When:
March 25th, 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!

Buying Your Next Home Before You Sell

Hosted by: Cynthia Flannigan, CFP®

Guest commentator: Lee Chieng

Certified Mortgage Advisor, General Mortgage Capital Corp

This Chalk Talk is designed for homeowners who are preparing for an important life transition: selling a long-time family home and purchasing a new home for the next chapter of retirement. But timing can be tricky. What happens if you find the perfect downsized home before your current home sells? Or if you want to avoid making your purchase contingent on selling first?

In this session, we’ll walk through:

1. What are the common obstacles homebuyers are facing when they decide to buy before they sell?
2. What are the financing options available?
   • Bridge loan
   • Equity line or equity loan
   • Pledged assets
3. The costs, timelines, and qualification requirements for each option
4. The advantages and potential risks to consider

Lee Chieng is an accomplished loan officer with a strong background in the mortgage industry. With over two decades of experience, she has been assisting clients in achieving their homeownership dreams since 2002. Lee possesses extensive knowledge of both traditional and non-traditional home mortgages, as well as expertise in government-backed loans such as FHA and VA.

In addition to her expertise in traditional, conventional, and government loans, Lee is well-versed in catering to the unique needs of investors and individuals with non-traditional income sources. She understands that not all borrowers fit the standard criteria and is proud to offer Non-QM loan programs tailored specifically for these situations. Lee is committed to providing options and solutions to clients who may have faced financial challenges in the past or have unconventional financial profiles.

Furthermore, Lee is highly knowledgeable in the complexities of reverse mortgages. She understands that homeowners in their golden years may have different financial needs and can benefit from a reverse mortgage. Lee’s reverse mortgage program is designed to provide financial flexibility and stability for seniors aged 62 and older. Whether her clients are looking to supplement their retirement income, cover healthcare expenses, or simply enjoy their retirement years to the fullest, she offers tailored solutions to meet their specific needs. Lee takes the time to educate her clients about the pros and cons of reverse mortgages, ensuring they have a comprehensive understanding of this specialized financial product.

Throughout her career, Lee has helped numerous clients with diverse backgrounds and unique circumstances achieve their homeownership goals. She believes in building trust and lasting relationships with her clients, always putting their best interests first. Lee’s commitment to providing exceptional service means that she goes the extra mile to educate her clients about the various options available to them. Her goal is to empower her clients to make informed choices that align with their financial objectives.

You may contact Lee at 415-569-2119 or by e-mail at lchieng@gmccloan.com to learn more!

The post Chalk Talk: Buying Your Next Home Before You Sell 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.

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.

At MainStreet, we help clients plan financially every day. But we’ve also seen what happens when someone enters retirement without a plan for how they’ll spend their time, find purpose, or stay connected. That emotional and lifestyle transition can be just as important as your investment portfolio.

Here are some questions worth asking as you prepare:

• What will a typical day look like in retirement?

• How will you spend your time—and with whom?

• What brings you joy, energy, or a sense of purpose?

• What hobbies or activities do you want to explore?

• How is your health, and what will it take to stay active?

From “What I Am” to “Who I Am”

As human beings, we go through several stages in life—childhood, young adulthood, career years—but retirement requires a shift many aren’t prepared for. We’re no longer defined by job titles or daily routines. Instead, it becomes a question of identity: Who am I now, and how do I want to live?

That’s why we were inspired by the work of Sara Zeff Geber, Ph.D., a retirement transition expert and founder of LifeEncore. She specializes in helping baby boomers and solo agers navigate this exact transition, beyond the numbers.

Sara encourages people to think in four categories:

• What you have (your resources—financial and otherwise)

• What you enjoy (travel, hobbies, volunteering, creativity)

• What do you want to learn (new skills, passions, or experiences)

• How do you want to live (your environment, community, and daily rhythm)

Your Retirement, Your Design

The beauty of this phase of life? There’s no one-size-fits-all model. You get to choose what it looks like—and how it feels. The earlier you start planning the non-financial side of retirement, the more fulfilling it can be.

It’s never too late to start asking the right questions—and it’s always the right time to build a life you love.

The post Non-Financial Side of Retirement … Are you ready? 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.

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