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October 9, 2025 • 13 minutes
People often say you should live without regrets. Yet for many, looking back with some sorrow over past choices is simply part of being human—especially in retirement. In fact, recent research shows that many retirees can point to specific planning steps they wish they had taken, steps that could have dramatically improved their financial readiness.
The vast majority of retirees have regrets. According to a survey conducted by Lincoln Financial Group, 62% of retirees would like to go back and plan differently for retirement. Bankrate puts the number of retirees regretting their financial choices at 74%!
Here are 15 ways today’s retirees say they would have planned differently, and how you can do better.
It’s one of the biggest regrets retirees face: fun costs money.
A recent Fidelity study found that two-thirds of pre-retirees (68%) have never created a retirement budget. That lack of planning shows up quickly once people stop working. Many assume they’ll spend less in retirement, but financial advisors see the opposite—especially in the first few years.
“Retirees often go out more—dinners with friends, vacations, hobbies,” says Mike Niemczyk of MLN Retirement Planning. “Without a plan, many find they’re spending faster than expected.”
Advisor John Soudan puts it this way: “When you retire, every day is Saturday. If your weekends usually mean golf and dinner out, imagine that seven days a week. You need to budget for it.”
The regret? Not planning ahead for the lifestyle you actually want. Or as Niemczyk warns, “Too many clients are running out of money before they run out of life.”
Takeaway: Decide what your version of “retirement fun” looks like, calculate what it costs, and make it part of your plan.
Explore these resources to help you plan for fun in retirement:
If there’s one regret that rises above all others, it’s this: not saving enough.
In fact, a study from the Transamerica Center for Retirement Studies shows that 78% of retirees wish they had saved more. And in a 2023 EBRI survey, 70% said the single best advice they’d give their younger selves was to save or invest more—and to start earlier.
The pain of not saving shows up in many ways: missing out on 401(k) matches, waiting too long to enroll, or failing to increase contributions over time. “Too many people put off saving until the very end,” says advisor Kerry Soudan of TREW Financial. “We see clients who only start thinking about retirement as they approach it—which leaves them with fewer options and greater stress.”
Saving adequately is imperative to your future financial security. And, while it is easier if you start saving in your twenties, it is never too late. Use the Boldin Retirement Planner to determine how much you need to save to support the life you want and discover strategies for achieving your goals.
Explore:
Not every retirement regret is about money. For many, it’s about time.
It’s surprisingly common to hear retirees say they wish they had stepped away from work sooner. After decades of saving and being financially responsible, the hardest leap isn’t building the nest egg—it’s trusting yourself enough to start spending it.
Hanging on to a paycheck for years after you could have retired often means trading time—your most precious resource—for security you may not actually need. And when retirees look back, that lost time can feel like the deepest regret of all.
Takeaway: If you’ve done the planning and your numbers work, don’t let fear keep you from enjoying the life you’ve earned. Retirement isn’t just about money—it’s about maximizing your time, energy, and joy while you have them.
If this is you, consider 9 ways to overcome the terror of spending your nest egg.
Skipping the occasional dinner out is manageable. But not knowing whether you can afford healthcare is a much bigger problem and a more serious retirement regret.
Healthcare consistently ranks as one of the top financial worries in retirement. Fidelity estimates that a 65-year-old couple retiring in 2025 will need about $315,000 over their lifetimes just to cover medical expenses, not including long-term care. Even with Medicare, many retirees face significant out-of-pocket costs: premiums, copays, prescriptions, and uncovered services. In fact, more than 1 in 5 retirees over 65 still carry medical debt.
For those considering early retirement, the concern is even sharper. Before Medicare eligibility at 65, private or marketplace plans can cost thousands per year, with premiums rising sharply with age. Many would-be retirees delay leaving work simply because they fear losing employer-sponsored coverage.
Takeaway: You can’t control rising medical costs, but you can plan for them. Incorporate healthcare into your retirement strategy the same way you plan for housing or travel. That means:
The Boldin Retirement Planner can give you a personalized estimate for health care costs. It also helps you figure out how to plan for a possible long-term care need and enable different “what if” scenarios for an early retirement. Seeing the numbers clearly can transform fear into confidence—and help you focus on living the life you want.
The Transamerica research suggests that a full 66% of retirees wish they were and had been more knowledgeable about financial planning.
There are a lot of considerations from investing, budgeting, debt and taxes…
Good thing you are reading articles like this one!
Many retirees look back and wish they had struck a better balance with their investments. Playing it too safe often meant their money didn’t keep up with inflation, eroding purchasing power over decades. And, research shows this may be an increasingly dire problem. Federal Reserve data shows that household balances in money market funds (a proxy for “safe cash-on-the-side”) have soared to nearly $5 trillion (from just under $2 trillion in 2018) — showing how many investors anchor too much in low-return, low-risk vehicles.
On the other hand, taking on too much risk — especially close to or in retirement — can leave you vulnerable to market downturns at exactly the wrong moment.
Retirement investment regrets aren’t just about numbers on a statement. They are about how these choices limited freedom. Being too conservative can mean saying “no” to travel, hobbies, or generosity because the money didn’t grow enough. Being too aggressive can mean sleepless nights and hard trade-offs after unexpected losses.
Quick Takeaway: Your investment mix should evolve as your life does. Boldin helps you see the long-term impact of different strategies, so you can find the balance between growth and security — and avoid second-guessing later.
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Some retirees look back and regret handing over the steering wheel. They paid thousands of dollars in fees to investment professionals and while the advice may have been fine, the cost added up and left them feeling like passengers in their own financial lives.
With the Boldin Planner, people often tell us they feel a new sense of empowerment. They still may choose to seek advice when needed, but now they understand their numbers, run their own scenarios, and make decisions with confidence.
