Retirement should feel like the reward for decades of hard work, not a source of late-night worry. Yet most of the pre-retirees and retirees I meet across Orlando and Central Florida arrive with the same handful of questions on their minds. After years of sitting across the table from families in Winter Park, Lake Mary, Dr. Phillips, Oviedo, and communities throughout Orange, Seminole, Lake, and Osceola counties, I have noticed that the same fifty questions come up again and again.
So I wrote them all down. This guide answers the 50 retirement planning questions I get asked most often, with answers tailored to people who are retiring in Florida, where the tax rules are friendlier than almost anywhere else in the country. Whether you are five years out or already retired, you can read straight through or jump to the question that is keeping you up at night.
A quick note before we begin: this is educational information, not personalized advice. Your situation is unique, and the right move for your neighbor may be the wrong move for you. Use this as a map, and then let’s build the plan that fits your life.
Knowing When You Are Ready to Retire
The first big question is rarely about investments. It is about timing and confidence. Before you can build a plan, you need to know whether you are truly ready and what “enough” actually looks like for your life in Central Florida.
1. How much money do I actually need to retire in Central Florida?
There is no single number that fits everyone, but a useful starting point is your annual spending multiplied by 25. If you expect to spend $60,000 a year above Social Security, you would aim for roughly $1.5 million in invested assets. The good news for Central Florida retirees is that Florida has no state income tax, so more of every withdrawal stays in your pocket compared with states like New York or California. Cost of living in Orlando suburbs such as Clermont, Kissimmee, and Sanford is moderate, though housing and insurance have climbed in recent years. The honest answer is that your number depends on your lifestyle, your housing situation, and how much guaranteed income you have. A personalized cash-flow plan beats any rule of thumb.
2. What is the “magic number” for retirement savings?
The idea of a single magic number is comforting but misleading. Two retirees with the same $1 million can have completely different outcomes depending on their spending, their guaranteed income, their tax situation, and when they retire relative to the market. A retiree with a pension and Social Security covering most expenses needs far less in savings than someone relying entirely on a portfolio. Instead of chasing a magic number, I encourage clients to focus on their income gap, which is the difference between guaranteed income and desired spending. Once you know that gap, you can size the portfolio needed to fill it reliably for 30 years or more. The number that matters is the one built around your actual life, not a headline.
3. Can I retire at 62, or should I wait?
You can retire at 62, but doing so usually means claiming Social Security early and locking in a permanently reduced benefit. If your full retirement age is 67, claiming at 62 can cut your monthly check by about 30 percent for life. That said, retiring at 62 can make sense if you have health concerns, a physically demanding job, or enough other assets to delay Social Security while you draw from savings. The key question is not just whether you can stop working, but how you will bridge income from 62 to whenever you claim Social Security and start Medicare at 65. For many Central Florida families, a few extra years of work or part-time income dramatically improve the long-term picture.
4. How do I know if I am financially ready to retire?
Financial readiness comes down to one test: can your guaranteed income plus sustainable withdrawals cover your expenses for the rest of your life, including healthcare and inflation? To answer that, you need a clear picture of three things. First, your real spending, not a guess but an honest monthly budget. Second, your income sources, including Social Security, pensions, and any annuities. Third, the gap between the two and whether your savings can fill it safely. I also look at your tax exposure, your healthcare bridge to Medicare, and your cash reserves for emergencies. When those pieces line up and you have a written plan that survives a bad market early on, you are ready. Readiness is a calculation, not a feeling.
5. What is a safe withdrawal rate from my savings?
For decades the common guideline has been to withdraw about 4 percent of your portfolio in the first year of retirement, then adjust that dollar amount for inflation each year. On a $1 million portfolio, that is $40,000 in year one. The 4 percent figure was designed to give a high probability of lasting 30 years through various market conditions. In today’s environment, some planners argue for a slightly lower starting rate to be safe, while others say a flexible approach that adjusts spending in down years can support a higher rate. The right number for you depends on your time horizon, your other income, and how comfortable you are adjusting spending. A withdrawal rate is a starting point, not a set-and-forget rule.
