Picture this: my neighbor, a successful executive who’d spent forty years climbing the corporate ladder, retired last spring with what seemed like a solid nest egg. Six months later, he’s back working part-time, not because he missed the office, but because he realized he’d made a crucial mistake with his healthcare coverage that left him scrambling to cover unexpected medical bills.

His story isn’t unique. After interviewing over 200 people for various articles, I’ve noticed a pattern: the smartest, most accomplished professionals often stumble into financial pitfalls right before retirement that cast shadows over what should be their golden years.

The thing is, these mistakes aren’t about not having enough money saved. They’re about timing, assumptions, and decisions made in those critical final working years that seem reasonable at the moment but create ripple effects for decades to come.

1. Taking Social Security too early

Here’s a question that haunts countless retirees: Why did I claim Social Security at 62? The answer usually involves needing the money immediately or fearing the system might collapse.

But here’s what happens: claiming at 62 instead of waiting until 70 means accepting a permanent 30% reduction in benefits. For someone living into their 90s, that decision could cost hundreds of thousands of dollars.

I recently spoke with a former teacher who took benefits early to help her daughter through a rough patch. Noble? Absolutely. But now, fifteen years later, she’s watching inflation eat away at her reduced benefits while her peers who waited are collecting significantly more each month.

The kicker? Social Security is often the only inflation-adjusted income retirees have.

2. Underestimating healthcare costs

Remember when we thought college tuition was expensive? Healthcare in retirement makes those costs look quaint. The average couple retiring today needs around $315,000 just for healthcare expenses, and that’s with Medicare. Without proper planning, medical costs become the monster under the retirement bed.

A former colleague discovered this the hard way when he retired at 63, two years before Medicare kicked in. His COBRA premiums ate through his first year’s retirement budget in eight months. He hadn’t factored in prescription costs doubling or his wife needing unexpected surgery. Now they’re dipping into their home equity just to cover medical bills.

3. Ignoring the impact of taxes on retirement income

Do you know how your retirement income will be taxed? Most people don’t, and it’s devastating. They assume retirement means lower taxes, but between required minimum distributions, Social Security benefits, and investment income, many retirees find themselves in the same or higher tax brackets.

I watched my father navigate this minefield after thirty years in sales management. He’d maxed out his 401(k) thinking he was being smart, only to realize those required distributions at 72 pushed him into a higher tax bracket, triggering taxes on his Social Security and increasing his Medicare premiums. One decision created a domino effect he’s still managing a decade later.

4. Not having a withdrawal strategy

Which account do you tap first? Your 401(k)? Your Roth IRA? Your taxable investments? The wrong sequence can cost you years of retirement security. Most people wing it, pulling money from wherever feels right at the moment.

The 4% rule everyone quotes? It’s outdated and doesn’t account for market volatility in your early retirement years. Retiring right before a market downturn and withdrawing too much can trigger something called sequence of returns risk, basically meaning you’re selling low when you should be preserving capital.

5. Failing to protect against long-term care costs

Seventy percent of people over 65 will need some form of long-term care, yet almost no one plans for it. At $100,000+ per year for nursing home care, it’s the expense that wipes out legacies and forces family homes to be sold.

Recently, I’ve been rethinking this myself after reading Jeanette Brown’s new course “Your Retirement Your Way”. The course reminded me that retirement planning isn’t just about money; it’s about designing a life that aligns with your values while protecting what you’ve built.

Long-term care insurance might seem expensive now, but watching families scramble to pay for care while dealing with health crises is heartbreaking.

6. Carrying debt into retirement

That mortgage you thought you’d have paid off? The car loan you justified because rates were low? Debt in retirement is like trying to run a marathon with ankle weights. Every payment is money not available for living expenses or emergencies.

One couple I interviewed refinanced their home at 58 to renovate for retirement. Smart move? They thought so until they realized their fixed income couldn’t comfortably cover the new payment plus rising property taxes and maintenance costs. They’re now considering downsizing not by choice, but by necessity.

7. Not adjusting investment risk appropriately

Still invested like you’re 40? That’s a problem. But so is being too conservative. The retirement risk zone, roughly five years before and after retirement, requires a delicate balance.

Too aggressive and a market crash devastates your portfolio. Too conservative and inflation erodes your purchasing power over a potentially 30-year retirement.

8. Overlooking inflation’s long-term impact

Remember when gas was under a dollar? Coffee was fifty cents? Inflation is the silent retirement killer. At just 3% annually, prices double every 24 years. That $50,000 annual budget at 65 needs to be $100,000 by 89 just to maintain the same lifestyle.

Fixed pensions and annuities sound secure until you realize they’re usually not inflation-adjusted. Twenty years in, that guaranteed income might cover your utilities but not much else.

9. Making emotional decisions with retirement accounts

Panic selling during market downturns. Lending money to adult children from retirement funds. Investing in a friend’s business venture. Emotions and retirement money don’t mix well. I’ve seen more retirement plans derailed by emotional decisions than by market crashes.

Being the family member everyone calls for advice, I’ve heard it all. The hardest conversations involve explaining why funding a grandchild’s education might mean choosing between medications in your eighties.

10. Retiring without a purpose or plan beyond finances

What will you do on Tuesday morning six months into retirement? This isn’t a financial mistake per se, but it becomes one when depression or boredom leads to overspending, poor health choices, or returning to work unprepared.

Jeanette’s course really drove this home for me. She emphasizes that retirement isn’t an ending but a beginning for reinvention. Without purpose, retirees often spend more trying to fill the void or make costly decisions like selling homes prematurely just for something to do.

Final thoughts

These mistakes aren’t inevitable. They’re preventable with planning, honest conversations, and sometimes admitting we need professional help. Retirement should be about freedom and fulfillment, not financial stress and regret.

Looking back, I wish resources like “Your Retirement Your Way” had been available when my father first retired. The course’s emphasis on aligning financial decisions with personal values while navigating the emotional aspects of retirement transition could have saved him years of stress.

The truth is, the decisions you make in your final working years echo for decades. But armed with awareness and the right guidance, you can avoid these pitfalls and create the retirement you’ve actually dreamed about, not the one that keeps you up at night.