When:
October  20th, 2026
3:30 pm Eastern; 12:30 pm Pacific
~45 minutes & Q/A included

How: Zoom Meeting
Recorded and available to retrieve for one
month

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

Email us for the recording!

Should You Do a Roth Conversion?
How to Think About It, and the Mistakes to Avoid

Hosted by: Anna Sergunina, CFP®

Guest commentator: Rob Colon, CFP®, EA

Tax Professional: MainStreet Tax Services

Should you convert part of your IRA to a Roth, and is this the year to do it? It’s the question we hear most in client meetings this fall, and many people get stuck debating it while the window for 2026 closes on December 31. Join Anna Sergunina, CFP®, and Robert Colon, CFP®, EA, the tax professional who prepares returns for MainStreet clients, for a practical conversation about how to think through the decision, the costs that go beyond the income tax, and the mistakes we see most often on real tax returns.

Meet Robert Colon, CFP®, EA

Rob is an independent tax professional and trusted partner of MainStreet Financial Planning. With over 15 years of experience in financial planning and accounting, he provides tax preparation and proactive tax planning services to MainStreet clients. As both a CFP® professional and an IRS Enrolled Agent, Rob works closely with our financial planners to help clients make tax-smart decisions that support their overall financial goals.

MainStreet Tax Services: Tax preparation and forward-looking tax planning for active MainStreet clients, built into your Money Roadmap so your planner and your tax preparer are working from the same plan.

Some of the topics we’ll discuss:

• Should you convert at all? The basic trade-off of paying tax now or later, and who pays it later, you or your heirs
• The years when converting makes the most sense, and when it doesn’t
• Costs beyond the income tax: Medicare premiums (IRMAA) and ACA health insurance subsidies
• How much to convert, without overshooting your tax bracket
• The mistakes we see most often
• Next steps, what documents to gather and what professionals to engage
• Your questions, answered live

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: Should You Do a Roth Conversion? How to Think About It, and the Mistakes to Avoid 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.

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.

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.

When:
August 7, 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

Sign Up by Clicking Here

The One Big Beautiful Bill: What It Means for You

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

Hosted by: Anna Sergunina, CFP®

Guest commentator: Rob Colon, CFP® an in-house tax expert

By now, you’ve likely seen headlines about the new legislation dubbed the “One Big Beautiful Bill” (OBBB) — a sweeping tax and policy package that’s stirring up plenty of questions.

At MainStreet, we know these changes can feel overwhelming. That’s why we’re dedicating this Chalk Talk: Real Money Questions. Expert Answers. session to breaking down what matters most — without the noise or the jargon.

Anna Sergunina, CFP®, will host this engaging conversation with Rob Colon, CFP®, who will walk through the key elements of the new law that could impact your financial life today and in the future. Whether you’re actively planning for retirement, raising a family, or just trying to understand what changed — this session is for you.

Rob will also share real-life examples and planning scenarios from recent client conversations, helping you understand how these changes might affect your own financial strategy.

Some of the topics we’ll discuss:

⁃ Changes to the State and Local Income Tax (SALT) deductions

⁃ Impacts on the child tax credit

⁃ Expiration of energy-efficient tax credits

⁃ Introduction of “Trump Accounts” for college savings

⁃ Updates to the standard deduction — and what it means for you

⁃ What’s permanent, what’s temporary, and what to watch

This Chalk Talk is open to clients and guests — and will be recorded and available for one month following the session.

Bring your questions. We’ll bring the clarity.

Save the date. Next Chalk Talk Session is scheduled for November 18^th, 2025

The post Chalk Talk: The One Big Beautiful Bill: What It Means for You appeared first on MainStreet Financial Planning.

The MainStreet Financial Planning Discussion Club

When:  Thursday, May 29th, 2025 at 3 pm ET | 12 pm PT

~30-45 minutes

Recorded and able to retrieve for one month

How: Zoom Meeting

Free for current clients, $10 for guests

Register Here!

Understanding Insurance Without the Overwhelm

Hosted by: Anna Sergunina, CFP®

Guest: Ramona Johanneson

Insurance can feel overwhelming, but it doesn’t have to be.
Join us for a practical, engaging conversation where we’ll cut through the complexity and help you feel confident about your coverage.

Ramona will share how to read between the lines of your policies and make informed decisions that truly protect you and your family.
We’ll cover:

• Auto Insurance: What coverage do you actually need?
• Umbrella & Liability: When it’s worth it—and how much is enough
• Homeowners Insurance: Key trends and red flags, especially in California.

This session goes beyond the basics to help you understand the “why” behind insurance coverage, so you can make confident choices that truly protect your financial future.

 Please forward your questions in advance to anna@mainstreetplanning.com

Coming Up

📅 Save the date for our next Chalk Talk: August 28, 2025 at 12pm PT / 3pm ET

Disclaimer: This is a group educational session. Strategies discussed may not apply to every situation. For personalized advice, please consult with your MainStreet financial planner.

The post Chalk Talk: Understanding Insurance Without the Overwhelm appeared first on MainStreet Financial Planning.

The MainStreet Financial Planning Discussion Club

When:  Thursday, November 21st at 6:45 pm ET | 3:45 pm PT

~30-45 minutes

Recorded and able to retrieve for one week

How: Zoom Meeting

Free for current clients, $10 for guests

Email us for the Recording!

Passing on Your Legacy: Planning for Smooth Asset Transfer

Hosted by: Vida Jatuils, CFP® &  Anna Sergunina, CFP®

Guest: Barry W. Finkelstein

Are you prepared for how your assets will pass to your loved ones? Join Anna Sergunina, CFP® and Vida Jaulis, CFP®, and guest estate planning expert Barry W. Finkelstein, as they provide insights into establishing a meaningful estate plan to ensure a smooth transfer of assets through trusts, wills, and essential directives.