6. How long will my retirement savings last?
How long your money lasts depends on four levers: how much you withdraw, how your investments perform, how taxes and fees chip away at returns, and how long you live. A 65-year-old today has a real chance of living into their 90s, so planning to age 95 or beyond is prudent. The single biggest threat is a steep market drop in the first few years of retirement combined with steady withdrawals, a danger known as sequence of returns risk. Two retirees with identical savings and withdrawal rates can have very different outcomes purely based on the order of their early returns. This is why a thoughtful withdrawal strategy and a cash buffer matter so much. A projection that stress-tests bad timing is far more useful than an average.
Social Security Questions
Social Security is the backbone of most retirement income, and the decisions around it are largely permanent. These are the questions that come up at nearly every first meeting.
7. When should I start taking Social Security?
This is the single most common question I hear, and the answer is almost never “as soon as possible.” You can claim as early as 62, but your benefit grows roughly 8 percent for every year you wait between full retirement age and 70. For someone whose full retirement age is 67, waiting until 70 can mean a benefit about 24 percent larger, guaranteed and inflation-adjusted for life. The right timing depends on your health, your family longevity, whether you are still working, your other income, and whether you are married. For couples, the higher earner delaying often protects the surviving spouse. The decision is permanent, so it deserves real analysis rather than a guess or a neighbor’s opinion.
8. How much will my Social Security benefit be?
Your benefit is based on your highest 35 years of earnings, adjusted for wage growth, and the age at which you claim. In 2026, the average retired worker receives about $2,071 per month, while the maximum benefit for someone claiming at full retirement age is $4,152 per month. If you wait until 70, the maximum rises to $5,251 per month. The most accurate way to see your own numbers is to create a free account at ssa.gov and review your earnings record and estimated benefits. I always encourage clients to check that record for errors, because a missing year of earnings can quietly lower your benefit. Once we have your estimate, we can model how different claiming ages change your lifetime income.
9. What is full retirement age in 2026?
Full retirement age, often shortened to FRA, is the age at which you qualify for 100 percent of your earned Social Security benefit. For anyone born in 1960 or later, full retirement age is 67. For those born in 1959, it is 66 and 10 months. Claiming before full retirement age permanently reduces your monthly benefit, while delaying past it earns delayed retirement credits up to age 70. Knowing your exact full retirement age is the foundation of any claiming decision, because every year early or late changes your check for the rest of your life. If you are not sure of yours, the Social Security Administration’s retirement age calculator will pin it down based on your birth year.
10. How much does waiting until 70 increase my benefit?
Between your full retirement age and age 70, Social Security adds delayed retirement credits worth about 8 percent per year. For someone with a full retirement age of 67, waiting the full three years to 70 increases the benefit by roughly 24 percent, and that increase is permanent and adjusted for inflation every year afterward. Few investments offer a guaranteed 8 percent annual increase with no market risk. The trade-off is that you give up checks during those waiting years, so delaying works best when you have other income or savings to live on and reasonable expectations about longevity. For a healthy person with a family history of long life, especially the higher earner in a couple, delaying to 70 is often one of the most powerful moves available.
11. Can I work and collect Social Security at the same time?
Yes, but if you claim before full retirement age and keep working, the earnings test may temporarily reduce your benefit. In 2026, if you are under full retirement age all year, Social Security withholds $1 for every $2 you earn above $24,480. In the year you reach full retirement age, the limit is much higher at $65,160, with $1 withheld for every $3 above it, and only until the month you hit full retirement age. Once you reach full retirement age, there is no limit at all, and you can earn any amount with no reduction. Importantly, withheld benefits are not lost forever. Your benefit is recalculated upward at full retirement age to account for the months that were withheld.
12. How are Social Security benefits taxed?
At the federal level, up to 85 percent of your Social Security benefit can be subject to income tax, depending on your combined income. The thresholds have not been adjusted for inflation in decades, so more retirees get caught each year. Here is the bright spot for our area: Florida does not tax Social Security benefits at all, because Florida has no state income tax. The new senior bonus deduction enacted for 2025 through 2028 can also reduce the federal tax bite for many retirees 65 and older. Managing which accounts you draw from, and when you do Roth conversions, can lower how much of your Social Security becomes taxable. Tax planning around Social Security is one of the highest-value moves we make together.