Quick Takeaway: Don’t pay for control you can take yourself. Tools like Boldin let you own your plan, know where you stand, and still bring in expert input on your terms — not at the cost of a lifetime of fees.
And when people realize how much control they’ve given up, the next regret quickly comes into focus: the true cost of paying AUM fees year after year.
One of the biggest financial regrets we hear is paying a lifetime of “assets under management” (AUM) fees. A seemingly small 1% annual fee can quietly drain hundreds of thousands of dollars from a portfolio over the course of retirement.
Think of it this way: Would you rather leave an extra $100,000 or more to your heirs — or pay it to an investment advisor? (The simple math is stark: 1% paid on $1 million over 30 years would be $300,000 in fees.) For many retirees, that’s the trade-off. It’s not that advice doesn’t have value — it can. But paying for it as a percentage of your wealth year after year often costs far more than people realize.
Quick Takeaway: Don’t let fees steal your future. With Boldin, you stay in control, get clarity on your plan, and can still seek expert input — without sacrificing a lifetime of wealth to AUM fees.
Of course, saving money on fees is only part of the equation. Even with full control, many people still wrestle with doubt: Did I get this right? Did I miss something important? That’s where another regret comes in — not getting a second opinion.
Most Boldin users find confidence in owning their own plan. Planning increases know-how and the projections are the closest thing you’ll find to a crystal ball. However, too many people worry about whether they’ve done their retirement planning “right.” They tinker, they adjust, they stress.
The Boldin Planner gives you control and clarity — but sometimes what’s missing is simple reassurance. And, planning is complicated! A second set of eyes never hurts.
Quick Takeaway:Boldin may be do it yourself, but that doesn’t mean do it alone. The Boldin Planner puts you in the driver’s seat, and a second opinion from a trusted expert can validate your work, catch blind spots, and give you the confidence to shift from stressing about retirement to actually looking forward to it.
Classes: Check out our weekly schedule of live classes. Or, watch recorded classes via the Planner’s classroom.
Coaching: Walk through your plan with a trained Boldin Coach. They’ll help you spot errors in your data and show you how to answer your questions using the Planner.
Advice from a CFP® Professional: Boldin Advisors gives you access to a Certified Financial Planner™ (CFP®) professional for a fixed fee Retirement Plan Review and fiduciary expertise.
Taxes are a major consideration for retirees. Uncle Sam can take a big bite out of your nest egg. “Many older Americans with 401(k) plans don’t realize those monies are taxed when cashed out,” Soudan says.
“If you have half a million in your 401(k) you might be hit with a 30 to 40% tax,” he adds.
However, with proper planning, there is a lot you can do to protect your money from taxes. It just takes some forethought.
The Boldin Retirement Planner enables you to see your potential tax burden in all future years and get ideas for minimizing this expense. It takes forethought, but Roth conversions, taxable income shifts and other strategies can result in significant lifetime savings.
Retirement isn’t a straight line. You need a financial plan flexible enough to fund your life even when surprises hit—because if there’s one certainty, it’s that the unexpected will happen.
Recent years have shown how quickly plans can be tested. Inflation has already strained many retired households, and research suggests most people hadn’t factored in just how much higher prices could climb. But inflation is only one curveball. Natural disasters, market downturns, fraud, unexpected health events, or adult children needing support—the list of potential disruptions is long.
The real regret isn’t that surprises happen—it’s being unprepared for them.
Takeaway: Build resilience into your retirement plan. That means stress-testing your finances under different scenarios, keeping cash reserves, considering insurance options, and running “what-ifs” so you can see how your plan holds up. A flexible strategy can turn fear of the unknown into confidence about the future.
Here is a list of 21 risks you face and how to plan for them.
One of the best ways to guard against life’s many risks is to ensure you’ve locked in reliable income sources for retirement. According to Lincoln Financial Group, more than a third of retirees regret not choosing investments that could have provided them with a steady stream of income.
Think of it this way: while you’re working, your focus is on saving. But once you retire, the challenge shifts to turning those savings into income you can count on. A predictable paycheck in retirement—whether from Social Security, pensions, annuities, or systematic withdrawals—doesn’t just cover bills. It delivers peace of mind, helping retirees feel secure enough to actually enjoy the years they’ve worked so hard for.
Debt, particularly credit card debt, increases your cost of living. The interest you pay increases the price of the goods or services and you have less money to spend and save.
The burden of debt can quickly erode your financial security, increase stress, and compromise your ability to enjoy a comfortable retirement, as your options for earning more money or extending your working years are significantly limited compared to when you are employed.
One third of retirees regret not paying off debts sooner.
One of the simplest and most costly mistakes is not taking full advantage of an employer match on retirement contributions. It’s literally free money — and once missed, it’s gone forever. Many retirees later realize that even small missed matches could have grown into tens of thousands of dollars over their careers.
Quick Takeaway:Always contribute at least enough to get the full match. It’s one of the easiest ways to supercharge your savings and avoid looking back on free money left behind.
Whether you are far from, approaching, or already in retirement, a written plan will help put your worries to rest. However, the Transamerica study found that only 18% of retirees have a written plan.
A written financial plan is likely to make you feel more confident about your finances (the Schwab Modern Wealth Survey showed that 63% of people with a written financial plan say they feel financially stable while only 28% of those with a plan feel the same level of comfort).
Boldin Users Know the Power of a Plan: A full 95% of Boldin subscribers with a financial plan report feeling very confident (48.6%) or somewhat confident (46.4%) about their financial future.
Creating a written plan takes time, but we strive to make it easier. The Boldin Retirement Planner is widely considered the online planning system. Forbes Magazine calls it “a new approach to retirement planning.” It is comprehensive, reliable, and will help you discover opportunities for more wealth and security.
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