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.

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.

These small, intentional moves aren’t just about staying organized in the short term—they also help you protect your long-term financial health, including your ability to continue building toward retirement.

1. Plan Ahead for Seasonal Spending

Think about what’s coming: back-to-school shopping, Halloween, Thanksgiving travel, holiday gifts. These expenses can quickly throw off your monthly cash flow—and may even lead to pausing retirement contributions or dipping into savings.

Take a few minutes to map out expected costs and start setting aside a small amount weekly. Even $25–$50 per week can ease pressure later. Look for early deals, repurpose gift cards, and make use of any unused credit card rewards. For more ideas, read our article on Joyful Holiday Spending.

2. Explore Extra Income Opportunities

If your summer schedule allows, consider bringing in a little extra income now to help offset upcoming expenses, without sacrificing your retirement savings goals. This could mean selling items you no longer use, offering a skill-based service, or trying out a small side project.

Even a few hundred dollars can go a long way in preserving your regular savings plan. Check out our tips on Using Credit Card Cashback Rewards for Holiday Spending for additional ways to stretch your money further.

3. Organize and Update Key Documents

Summer is also a great time to review the paperwork side of your financial life. Make sure your beneficiary designations are current, check your insurance coverage, pull your credit report, and revisit estate planning documents. These foundational pieces are essential to protecting the retirement future you’re working toward—and they’re often overlooked during busier seasons.

Final Thought

A quick summer check-in doesn’t require an overhaul. These thoughtful steps—planning seasonal spending, exploring flexible income options, and staying organized—can help you feel more in control today while staying aligned with your retirement goals.

If you’d like to review your progress or make sure your short-term decisions are supporting your long-term plans, we’re here to help.

The post 3 Smart Summer Moves to Keep Your Financial Plan (and Retirement Goals) on Track appeared first on MainStreet Financial Planning.

Retiring or furloughed before age 65 is a long-term goal or a dire situation for many older workers who find themselves in the middle class these days.  With the exception of many government workers and military retirees, health insurance and its attendant cost is the number one worry for early retirees, either by design or default.

There are several options for health care coverage prior to Medicare, and most are costly in comparison to employer-provided plans, where premiums are shared with an employer.

In our experience, there are five options for potential early retirees to study and monitor as they approach the need for health care services in the independent retired phase before age 65:

• COBRA – which provides the same coverage from the most recent employer for up to 18 months in most situations. The cost is usually double pre-retirement costs.
• Private – Going directly to an insurer for an individual medical plan with various co-pays and deductibles is pretty easy, but usually very costly. It’s not unusual for individuals to pay $1,200 to $2,000 a month for good coverage with low deductibles.
• Health Insurance Marketplace – These are the options available under the Affordable Care Act, providing comprehensive coverage and sometimes being subsidized at lower income levels. Click here to learn more. 
• Spouse – Having a working spouse with health care benefits can provide coverage for an early retiree.
• Medical Sharing – These are faith-based programs that reimburse for covered expenses out of a fund pool that is contributed to on a monthly basis. Pre-existing conditions and some conditions (pregnancy out of wedlock) may not be covered in several of these plans based on a certain belief system.

Here’s what you can do to plan ahead as you search out these alternatives:

1. Talk to recent retiree colleagues and ask for their experiences and how they scoped out the health care alternatives.
2. Talk to fellow church or social club members to ask about their health care decisions and their experience with the alternatives we’ve mentioned.
3. Contact your county Area Agency on Aging for a referral to decision helpers. They provided that information to me when I needed to assist a family member located in another state.
4. Talk to your physician or office staff and ask them for their opinion on how to pay for medical services.
5. Finally, ask other family members and relatives for their opinion about obtaining local medical services as it pertains to cost and value for premiums or cost-sharing contributions

Good luck and happy hunting. Remember that you can contribute to lower costs by exercising and eating healthy.

The post Retiree Health Insurance Before Age 65 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.

While this fire was nothing compared to the devastating fires in the Los Angeles area, it was an eye-opening experience. I want to share some key lessons learned to help you review your own insurance coverage and emergency preparedness.

Key Takeaways & Insurance Considerations

1. Ensure Your Home Can Alert You in an Emergency

• Many neighbors close to the fire didn’t wake up when we knocked on their doors.
• Having a working doorbell is crucial. If you have a two-story home, make sure you can hear it from upstairs.
• Regularly check that your fire alarms are functioning properly and have one in each room, hallways and maybe even in the garage.
• Keep a fire extinguisher in an easily accessible location and ensure everyone in your household knows how to use it.

2. Never Use an Extension Cord for Appliances

• Fire investigators determined the fire started because a mini fridge was plugged into an extension cord and then into a 46-year-old garage outlet.
• Always plug appliances directly into a wall outlet—extension cords are not designed to handle high loads for extended periods.