13. What is the best Social Security strategy for married couples?
For married couples, Social Security is a household decision, not two separate ones. A common and effective strategy is to have the lower earner claim earlier if needed for cash flow, while the higher earner delays as long as possible, ideally to 70. The reason is survivor benefits. When one spouse passes away, the survivor keeps the larger of the two benefits, so maximizing the higher earner’s check protects whoever lives longer. Coordinating claiming ages, spousal benefits, and longevity expectations can add tens of thousands of dollars over a couple’s joint lifetime. This is exactly the kind of analysis worth running carefully, because the choices are largely permanent once made.
14. What happens to Social Security when my spouse passes away?
When one spouse dies, the surviving spouse does not keep both Social Security checks. Instead, the survivor receives the larger of the two benefits, and the smaller one goes away. At the same time, the survivor often shifts from filing jointly to filing as a single taxpayer the following year, which can push the same income into higher tax brackets. This combination, sometimes called the widow’s tax trap, can mean a meaningfully higher tax bill on a lower household income. Planning ahead, by having the higher earner delay benefits and by building tax-flexible accounts like Roth IRAs, can soften this blow. It is one of the most overlooked risks in retirement, and one I make sure every married couple understands.
Taxes in Retirement
Taxes do not stop when your paycheck does. The good news is that retiring in Florida gives you a major head start, and smart planning can shrink your tax bill even further.
15. Does Florida tax retirement income?
This is one of the best reasons to retire in Central Florida. Florida has no state income tax, which means the state does not tax your Social Security, your pension, your 401(k) or IRA withdrawals, or your investment income. There is also no state estate tax and no state inheritance tax. Compared with high-tax states, a retiree pulling $80,000 a year from various sources can save thousands annually simply by living in Florida. You will still owe federal income tax on most of that income, but eliminating the state layer is a powerful and permanent advantage. It is a major reason retirees relocate to Orlando suburbs like Lake Nona, Winter Garden, and Clermont, and a real benefit for those who are already here.
16. What is the new senior tax deduction for 2026?
Starting with the 2025 tax year and running through 2028, taxpayers who are 65 or older can claim a new bonus deduction of up to $6,000 per person, or $12,000 for a married couple when both spouses qualify. This is on top of the regular standard deduction and the existing additional standard deduction for seniors. It is available whether you itemize or take the standard deduction. The catch is an income phase-out: the full deduction applies below $75,000 of modified adjusted gross income for singles and $150,000 for joint filers, then shrinks above those levels. Because the benefit fades as income rises, managing your taxable income, including the timing of withdrawals and Roth conversions, can help you keep more of this temporary break while it lasts.
17. What is a Roth conversion and should I do one?
A Roth conversion means moving money from a traditional IRA or 401(k) into a Roth IRA and paying income tax on the amount converted now, so that all future growth and withdrawals come out tax-free. The appeal is paying tax at today’s known rates rather than unknown future ones, and reducing future required minimum distributions. Conversions are especially attractive in the lower-income years between retiring and starting Social Security or required distributions, when you may be in a temporarily low tax bracket. Living in Florida helps, since there is no state income tax on the conversion. Conversions are not free, though. They raise your taxable income for the year and can affect Medicare premiums, so they should be sized carefully, often over several years.
18. What is the “401k tax bomb”?
The 401(k) tax bomb refers to the large tax bill that can build up inside a traditional 401(k) or IRA. Every dollar in those accounts is pre-tax, meaning you have never paid income tax on it. When you retire, required minimum distributions eventually force money out whether you need it or not, and that income can push you into higher brackets, increase the taxable portion of your Social Security, and raise your Medicare premiums. A married couple with a seven-figure IRA can face surprisingly steep tax bills in their 70s. Defusing this bomb usually involves strategic Roth conversions in your 60s, charitable giving strategies, and careful withdrawal sequencing. The goal is to spread the tax over time at lower rates instead of getting hit with it all at once.
19. What are required minimum distributions (RMDs)?
Required minimum distributions, or RMDs, are amounts the IRS requires you to withdraw each year from traditional retirement accounts once you reach a certain age. Under current law, RMDs now begin at age 73 for most people, rising to 75 in future years under the SECURE 2.0 law. The amount is based on your account balance and a life-expectancy factor, and the withdrawal is taxed as ordinary income. Missing an RMD can carry a penalty, so the deadlines matter. Roth IRAs have no required distributions during your lifetime, which is one reason Roth conversions can be so valuable. Planning for RMDs before they begin, rather than reacting to them, gives you room to manage your tax bracket and avoid unwelcome surprises.
