One of the most common concerns I hear as a financial planner is “Can I really afford to spend this money?” Even clients with substantial savings often struggle to shift from a saving mindset to a spending mindset in retirement. Years of financial discipline can make it emotionally difficult to draw from investment accounts, even when their plan clearly shows they can afford to do so.

Research has consistently found that most retirees naturally spend less as they age. After adjusting for inflation, spending generally declines by about 1% to 2% per year, meaning many retirees are worrying about overspending at a time when their expenses are likely to decrease on their own.

There are three often-used phases of retirement spending that you’ve probably heard from MainStreet if you’ve been a client for a while:

• The “Go-Go” Years: Early retirement is often the most active. Travel, hobbies, home projects, and time with family can make these some of the highest-spending years.
• The “Slow-Go” Years: As lifestyles become more settled, discretionary spending often decreases, even as healthcare expenses gradually increase.
• The “No-Go” Years: Later in life, travel and entertainment expenses typically decline significantly. While medical costs become a larger portion of the budget, total household spending often continues to trend downward.

Despite these natural spending patterns, many retirees spend less than they comfortably could. They worry about market downturns, inflation, healthcare costs, or simply running out of money. These concerns are understandable, but they can sometimes prevent retirees from fully enjoying the financial security they’ve spent decades building.

One of the most valuable roles of a financial plan is providing confidence, not just about avoiding financial mistakes, but about making the most of retirement. A well-designed retirement plan can help answer questions like:

• Can I take that dream vacation?
• Is it okay to help my children or grandchildren financially?
• Can I replace my car or renovate my home?
• Can I spend more now without jeopardizing my future?

Sometimes, the greatest value of a retirement plan isn’t telling someone they need to spend less. It’s showing them that they can responsibly and confidently spend more. I have recently “given permission” to clients to buy the business class ticket, buy the car they’ve always dreamed of and to get the nicer Airbnb on their European vacation.

So how do you start giving yourself permission to spend?

Here are a few simple ideas:

• Create a “yes” fund. Set aside a specific amount each year for travel, hobbies, or family experiences. When you’ve already planned for it, spending becomes much easier.
• Plan your spending with the same intention you used to save. At the beginning of each year, choose one or two experiences or purchases that would make retirement more meaningful, then commit to following through if your financial plan supports those decisions.
• Ask yourself one simple question: “If not now, then when?” If your financial plan shows you’re on track, remind yourself that your savings were meant to support your life, not simply grow your account balance.

The goal isn’t to leave retirement wishing you’d saved more when you already had enough. It’s to use your savings intentionally to support the life you’ve worked so hard to create. A thoughtful financial plan can provide something many retirees need most: permission to enjoy the retirement they’ve earned.

Source:

-The Go-Go, Slow-Go, and No-Go framework is generally credited to Michael Stein’s book “The Prosperous Retirement”

-Vanguard, The Vanguard Retirement Outlook: Strong National Progress, Opportunities Ahead (2025).

The post Spending in Retirement – Giving yourself permission to spend what you’ve saved. appeared first on MainStreet Financial Planning.

I have some version of this conversation almost every week. Someone sits down with me, newly retired or a year or two out, with money in three places. A brokerage account, a traditional IRA or 401(k), and usually a Roth. They ask which one to live on first, and most already have an answer in their head from something they read. Spend the brokerage account first, then the IRA, and save the Roth for last.

It’s a clean rule. And for a lot of couples, it quietly hands the IRS thousands of dollars they never owed.

Walk through it with me. Say you both retire at 63 with $1.2 million in a traditional IRA, $400,000 in a brokerage account, and $150,000 in a Roth. Social Security hasn’t started. You need about $80,000 a year to live on, and if you don’t know that number yet, figure out what you’ll spend in retirement first, because the whole plan rests on it.