3. Check Your Insurance Coverage for Garage Contents

• If you store valuable items in your garage, ensure you are including their value in the personal property section of your homeowner’s, condo, or renters’ policy.
• The HOA’s insurance typically won’t cover your personal belongings, even in accidental fires.

4. Know How Your Auto Insurance Covers Fire Damage

• If your car is damaged in a fire, repair or replacement will generally fall under your personal auto policy’s comprehensive coverage. This type of coverage kicks in when there is damage to your car (vs. collision insurance when you are in an accident)
• Most policies have a deductible so make sure this fits with how much you are afford.

5. Understand Who Pays for Garage Repairs

• The HOA will cover rebuilding the garage structure, but there is a deductible that the HOA has to pay.
• If you’re found responsible for the fire, that deductible will likely be passed on to you.
• Make sure you have Loss Assessment coverage in your condo policy to cover this type of claim.

6. Keep a Home Inventory for Easier Claims

• Take photos or videos of your belongings and store them in a secure digital location. This makes it easier to file claims and prove what you owned.
• Read this article to check out home inventory apps as an easy way to document your belongings. The app Encircle is a favorite among our staff.

7. Make an Emergency Evacuation Plan

• Decide what you would grab if you had 5 minutes, 15 minutes, or more time to evacuate.
• If you live on the second floor, ensure you have a safe exit plan.
• Exchange phone numbers with your neighbors for quick communication.

8. Have a Safety Plan for Pets

• If you have pets, make sure you have an evacuation plan that includes their needs.
• Know where your pet carrier is stored and keep it easily accessible.

Review Your Insurance Coverage

Given the recent fires, now is a great time to review your homeowners or renters’ insurance policy to ensure you have sufficient coverage.

• If you own a condo, check out my article: Five Things to Know When Buying Condo Insurance.
• If you own a home, you may want to read: Rising Inflation Could Mean Your Home Is Underinsured.
• If you rent, make sure your renters’ insurance covers:
  • Personal property replacement
  • Liability for accidental damages
  • Additional Living Expenses (aka ALE) for temporary hotel or rental stays if your home becomes uninhabitable

If you have any questions about your coverage, schedule a meeting with your financial advisor or insurance agent.  Now is the time to prepare —before an emergency happens.

The post Lessons from a Garage Fire: Reviewing Your Insurance Coverage appeared first on MainStreet Financial Planning.

1. Freeze Your Credit

If you temporarily unfreezed your credit for a loan or new credit card last year, be sure to re-freeze it now. Freezing your credit is an effective way to protect against identity theft and unauthorized access to your financial accounts.

2. Update Your Home Inventory

Take a few moments to review and update your home inventory, whether you keep it in an app, a spreadsheet, or through photos on your phone. Removing items you no longer own and adding new purchases will ensure your inventory is accurate and ready for insurance purposes if needed.

3. Scrutinize Your Credit Report

Visit annualcreditreport.com to get your free credit reports from the three bureaus: Experian, TransUnion, and Equifax. Verify that the information is accurate and that all your credit cards, store accounts, and loans are properly listed. This will help catch any errors or fraudulent activity. If you notice discrepancies, file a dispute with the relevant credit bureau.

4. Verify Your Social Security Earnings

Your Social Security benefits are based on your earnings record, so it’s crucial to ensure your reported income is correct. Log into myssa.gov to view and confirm your earnings history. If you notice any errors, you can easily request a correction online. For 2024, the maximum taxable earnings subject to Social Security tax is $168,600. Double-checking this annually ensures your record stays accurate for future benefit calculations.

5. Review Your Estate Planning Documents

Take some time to review the key documents in your estate plan, such as your will, power of attorney, and property deeds. Whether they’re stored in physical files or securely stored digitally, it’s important to confirm they’re updated and easy to access should you need them.

6. Revise Your Annual Budget

Look over your budget from the previous year and make adjustments for 2024. Tools like Tiller, Monarch, or YNAB can help you track your spending and ensure you stay within your financial goals. While inflation can increase certain costs, staying aware of your spending is the key to preventing your expenses from creeping up.

7. Prepare for Tax Season

Organize your tax documents in one central location—whether it’s a folder, box, or basket—to avoid scrambling when it’s time to file. You’ll receive a mix of mailed forms, emailed notices, and online documents, so keeping everything in one place will save you time and hassle when tax season arrives.

By checking these key items annually, you’ll stay on top of your financial health and be ready for whatever the year brings. Starting the year with these updates will give you peace of mind, knowing your finances are secure and organized.

The post Start the Year Strong: Get Your Financials in Shape for 2025 appeared first on MainStreet Financial Planning.