20. How can I reduce taxes in retirement?
Tax reduction in retirement is less about any single trick and more about coordinating many moving parts. The main levers are which accounts you withdraw from and in what order, the timing of Roth conversions in low-income years, managing capital gains, using qualified charitable distributions if you give to charity, and taking advantage of deductions like the new senior bonus deduction. Living in Florida already removes state income tax from the equation, which is a significant head start. The biggest savings usually come from multi-year planning rather than year-by-year reactions, because the decisions you make in your 60s shape the tax bills of your 70s and 80s. A coordinated tax strategy can be worth more than a percentage point of investment return.
21. What is IRMAA and how does it affect my Medicare premiums?
IRMAA stands for the income-related monthly adjustment amount, and it is essentially a surcharge on your Medicare Part B and Part D premiums when your income exceeds certain thresholds. Medicare looks back at your tax return from two years earlier to decide whether you owe it, so your income at 63 can affect your premiums at 65. The surcharge climbs in tiers, and crossing a threshold by even one dollar bumps you to the next tier. This is why large one-time income events, like a big Roth conversion or a property sale, need careful planning. For many retirees, managing income to stay under an IRMAA threshold is a real and avoidable cost. We watch these brackets closely whenever we plan withdrawals or conversions.
22. Should I move to Florida to save on retirement taxes?
For many retirees, Florida is one of the most tax-friendly states in the country, and taxes are a legitimate reason to consider relocating. With no state income tax, no tax on Social Security or retirement withdrawals, and no state estate or inheritance tax, Florida lets you keep more of your money than most states. Add a generally mild climate and the homestead exemption that reduces property taxes on your primary residence, and the appeal is clear. That said, taxes should be one factor among several, including housing costs, insurance, proximity to family, and healthcare access. If you are weighing a move to the Orlando area or already calling Central Florida home, the tax advantage is real and worth building your plan around.
Retirement Income and Withdrawals
Saving for retirement and spending in retirement are two different skills. This section covers how to turn a lifetime of savings into a paycheck that lasts.
23. How do I turn my savings into a paycheck?
After decades of saving, the hardest mental shift is learning to spend wisely, turning a pile of assets into a dependable monthly income. The most common approaches combine a few sources: Social Security as your guaranteed base, possibly an annuity or pension for additional guaranteed income, and systematic withdrawals from your investment accounts for the rest. Many retirees keep one to two years of spending in cash so they never have to sell investments at a bad time. The right blend depends on how much guaranteed income you want versus how much market exposure you are comfortable with. A written income plan that names exactly where each month’s money comes from removes a surprising amount of stress.
24. What is sequence of returns risk?
Sequence of returns risk is the danger that a market downturn early in retirement does lasting damage, even if average returns over time look fine. The reason is that withdrawing money from a falling portfolio locks in losses, leaving less to recover when markets rebound. Two retirees can earn the same average return over 30 years, yet the one who hit a bad market in their first few years can run out of money while the other thrives. This is why the years right around retirement are so critical. Strategies to manage it include holding a cash buffer, having some guaranteed income, and being willing to trim spending in down years. Protecting against bad timing early is one of the most important jobs of a retirement plan.
25. Which accounts should I withdraw from first?
The conventional order is to spend taxable brokerage accounts first, then tax-deferred accounts like traditional IRAs and 401(k)s, and Roth accounts last, allowing the tax-free Roth money to grow as long as possible. But the conventional order is not always optimal. In low-income years, it can pay to deliberately pull from or convert tax-deferred money to fill up lower tax brackets, even if you do not need the cash, to reduce future required distributions. The best sequence depends on your bracket each year, your Social Security timing, and your future RMD picture. This is where coordinated planning shines, because thoughtful withdrawal sequencing can add years of longevity to a portfolio purely through tax efficiency.