The IRS won’t make you start pulling from that IRA until your required age, which is 73 if you were born before 1960, and 75 if you were born in 1960 or later. For most people retiring in their early 60s today, that’s 75, so the account can sit and grow for more than a decade. Spend the brokerage account down first and the IRA grows untouched the whole time, until the year you hit that age and the government makes you start taking money out whether you need it or not. Those required withdrawals can run $60,000 a year or more, they pile on top of your Social Security, and by then you’ve lost the room to do much about the tax bill.

I call the years in between, from the day you stop working to the year those withdrawals start, your golden years. Your income is the lowest it will ever be, and most people let those years slip by without using them. In 2026, a married couple can have about $130,000 of income, after the standard deduction, and still stay in the low 12% tax bracket. If you’re living on $80,000 from the brokerage account and showing little else on your tax return, you’ve got a big, empty stretch of that 12% bracket going to waste.

That empty space is the opportunity. Instead of leaving the IRA to grow into a tax problem later, you take money out of it now on purpose, or convert a piece to your Roth, filling that low bracket while you’re sitting in it. The difference, in plain numbers: pull $50,000 out of the IRA at 12% and the tax is about $6,000. Leave it, and that same $50,000 can come out later at 22%, once Social Security and the required withdrawals are both running, for a tax of about $11,000. Same money, nearly double the tax for waiting.

And this isn’t a plan you build once and file away. The brackets move, the rules change, and your life does too, so the smart move shifts a little from one year to the next. Some years you fill more of the bracket, some years less.

So when someone asks me which account to spend first, my real answer is that the order is its own decision, worth mapping out and keeping current, not a rule of thumb you set once and forget. If you’re in your golden years now, or you can see them coming, it’s worth a look before December, while this year’s room in the bracket is still open. That kind of year-by-year planning is the heart of what we do inside a Money Roadmap, and it’s why the clients we work with come back to it with us every year.

The post Is There Room Left in Your Tax Bracket? appeared first on MainStreet Financial Planning.

Here are four important retirement planning options to review before age 65.

1. Super Catch-Up 401(k) Contributions: A Limited-Time Opportunity

Along with traditional contributions, the current rules allow individuals age 50 and older to make additional catch-up contributions of up to $8,000 to retirement plans each year. However, for individuals ages 60–63, recent rule changes allow for a “super catch-up” contribution of up to $11,250 each year.

These additional allowed amounts create valuable opportunities to boost retirement savings.

Planning question: Will you maximize your retirement contributions during these years?

2. Medicare Enrollment: Missing It Can Be Expensive

Turning 65 triggers one of the most important retirement deadlines: Medicare enrollment.

Medicare is a federal health insurance program designed primarily for individuals aged 65 and older. So, whether you need the coverage immediately or not, failure to enroll within the proscribed window may increase your healthcare costs in the future.

While decisions around Medicare can be complicated, especially if you plan to work past 65 or you already have insurance coverage, it’s important to be aware of, investigate, and understand the process because delaying enrollment may result in a permanent premium increase of 10% for each full year of non-enrollment. And, unlike many penalties that disappear over time, this one may follow you indefinitely. So, ask for help if you have questions about Medicare or Medicare enrollment.

Planning question: Will you review Medicare and evaluate enrollment timing implications before age 65?

3. HSA Contributions: Stop When Medicare Starts

Health Savings Accounts (HSAs) are tax-efficient savings tools. Contributions can be tax-deductible, growth can be tax-deferred, and qualified withdrawals can be tax-free.

However, once you begin Medicare, IRS rules require you to stop all HSA contributions.

To avoid unintended excess contributions to your HSA and triggering tax penalties of up to 6%, consider stopping HSA contributions six months prior to enrolling in Medicare.

Planning question: Will you coordinate your HSA strategy with your Medicare timeline?

4. Medicare Premiums: What is IRMAA?

To determine premiums, Medicare looks back at your income from the previous two years on an annual basis. In other words, financial decisions you make at ages 63 and 64 are used to determine your Medicare premium costs at 65 and 66.

