A Reminder About the Intersection of Money and Life

Hazy nighttime Cubs game at Wrigley Field indicating some of the best memories I've had and spent money on.

By now, you should know that I love Chicago.

It’s where I’m from, where I’ve chosen to raise my family, and where I primarily invest in real estate.

Last night was a good night for Chicago sports fans.

My favorite team, the Chicago Cubs, won a playoff series for the first time since 2017.

While watching the game at home, I couldn’t help but think of how different my life is today than it was in 2017.

Back then, I had season tickets and rarely missed a game. My wife and I were just about to get married. Life was good and about as easy as can be.

From a financial perspective, we were pretty boring.

By the way, being boring with money is not a bad thing.

When it comes to money, boring is good.

Back in 2017, my wife and I each made good incomes as attorneys. More importantly, we were happy saving a lot of the money we earned.

We rented an apartment and had minimal expenses besides travel and our social lives.

At that time, we had a good amount of savings because we were planning to buy a house after the wedding.

Our only investments were in retirement accounts, like a Roth IRA and 401(k). We didn’t own any real estate.

Life’s a bit different for me now.

I don’t have season tickets anymore. We don’t travel as much.

We have three kids and different financial priorities.

Life is better than ever, but maybe not as easy as it was in 2017.

OK, what does all this have to do with baseball?

Last night at home, while watching the Cubs pull out a stressful victory, I started thinking about these things. I wasn’t in the crowd like in 2017, but I knew exactly how the fans were feeling.

Each pitch was tense. The crowd went nuts after every Cubs hit or strikeout by a Cubs pitcher. Whenever the San Diego Padres had a rally going, every Cubs fan was nervous.

In the end, the Cubs pulled out the victory and thousands of people now have memories they’ll never forget.

There’s nothing better than playoff baseball. I love it and hate it at the same time.

Watching the game, I thought of some of my favorite baseball memories. It was a good reminder of why it’s so important to think and talk about money.

We say it a lot around here: money is only a tool. When used properly, you can use money to build lifelong memories. You can create stories that you’ll remember for the rest of your life.

Stories like the ones I have from 2016 when the Cubs won the World Series.

That’s when I met Phil and April.

My nice friends, Phil and April.

Throughout that World Series run, we sat next to the nicest couple in the world, Phil and April.

Phil was a diehard Cubs fan. April was more reserved.

Both were smart and very friendly. They were enjoyable people to sit with.

We chatted baseball, mostly. Pitching changes. Send the runner. Question the manager. That sort of thing. Completely normal, unremarkable stuff. 

Until Game 5.

Game 5 was played on a crisp, October evening. Jackets and beanies weather in Chicago. Phil and April were sitting next to my brother and I, as usual.

Mike Napoli was playing first base for Cleveland. Around the 3rd inning, a jerk four rows in front of us taunted Napoli with a crude, juvenile insult.

It was apparent the jerk was doing his part to keep Old Style in business for another year.

None of us liked what this jerk yelled.

Phil especially didn’t like it.

Phil was nice…and tough.

Phil did what the rest of us were thinking but were too scared to do ourselves.

Phil stood up. In so many words, Phil sternly recommended that the jerk knock it off and show some class.

The jerk turned around, aggressively scanning the crowd for the man who had publicly shamed him. The jerk had that unmistakable look in his eye that meant, “Let’s dance.”

My brother and I were a bit worried for our nice… and all of a sudden tough…friend, Phil. 

Phil’s wife, April, did not look worried. She sat there like nothing strange was happening. Almost like she had seen this movie before.

When the jerk locked eyes with Phil, he immediately saw that Phil was not backing down. If anything, Phil looked a little too eager.

Well, the jerk was sloppy, but he had enough sense to recognize that he wanted no piece of Phil. He wisely turned back around and sat down quietly. 

That was the last we heard from the jerk that night.

