Financial Moves Americans Regret the Most, Broken Down by Generation
Everyone has taken a wrong turn with money at some point, but the choices people look back on with the most regret often depend on the era they grew up in. Boomers focus on retirement security. Millennials think about debt and the plans they postponed. Gen Z is already noticing the long-term effects of early financial decisions. Different costs, job markets, and expectations shaped how each group learned to spend and save.
Looking at these regrets helps explain why people approach money the way they do today. It also gives a clearer sense of what to watch out for, no matter your age. Here’s how the most common regrets sort out across generations.
Boomers: Not Saving for Retirement Early Enough
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Among baby boomers, 37% say they regret not starting their retirement savings sooner, the highest of any generation surveyed by Bankrate. That delay now limits how far their savings can stretch, especially for those who rely heavily on fixed incomes in later years.
Boomers: Carrying Debt Into Retirement
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Many boomers find themselves managing credit card balances even after leaving the workforce. With fewer ways to boost income and rates climbing, repayment gets tougher. Roughly 13% name this as a key regret. For some, that debt lingers far longer than they ever expected.
Boomers: Underestimating Health Care Costs
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Healthcare in retirement rarely costs less than people expect. Fidelity estimates that a 65-year-old retiring in 2024 will incur around $165,000 in medical expenses. Boomers who skipped long-term care planning or underinsured themselves are now facing bills they didn’t fully anticipate, sometimes forcing tough trade-offs to cover essentials.
Boomers: Missing Out on Market Gains
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Some boomers kept their money out of equities and missed decades of potential growth. The S&P 500 averages about 10% annual returns over the long term. Those who stuck to conservative strategies missed decades of potential compounding, especially if they didn’t use retirement plans like 401(k)s.
Boomers: Overspending During Peak Earnings
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Many boomers now say they didn’t make the most of their peak earning years. Rather than build a bigger savings cushion, they upgraded homes, bought new cars, and took costly trips. That lifestyle inflation now makes retirement less flexible than it could have been with tighter budgeting early on.
Millennials: Struggling With Long-Term Student Debt
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Millennials experienced college during a period of rising tuition and stagnant wage growth. Many borrowed heavily without fully understanding the long-term impact. For some, like those profiled in GOBankingRates, student loans that started at around $18,000 ballooned to over $30,000 due to interest, delaying other financial goals.
Millennials: Giving Up Control Over Household Finances
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Some millennials regret leaving financial decisions entirely to a spouse or partner. In one reported case, a woman discovered her husband had misled her about their financial situation. Experts advise shared budgeting and monthly financial reviews to ensure both partners stay informed and aligned on savings and spending.
Millennials: Letting Credit Card Debt Build Up
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Millennials often turned to credit cards during periods of economic instability, including the Great Recession and the COVID-19 pandemic. What started as manageable balances grew with high interest rates. One couple accumulated $50,000 in debt over several years..
Millennials: Skipping Insurance on a Major Asset
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A millennial couple who bought a condo in 2007 without private homeowners’ insurance lost over $100,000 when a fire destroyed the property. They relied solely on their homeowners association’s policy, which didn’t cover their unit. That experience led to long-term financial damage due to underinsuring the property.
Millennials: Avoiding Financial Planning Help
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Many millennials didn’t consult financial professionals early on. Some now say they would have made more strategic choices had they sought advice. Planners recommend periodic check-ins, especially in your 30s and 40s, to assess progress toward goals and adjust for changes in income, expenses, or savings capacity.
Gen Z: Not Building an Emergency Fund
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According to Bankrate, 21% of Gen Z say not saving for emergencies is their biggest money misstep. Many young adults ended up turning to credit cards or pulling from retirement accounts when an unexpected expense appeared. The issue often wasn’t a lack of motivation. It was the absence of a basic plan for handling a tough month, a medical bill, or a sudden repair.
Gen Z: Opening Credit Accounts Too Early
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Turning 18 often came with pre-approved offers that made credit seem easier to handle than it actually was. Missed payments, maxed-out cards, and damaged credit scores followed for many. The challenge wasn’t the availability of credit. It was being done without knowing how to manage it responsibly. Financial planners often suggest beginning with secured cards and low limits to build good habits early.
Gen Z: Borrowing for College Without a Clear Plan
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A number of Gen Z students took on loans without calculating future earning potential or building a backup strategy. Many now feel uncertain about whether their degree will lead to sufficient income to manage repayments. The regret often lies in not evaluating cost versus outcome.
Gen Z: Tapping Retirement Accounts for Emergencies
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Using retirement savings like a backup bank account came with penalties and long-term consequences. Early withdrawals often triggered fees, and more importantly, erased the compound growth those dollars could have earned. Rebuilding that balance takes time. Many regret trading for quick cash in a crisis.
Gen Z: Waiting to Start Retirement Contributions
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Only a small share of Gen Z cite skipping retirement contributions as their biggest financial mistake, but those who do now realize the missed opportunity. Even tiny amounts invested early could have grown for decades. Waiting just a few years can shrink the future balance by tens of thousands.