Higher-income retirees may pay additional surcharges called Income-Related Monthly Adjustment Amounts (IRMAA). Be aware that large Roth conversions or retirement account distributions, significant capital gains, or unusual income events that add to your income could result in increased Medicare premiums. Reference Basics of Roth IRA Conversion resource.

This does not mean you should avoid these strategies. It simply means that you should understand how using them may impact your healthcare costs at a later date.

Planning question: Will you look ahead at how today’s income decisions may affect future Medicare costs?

Here is a helpful resource to get a handle on Spending in Retirement.

The Bottom Line

As you move closer to age 65, you have a number of important options that can save money, reduce taxes, and improve long-term outcomes – some options come with expiration dates, while others help you plan to avoid possible negative consequences. Retirement planning isn’t just about building assets. It’s also about understanding the timing of key deadlines, so you can make informed decisions for your financial future.

The post Retirement Planning? What to Do Before Age 65 appeared first on MainStreet Financial Planning.

Why Consider a Roth IRA Conversion?
• Tax-free growth – Your investments can grow without future tax burdens.
• Tax-free withdrawals – You and your heirs can enjoy tax-free distributions in retirement.
• No required minimum distributions (RMDs) – Unlike Traditional IRAs, Roth IRAs do not require withdrawals during your lifetime.

Key Considerations Before Converting

Do you need these funds within the next 5 years?
• Withdrawals of converted funds within five years may be subject to taxes and penalties. If you’ll need access to the money soon, this may not be the best option.

Will the conversion push you into a higher tax bracket?
• The amount converted is taxed as ordinary income. A large conversion could push you into a higher tax bracket. To manage this, consider converting smaller amounts over several years.

How will you pay the taxes on the conversion?
• Using cash from outside your IRA to pay the tax bill helps maximize tax-free growth.
• If you use IRA funds to cover taxes, your investment balance shrinks.

Will your tax rate be higher now or in the future?
• If you expect to be in a higher tax bracket later, converting now at a lower rate may save money in the long run.
• If your current tax rate is higher than your expected future rate, conversion may be less beneficial—unless you have a long time horizon for growth.

Who is your Roth IRA for?
• If you don’t anticipate needing these funds for your own lifestyle, a Roth IRA conversion can be earmarked for the next generation, allowing up to 10 additional years for tax-free growth.
• However, this remains your asset first and can support your needs if circumstances change.

Final Thought: No Do-Overs
Once you complete a Roth IRA conversion, it cannot be reversed. You must pay taxes on the converted amount in the year of the conversion.

A Roth conversion isn’t inherently “good” or “bad”—it’s a timing decision. The right answer depends on your current tax situation, future expectations, and how this move fits alongside the rest of your financial plan. Thoughtful planning, often done over multiple years, can turn this into a powerful tool rather than an expensive mistake.

The post Basics of a Roth IRA Conversion appeared first on MainStreet Financial Planning.

We’re so grateful when you share MainStreet Financial Planning, Inc. with your friends, family, and colleagues. Your trust means everything to us.

At MainStreet Financial Planning, we don’t manage investments or sell financial products. Instead, we provide objective, flat-fee financial advice that focuses entirely on helping clients make informed, confident decisions about their money. Our only motivation is your success — not commissions or asset-based fees.

If you know someone who could benefit from retirement planning or unbiased, professional financial guidance from a fee-only fiduciary, here’s how to connect them with our team.

Who We Help

We work with individuals, couples, and families who want to feel confident, organized, and in control of their financial future.

Our specialty is retirement planning — helping people in their 40s, 50s, and 60s move from saving to spending with clarity and confidence. We also guide younger families building toward long-term goals like college savings, home buying, and financial independence.

Many of our clients are do-it-yourself investors — smart, proactive people who prefer to manage their own investments but want a second set of eyes and a trusted guide to keep them on track. We help them simplify, focus, and make informed decisions so they can feel confident about their next steps.

