I Asked ChatGPT the Biggest Money Mistakes Parents Make — and Why They’re So Costly
Written by
Laura Bogart
Edited by
Kristen Mae
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As a parent, you want to set your children up for success in all aspects of life — including personal finance. You’re their first role model in money matters, which only compounds the pressure to get things right. But the decisions you make about your own finances can also have long-term consequences for your children, often in ways that are easy to miss.
So what is a well-meaning parent to do? For starters, you can learn about the most common money mistakes parents make — and why they tend to be so costly over time. While a financial planner can help you build a strategy tailored to your family, tools like ChatGPT can offer a high-level explanation of mistakes you’ll want to avoid.
A Note of Encouragement
When I asked ChatGPT to share the biggest money mistakes parents make and why they’re so costly, its response struck a surprisingly empathetic tone. It acknowledged that it’s hard to be a parent and that these mistakes are often driven by good intentions.
“Parents often make money decisions under pressure, love, fear or guilt — so the mistakes are understandable,” it wrote. “But some are especially costly because they compound over years or shape children’s lifelong money habits.”
1. Not Planning for Their Own Retirement
The AI noted that parents often prioritize their kids’ needs — such as college, activities and housing — while assuming they’ll “figure retirement out later.”
ChatGPT was blunt about why this can be costly both financially and emotionally: “There are no loans for retirement.” Just as they can’t turn back the clock to their grown children’s precious baby years, parents can’t recover the time their investments and contributions to retirement accounts could have spent compounding.
Parents who can’t support themselves in retirement often end up becoming a financial burden on their adult children.
“Helping kids at the expense of retirement often hurts both generations,” the AI wrote.
2. Paying for Everything Instead of Teaching Responsibility
For parents who grew up with financial instability, giving their children an easier life can feel like an expression of love. But there’s a difference between providing your children with stability and spoiling them — while inadvertently preventing them from learning money management.
“Kids don’t learn budgeting, trade-offs or delayed gratification,” ChatGPT said. “Adult children may struggle with debt, dependence or entitlement. Short-term comfort can create long-term financial dysfunction.”
Though I didn’t ask ChatGPT for solutions, I know parenting in the digital age does come with certain advantages, such as apps that help kids gain financial literacy. Popular money apps like Cash App’s Families feature let teenagers manage money by setting savings goals, receiving direct deposits and even using a prepaid Visa debit card responsibly — all with parental supervision.
When used thoughtfully, these modern tools can spark conversations about smart decision-making with money. Meanwhile, teens build confidence managing money well before they enter adulthood and are faced with all the financial responsibilities that come with it.
3. Overextending for Education Without a Plan
This mistake is understandable, since education is a gateway to professional success. However, ChatGPT warned that the parental belief that “any education at any price is worth it” can lead to risky decisions, such as subsidizing degrees with low ROI — which is a polite way of saying that a master’s degree in basket weaving may not be the most sound financial decision.
The AI cautioned against taking on Parent PLUS loans and private debt that can debilitate parents’ cash flow, forcing parents to delay retirement, work longer than planned or take on unnecessary additional stress.
“Education is an investment,” the AI said. “Ignoring return on investment can damage the whole family.”
4. Indulging in Lifestyle Inflation “for the Kids”
Between social media influencers and their peers, children are bombarded with messages about what they’re supposed to want — the latest gadget, the most elaborate vacation, the must-have experience.
Parents who want their children to fit in may try to stretch their budgets to keep up, even when they really can’t afford it. ChatGPT warned that taking on higher expenses just to keep up with the Joneses can “lock families into fragile finances. Stress increases while savings decrease.”
Worse, kids may internalize the idea that spending equals love or success — a lesson that can set them up for overspending and disappointment in adulthood.
5. Failing To Protect the Family Financially
Insurance and estate planning are rarely top of mind for busy parents. It’s easy to procrastinate or assume nothing will happen. Unfortunately, sooner or later, something will — and without life insurance, disability insurance or an estate plan, families can face severe financial disruption during already difficult moments.
“Medical events or death become financial crises,” ChatGPT said. As if this weren’t grim enough, it also noted that without estate planning documents, courts may ultimately decide guardianship and asset distribution.
Protecting your children financially means planning for scenarios you hope never occur. As ChatGPT put it: “Protection planning is about love, not pessimism.”
The Bottom Line
ChatGPT identified a clear throughline among these parental mistakes: Short-term thinking, emotional decision-making and avoiding discomfort now — only to create greater hardship later.
“The most financially successful families aren’t the ones who spend the most,” the AI said. “They’re the ones who align money with values and teach those values early.”
For parents, that may be the most important takeaway of all.
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