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.

When:
June 5th, 2026
3:00 pm Eastern; 12:00 pm Pacific
~45 minutes & Q/A included

How: Zoom Meeting
Recorded and able to retrieve for one week

Cost: Free to ongoing clients; $10 per session for guests

Email us for the recording!

Bridging the Gap to Medicare: Health Insurance Strategies for Early Retirement

Hosted by: Cynthia Flannigan, CFP®

Guest commentator: Matt Allen
Founder, Iconic Insurance

Thinking about retiring before age 65? One of the biggest challenges early retirees face is navigating health insurance before Medicare begins. Join us for a practical conversation with Matt Allen, Founder of Iconic Insurance, as we break down ACA plans, COBRA, tax credits, private insurance options, and smart strategies to help manage healthcare costs and retire with more confidence.

Matt Allen is the Founder at Iconic Insurance, where he specializes in helping and educating self-employed individuals, small business owners, and early retirees navigate the complexities of health insurance. With over a decade of experience, Matt has developed a deep understanding of the challenges that come with securing health insurance coverage outside of employer-sponsored plans.

Iconic Insurance Mission Statement: “We empower people to confidently navigate the healthcare system.”

Some of the topics we’ll discuss:

• Understanding ACA marketplace plans and subsidies
• How COBRA works and when it makes sense
• Private insurance alternatives before Medicare
• Strategies to manage healthcare costs in early retirement
• Tax credit opportunities and income planning considerations
• Common mistakes early retirees make with health insurance

Disclaimer: This is a broad group session and certain strategies may or may not be appropriate for specific situations. MainStreet makes no claim that all member posted information is accurate or should be acted upon without professional and individual financial planning, tax and/or legal advice.

The post Chalk Talk: Bridging the Gap to Medicare: Health Insurance Strategies for Early Retirement 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.

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.

My Own Life Insurance Journey

Like many, I bought my first life insurance policy in my 20s—mostly because I knew it was the “responsible” thing to do.

When our son was born, my needs changed dramatically. Suddenly, we had childcare costs, a growing list of family expenses, and his future education to plan for. I added more coverage.

Later, when our daughter arrived, I was already in my 40s—and by then, we had also taken on a bigger mortgage. For many families, that timing might feel “late in life” to be adding coverage. But with the right strategy, it doesn’t have to be overwhelming. I built a laddered approach—adding policies with different lengths and different amounts—to match our obligations. Because coverage phases out as those obligations (like tuition and the mortgage) go away, the overall cost stays manageable, even starting later.

This laddered strategy saved about 15–20% on premiums compared to buying one big 30-year policy, while giving me the most protection during the years my family needs it most.

Are You Over- or Under-Insured?

The most important step is to ask: Does your coverage still fit your life today?

• Over-insured? If your mortgage is nearly gone, your kids are financially independent, and retirement savings are solid, you might be paying for more insurance than you need. Many people also forget they have life insurance through work—coverage they’ve never factored into the bigger picture. If you’re considering canceling, read: Three Considerations If You Are Thinking to Cancel Your Life Insurance Policy.
• Under-insured? If you still have tuition to cover, debts to pay, or parents who rely on you financially, your current coverage may fall short. Ask yourself: Do You Have Enough Life Insurance?.

Term Insurance: Still Worth Considering

If you bought a 20- or 30-year term policy years ago, it may be close to expiring. When the term ends, so does the coverage. If your responsibilities are still significant, this could be the time to add more. Even in your 40s or 50s, shorter-term coverage—like a 5- or 10-year term—can still be surprisingly affordable.

And don’t assume term is just for your younger years. Sometimes adding new coverage later makes perfect sense if your financial needs have grown. Not sure how much protection you need right now? Start here: Calculating the Need for Life Insurance.

Permanent Insurance: Does It Still Fit?

Permanent insurance (whole life, universal life) is usually set up with long-term goals—estate planning, leaving a legacy, or lifelong protection. For some families, these policies remain useful well into retirement. Others may find that their original purpose no longer applies.

Permanent policies can also provide flexibility. Over time, they build cash value, which can sometimes be accessed through policy loans—for example, to help cover a child’s college costs. But it’s important to remember: tapping that cash value comes at a cost, reduces the death benefit, and should always be carefully evaluated. For more perspective, read: Is Whole Life Insurance an Investment?.

Review as Life Changes

Your financial life won’t stay the same—and neither should your insurance. I’ve adjusted my coverage as our family grew and our mortgage changed, and I encourage others to do the same. Make a point to review your policies every few years or whenever you hit a major milestone.

The right coverage gives you peace of mind that your family is protected. And making sure it evolves alongside your life is one of the smartest financial moves you can make.

Further Reading on Life Insurance

• Three Considerations If You Are Thinking to Cancel Your Life Insurance Policy
• Is Whole Life Insurance an Investment?
• Do You Have Enough Life Insurance?
• Calculating the Need for Life Insurance

The post Life Insurance and the Sandwich Generation: Do You Have the Right Coverage? appeared first on MainStreet Financial Planning.

For these clients, it’s not just the delivery of a solid, financial plan.  We also have a conversation around who is going to be in “Circle of Support”—a mix of people who could offer emotional, practical, and professional support during this next chapter of life.

If you’re facing retirement without family, considering a similar move—or just wondering how to strengthen your connections in retirement—here are five steps to help you build a support network without relying on family.

1. Reflect on Your Needs and Strengths

Begin by thinking about the kind of support you want or need in this next stage of life:

• Emotional: Companionship, encouragement, or a trusted friend to talk to.
• Practical: Help with errands, home maintenance, or rides to appointments.
• Professional: Advisors who can support your financial, health, or legal decisions.