About MainStreet Financial Planning

MainStreet Financial Planning, Inc. is a 100% women-owned, women-led, fee-only, fiduciary firm founded in 2002.

We are a virtual financial planning firm, serving clients across the U.S. and worldwide. Whether you live in California, Maryland, Tennessee, New York, Virginia, Washington, DC or abroad, our secure online process makes it easy to get professional guidance from anywhere.

Here’s what makes us different:

• Retirement-focused advice. We help clients understand what retirement really costs — and how to make their savings last.

• Flat, transparent fees. No asset minimums, no AUM fees, and no commissions — ever.

• Virtual and flexible meetings. Meet with your CERTIFIED FINANCIAL PLANNER™ professional wherever life takes you.

• Independent fiduciary guidance. We’re paid only by our clients, and we always act in your best interest.

• Women-led team. Compassionate, approachable, and deeply experienced in guiding families through life’s biggest financial transitions.

We believe financial planning should be accessible, understandable, and empowering — not intimidating.

What We Do

As a flat-fee, fiduciary financial planning firm, we help clients organize their finances, clarify goals, and make confident decisions in every area of their financial life:

• Retirement income and distribution strategies

• Cash flow and budgeting

• Investment allocation and portfolio organization

• College savings and education funding

• Tax and insurance planning

• Managing life transitions such as career changes, inheritance, or downsizing

We offer three main service options:

• Money Roadmap (one-time financial plan): $4,400 for individuals / $5,800 for couples

• Money Roadmap Navigator (ongoing financial planning): includes comprehensive planning, accountability, and ongoing support — $2,000 for individuals/$2,500 deposit for couples, plus $210/month for individuals or $265/month for couples

• Hourly financial planning: $425/hour (ideal for targeted questions, plan updates, or second opinions)

Meet Our Financial Planners

Our team of CERTIFIED FINANCIAL PLANNER™ professionals brings decades of experience helping clients simplify their finances and build financial confidence:

• Anna Sergunina, CFP® – President & CEO, Financial Planner

• Cynthia Flannigan, CFP® – Financial Planner

• Vida Jatulis, CFP® – Financial Planner

• Katherine Edwards, CFP® – Financial Planner

• Jennifer Bush, CFP® – Financial Planner

Learn more about our advisors on our Meet the Team page.

Making a Referral Is Easy

1. Think of someone who could benefit from financial clarity, retirement planning, or a flat-fee second opinion — a friend, family member, or colleague.

2. Share your experience. Tell them how our planning process helped you feel more organized and confident. You can also share our Google Reviews so they can see what other clients have said.

3. Email an introduction to info@mainstreetplanning.com. We’ll take it from there and make sure your friend receives a warm, no-pressure welcome.

Sample Email You Can Send

Subject: Introduction to MainStreet Financial Planning

Hi [Friend’s Name],

I wanted to introduce you to my financial planner, [Advisor’s Name] from MainStreet Financial Planning. They’ve helped me get organized and feel more confident about my financial future.

I thought of you because you mentioned [planning for retirement / wanting a second opinion / looking for financial clarity]. Their team works virtually, charges flat fees, and focuses on helping clients like us — smart do-it-yourselfers who want a clear plan and expert guidance along the way.

[Advisor’s First Name] – meet [Friend’s First Name]. I’ll let you two take it from here!

Best,

[Your Name]

A Personal Thank-You

Your referrals are the heart of our growth and the greatest compliment we can receive. Each introduction allows us to help another family feel organized, confident, and ready for the next stage of life.

As a small token of our gratitude, we make a charitable contribution to your favorite nonprofit for every new client referred by you, through our partnership with TisBest Philanthropy. It’s our way of saying thank you and ensuring that your referral creates a positive ripple effect in the community.

It’s truly a win for everyone.

Thank you for trusting us — and for sharing MainStreet Financial Planning with the people you care about most.

