Retirement Mistakes My Boomer Parents Made That I'll Avoid
We inherit many traits from our parents, but these retirement mistakes don’t have to be among them. Here's how Gen Xers and Millennials can thrive in retirement.
"Can I borrow money?"
It’s not an uncommon question. But when it comes from a parent, it can stop you in your tracks.
Growing up, money typically flows one way: parents help kids. So when the direction flips, even for understandable reasons, it can feel disorienting. It’s like a bad version of opposite day.
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When my mother and stepfather hit a rough financial patch, I did what I could. Family is family, after all. That moment didn’t make me judge their decisions. But it has made me think more seriously about my own.
Many people their age, baby boomers, would admit to making mistakes. A recent Nationwide survey found that 55% of recent retirees say they have regrets about how they saved for retirement. More than a quarter wish they had started earlier, and 13% wish they had contributed more each year.
We’re told to honor our parents. That’s good advice for most things, just maybe not always when it comes to money. Here’s where I plan to take a different path.
"For many in my parents’ age group, money has long been a taboo topic."
Retirement was the plan. Planning wasn’t.
My mother and stepfather are both past traditional retirement age — and still working.
There are positives to that: purpose, routine and staying active. But underneath it lies a more practical reality: a lack of retirement preparedness.
As Lawrence Pon, CFP® and founder of Pon & Associates, puts it: “The most common retirement planning mistake is not retirement planning.”
In fact, only about 40% of boomers are considered “retirement ready,” according to Vanguard, and those tend to be higher-income households.
The issue isn’t just whether people saved. As Pon explains, it’s whether they consistently took advantage of the tools available to them – things like employer matches, maximizing retirement plan contributions, catch-up provisions and other tax-advantaged accounts, such as health savings accounts.
Individually, these decisions don’t seem dramatic. Over decades, they are.
In fairness, my parents’ generation lived through the shift from pensions to self-directed retirement accounts (not to mention 16% mortgage rates in the 1980s). The system changed, but the mindset didn’t always keep up. So some people operated as if things would work out on their own. For many, they didn’t.
What’s interesting is how that mindset may be shifting. The Northwestern Mutual 2026 Planning & Progress Study found Gen Z to be the most confident generation, with 58% expecting to be financially prepared for retirement, while millennials are roughly in line with boomers at 55%. That likely reflects greater access to information, tools and investment options.
For me, the takeaway is simple: retirement isn’t a finish line. It’s a long phase of life that requires ongoing attention and not something to figure out later. Or put another way: what you delay now doesn’t disappear. It just shows up later.
"[Social Security is] meant to be longevity insurance.... The real risk isn’t dying early. It’s living a long time and running short." — Natalie Pine
Treating Social Security like a discount coupon
Without enough saved for retirement, the pressure is often to claim Social Security early. That’s exactly what happened in my parents’ case, as well as in many households.
According to Northwestern Mutual, more than a third of boomers plan to claim benefits as soon as they’re eligible at 62, even though it permanently reduces their monthly income.
Claiming early can cut benefits by roughly 30% compared to waiting until full retirement age. On the flip side, delaying benefits increases them by about 8% per year up to age 70.
"Many people don’t realize how quickly they reach the breakeven threshold where they have gotten more out of the system by waiting than claiming early," says Patrick Fontana, CFP® and founder of Fontana Financial Planning.
There are situations where claiming early makes sense. But broadly speaking, this is one of the most important financial decisions people make and one of the easiest to get wrong.
"It’s really meant to be longevity insurance," says Natalie Pine, CFP® and managing partner at Briaud Financial Advisors. "For most couples, especially if one spouse earned more, it often makes sense to delay until 70. The real risk isn’t dying early. It’s living a long time and running short."
I can’t say with certainty what my circumstances — or that of the program itself – will be when I become eligible. But my goal now is to delay as long as possible for the credit rather than the discount.
Not getting an outside perspective
In my family, there was an implicit belief that things were being handled. My stepfather worked in finance, so the assumption — spoken or not — was that expertise in one area translated to a complete plan.
But retirement planning involves many moving parts. And once you factor in behavior, taxes, income strategy and long-term decision-making, it becomes clear that it’s often better to have a qualified outside perspective.
A 2025 Gallup survey found U.S. adults are most likely to turn to friends and family (43%) or financial advisers and planners (41%) for financial guidance. But the issue isn’t just whether you seek help, it’s whether you’re getting the right kind.
"A lot of people default to someone they know locally or someone focused only on investments. But retirement planning is bigger than that," Pine says. "A fee-only, fiduciary planner who looks at the whole picture tends to lead to better outcomes."
Read: How to Find a Financial Adviser for Retirement Planning.
Talk to my kids about money before someone like MrBeast does
I don’t remember many real conversations about money growing up. At least, not beyond the standard noncommittal responses when asking to buy something, like "we’ll see" or "maybe next payday." (Some of which, I’ll admit, I now use with my own kids.)
Part of that is generational. For many in my parents’ age group, money has long been a taboo topic. Though that’s starting to change. A Bankrate survey found that only 33% of boomers feel comfortable sharing their bank account balance with family or close friends, compared to 41% of millennials and 52% of Gen Z.
But keeping money conversations close to the vest can create problems for families later.
As Pine puts it: "Another mistake is simply not talking about money as a family. You don’t need to share every detail, but explaining your values and decisions can prevent confusion or even conflict later on."
This goes beyond estate planning. It’s also about making sure my kids are prepared to make good financial decisions.
If I had to guess, younger people today are far more comfortable sharing financial details because they are exposed to more conversations about money, from social media to podcasts. Even MrBeast has entered the financial space with a money app.
Nothing against MrBeast, but I’d prefer to get there first. That’s why money now comes up in our house beyond just shopping. It includes budgeting, the importance of investing and how to make decisions with it.
Yet, I know every generation tends to critique the one before it. So if history is any guide, I won’t be surprised to read one day something my kids have written about the financial mistakes I made — and how they plan to avoid them.
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