If you’re asking “will my money last?” through retirement, consider these 7 things most retirees forget
Most of us dream about a comfortable, worry-free retirement—days filled with hobbies, travel, and maybe a few lazy mornings. But the lingering question in so many minds is: “Will I outlive my savings?”
It’s a valid concern because retirement planning is rarely a straight path. Life throws curveballs, medical expenses show up, market conditions shift, and sometimes, we forget to consider the most basic factors that can make or break our financial security.
Today, I want to walk through seven things that many retirees overlook, and why each one matters for anyone who wants to ensure their nest egg truly lasts.
Let’s dive in.
1. Reevaluate your timeline
One of the most common oversights I’ve seen (and personally heard from older relatives) is underestimating how long retirement might last.
We’re living longer now than ever before, thanks to medical advancements and healthier lifestyles. A couple of decades ago, retirement might have been a 10- or 15-year period for the average person.
Now, it’s not unusual to spend 20 or even 30 years in retirement.
That’s a huge chunk of time to fund, especially if you retire early. So it’s essential to reevaluate your timeline with the possibility that you might live longer than you expect.
Consider how your spending patterns could change, whether you’ll want to work part-time for a while, or if you’ll need to budget for age-related healthcare costs that weren’t on your radar.
The more you view retirement as a long-term journey rather than a short pitstop, the better you’ll be able to plan for it.
2. Keep an eye on inflation
We’ve all heard stories from our grandparents about how cheap things used to be. A loaf of bread for a quarter. A new car for a few thousand bucks.
Inflation is an invisible force that quietly erodes your purchasing power over time, yet I’ve noticed many retirees forget to factor it into their long-term planning.
Even a small annual inflation rate can take a major toll on a fixed income, especially over two or three decades.
According to Warren Buffett, cash is almost always the worst investment. He’s referring to how inflation will inevitably decrease the real value of your savings.
It doesn’t mean you should never hold cash, but it underscores the importance of investing your money in ways that can potentially outpace inflation—whether that’s through stocks, bonds, real estate, or other assets.
Sitting on large sums of money under a figurative mattress might feel safe, but it can make your savings vanish faster than you think when living costs keep climbing.
3. Anticipate lifestyle shifts
I once had a chat with a family friend who retired from a high-pressure marketing career.
She was convinced she’d spend all her days gardening and reading. But two years in, she discovered a love for traveling. Suddenly, her annual budget had to expand to accommodate cruises, plane tickets, and a whole new set of expenses she hadn’t originally planned for.
Retirement often offers us the freedom to explore new passions or revisit old ones we never had time for.
It might be golf, photography, volunteering abroad—whatever it is, these interests can shape your spending. Many retirees forget to account for these possible changes in lifestyle.
It’s not just about paying the bills or setting aside money for medical needs. Sometimes, you’ll need room in your budget for new experiences or side projects that pop up.
So think beyond your current expectations. Even if you have a specific retirement vision in mind, remember that tastes and opportunities can evolve.
4. Plan for healthcare and emergencies
Nobody likes thinking about potential health issues or sudden emergencies, yet these can be some of the most significant expenses in retirement.
My grandfather used to joke, “The only exercise I’ll do when I’m older is walking to the fridge.”
But life had other plans—he ended up with a sports injury in his late 60s that required physical therapy, leading to unexpected medical costs.
It’s crucial to build a financial cushion for health-related surprises. Research from the Center for Retirement Research at Boston College has pointed out that out-of-pocket healthcare costs can substantially rise after age 70.
Even with the best insurance, there are deductibles, co-pays, and procedures that may not be covered.
Whether it’s a surgery, home care, or the possibility of assisted living, acknowledging these potential expenses is far wiser than hoping they never show up.
5. Understand the psychology of spending
It’s easy to see retirement as this giant, open-ended vacation. Many folks retire and, after a lifetime of working, feel compelled to indulge in experiences they postponed for years.
There’s absolutely nothing wrong with this—retirement should be enjoyed—but there’s a psychological component that often leads people to overspend in the early years.
As Greg McKeown has said, “If you don’t prioritize your life, someone else will.” Similarly, if you don’t keep tabs on your spending priorities, lifestyle creep can sneak in.
You might start saying yes to every trip or family request, or picking up a new luxury hobby without a second thought. Over time, these “little” indulgences add up.
Learning to recognize the difference between spending on what truly matters and simply spending because you can is key to making your money last.
6. Review your investment strategy
I’ve mentioned this before in a previous DM News post, but it bears repeating: Just because you’re retired doesn’t mean your money should stop working.
Too many retirees stash all their funds in ultra-conservative instruments because they fear losses.
While caution is understandable, you also want to outpace inflation and keep growing your nest egg—even if at a more moderate pace.
A balanced portfolio that includes growth-oriented assets, like dividend-paying stocks or carefully chosen mutual funds, can help you maintain a solid financial footing throughout retirement.
As you age, your risk tolerance may change, but that doesn’t mean you should avoid all risk. It’s about tailoring your investments to your comfort level and your timeline.
Consulting a trusted financial advisor could be a worthwhile step here, especially if you’re unsure how to strike that balance between safety and growth.
7. Communicate your plans
Last but not least, one thing I’ve seen retirees forget is the importance of communicating their financial realities and estate plans.
This is especially critical if you have a spouse, children, or other dependents who might be impacted by your financial decisions.
We sometimes assume family members know exactly what’s going on, but it’s amazing how often miscommunication about finances leads to stress, disagreements, or even legal complications down the line.
Setting up a will, talking about who will handle finances if you’re incapacitated, and discussing how you plan to pass on any inheritance can save a lot of confusion later. It’s not the easiest conversation, but it’s one of the most important.
Clarity about money and future intentions can spare your loved ones from guesswork and potential conflicts if an emergency arises.
Putting it all together
Retirement is a significant milestone, a time to finally enjoy the fruits of your labor.
But it’s also a stage in life that demands careful thought and ongoing attention. Here at DM News, we see it all the time: people underestimate how retirement expenses can creep up, or they skip the tough questions about health, family, and changing desires.
These are the details that often determine whether your money goes the distance.
If you keep tabs on factors like your time horizon, inflation, lifestyle changes, healthcare costs, and investment strategies, you’ll be far ahead of the pack.
And don’t forget the human side of it all—the psychology of spending and the need for honest communication. As Gary Vaynerchuk once put it, “The future is everything I care about.”
Focusing on these sometimes-forgotten essentials will help secure that future, so you can enjoy retirement rather than stress about it.
At the end of the day, retirement is about living life on your own terms. And part of that freedom comes from knowing your money will be there when you need it most.
By remembering these seven things, you’re setting yourself up for a more confident, fulfilling, and financially secure journey ahead.