The post Share MainStreet: Help Your Friends Find a Flat-Fee Fiduciary Financial Planner They Can Trust appeared first on MainStreet Financial Planning.

I am sharing these key takeaways from Michael Finke’s research with you so that you can ponder what your own happy retirement looks like.

Social Connection = The Secret Ingredient

• Spousal relationship quality is the strongest predictor of life satisfaction.
  • A poor-quality marriage lowers life satisfaction below that of being unmarried.
  • A very close marriage substantially boosts satisfaction
• Friends also significantly increase life satisfaction—the number and frequency of contact with friends both matter.
• Other family (beyond spouse and children) has a smaller but still positive effect.
• Children: Neither the number of children nor contact with them significantly impacts retirees’ life satisfaction. (So, moving across the country to be closer to your kids might not deliver the joy you are expecting.)

Tip:  Create a retirement budget that allows for leisure spending; going out to dinner with friends, traveling to connect with friends, and doing hobbies that provide an opportunity to socialize.\

You Do Not Need to be Rich to be Happy

• Retirees don’t need to be rich to be happy – they need to feel financially secure
• Anxiety about money reduces life satisfaction
• High financial anxiety = 23% lower odds of life satisfaction

Tip:  Structure your money and investments so that you feel comfortable spending in retirement (guaranteed income, lower risk investments, etc.)
Learn how to estimate and structure your retirement spending realistically.

Health is Wealth

• Poor health is the number one cause of retirement dissatisfaction.
• Retirees in excellent health score dramatically higher on life satisfaction than those in poor health.

Tip: Invest in wellness, prevention, and active living for yourself. Make it part of your financial plan!

The Risk of Cognitive Decline is Real

• Cognitive decline affects financial decision-making.
• Financial intelligence peaks in your 50s and declines by your 70s
• Confidence does not decline with age

Tip:  Simplify your finances, appoint a durable power of attorney early, and create a withdrawal strategy that doesn’t rely on frequent decision-making.
Read about transitioning from saver to confident retirement spender.

 Consider Community Living

• Retirees in community-based housing report 25%-30% higher life satisfaction
• We think that our home is a safe haven for aging, but aging in place can increase isolation.
  • Friends move away.
  • Driving becomes difficult
  • Home becomes harder to manage
• Retirees living alone after age 82 report lower life satisfaction

Tip: Make sure that your retirement living plan will allow you to continue to connect with people as you age.

While financial security is important, research shows that money alone isn’t what makes retirement truly satisfying.  Did the science behind a happy retirement change the way you are thinking about your retirement plan?

Resources:

“Spending, Relationship Quality, and Life Satisfaction in Retirement” (Finke, Ho & Huston, 2018)

3 Signs You’ll Be Happy In Retirement

Podcast: The Long View; EP23 Michael Finke: Here’s What Makes Retirees Happy

The post The Science Behind a Happy Retirement appeared first on MainStreet Financial Planning.

The truth is, figuring out retirement spending doesn’t start with a magic formula. It starts with looking closely at the life you live today — and the one you imagine for the future. That process is simpler than most people think, but it requires a willingness to pull out the numbers and see them for what they are.

Step 1: Look at today’s spending

The best predictor of your retirement lifestyle is how you spend money right now.

Begin by asking:

• What do I spend each month on housing, food, transportation, and healthcare?
• Which costs are essential versus optional?
• How consistent is my tracking — do I actually know what I spend?

This step may feel basic, but it’s powerful. Using credit card and bank statements to ground your answers in reality helps you “feel” the numbers, not just guess at them. If you need tools to make that easier, see 3 Alternatives to the “Mint” Budgeting App.

Step 2: Separate fixed and variable expenses

A simple but powerful way to think about money is to split your expenses into two buckets:

• Fixed expenses: Mortgage or rent, property taxes, insurance premiums, utilities, basic groceries. These are your non-negotiables — they don’t go away just because you retire.
• Variable expenses: Travel, dining out, hobbies, gifts, entertainment. These are the lifestyle choices that make retirement fun, and they can flex up or down depending on your circumstances.

