Parents reflect on their biggest money regrets

I recently asked my mother, "Do you have any regrets about the money decisions that you made with me?"

Her response: "Too many to name now. Real Housewives is about to come on. I'll email you later."

She never did. And I suspect that she avoided following up with me because she didn't want to be bothered with the weight of regret. But if she had taken the time to list a few things, she probably would have said something about how she spoiled me too much — that she shouldn't have bought me so many Barbies or that new Dodge Shadow when I turned 16. I believe that my mom thinks that all of those purchases somehow added up to my penchant for spending rather than saving.

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She may be right. But I'm sure that a nurture-nature combination was at play. Besides, I've long since let my mother off the hook for whatever bad money habits that she might have passed along to me … now if only I could get her to let herself off the hook too.

But that's the thing about parents: Their wouldas, couldas, and shouldas can haunt them for a lifetime. In fact, I've yet to meet a parent who isn't somehow saddled with the things they wish they'd done differently with their kids.

When I asked other parents of grown kids the same question that I asked my mother, their responses were thoughtful and surprising. What wasn't surprising, however, is the fact that not a single one of them said, "Regrets? I have none."

"I should have … invested more in my family"

"Looking back, I'd have spent more time with my three boys when they were younger. I was a small business owner, and at various points in their lives, I ran a construction business, a farm equipment company, and a car dealership. The construction business was especially expensive — I paid $5,000 a month to Caterpillar alone. So I worked a lot of hours, overseeing projects, drumming up new business, and securing high-paying contracts to make sure that my expenses at home and work were always covered. When you've got 50 employees looking to you for a check every week, you feel responsible for their families, too.

But, in hindsight, I would have cut back on my hours — even just a little bit — so I could go to a few extra baseball games. Our family would have still had a comfortable life, even if I hadn't been working so much. I also wish that I'd put more money into travel. Although we took some small road trips, I really should have sprung for a big cross-country vacation to Washington to see the big timber." —Bill West, 80, retired

What Bill's son has to say … "It's true. Sometimes Dad would go to work on a Monday, and we didn't see him again until Saturday. And those road trips we took were actually business trips disguised as vacations! Dad would talk business during the day with equipment dealers and farmers — and then we'd go to a ball game in the evening before driving back home.

For years, up until my mid-30s, I worked nonstop, just like my dad. I had a slogan that no job was too small. If somebody wanted to pay me to teach an extra class at a different university or provide counseling somewhere, I said yes. It didn't matter if I never had a weekend or an evening off. But since getting married and having two kids, I've slowed down. I make it home for dinner most evenings, and I only travel for work five days a month. Before I had children, I was away nearly three times as much.

But my father's hard work ethic also had a positive impact: He was always practical with money, and I try to be the same way — when my boys get older, I'll pass that along to them, as well. Dad drove the same jeep for 15 years, and he believed in living slightly below your means. People say that you should have three months' worth of living expenses saved up. Well, I have five. Instead of putting 10 percent of my income into retirement, I put in 20." —Steve West, 43, professor and counselor

"I should have … been better about teaching proper budgeting"

"I regret that my two youngest kids, who are in their early forties, can't follow a budget as adults. When I was their age, I had a financial plan — and I worked that plan. The very first thing that I did with every paycheck was to put 20 percent to 25 percent of it into savings. I started with just $20 from each check, and then I gradually put away more. Thanks to this approach, I'm confident that I won't outlive my retirement savings.

But although I was smart about my own budgeting, when it came to my kids, I wish that I'd taken the time to sit down with them as early as junior high school to show them my budget, so they could see how it was done. I also wish that I'd taught them to save for retirement as soon as they got their first jobs.

My daughter Consuelo started working part-time at the skating rink when she was in junior high school. At such an early age, it's not like she had any overhead back then, so I encouraged the bad habit of letting her spend most of her money on frivolous things. I made sure she put a little aside in a savings account, but we're talking $10 a check, so it wasn't much.

It wasn't until she was in her mid-20s that I finally sat her down and showed her how to create a budget, line-by-line and expense-by-expense, including retirement savings — but by then, she'd already been doing what she wanted with her money for more than a decade. And you know the saying about old habits dying hard. Well, I wish I hadn't waited so long to take the hands-on financial approach with my daughter." —Irene Holland, 63, retired

What Irene's daughter has to say … "If there was one thing that Mom taught us, it was how to save: From the time I was 12 years old until I graduated from high school, I always had after-school and summer jobs. And although I had to put aside a portion of my paychecks into my savings account, my mom wasn't strict about me taking out the money to do things like go shopping or eat out with friends. It was never clear what, exactly, I was supposed to be saving my money for. So when I went away to college, the savings account was mine to master — and I blew through it in my first year.

I've always had a little bit of a rebellious streak, so it doesn't matter how much or how often you tell me not to do something … if I want to do it, I will. I see a little bit of that rebel in my 18-year-old daughter, but I'm not worried about her blowing through her money when she heads to college. She's a real miser! She worked part-time in high school, and she hoarded her checks like there was a disaster coming. She just really gets the concept of having money set aside for a rainy day.

I laugh because she likes to play broke so that I will foot the bill. But I'm hip to her game. Lately, I've been making her dip into her own account when she wants to eat out with friends because I want her to know what it's like to spend wisely!" —Consuelo Cooks, 41, customer service associate

"I should have … taught my son about the pitfalls of credit card debt"

"My oldest son, Anthony, was lucky to get a full scholarship for college. The problem was that he was responsible for covering his own incidentals and day-to-day expenses — and he made ends meet by using credit cards … one too many of them. When I realized what he was doing, I was taken aback.

Still, I didn't intervene.

I don't know why — maybe it was because I felt guilty about not being able to help him out more financially. In hindsight, I wish I'd spoken up and said, 'Son, maybe it's time to slow down with the credit cards,' or sat down with him to make sure that he was truly using them for school-related purchases." —Angel Suliveras, 59, social worker

What Angel's son has to say … "Money was often tight growing up, so I was happy when I got a full scholarship to a university. My freshman year I applied for every credit card under the sun — and quickly got myself in a mountain of debt. Even if my parents had warned me against applying for the credit cards, it likely would've sounded like just another 'do this, don't do that' rule to rebel against.

I'm teaching my kids early about the importance of maintaining good credit. For example, if my son Luca wants a bike, he'll have to use the money he's saved up in his savings account or piggy bank to buy it. If he doesn't have all the money, then we'll loan it to him on credit, and he'll have to pay us back with the allowance he makes from his chores. Right now, he's only five, so we give him a few dollars here and there for things like pulling weeds and emptying the garbage cans. The idea behind loaning him the cash for a big-ticket item will be for him to feel the pain of earning money that you can't keep because you owe it to someone else. —Anthony Suliveras, 38, health-care analyst

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