Someone in Chicago analyzes his relationship with money during tax season

An advice column where Chicago can ask questions on how to navigate life transitions, relationships, family, finance and more.

I remember a devastating morning in 2009 when my mom was dropping me off at school.

Earlier that week, I had been accepted into my high school’s National Honor Society. All I needed was orientation and $30 for dues, and then I could walk around in those fancy polo shirts all overachieving nerds wore.

Before I said goodbye, I asked my mom for the money and she dropped one of her famous phrases, “Mijo, no tengo ningún cinco.” (“Son, I don’t even have a five.”). I’ve heard that rejection for years, but that particular morning, it brought me to immediate tears.

You see, before we left home, we got a call from the hospital. My dad had been in a coma for weeks and was going into surgery with low chances of making it. My mom wanted the family together, but I insisted I had to go to school to turn in a very important essay. (Nerd.) We argued but she eventually saw through my adolescent denial and understood I’d rather be in school than lose my dad before 10 a.m.

You might be thinking, “What a brat, making his mom feel bad the day her husband could die.” I thought that, too.

But, I realize now, I could only take so much defeat in one morning.

“Your dad’s gonna die. And, oh yeah, you’re poor.”

That was 17-year-old me. At 18, I was having a different experience with money.

I moved away for college and got a $7,000 refund thanks to my scholarships.

And y’all, I went through what seemed like an unlimited amount of cash in about two months.

I got my parents (my dad survived) a new AC unit — part of my “raised right, thoughtful son” side. But I was also a teenager who never had more than $40 to spend at the mall before. So, I went on multiple shopping sprees, paid for my friends at restaurants and, when I dropped my two-month-old laptop, I easily bought a new one. (Brat.)

Within two years, money had kicked me at my lowest and made me feel a blissful — but temporary — high.

That’s why I think people take money very personally. Whether we are struggling or thriving, we look back at our experiences, look at how others use their money and think, “If I had that money, I would [insert how you’re better here].”

That’s especially true when a large sum of cash comes (or goes) our way during tax season. We want to prepare for the bad, and set ourselves up to live within the comfort money can offer. But financial comfort is different for everyone.

Personally, I like to divide my refund between treating myself to something special and paying off a scary debt. Whatever is left over goes to savings.

For more perspectives, I asked Chicagoans what the best way to spend a refund is, and here’s what some said:

Why do you need to spend it? Invest it in the stock market, let it grow, throw it in retirement accounts. Pay off bills and debt with it. Use it to make your life better. Don’t let it fatten up some company owner’s pocket.

— Dan

Depending on your tax bracket, you’re either investing in stocks or finally able to afford two bags of groceries.

— Brian

Principal-only house payment.

— John

Stock up with food and household items and save the rest. Especially at this day and time.

— Barbara

New kayak and paddle.

— Diane

I’m putting some of it into savings, and the rest of it will be put in my travel fund.

— Heather

The best way is not to spend it. It’s money you didn’t have anyway. Invest it. Sow for the future.

— Patricia