To get a sense of balance between these categories, many clients also find the 50-30-20 Rule of Thumb helpful — it’s a quick way to compare essentials, lifestyle, and saving against what you’re currently spending.

Step 3: Ask what carries over into retirement

Not all expenses disappear when you stop working. Some shrink, some grow, and others surprise you.

Ask yourself:

• Will I still have a mortgage, or will the house be paid off?
• How will healthcare costs change once I’m on Medicare?
• Will I travel more — or spend less on commuting and work clothes?
• What new hobbies, family support, or giving might I want to add?

You don’t need perfect answers. Even rough estimates highlight what will stay the same, what will change, and what could catch you off guard.

Step 4: Don’t forget the surprises

Even the most careful planners underestimate certain costs:

• Healthcare and long-term care: Premiums, prescriptions, and in-home or assisted care can be significant. Genworth estimates median costs at $5,000–$10,000+ per month.
• Home maintenance: Roofs, HVAC systems, and other big-ticket repairs don’t vanish in retirement.
• Lifestyle creep: More time can mean more spending on hobbies, entertainment, or family experiences.

Step 5: Put it all together with a worksheet

After walking through these steps, the next move is to put your numbers in one place. A Retirement Spending Worksheet helps you:

• Capture today’s fixed and variable expenses.
• Decide which ones continue into retirement.
• Estimate how your costs shift — higher in some areas, lower in others.
• Create a simple snapshot you can revisit every year.

You don’t need perfect answers — even ballpark numbers bring clarity and confidence.

FAQ

Here are some of the most frequently asked questions I hear from clients — they’ll help you gauge if you’re on track as you work through this exercise with the worksheet.

Q: How much does the average retiree spend per month?

A: According to the U.S. Bureau of Labor Statistics, consumer units with a reference person aged 65 or older reported average annual expenditures of about $49,872 in 2020–2021. That works out to roughly $4,150/month.

Q: Will my expenses go down in retirement?

A: Some will (commuting, payroll taxes), but others rise (healthcare, hobbies, travel). That’s why separating fixed and variable expenses matters.

Q: How often should I update my plan?

A: At least once a year, or after big life changes such as paying off a mortgage or a health shift.

Q: What if I don’t know exact numbers?

A: Use ranges or estimates. Clarity, not perfection, is the goal.

Figuring out retirement spending starts with looking at today, separating fixed from variable, and asking which expenses carry forward. From there, you can begin to see your future life with more clarity.

At MainStreet, the clients we work with often find this exercise to be a turning point. What feels vague and overwhelming at first becomes tangible once the numbers are laid out side by side. And while the worksheet itself is simple, the act of doing it is where the real value lies. Pulling out credit card and bank statements, writing down real spending categories, and comparing them to what life might look like in retirement helps make the numbers real.

That’s exactly what the Retirement Spending Worksheet is designed to do — take your best guesses and your real numbers, and turn them into a snapshot you can build on with confidence.

Next step: Download our worksheet and sketch out your numbers. The moment you see them on paper, you’ll feel more in control of your retirement.

Fill out the form to get the worksheet link sent to you and to join our MainStreet Inbox Club

The post How Do I Figure Out What I’ll Really Spend in Retirement? appeared first on MainStreet Financial Planning.

These rules of thumb are helpful—they give you a place to start. But they’re also overly simplistic. If you stop at the quick math, you risk overlooking some of the biggest financial realities of retirement: healthcare, long-term care, home maintenance, and lifestyle goals.

So let’s recap the three most common rules you’ve probably heard—and then talk about why they all fall short in the same way.

Rule #1: The 25X Rule

This rule says you should aim to save 25 times your expected annual retirement expenses.

• Spend $80,000 a year? Aim for $2 million.
• It’s a simple, powerful way to connect your lifestyle to your savings target.

