Financial Habits of Chicago Men: Spending, Saving Money

No one likes talking about money.

It’s taboo. It’s gauche. And it’s a source of boundless curiosity.

So today, we’re pulling back the curtain so you can see how other guys in your tax bracket — as well as outside of it — choose to spend their money.

Below, we ask three Chicagoans to share their habits and thoughts: how much they make, how they spend it and how life would be different if they had a little more.

Manager at a Public Relations Agency, 31
“If it weren’t for my fiancé, I wouldn’t consider my financial future whatsoever.”

Annual income: $60,000 ($170,000 combined HHI)
Neighborhood: River North
Marital status: Engaged, no kids
Rent: $2,400/month for a 2BR/2BA
Groceries: $135/week
Credit cards: 1
Investment plan: “Just a 401(k).”
Dining out: “Probably four nights a week.”
Overspends on: “Entertainment, travel and staple pieces of clothing.”
Hates overspending on: “Food.”
Last ‘splurge’ purchase: “Mardi Gras in New Orleans.”
Next ‘splurge’ purchase: “More leather jackets.”
Spender or saver? “Definitely a spender.”

What’s currently your biggest worry related to money?
“That we’ll never save enough to finally invest in a home. We have the cash flow, but we’re still enjoying life a lot. We continue to talk about how badly we want to own a place, but we don’t have any money to show for it to make that happen.”

Any financial regrets in the past five years?
“I borrowed money from an uncle when I was unemployed. That was the worst decision, because I could have probably survived without it and now I owe him. It’s always weighing on my shoulders every time I spend any money.”

If you made more money, how would your life be different?
“It probably wouldn’t. If I made more money, I’d have more expenses, I have a feeling. I’d fill it in with clothing or additional travel or a house cleaner once a week instead of living the exact same way and saving more.”

How do you think you compare to other Chicagoans in terms of income and happiness?
“I’m not at the bottom. I’m definitely not at the top. I’m sort of comfortably floating in the middle area. I have enough money to go out and have fun and pay rent and all of that, so I think overall I’m doing OK. From a happiness level, I’m probably above par. I’ve got a really good thing going.”

What financial advice would you give your 20-year-old self?
“Put $50 from every paycheck away into an account that you cannot withdraw from. You will not miss that money, and it will help.”

Real Estate Broker and
Small Business Owner, 33
“We’re at a point in our lives where we want to invest in ourselves. It sounds a little hokey, but that’s a decision we made.”

Annual income: $130,000 ($145,000 combined HHI)
Neighborhood: Andersonville
Marital status: Married, no kids
Rent: $2,400/month
Groceries: $350/week
Credit cards: 1
Investment plan: “All in on two small businesses and we invest in real estate.”
Dining out: “One night a week.”
Overspends on: “Travel. I’ve never once regretted anything I’ve spent abroad.”
Hates overspending on: “Surprises, like blowing a tire or someone getting sick.”
Last ‘splurge’ purchase: “A new cannabis pipe. It was $100.”
Dream purchase: “A Land Rover Defender.”
Spender or saver? “Definitely a saver.”

How are you saving for the future?
“We’ve got a large step-by-step plan. Step one is to build businesses and continue to invest and amass some liquidity. Step two would be to sell said businesses and purchase more property, and step three is more traditional: diversifying with stocks and bonds and all that.”

What’s currently your biggest worry related to money?
“I have two worries. One is a real estate market downturn before I’m liquid enough to take advantage of it. And the second thing is we don’t have health insurance. We’ve been without health insurance for a while, because with the new changes, we just flat-out can’t afford it. We’re one bus accident away from a really bad situation, and that freaks my shit out.”

Any financial regrets in the past five years?
“I have only been doing this — understanding my ass from my elbow when it comes to finances — for about five years. I’m really frustrated that I didn’t have somebody come into my life 10 years ago and explain this. There are books I should have had in my hands sooner, and there are people I should have been taking to coffee sooner. But at the same time, I’m proud of what I’ve been able to do.”

If you made more money, how would your life be different?
“I would be a dad. We want to prepared, we want to be good parents and we want to be around, but we need money. We’re hoping to start taking a swing at it at the end of this year.”

How do you think you compare to other Chicagoans in terms of income and happiness?
“Statistically, I know I’m not anywhere near the top 1 percent, but I know I’m higher than most people. On the other hand, I’m not a very exciting person to hang out with. I wouldn’t say I’m unhappy. I have an amazing wife and partner and a great reputation in the industry, but I do not have time. I don’t have any hobbies, and if we talked I’d only talk about work and that’s not cool.”

What financial advice would you give your 20-year-old self?
“It would be to read a frickin’ book on money.* Don’t overthink it. And buy something like YNAB [a budgeting software]. It costs $60, which is ridiculous, but it’s a game-changer.”

*Ed note: He suggests reading the first chapter of “Rich Dad Poor Dad” by Robert Kiyosaki and Sharon Lechter and “I Will Teach You to be Rich” by Ramit Sethi.

Lawyer, 49
“I could probably retire tomorrow if I wanted to. But I don’t.”

Annual income: $5,000,000
Neighborhood: Bucktown
Marital status: Married, two kids (elementary school)
Owns: Two homes (one in Bucktown, one in Michigan)
Groceries: $750/week
Credit cards: 2
Investment plan: Stocks, bonds and real estate. “I use an outside advisor.”
Dining out: “Probably four nights a week.”
Overspends on: “Vacations.”
Hates overspending on: “Parking.”
Last ‘splurge’ purchase: “World Series tickets. I took my uncle.”
Spender or saver? “If I had to pick one, a saver. But I do consider myself both.”

What’s one thing you want to purchase right now that’s out of your means?
“Honestly, I’d say nothing. I could say a private plane, but I don’t really want to purchase one. That sounds sort of pretentious, but anything that I want, I buy.”

How are you saving for the future?
“I have fully funded my daughters’ colleges already in what’s called a Bright Start account. I have estate-planning advice that allows me to maximize the amount of money that would be available if something happens to me. I have life insurance, and I try to be smart in terms of my estate and tax planning to minimize the cost if something were to happen to me and to maximize the amount of money that would be available to my family.”

What’s currently your biggest worry related to money?
“The economy falling apart would probably be my biggest concern. I’m well positioned but having some sort of catastrophic financial crisis that would cause the markets to go crazy would both hurt my ability to earn current income as well as my savings. Other than that, I don’t have any real worries about retirement or what the future holds.”

Any financial regrets in the past five years?
“My regret would be not investing more aggressively in the stock market and real estate. That’s in hindsight, of course. I’m pretty conservative, but knowing what I know now, I probably would have been more aggressive.”

If you made more money, do you think your life would be different?
“No. I might retire earlier, I guess … I don’t know if I’ll ever want to do nothing, but there will come a time when I don’t want to work as hard. I’m not there yet, but there is a tradeoff even now with a lot of [work] travel and spending time with the family. If I made a lot more money and were able to not travel as much, I might do that.”

How do you think you compare to other Chicagoans in terms of income and happiness?
“I’d like to say that I both make more money and am happier than the average Chicagoan.”

What financial advice would you give your 20-year-old self?
“Do what you love and monetary success will follow. And don’t sweat the small stuff. Just focus on what you enjoy doing.”