Why did you choose a career in financial planning?

I learned early on in my adulthood that to be truly satisfied in my career, I had to
be learning something new, helping others, or making a meaningful impact. A
career in financial planning ensures that all three of those criteria are met every
single day. I love what I do!

Tell us a little about your family.

My husband is a career military officer, most recently serving at Fort Polk,
Louisiana, and I have three active sons. I am lucky to be surrounded by laughter,
noise, and a bit of chaos each and every day.

What do you enjoy doing when you’re not working?

I enjoy boating, fishing, and spending time outdoors. Some may say I am solar-
powered.

What’s one thing on your bucket list?

I want to own a lake house where my children and one day my grandchildren can
gather and make memories.

What’s a fun fact most people don’t know about you?

I have my motorcycle license!

What is the best financial advice you’ve ever received?

A goal without a plan is just a wish. Putting dollar amounts to our financial goals
has changed our trajectory. We are first-generation wealth builders with goals of
funding our children’s education and retiring early and comfortably.

If you could spend a day doing anything, what would it be?

I would choose to spend it boating with family and friends. It doesn’t get better
than that!

The post EMPLOYEE SPOTLIGHT – Lindsay Wilson appeared first on MainStreet Financial Planning.

Why did you choose a career in financial planning?

Growing up, my family rarely discussed money, so I didn’t know much about managing it or how important that process was. But once I learned, I wanted to share my knowledge with others—to help them avoid some of the mistakes I made along the way. A career in financial planning felt like the perfect way to combine my passion with work that empowers people to build more secure lives.

Tell us a little about your family.

Most of my family lives in Kentucky and the surrounding states, but I’m very fortunate to live not too far from my daughter in southern CA. She’s all grown up, she’s so much fun to be with and I’m so proud of her and her accomplishments.

What do you enjoy doing when you’re not working?

When I’m not working, I enjoy a wide range of hobbies from designing fashions to building furniture to painting to you name it – I love learning new things.

What’s one thing on your bucket list?

I’m a recent transplant to CA so I want to explore and enjoy the beaches, the sunsets, and the beautiful weather.

What’s a fun fact most people don’t know about you?

I once renovated a 100-year-old house in Kentucky. I added modern furnishings and stained-glass windows that I made myself and later sold it to a designer who purchased everything including the furnishings for above my asking price.

What is the best financial advice you’ve ever received?

Mind your money—because if you don’t someone else will and then they will control your future.

If you could spend a day doing anything, what would it be?

Hanging out with my kid – we have so much fun together.

The post EMPLOYEE SPOTLIGHT – Patricia Stallworth, CFP® 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.

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.

1. Use Your Tax Return as a Guide

Before you file it away, take a quick look at what actually happened last year:

• Where did your income really come from?
• How much did you pay in taxes?
• Did anything surprise you (a big refund or an unexpected bill)?

Ask yourself: Was this what I expected?

If not, that’s helpful. It usually means there’s something worth adjusting now—not next year.

2. Adjust Withholding or Estimated Payments

If you owed more than you expected or got a much bigger refund than you planned, it’s probably time to fine-tune things:

• Update your paycheck withholding
• Revisit estimated tax payments (especially if you’re retired or self-employed)

The goal here isn’t perfection. The goal is just to avoid big surprises and smooth out your cash flow.

3. Revisit Your Tax Strategy for This Year

Now that you’ve seen how last year played out, you can be more intentional this year.

A few things to think about:

• Does a Roth conversion make sense this year?
• Should you shift income between years if you have flexibility?
• Are there opportunities to realize gains or losses more strategically?

4. Update your Contributions

This is one of the easiest things to review and update during your “spring cleaning.” Be sure to increase your contributions to your 401k and/or IRA’s to max out for the year.

For 2026, contribution limits have increased to:

• 401(k): $24,500 (+ $8,000 catch-up if 50+, or up to $11,250 if ages 60–63)
• IRA (Traditional or Roth): $7,500 (or $8,600 if 50+)
• HSA: $4,400 individual / $8,750 family (+ $1,000 catch-up if 55+)

If you can:

• Increase your automatic contributions
• Revisit your IRA or HSA funding plan
• Make sure your savings still match your current income

Even small changes now can make a noticeable difference by the end of the year.

5. Clean Things Up and Simplify

This is the “spring cleaning” part. Take a little time to:

• Consolidate old retirement accounts
• Double-check your beneficiaries
• Organize important documents
• Cancel or unsubscribe from things you don’t use anymore

6. Revisit Your Investment Mix

The market has moved around a lot over the last year and your portfolio can drift more than you realize. After tax season is a great time to:

• Review your allocation
• Rebalance if needed
• Make sure your investments still line up with your timeline (especially if retirement is getting closer)

Filing your taxes isn’t really the finish line—it’s more like the starting point for making smarter decisions this year. A few small, intentional adjustments now can go a long way toward reducing taxes over time, improving cash flow and feeling more confident about what’s ahead. If you have questions about any of this, feel free to reach out! We’re always happy to help you get things organized and on track for the year ahead.

The post Spring Cleaning for Your Finances: What to Do After You’ve Filed Your Taxes appeared first on MainStreet Financial Planning.

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.