Rule #2: The 70–80% Income Replacement Rule

This shortcut suggests you’ll need about 70–80% of your pre-retirement income to maintain your lifestyle.

• Earn $100,000 now? Plan for $70,000–$80,000 in retirement.
• The logic is that some expenses (commuting, payroll taxes, retirement savings) disappear when you stop working.

Rule #3: The 4% Withdrawal Rule

This rule assumes you can safely withdraw 4% of your portfolio each year without running out of money.

• A $1 million portfolio → ~$40,000/year.
• It accounts for market downturns and inflation by relying on long-term averages.

Where These Rules Fall Short

On paper, these rules make sense. In real life, retirement is messy. And here’s where most people stumble: estimating future expenses correctly.

• Tracking: Very few of us have a reliable system for tracking spending. Some use spreadsheets, some use apps, but many don’t track at all. And even among those who try, it’s tough to stay consistent. According to Investopedia, while 86% of Americans say they budget, only about 22% actually stick with it long-term (Investopedia). Without reliable data today, projecting tomorrow is nearly impossible.
• Emotion: Spending isn’t just math—it’s emotional. It reflects priorities, and those priorities change. One year it’s travel, the next it’s helping kids, later it may be healthcare or downsizing.
• Life stages: Retirement unfolds in phases. What you spend at 65 looks very different from what you spend at 85.
• Long-term care: The biggest blind spot. According to Genworth’s 2024 Cost of Care Survey, median costs range from $5,000–$10,000+ per month for assisted living or in-home care (Genworth). Yet it almost never gets included in a “25X” calculation or a 4% withdrawal plan.
• Big-ticket surprises: Roof replacements, major dental bills, car purchases—expenses like these don’t fit neatly into a monthly budget but are very real.

The Bottom Line

The 25X Rule, the 70–80% Rule, and the 4% Rule are useful. We share them with clients all the time because they provide a sense of direction when retirement feels overwhelming. But here’s the truth we’ve seen over and over again: they give comfort, not clarity.

Comfort comes from a simple formula that tells you you’re “on track.” Clarity comes from knowing your plan accounts for healthcare, long-term care, home repairs, shifting priorities, and those big expenses you don’t see coming.

That’s why my message is always the same: start with the shortcuts—but don’t stop there. Ask yourself:

• What expenses am I not accounting for?
• How will my priorities change over time?
• What surprises could throw off my plan?
• What big ticket items are coming up?

That’s when retirement planning shifts from being about numbers on a page to building a roadmap that supports the life you actually want to live. And that’s the point: not just reaching retirement, but being able to enjoy it with confidence.

The post The Retirement Rules Everyone Quotes—And the Gaps They Miss appeared first on MainStreet Financial Planning.

Here’s what you need to know to avoid Medicare late enrollment penalties while continuing to work past age 65.

Understanding Medicare Parts and Potential Penalties

Medicare consists of several parts, and not all of them are mandatory at age 65. But delaying enrollment in certain parts without proper coverage can result in permanent financial penalties.

Do You Need to Enroll in Medicare at Age 65?

That depends on your current health insurance:

• If your employer (or your spouse’s) has 20 or more employees, and you’re actively working, you can delay enrolling in Medicare Part B and D without penalty. The employer’s plan is considered creditable coverage, meaning it meets Medicare’s standards.
• If the employer has fewer than 20 employees, you generally must enroll in Medicare when you turn 65. In this case, Medicare becomes your primary insurance, and delaying could lead to gaps in coverage and penalties.

When You Retire: Use the Special Enrollment Period (SEP)

Once you stop working or lose employer coverage (whichever happens first), you enter what Medicare calls a Special Enrollment Period. This allows you to sign up for Medicare without facing penalties.

• You have 8 months to enroll in Part B after your employment or group coverage ends.
• You have 63 days to enroll in Part D after your drug coverage ends.