26. What is the 4% rule and does it still work?
The 4 percent rule is a guideline suggesting you can withdraw 4 percent of your portfolio in the first year of retirement, then adjust that amount for inflation annually, with a high chance of lasting 30 years. It came from research on historical market data and remains a reasonable starting point. Critics note that it assumes a fixed approach and specific market conditions, and that a flexible retiree who adjusts spending in bad years can often support more, while a very early retiree planning for 40 years may want less. I treat the 4 percent rule as a sanity check rather than a hard law. Your actual sustainable rate depends on your timeline, your other income, and your willingness to adapt.
27. Should I pay off my mortgage before I retire?
Paying off the mortgage before retirement is partly math and partly peace of mind. The mathematical answer depends on your interest rate versus what your money could earn invested, and on the tax picture. But for many retirees, the emotional value of entering retirement with no mortgage payment is worth a great deal, because it lowers the fixed expenses you must cover every month regardless of the markets. A lower required income also reduces how much you must withdraw, which can ease taxes and sequence risk. The downside is tying up cash in home equity that is not easy to access. There is no universal right answer, so we look at your rate, your reserves, and how much a paid-off home would help you sleep at night.
28. How much cash should I keep in retirement?
A common guideline is to keep one to two years of living expenses in cash or near-cash, separate from your invested portfolio. The purpose is not investment return but protection: when markets fall, you can spend from cash instead of selling investments at depressed prices, which directly defends against sequence of returns risk. Too little cash leaves you forced to sell at the worst time, while too much cash sitting idle drags on long-term growth and loses ground to inflation. The right reserve depends on your guaranteed income and your comfort level. For most retirees, a cash buffer paired with a clear plan for when to refill it strikes the right balance between safety and growth.
29. What is a bucket strategy?
The bucket strategy organizes your money by when you will need it. The first bucket holds near-term spending, typically one to three years, in cash and stable assets. The second bucket holds intermediate money, often in bonds, for roughly years three through ten. The third bucket holds long-term money in stocks for growth you will not touch for a decade or more. As you spend from the first bucket, you periodically refill it from the others, ideally selling from whichever has performed well. The appeal is psychological as much as financial: knowing your next few years of income sit safely in cash makes it far easier to leave your growth investments alone during a downturn. Many of my Central Florida clients find this framework calming and easy to follow.
30. How do I plan income that lasts 30 years?
Planning income for three decades means designing for longevity, inflation, and bad market timing all at once. The foundation is guaranteed income that covers your essential expenses, from Social Security and possibly an annuity, so the basics are always met no matter what markets do. On top of that, a growth-oriented portfolio funds your discretionary spending and keeps pace with rising costs over time. A cash buffer protects the early years, and a willingness to adjust spending modestly in down markets adds resilience. The biggest mistakes are underestimating how long you will live and forgetting that prices in 25 years will be much higher than today. A plan built for a long, inflation-adjusted life span is far safer than one built for averages.
Investments and Risk
Your investment strategy should change as you move from building wealth to living on it. The goal shifts from maximum growth to reliable, protected income.
31. How should I invest my money in retirement?
Investing in retirement is a shift from pure accumulation to balancing growth, income, and protection. You still need growth, because a retirement that lasts 30 years must outpace inflation, so stocks remain important even after you stop working. At the same time, you need stability and accessible cash so a market drop does not force you to sell at the wrong moment. Most retirees land on a diversified mix of stocks for long-term growth, bonds for stability and income, and cash for near-term spending, with the exact proportions tied to your risk tolerance and income needs. The goal is not to chase the highest return but to build a portfolio that funds your life reliably across good markets and bad.
32. How do I protect my savings from a market crash near retirement?
The years just before and after you retire are the most vulnerable to a market crash, because you have the most money at risk and the least time to recover before you start withdrawing. Protection comes from a few layers working together: holding one to two years of cash so you are not forced to sell, keeping a meaningful allocation to stable assets, considering guaranteed income sources for your essential expenses, and not taking more market risk than your plan actually requires. The aim is not to predict crashes, which no one can do reliably, but to build a portfolio that can absorb one without derailing your retirement. A plan that survives a bad first few years will survive almost anything.