Also, consider what you bring to the table. Do you have time to help others? A skill to share? Support networks are most rewarding when they’re mutual.

2. Reconnect and Strengthen Relationships

You may already have people in your life who could be part of your circle—you just need to nurture the connection.

• Reconnect with old co-workers, friends, neighbors you’ve lost touch with.
• Strengthen your current friendships by scheduling regular calls, planning outings, or sharing experiences together.

Even small steps—like inviting someone for coffee—can lead to meaningful connections over time.

3. Expand Your Network with Intention

When you’re ready to meet new people, seek out opportunities based on shared interests:

• Hobbies: Join local clubs or online groups focused on something you enjoy.  If you love hiking, join a local hiking group.  If you love theater, volunteer to paint scenes at the local theater.  Join a book club, craft or gardening club to meet your kind of people.
• Community resources: Check out offerings at your local senior center or community center. Many offer fitness classes, art workshops, or lifelong learning courses.
• Support groups: If you’re facing a specific challenge—like caregiving, chronic illness, or grief—there are groups filled with people who understand.
• Online tools: Sites like Meetup.com, NextDoor or Facebook Groups can help you connect with like-minded people in your area.

And remember—if you don’t find something that fits, create your own.

4. Communicate Clearly and Set Boundaries

Building a support system means inviting people into your life—but also setting healthy expectations.

• Be honest about what kind of help you’re seeking.
• Understand that not everyone will have the capacity to meet those needs—and that’s okay.
• Clarify your own limits, too, so you don’t become overwhelmed by trying to be everything to everyone.

Healthy boundaries make relationships stronger and more sustainable.

5. Make It Mutual

Support isn’t just about what you receive—offering your time, presence, or skills helps relationships flourish. Whether it’s helping a friend with tech, offering to walk a neighbor’s dog, or simply listening when someone’s had a hard day, reciprocity creates a sense of community and purpose.

You’re Not Alone

Retirement without family can feel uncertain—but it doesn’t have to be lonely. By reflecting on your needs, reaching out to others, and being open to new experiences, you can build your own Circle of Support.

Start by reaching out to one person today. You may be surprised by how ready others are to connect—and how fulfilling this next chapter can truly be.

Other Helpful Resources:

Creating Your Solo Aging Plan

Navigating Solo Network and Resources Library

Solo Aging and the Importance of Building a Local Support Network 

How to Build Your MicroBoard (And Be the Chair of Your Board!)

13 Ways to Live a Dynamic Life 

With the increasing awareness of Solo Aging, help with planning can also be found through many organizations around the country, including senior centers, area agencies on aging, and county offices of aging.

Online search suggestions:  Search “solo aging”, “childfree”

The post Facing Retirement Without Family: How to Build Your Circle of Support appeared first on MainStreet Financial Planning.

One of his biggest goals? Hiking a portion of the Appalachian Trail (AT) as a way to disconnect, reflect, and prepare for his next chapter after service. But a trip like this doesn’t just happen—it takes thoughtful financial and logistical planning. Here’s how we made it work:

Two Years of Intentional Planning

When we moved to Kentucky from Hawaii two years ago, we knew this would be our final duty station. That’s when my husband began outlining his retirement timeline, carefully saving his leave, and considering how he wanted to transition into post-military life.

As the AT hike became a serious goal, we began discussing the financial aspects. His sisters had hiked a portion of the trail a few years ago and shared valuable insights. From there, we created a checklist of essential gear, food supplies, and tracking equipment. Instead of making large, last-minute purchases, we spread out our expenses over two years, buying items gradually to avoid financial strain.

The Cost of Hiking the Appalachian Trail

According to Google, the average cost for an Appalachian Trail thru-hike ranges from $5,000 to $7,000, including gear, resupply packages, and town expenses. The estimated monthly cost is around $1,000 for food, lodging, and other essentials.

For our trip, we carefully budgeted and planned ahead:

• Gear & Resupply Packages: We spent approximately $4,000 on gear and pre-planned resupply shipments to help manage costs and ensure my husband has the essentials on the trail.
• Town Expenses: We estimate spending around $1,000 on hostel stays, laundry, meals, and transportation (shuttles/Ubers) when my husband stops in towns along the way.

By spreading out these costs over two years, we avoided large financial burdens and ensured my husband could fully enjoy this experience without financial stress.

Aligning the Hike with Retirement Logistics

Once he received his retirement orders, we mapped out key dates—his Change of Responsibility ceremony, VA appointments, potential Career Skills Program (CSP) opportunities, and his official retirement ceremony. All of these factors impacted when he could embark on the trail. Initially, he hoped to hike for 60 days, but after reviewing his commitments, he adjusted his plan to a 35-day trek.

Involving Our Son in the Journey

As we fine-tuned our plans, we realized this experience could be even more meaningful. Our 17-year-old son decided to join his dad for 50 miles of the hike during spring break. We factored this into our financial and travel planning, ensuring I could pick him up at a designated spot while my husband continued his journey.

More Than a Hike—A Financial and Life Transition

For us, this Appalachian Trail journey isn’t just about the hike—it represents a carefully planned transition into retirement. By budgeting for this adventure in advance, aligning it with our financial goals, and ensuring my husband has the time and resources to pursue his dream, we’ve set the stage for an exciting new chapter.

At MainStreet Financial Planning, we believe financial planning isn’t just about numbers—it’s about making dreams achievable. Whether it’s planning for retirement, a big life goal, or a career transition, having a solid financial strategy makes all the difference.

Are you preparing for your next big life adventure? Let’s plan it together.

The post Financial Planning for Life’s Big Adventures: How We Prepared for My Husband’s Appalachian Trail Hike appeared first on MainStreet Financial Planning.