Failing to enroll within these windows can trigger the penalties listed above.

Key Steps to Avoid Penalties

1. Confirm Your Employer Coverage Is Creditable
   Talk to your HR or benefits administrator to confirm whether your current plan counts as creditable coverage for Medicare Parts B and D.

• Creditable coveragemeans the employer health plan is at least as good as Medicare.
• If your current employer coverageis creditable, you may be able to delay enrolling in Medicare Part B and/or Part D without penalties.
• If it’snot creditable, you need to enroll in Medicare when first eligible to avoid penalties and coverage gaps.

1. Gather the Required Paperwork
   When you retire and apply for Medicare Part B, you’ll need to submit Form CMS-L564 (Request for Employment Information), signed by your employer. This proves you had coverage and qualifies you for penalty-free late enrollment.
2. Time Your Enrollment Carefully
   Enroll during your Special Enrollment Period instead of using the General Enrollment Period (January 1–March 31), which may result in a coverage gap and penalties. Also, COBRA isn’t considered group health plan coverage, so again, use the Special Enrollment Period!

Should You Enroll in Medicare Part A at 65?

Many people enroll in Medicare Part A at 65, even while working, because:

• It’s free if you or your spouse worked and paid Medicare taxes for at least 10 years.
• It can serve as secondary insurance to your employer plan.

However, if you have a Health Savings Account (HSA) and want to continue contributing to it, do not enroll in any part of Medicare, including Part A. Once you enroll, you can no longer contribute to your HSA.

Working past 65 doesn’t mean you’ll be penalized by Medicare — but it does require some proactive planning. By understanding your coverage, and acting during the correct enrollment windows, you can avoid costly mistakes and ensure a smooth transition when you’re ready to retire.

Go to www.medicare.gov for more information and download the Medicare and You handbook. These resources can answer many of your questions about enrolling for Medicare.

The post How to Avoid Medicare Penalties When Working Past 65 appeared first on MainStreet Financial Planning.

Thanks to the SECURE Act 2.0, the starting age for RMDs has recently changed:

• If you were born between 1951 and 1959, your RMDs begin at age 73
• If you were born in 1960 or later, they begin at age 75

This gives many retirees a bit more time to plan—whether that’s converting to a Roth IRA, using taxable accounts first, or simply letting your money grow a little longer. We covered this in more detail in our article, SECURE Act 2.0 May Change Your RMD Age.

How do RMDs work?

Each year, the IRS uses your prior year’s December 31 account balance and a life expectancy factor to calculate your required withdrawal. You can withdraw more if you’d like, but not less. If you don’t take your RMD by the deadline, you could face a steep penalty—50% of the amount you were supposed to withdraw (though recent law changes now allow for more leniency if corrected promptly).

And keep in mind, RMDs are taxable as ordinary income, so they can impact your overall tax picture, Social Security taxation, and even Medicare premiums. That’s why we always encourage building RMDs into your broader retirement income strategy.

Charitable Giving Strategy: QCDs

If you’re charitably inclined, there’s a smart way to meet your RMD and support a cause you care about: the Qualified Charitable Distribution (QCD). This allows individuals age 70½ or older to donate directly from their IRA to a qualified charity—up to $100,000 per year. QCDs count toward your RMD and don’t increase your taxable income.

We go deeper on how this works in our article, Give Your Way: Exploring the Many Paths to Charitable Giving.

3 Tips to Stay Ahead of RMDs:

1. Track your age and know when your RMDs begin—missing one is costly.
2. Set a reminder for the December 31 deadline each year (except for your very first RMD, which can be delayed to April 1).
3. Work with your financial planner to coordinate withdrawals with your other income sources and tax planning opportunities.

The truth is, RMDs aren’t just about following IRS rules—they’re a key part of managing your retirement income wisely. With the right strategy in place, you can turn RMDs into a tool for reducing taxes, supporting causes you care about, and staying in control of your financial future.

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