buddies from Michigan.

“Who’s down for Indy??”

I got crickets.

When I followed up with "don't all jump at once," I was met with very reasonable excuses: Easter weekend plans, too much travel recently, kids.

Hey, I get it. It's a last-minute spontaneous thing that could run anywhere from $1k to $2,500 depending on whether we made it to the national championship. People had life things happening and couldn’t drop everything for basketball.

But I was bummed.

I had pretty much accepted my fate until I was texting my friend Alex about another trip we were planning and it hit me that we used to go to Michigan basketball games together. Why hadn’t I asked him sooner? So I sent him a text:

10 minutes later Alex was in. But should I actually do it?

The logical part of the brain started kicking in. Do I really need to drop upwards of $2,000 this weekend? I went to the football national championship a few years ago, do I really need to do this too?

But as I thought it through, I kept coming back to what actually matters.

I work for myself and can work from anywhere. That means no PTO to request, no one to answer to, and no obligations keeping me home. If we made the championship, I'd just work from the hotel room for a few extra days. This is exactly the type of thing I designed my life to be able to do and here it was, staring me in the face.

Looking at the decision through that lens made it an easy choice. We were headed to Indy.

—

What surprised me about the weekend was that while I loved the actual games, my favorite moments weren't inside Lucas Oil Stadium.

Take Friday night. Everyone we talked to before the trip had said the same thing: You have to go to St. Elmo's. Get the shrimp cocktail. 

So after hearing it three times, we were set on making it happen.

We walked up at 5 PM straight into a bouncer in a suit and tie standing in front of a red carpet, who told us they were at full capacity. Bar seating was first-come, first-served but it was packed. We walked away feeling like we had missed our shot.

At the corner of the block we started thinking through a backup plan, but Alex wasn't having it.

His take was simple: we just need to get in the door and figure the rest out from there. So we went back, talked our way past the bouncer saying we wanted to check on late reservations, and once we were inside we found a lounge tucked in the back that wasn't nearly as packed as advertised. We grabbed two seats and ordered our first round of old fashions.

30 minutes later, we ordered the shrimp cocktail.

I’m not a big cocktail sauce guy but this was a famous dish so I figured it must taste good.

I took one bite and it hit like a slap in the face.

My sinuses immediately cleared and my eyes started watering. It was delicious, but damn I wish someone would have told me how spicy it was beforehand. And because St. Elmo's sits right in the middle of everything Final Four, we had a front row seat to people watch all the March Madness Celebrities. Ernie Johnson from the TNT broadcast walked in with an entourage. Bruce Pearl, the hall of fame coach was dressed in his full suit. Then our guy Jalen Rose walked in with his Michigan Varsity jacket on.

It was one of those nights that felt like it wasn't supposed to happen but ended up being one of the best of the whole weekend.

Between the Uber rides, cocktail bars, fan festivals, and spending a Sunday at a local rock climbing gym, there were so many of these in-between moments that became my favorite part of the trip.

Don't get me wrong, I'm pumped my Wolverines brought home the trophy and that made the weekend much sweeter. But looking back, I just loved exploring a new place with one of my best friends …. as cheesy as that sounds.

I’m glad my 30 year old self pulled the trigger on going to Indy. That 10 year old skipping school to watch the games would have killed him if he didn’t.

Thank you for reading! As always please reply and let me know what resonated, what didn’t, or what you question. I love chatting about this stuff!

Cheers,

Andrew