• Transfer cash held in digital wallets like Venmo, PayPal and Cash App to your bank account monthly.
  • Benefit: Funds held in these apps are not FDIC insured. Moving them protects your money—and allows it to earn interest.
• Vacuum out your dryer vent at least annually.
  • Benefit: Your dryer runs more efficiently, and more importantly, you significantly reduce the risk of a house fire.
• Make a credit card payment twice a month.
  • Benefit: Your credit score could increase by lowering your credit utilization rate before the lender reports your balance to the credit bureaus.
• Take photos of your ID, passport, and credit cards and store them in a hidden folder on your phone.
  • Benefit: If items are lost or stolen, you’ll have quick access to important details and customer service numbers securely stored in a password-protected Hidden/Locked/Secure folder.
• Write a postcard to a friend you haven’t spoken to in a while. A stamp for the standard domestic postcard (4 ¼” high by 6” long) costs $0.61.
  • Benefit: Staying socially connected can reduce loneliness and positively impact your long-term health and happiness!

At the end of the day, progress doesn’t come from grand resets—it comes from small, repeatable choices that quietly stack in your favor. Whether it’s reconnecting with someone you care about, protecting your money, improving your safety, or strengthening your financial footing, these simple to-dos are easy to overlook but powerful when practiced consistently.  If your New Year’s intentions wobbled a bit, that’s okay—consider this your reminder that a reboot is always available, and even the smallest habits can make a meaningful difference over time.

Related reading:

Good Habits Need Good Techniques — a practical look at how to build habits that actually last.

The post Good Habits for the New Year appeared first on MainStreet Financial Planning.

Here are four smart year-end check-ins to complete before December 31st.

1. Review Your Spending Plan

• Look over your 2025 expenses. Are there new recurring costs that should be added? Any unused subscriptions or services that can be canceled?

• Identify areas where spending could be reduced or redirected to better support your 2026 financial goals.

• If you’re not currently using a budgeting system, here’s a great place to start:

  3 Alternatives to the Mint Budgeting App

• Consider using a budgeting or cash-flow app to simplify tracking the flow of money throughout the year.

2. Strengthen Your Emergency Fund

• Aim for 3–6 months of essential expenses saved in a high-yield savings account.

• Reevaluate your target amount based on life changes in 2025—job transitions, higher expenses, more dependents, or fewer earners.

• If your emergency fund is below your target, set a plan for steady monthly contributions in 2026 to rebuild your reserves.

3. Check In on Your Investments

2025 Retirement Contribution Limits

• 401(k)/403(b)/TSP employee deferrals: $23,500
• IRA (Traditional or Roth): $7,000
• Catch-up contributions (age 50+):
  • $7,500 for workplace plans

  • $1,000 for Traditional and Roth IRAs

• Special catch-up for ages 60–63: $11,250 (if your employer plan allows it)

Year-End Investment Actions

• If you aren’t maxing out your accounts, consider increasing contributions by 1% for 2026—small increases compound significantly over time.

• Review your portfolio allocation. Market swings throughout the year shift your mix of stocks, bonds, and cash.

  A year-end rebalance helps realign your investments with your risk tolerance and long-term goals.

• Not sure whether your portfolio is positioned correctly? Reach out to our team—we’re happy to help.

4. Review Your Required Minimum Distributions (RMDs)

If you are age 73 or older in 2025, or if 2025 is your first RMD year, this is a key item to address before December 31st.

What to know:

• If you turned 73 in 2024, your 2025 RMD must be taken by December 31, 2025.

• If you turn 73 in 2025, this is your first RMD year:

  • You may take your RMD anytime in 2025 or delay it until April 1, 2026.

  • But delaying means taking two RMDs in 2026, which may increase your taxable income.

• Confirm that all RMDs are withdrawn from the correct retirement accounts (IRAs, 401(k)s, 403(b)s, etc.).

• The penalty for missed RMDs is 25% of the amount not withdrawn (reduced to 10% if corrected promptly).

If you need help calculating or coordinating your RMDs, our team is here to walk you through the process.

Additional Resources to Support Your 2025 Wrap-Up

• 5 Year-End Tax Moves to Make Now (Anna Sergunina)

• 5 Ways to Get Organized in the New Year (Cynthia Flannigan)

• One Financial Habit to Change (Cynthia Flannigan)

The post Review These 4 Financial Tips Before December 31, 2025 appeared first on MainStreet Financial Planning.

When:
November 18th 2025
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!

When Health Meets Wealth:
Planning for a Longer, Stronger Life

(For anyone curious about the sweeping tax changes and how they may impact your family)

Hosted by: Anna Sergunina, CFP®

Guest commentator:  Dr. Pamela E Wilson

What if your health plan and financial plan worked together?

What if your financial plan and your health plan worked together?

Join Anna Sergunina, CFP®, and Dr. Pam Wilson, physician and founder of the F.I.R.S.T. Method™, for a special Chalk Talk on the intersection of longevity medicine and financial readiness.

You’ll learn how to reset your habits, energy, and mindset—so you can live longer, feel better, and enjoy your retirement years with confidence. Together, Anna and Dr. Pam will show how aligning your health and money decisions can help you build a longer, stronger, and more fulfilling life.

About Dr. Pam E. Wilson:

Dr. Pam Wilson is a physician with over 30 years of experience helping people restore energy, rebuild health, and move with strength and purpose. She created the F.I.R.S.T. Method™ and is the author of the upcoming book Think. Fuel. Move. — a proven framework for transforming mindset, metabolism, and movement for lasting health. 

Some of the topics we’ll discuss:

1. How Health Impacts Financial Independence
2. Longevity Planning: Living Well, Not Just Longer
3. Habits That Pay Dividends — in Health and Money
4. Creating a Holistic Health Plan for Your Future

The post Chalk Talk: When Health Meets Wealth: Planning for a Longer, Stronger Life appeared first on MainStreet Financial Planning.