In many cases, estate planning documents are established without a full understanding of how they work, when they come into play, and how tools like trusts can facilitate the efficient transfer of assets to the next generation. This session will take you beyond the basics, empowering you with the knowledge to make informed decisions tailored to your unique life stage and family needs.

Topics we’ll cover include:
1. The essential documents for effective asset transfer, including trusts, wills, and powers of attorney.
2. Planning for minor children: setting up trusts to protect and support young beneficiaries.
3. Understanding how asset transfer evolves as children reach adulthood.
4. Choosing the right successor trustees, executors, and healthcare agents.
5. Structuring inheritances to ensure they support, rather than burden, your beneficiaries.

Join us for this insightful session to gain peace of mind, fully understand your estate plan, and ensure your legacy supports your loved ones at every stage of life!

About Barry W. Finkelstein

Barry Finkelstein is a California native and opened his last office in Alameda in 2000, focusing exclusively on estate planning for individuals and families throughout the Bay Area.  Barry is passionate about estate planning because he feels that there is so much about what happens to us and our stuff if we become incapacitated and after we die that most people don’t know or understand, which is why he loves doing presentations like this one, to help people make that rough transition as smooth as possible.  Barry is an avid cyclist who loves to do volunteer work and lives in Mountain View with his wife Susan and their two cats.

The post Chalk Talk: Passing on Your Legacy: Planning for Smooth Asset Transfer appeared first on MainStreet Financial Planning.

The MainStreet Financial Planning Discussion Club

When:  Thursday, October 10th at 3pm Eastern; 12pm Pacific

~30-45 minutes

Recorded and able to retrieve for one week

How: Zoom Meeting

Free for current clients, $10 for guests

Email us for the recording!

College Funding Planning

Hosted by: Vida Jatuils, CFP® &  Anna Sergunina, CFP®

Is your child heading to college in the next 0-5 years? Now is the time to start planning! Join Vida Jatulis, CFP®, and Anna Sergunina, CFP®, as they guide you through key strategies for funding your child’s education and developing a comprehensive timeline of actions to take.

We’ll cover crucial steps, deadlines, and discussions you should have over the next few years while your child is still in high school. Key topics include saving strategies, estimating costs, tax planning, and financial aid. Plus, we’ll help you map out the important conversations to have with your teen about college money.

Things we will discuss:

1. Is it too late to start saving?
2. Estimating the cost of college and creating a cash flow plan.
3. How to have the college money talk with your high schooler.
4. Tax planning strategies to reduce college expenses.
5. Is it worth spending money on test prep or AP tests?
6. Understanding aid, loans, and how to tap into investments.

Don’t miss this opportunity to build a solid college funding plan and stay on track with key financial decisions over the next 0-5 years!

College Funding Plan

The post Chalk Talk: College Funding Planning appeared first on MainStreet Financial Planning.

The MainStreet Financial Planning Discussion Club

When:  Thursday, June 27th at 6pm Eastern; 3pm Pacific

~30-45 minutes

Recorded and able to retrieve for one week

How: Zoom Meeting

Free for current clients, $10 for guests

Email us for the recording!

Navigating the Non-Financial Side of Retirement

Hosted by: Anna Sergunina, CFP®

Guest: Luanne Mullin, Retirement Counselor

Retirement is a complex and exciting phase of life that we spend years working, saving, investing, and preparing for. But how do you create a path that ensures you are truly ready and confident in your decisions, especially the non-financial ones?

In this discussion, we’ll cover essential topics to help you prepare for this transition.

• The Nature of Transitions: How do we recognize and embrace change, whether we initiate it or happens to us?
• Mapping Your Future: What steps can you take to move forward with confidence and purpose?
• Risk-Taking and Momentum: How can embracing risks lead to growth and new opportunities?
• Exploring New Possibilities: What are the unique challenges and opportunities for those over 50.

Let’s get started on making your retirement as fulfilling and secure as possible!

Readings:

Beyond savings: Why retirement lifestyle planning is important

Retiring Soon? How to Ensure a Successful Transition

Please forward your questions in advance to anna@mainstreetplanning.com

The post Chalk Talk: Navigating the Non-Financial Side of Retirement appeared first on MainStreet Financial Planning.

The MainStreet Financial Planning Discussion Club

When: Tuesday 3-19-24 at 7:30pm Eastern; 4:30pm Pacific

~30-45 minutes

Recorded and able to retrieve for one week

How: Zoom Meeting

Free for current clients, $10 for guests

Email us for the recording!

Continuing Care Retirement Communities

Hosted by: Jennifer Bush, CFP®

CCRCs are retirement communities (aka life plan communities) for people 60+ who want an all-in-one solution to aging in place. Residents start out living independently in an apartment, duplex, or single-family home, and later transition to assisted living, memory care, or skilled nursing if needed. A perfect choice for those who want the security of knowing they won’t have to move should their health needs change. Join us for a deeper dive to see if a CCRC or life plan community is right for you. We will explore:

• Lifestyle benefits
• Payment Structures
• Financial contracts
• How to prepare for the move
• Things to include in your research.

 Please forward your questions in advance to jennifer@mainstreetplanning.com

Readings:

Where You Live Matters: Continuing Care Retirement Communities

Niche Retirement Communities Are Growing — Are They Right for You?

Back to School: University-Based Senior Living Trend Nears Next Evolution 

How to Know If a CCRC’s Healthcare Center Will Meet Expectations

The post Chalk Talk: Continuing Care Retirement Communities appeared first on MainStreet Financial Planning.