I once had a conversation with my aunt at a family dinner that stuck with me more than I expected. She was six months into retirement—something she’d looked forward to for years—but her energy wasn’t quite as relaxed as I thought it would be. After a glass of wine and some coaxing, she finally said it: “It’s not that I didn’t save. I just didn’t know what it would actually feel like to stop earning.”
And there it was.
Retirement struggles don’t usually happen because someone forgot to plan. They happen because real life doesn’t line up neatly with a calculator. Expenses shift. Emotions flare. The rules feel different. The systems that worked for decades suddenly feel shaky. It’s not failure—it’s adjustment. And it’s incredibly common.
So let’s have the real conversation. This is a clear, helpful breakdown of why even thoughtful, successful people sometimes hit financial bumps in retirement—and what you can do (or start doing now) to prevent the most common ones. Because this next phase of life should be one you get to enjoy, not one you’re constantly trying to manage.
Let’s start here, because it affects everything else.
A lot of people plan for retirement as if it’s a 10- or 15-year stretch. But the reality? A 65-year-old woman today has a 50% chance of living into her 90s. That’s nearly three decades of retirement—longer than some people spend working at a single job.
The problem is, if you only planned financially for a 20-year retirement, those extra years start to feel stressful, fast. This is especially true for women, who not only tend to live longer but also may carry the financial brunt of caregiving or interrupted careers.
The fix: Shift your mindset. Retirement is not one long vacation—it’s a whole new financial life stage. Planning for 30 years (instead of 20) might feel aggressive, but it’s safer—and more freeing—long term.
Also, consider phased retirement if it works for your lifestyle. Keeping part-time income flowing in those first five years can take a lot of pressure off your long-term assets.
Here’s a sneaky one. A lot of people assume their spending will naturally go down in retirement. And in some categories, it might. But not by much. And definitely not automatically.
Inflation is becoming an even bigger headache for retirees, according to the 2025 U.S. Retirement Survey by asset manager Schroders. The survey found that 92% of retirees are concerned about inflation eroding their savings—a slight bump from 89% reported last year. Plus, nearly half (45%) of respondents admitted their retirement expenses were higher than they expected.
Here’s what tends to happen: once people have more free time, they also tend to spend more—on travel, home updates, hobbies, or helping out family. You’re not waking up at 6 a.m. to go to the office anymore. You’re living. But without new income coming in, those little lifestyle boosts start to compound.
The fix: Run your numbers based on your actual retirement lifestyle, not your idealized version. Create a “core needs” budget and a “lifestyle add-ons” budget. That way, if you need to trim later, you know exactly where to cut—and what’s still sustainable.
Another fix that worked for one of my clients: simulate your retirement budget for six months before you retire. Live off your projected retirement income and see how it feels. It’s a much safer place to tweak than two years into the real thing.
Health care is the big one. It’s also the category that causes the most panic—especially once people realize Medicare isn’t quite the blanket coverage they thought it would be.
Between premiums, deductibles, prescriptions, and out-of-pocket limits, most retirees spend far more on health care than they anticipated. A Fidelity report from 2023 estimated that an average retired couple could need around $315,000 for health care costs in retirement. And no, that doesn’t include long-term care.
The fix: Start factoring in health care as its own line item in your retirement plan—not just as part of your general budget. Learn the differences between Medicare Parts A, B, D, and Advantage. Consider supplement plans early. And yes, long-term care insurance could be worth a look if your family has a history of chronic illness or you’re concerned about protecting assets later in life.
If you're still working, use an HSA (Health Savings Account) to stockpile for future costs—it’s one of the few triple-tax-advantaged accounts that exists.
Retirement comes with a weird emotional cocktail: freedom, uncertainty, nostalgia, sometimes a little panic. And when those emotions aren’t acknowledged, they tend to show up in money decisions.
Maybe you give away too much to adult kids because you want to feel helpful. Or maybe you hold everything in cash because you’re afraid of losing money in the market—even though that cash is slowly losing value to inflation.
The fix: Slow down. Check your motives. Is the decision driven by facts or by fear?
Talk to someone—whether it’s a financial advisor or a trusted peer. Set boundaries around financial support for family (yes, even the ones who say they’ll pay you back “next quarter”). And keep at least a portion of your investments working for you. Just because you’re retired doesn’t mean your money should be.
Here’s a common trap: You spend 30 years building up your retirement accounts… but when it’s time to start using that money, you don’t have a plan. So you wing it. And unfortunately, winging it can get expensive.
The order in which you withdraw from accounts—Roth IRA vs. 401(k) vs. taxable accounts—can have a huge impact on taxes, health care premiums, and how long your money lasts. It’s not just about how much you take out—it’s about when and from where.
The fix: Work with a tax-aware financial planner (or dig into the research) to create a withdrawal sequence that minimizes taxes and preserves your savings. Consider “filling up your tax brackets” early in retirement by taking strategic withdrawals before Social Security or RMDs kick in.
And yes—speaking of that—don’t forget about Required Minimum Distributions (RMDs), which kick in at age 73. If you don’t plan for them early, you could end up with a higher tax bill than expected.
Social Security is one of the most misunderstood pieces of the retirement puzzle. A lot of people take it at 62 because they’re nervous, or because they think, “I’ve earned this—why wait?” Others delay as long as possible without realizing they’re tapping other accounts harder than necessary.
Here’s the nuance: timing matters a lot. Taking benefits early reduces your monthly payout, permanently. But waiting too long, if you don’t have the savings to bridge the gap, can create unnecessary pressure on your other assets.
The fix: Run the numbers based on your health, income needs, and marital status. For some people, waiting until 70 is the best move. For others, it’s better to claim at full retirement age (usually 66 or 67) and preserve other savings. If you're married, there are spousal strategies worth exploring—especially if one partner has significantly higher earnings.
Delaying Social Security from age 62 to 70 increases your benefit by about 8%—but the trade-off only works if you live long enough to benefit from the higher payments.
One thing I’ve noticed from working with retirees (and watching my own parents navigate this stage of life) is that the people who feel most financially stable aren’t always the ones with the biggest nest eggs. They’re the ones who planned for flexibility.
Things change. Plans shift. A child moves back in. A spouse gets sick. A housing market spikes. The retirees who’ve built in margin—mentally and financially—don’t just weather the changes better. They actually enjoy retirement more.
The fix: Instead of setting one rigid financial plan, build a “Plan A” and a “Plan B” for your retirement income. Include flexible spending categories you can adjust. Keep a modest cash reserve. And revisit your plan yearly, not just once when you retire.
You didn’t work this hard just to feel stressed or limited. Retirement isn’t just about not working—it’s about building a life that reflects your values, energy, and purpose. But that kind of freedom takes strategy.
The good news? You don’t need to get it perfect. You just need to stay curious, stay flexible, and stay connected to what actually matters to you. A plan that worked for your neighbor may not work for your life—and that’s okay.
It’s never too early to start planning smarter, and it’s never too late to shift the plan.