33. What is the right mix of stocks and bonds for a retiree?
There is no single correct mix, because the right allocation depends on your income needs, your other guaranteed income, your time horizon, and how you handle market swings. An old rule of thumb suggested subtracting your age from 100 to get your stock percentage, but with longer life spans many planners now lean toward holding more stocks than that for growth. A retiree whose essential expenses are fully covered by Social Security and a pension can afford more stock exposure, while someone relying heavily on their portfolio may want more stability. The key is matching your investments to your actual spending timeline, keeping near-term money safe and long-term money growing. Your allocation should serve your income plan, not the other way around.
34. How does inflation affect my retirement?
Inflation is the quiet threat that erodes your purchasing power year after year. Even at a modest 3 percent annual rate, prices roughly double over 24 years, so a comfortable income today may feel tight midway through a long retirement. This is why simply holding all your money in cash, while it feels safe, is actually risky over decades. To keep up, your plan needs growth assets like stocks, income sources that adjust over time, and Social Security, which does include annual cost-of-living increases. The 2026 cost-of-living adjustment, for example, raised benefits by 2.8 percent. Building inflation directly into your projections, rather than assuming today’s prices forever, is one of the most important and most overlooked parts of retirement planning.
35. Are annuities a good idea?
Annuities can be a good idea for the right person and the wrong choice for someone else, which is why they spark such strong opinions. At their core, annuities let you convert a lump sum into guaranteed income, often for life, which can be valuable for covering essential expenses and reducing the worry of outliving your money. The trade-offs are that some annuities carry high fees, complexity, or limited access to your principal, and not all are created equal. The right question is not whether annuities are good or bad in general, but whether a specific annuity solves a specific problem in your plan, such as creating a guaranteed income floor. When used thoughtfully and chosen with care, they can bring real peace of mind.
36. What is a fixed indexed annuity?
A fixed indexed annuity is a contract with an insurance company that credits interest based partly on the performance of a market index, while protecting your principal from market losses. In strong market years, you earn a portion of the index’s gain up to a cap or participation rate, and in down years, you typically do not lose value due to market declines. The appeal is a blend of some growth potential with downside protection, which can suit retirees who want to avoid steep losses. The trade-offs include caps that limit your upside, surrender charges for early withdrawals, and varying contract terms that require careful reading. As with any annuity, the details matter enormously, so it is essential to understand exactly how a specific contract works before committing.
Your 401(k), IRA, and Rollovers
Your 401(k) and IRA are likely your largest assets, so what you do with them deserves careful thought. Here are the questions I hear most about these accounts.
37. What should I do with my 401(k) when I retire?
When you retire or leave a job, you generally have a few choices for your 401(k): leave it in the employer plan if allowed, roll it into an IRA, roll it into a new employer’s plan, or cash it out, which is usually the worst option due to taxes and lost growth. Many retirees roll the balance into an IRA to gain more investment choices and more control over withdrawals and tax planning. Others keep the 401(k) if it has strong, low-cost funds or special features. The right move depends on the quality of your plan, the investment options, the fees, and your overall strategy. This is a decision worth getting right, because it sets the foundation for how your largest account will be managed for decades.
38. Should I roll my 401(k) into an IRA?
Rolling a 401(k) into an IRA is a common move, and it offers some real advantages: a much wider range of investment options, often lower costs, easier coordination of withdrawals, and more flexibility for Roth conversions and tax planning. A direct rollover, where the money moves straight from one custodian to another, avoids taxes and penalties. That said, an IRA rollover is not always best. Some 401(k) plans offer institutional pricing, unique funds, or earlier penalty-free access if you separate from service at 55 or later. There can also be creditor-protection differences. The decision should weigh your specific plan’s quality against the flexibility an IRA provides. For many retirees the IRA wins, but it is worth confirming rather than assuming.
39. What is the difference between a traditional and Roth IRA?
The core difference is when you pay taxes. With a traditional IRA, you typically get a tax deduction when you contribute, your money grows tax-deferred, and you pay ordinary income tax on withdrawals in retirement. With a Roth IRA, you contribute after-tax dollars with no upfront deduction, but your money grows tax-free and qualified withdrawals in retirement are completely tax-free. Roth IRAs also have no required minimum distributions during your lifetime, which makes them powerful for tax planning and for leaving money to heirs. The general principle is that traditional accounts favor you if you expect a lower tax rate later, while Roth accounts favor you if you expect the same or higher rates. Most well-built plans use a mix of both for flexibility.