Our nice (and tough) friend, Phil had restored order.

chicago cubs sing lit up reminding me of why we spend money.
Photo by Dastan Eraliev on Unsplash

Phil’s on TV!

On the day of the Cubs’ championship parade, my brother called me excitedly, “Phil’s on TV! Phil’s on TV!”

It didn’t register right away who he was talking about.

When I turned on the TV, sure enough, there was Phil, our World Series friend. I was so confused. Phil was giving an interview on set with the Cubs announcers.

Our nice (and tough) friend, Phil? On TV? 

I turned up the volume and listened to Phil talk about his experience watching the Cubs win the World Series. Maybe I was hoping he’d mention his nice friend, Matt. (He didn’t.)

I still couldn’t figure out why Phil was on TV. 

Why won’t they just put his name on the screen already!? 

It wasn’t until the end of the interview that I learned who Phil was.

All I could do was laugh. 

Our nice, and confirmed tough, friend Phil is better known as World Wresting Entertainment (WWE) champion and icon, CM Punk.

Oh, and his wife?

WWE champion and bestselling author, AJ Mendez.

Unknowing watching the Cubs win the World Series with two celebrities with a combined 3.5 million Instagram followers?

Yup, that’s a story I’ll be telling for a while.

A memory I wouldn’t trade for anything. 

As much fun as the World Series was, my favorite Cubs memory actually took place during the 2015 season, the year before they won the World Series.

It was during the 7th inning of Game 4 of the NLDS. This was the game where the Cubs knocked the rival St. Louis Cardinals out of the playoffs.

In the 7th inning, with the Cubs up 5-4, Kyle Schwarber hit one of the most epic home runs in Cubs history, landing his moonshot on top of the new right field video board.

It was such a feat, the ball is now enshrined where it landed.

The entire stadium was rocking so loud, you could feel the ground shaking beneath your feet. Every fan was jumping up and down, hugging anyone close enough to touch.

We were all dancing like nobody was watching. That moment was pure happiness. 

I was there with my mom.

A lifelong Chicagoan, she too was jumping up and down and high-fiving all the other diehard fans in our section.

After the game, we met up with my wife at a restaurant and relived the victory over Champagne.

That day with my mom and my future wife is one of the best memories I have.

clear wine glass holding champagne, one of the best memories I have with my mom and spent money on.
Photo by Oliver Sherwin on Unsplash

What does this have to do with money?

What does any of this have to do with money?

When I say money is a tool to create stories and memories, this is what I mean.

My brother and I still joke about our nice friends, Phil and April. I wouldn’t trade that memory with my mom for anything.

These are the types of experiences that I want more of.

These memories, and the desire for more like them, continue to motivate me today.

I want to be good with money, not so I can stash it in the bank, but so I can use that money to create joy for me and my family.

Beyond that, watching the crowd at Wrigley Field last night reminded me of why I started a personal finance blog.

It excites me to try and help people make intentional money decisions for meaningful experiences with meaningful people.

Talking money is really just talking life.

You may not be a baseball fan, but this conversation illustrates a foundational concept of Think and Talk Money.

Yes, we discuss money.

But, we’re really talking about our lives and our experiences.

Money is just a tool to help us. 

And before you get cynical on me, of course money is not required for good experiences. That’s not the point.

What I’m suggesting is that if we’re all spending so much of our time each week at work, shouldn’t we spend some time thinking about the money we earn so we can maximize experiences like I had with my mom? 

Think and Talk Money is all about awakening that thought process so we can use the tool of money to fuel meaningful lives.

You might not use that tool to get Cubs tickets.

But, what if you started thinking about money as just a currency that you trade to get your time back so you can do more of what you want with who you want?

Whatever it is that you’re after in life, thinking and talking about money will help get you there.

Have you used money as a tool recently to create stories and memories?

Let us know in the comments below.

Disclosure: This page contains affiliate links, meaning I receive a commission if you decide to purchase using my links, but at no additional cost to you. Please read my Disclosure for more information.

© 2025 Matthew Adair

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