40. How much can I contribute to retirement accounts in 2026?
For 2026, you can contribute up to $24,500 to a 401(k), 403(b), or similar workplace plan through salary deferrals. If you are 50 or older, you can add a catch-up contribution of $8,000, bringing your total to $32,500. The IRA contribution limit is $7,500, with an extra $1,100 catch-up for those 50 and over, for a total of $8,600. These limits let diligent savers add meaningful amounts in their final working years. Keep in mind that income limits can affect Roth IRA eligibility and the deductibility of traditional IRA contributions. If you are still earning income in your 60s, maximizing these accounts can be one of the most effective ways to boost your retirement readiness.
41. Can I still contribute if I am over 60?
Yes, and 2026 brings an especially generous opportunity. Thanks to the SECURE 2.0 law, workers who are 60, 61, 62, or 63 during the year qualify for a higher super catch-up contribution to their workplace plan. For 2026, that means people in this age band can contribute up to $11,250 in catch-up on top of the standard limit, for a total 401(k) contribution of up to $35,750, if their plan allows it. This is a powerful way to pack extra savings into the final stretch before retirement. One new wrinkle: starting in 2026, higher earners whose prior-year wages with the employer exceeded $150,000 must make their catch-up contributions on a Roth basis. For many late-career savers, that is actually a smart outcome anyway.
42. What happens to my retirement accounts when I pass them to my kids?
Leaving retirement accounts to your children changed significantly under the SECURE Act. Most non-spouse heirs, including adult children, must now empty an inherited traditional IRA or 401(k) within 10 years of your death, rather than stretching withdrawals over their own lifetimes. Because those withdrawals are taxable, a large inherited IRA can land on your children during their peak earning years and push them into high tax brackets. This makes proactive planning valuable. Strategies like Roth conversions during your lifetime, since inherited Roth accounts are generally tax-free to heirs, and coordinating beneficiary designations carefully, can preserve far more of your legacy. Naming the right beneficiaries and keeping those designations current is one of the simplest yet most important steps you can take.
Healthcare and Long-Term Care
Healthcare is the expense most retirees underestimate. Planning for it, including the gap before Medicare and the risk of long-term care, protects everything else you have built.
43. What will healthcare cost me in retirement?
Healthcare is one of the largest and most underestimated expenses in retirement. Even with Medicare, you face premiums, deductibles, copays, and costs Medicare does not cover, such as most dental, vision, and hearing care. Estimates for a typical 65-year-old couple retiring today run into the hundreds of thousands of dollars in total lifetime healthcare costs, not counting long-term care. Premiums also rise with income through the IRMAA surcharge, which is why income planning and healthcare planning go hand in hand. Budgeting realistically for medical costs, and building in a cushion for the years when health needs grow, keeps healthcare from derailing an otherwise solid plan. It deserves a dedicated line in every retirement projection, not an afterthought.
44. How does Medicare work and when do I sign up?
Medicare is federal health insurance that generally begins at age 65. It has several parts: Part A covers hospital care, Part B covers doctor visits and outpatient care, Part D covers prescriptions, and you can choose either Original Medicare with a supplement, or a Medicare Advantage plan that bundles coverage. Your initial enrollment window spans the three months before your 65th birthday month, that month, and the three months after. Missing your enrollment window can trigger lifelong late penalties, so the timing is important, especially if you are not still covered by an employer plan. Because the choices between Original Medicare, supplements, and Advantage plans carry long-term consequences, it is worth understanding your options well before you turn 65.
45. What about health coverage if I retire before 65?
Retiring before 65 means bridging the gap until Medicare begins, and that gap is one of the biggest hurdles for early retirees. Your main options include coverage through the Affordable Care Act marketplace, where managing your taxable income can qualify you for premium subsidies, continuing your employer plan temporarily through COBRA, or joining a spouse’s plan if available. Marketplace subsidies are based on income, so retirees who can control their reported income, for instance by drawing from cash or Roth accounts, may qualify for substantial help with premiums. This bridge period needs to be planned carefully, because health coverage from, say, 62 to 65 can be expensive without a strategy. We build this gap directly into early-retirement plans.
46. Do I need long-term care insurance?
Long-term care, meaning help with daily activities due to aging or illness, is a real and expensive risk: a large share of people will need some form of it, and costs for care at home or in a facility can run into thousands of dollars per month. Long-term care insurance is one way to protect against that risk, but it is not the only one. Some retirees self-insure by earmarking assets, others use hybrid policies that combine life insurance or annuities with long-term care benefits, and some rely on a combination. Whether you need a policy depends on your assets, your family health history, and how you want to protect your spouse and heirs. The key is to make a deliberate decision rather than simply hoping the need never arises.
Estate, Legacy, and Working With an Advisor
A complete plan looks beyond your own lifetime. These final questions cover protecting your legacy and deciding whether to go it alone or get professional help.
47. What estate planning documents do I need?
At a minimum, most retirees should have four core documents: a will that directs where your assets go, a durable power of attorney that lets someone manage your finances if you cannot, a healthcare surrogate or medical power of attorney for medical decisions, and a living will or advance directive that states your wishes for end-of-life care. Many families also benefit from a revocable living trust, which can help avoid probate and keep matters private. In Florida, having these documents properly drafted under state law is important, and keeping your beneficiary designations on retirement accounts and life insurance current is just as critical, since those override your will. Estate planning is not only for the wealthy. It is how you protect your family from confusion and conflict.
48. How do I leave money to my family the right way?
Leaving a legacy well is about more than the dollar amount. It involves choosing the right accounts to pass on, since a Roth IRA is generally tax-free to heirs while a traditional IRA is taxable to them under the 10-year rule. It means keeping beneficiary designations current, because those control who receives your retirement accounts regardless of what your will says. For larger estates or blended families, trusts can provide control and protection. And it often means having open conversations with your family so your intentions are understood. Thoughtful planning can dramatically increase how much of your hard-earned money actually reaches the people you love, rather than being lost to taxes or tied up in probate. The right way is the way that reflects your values and minimizes friction for those you leave behind.
49. Do I really need a financial advisor, or can I do this myself?
Plenty of disciplined people manage their own finances successfully, especially during the saving years when the main task is to invest steadily and avoid mistakes. Retirement, though, is more complex, because you are juggling withdrawal strategy, Social Security timing, tax planning, healthcare, and estate decisions all at once, and the choices are often permanent. A good advisor earns their fee not by picking hot investments but by coordinating these pieces, helping you avoid costly errors, and keeping you steady when markets get scary. If your situation is straightforward and you enjoy managing it, doing it yourself can work. If it feels overwhelming, or the stakes of getting it wrong are high, professional guidance can pay for itself many times over. The honest answer depends on your complexity, your confidence, and your time.
50. How do I choose a retirement financial advisor in Orlando?
Choosing the right advisor matters, so look for a few key things. First, umake sure they are going to put together a strategy for you that gives you clarity. Second, look for genuine experience with retirement income planning specifically, not just investing, including Social Security, tax strategy, and withdrawal planning. Third, make sure they explain things clearly and listen to your goals rather than pushing products. It also helps to work with someone who understands the Central Florida landscape, from our tax advantages to local cost-of-living realities. Ask about their process, and how they will coordinate the moving parts of your plan. The right fit is someone you trust to guide you through decades, not just one transaction.
Your Next Step Toward a Confident Retirement
If you read this far, you clearly take your retirement seriously, and that puts you ahead of most. These 50 questions cover the landscape, but your retirement is not a list of general answers. It is a specific plan built around your savings, your family, your goals, and your life here in Central Florida.
I help pre-retirees and retirees across Orlando, Winter Park, Lake Mary, Dr. Phillips, Oviedo, and surrounding communities, as well as clients nationwide through virtual meetings, turn these questions into a clear, written retirement income plan. If you would like to talk through your own situation, I would be glad to help.
Let’s build a retirement you can feel confident about. Reach out to schedule a conversation, and let’s start with the question that is on your mind right now.
Disclaimer
This article is for educational purposes only and does not constitute personalized financial, tax, or legal advice. Tax laws, contribution limits, and benefit figures referenced reflect 2026 amounts and are subject to change. Individual situations vary, and you should consult a qualified financial advisor, tax professional, or attorney before making decisions. Roger Fishel Financial provides retirement income planning services to clients in Orlando, Central Florida, and nationwide.