Financial help

Financial help for individuals is available through FEMA. There are three ways to apply:

1. Online at DisasterAssistance.gov. This is the fastest and easiest way to apply.
2. Through the FEMA App for mobile devices.
3. By calling the FEMA helpline at 1-800-621-3362, 4 AM to 10 PM (PST).

For help with applying see this video on how to apply: FEMA Accessible: Registering for Individual Assistance 

Loan Forbearance

(Mortgage, Auto, Personal):

You are expected to continue to pay your loan obligations, even if the home, auto, or other item was destroyed. Call each lender directly and see if there are accommodations that can be made, such as a hardship forbearance.  A hardship forbearance may include skipping some months of payments (the amount will vary by provider) and having the maturity date pushed into the future.  Note that interest will most likely still accrue and increase during the forbearance period.

Automobile

Automobile: Fire victims who need to replace lost or damaged DMV-related documents can do so free of charge at assistance centers in the impacted areas. Fire victims also can receive support at local DMV field offices, by calling DMV customer service at 1-800-777-0133 or by visiting www.dmv.ca.gov.

Vital Records

The California Department of Public Health (CDPH) is working with those who have lost vital records as a result of the disaster. Birth, death, and marriage records should be requested from the county recorder’s office in the county where the event occurred. For more information visit the CDPH website for a list of county recorders. Or you may call 916-445-2684

Things to remember!

• Document Everything!  When it is safe for you to return to your property, take videos and photos.  Keep a journal with a timeline from the date of the fire to the present day, documenting expenses for food, shelter, clothing, medications, and transportation.  Save receipts to submit supplement your insurance claims.
• Ensure continued mail service: USPS mail forwarding.  If you’re moving, submit a permanent change of address request so your USPS® mail is properly rerouted to your new address. If you’re only relocating for 15 days up to 1 year (like going to school or staying with family or friends), submit a temporary change of address request.  If your housing situation is in flux, you may want to rent a P.O. Box for consistent mail delivery while you and your family are moving around.
• Medications – contact your doctor and local pharmacy if you need refills on prescriptions.  Refer to your medical insurance policy, especially if you must move out of your home, with regards to in/out of network providers.
• Pets – Check with your Veterinarian to get copies of your pet’s records and prescriptions.  If you need to re-locate, see if they will call the Veterinarian in your new area as a reference if there is a shortage of veterinarians taking new patients.

If your home burned

If your home burned, then documenting your home’s condition and furnishings may be difficult.  Check your and your extended family/friends’ social media (Facebook, Instagram, etc) for recent photos to help with your insurance claims.

California Fire Foundation’s Supplying Aid to Victims of Emergency (SAVE) program provides a $250 gift card to eligible survivors of fire and natural disasters by firefighters on the scene who are enrolled in the SAVE program.  Contact the California Fire Foundation at save@cpf.org or (916) 641-1707. 

Tax Return Deadlines and Info:

In response to the recent wildfires, CDTFA has extended the January 31 sales and use tax filing deadline for Los Angeles County taxpayers until April 30, 2025. Relief and extensions beyond Los Angeles County are also available upon request. See the State of Emergency Tax Relief page for more information and a list of all tax programs covered by this relief.

Tax relief in disaster situations

The Internal Revenue Service announced tax relief for individuals and businesses in parts of California affected by wildfires and straight-line winds that began on Jan. 7, 2025. These taxpayers now have until Oct. 15, 2025, to file various federal individual and business tax returns and make tax payments.

The state of California has extended the application deadline for state financial aid programs.  If you have a current or rising college student and are planning on filing the FASFA for potential financial aid – please look at this website

Be sure to use the Free Application for Federal Student Aid on the California Student Aid Commission’s website at by May 2, 2024.

General info websites or resources:

CA government 2025 Los Angeles Fires

A list of free and discounted resources for victims of Los Angeles-area fires

Los Angeles Wildfire Recovery: Financial Resources and Steps for Homeowners – Abacus Wealth

If you are suffering from the LA Fires and need Financial planning help, please reach out!

The post LA Fires 2025 Resources: Beginning Steps to Recovery appeared first on MainStreet Financial Planning.

1. Healthcare
Open enrollment is an excellent time to reassess your healthcare needs for the upcoming year. Here are a few items to review for your healthcare benefits:

Consider if you need to change the type of healthcare plan you will have for the upcoming year. If you have an upcoming surgery or a baby on the way, a lower-deductible health plan might be beneficial. Conversely, if you are generally healthy and don’t anticipate significant medical needs, a high-deductible health plan could be more cost-effective.

If you do choose the HDHP, you may also have the option to open a Health Savings Account (HSA) where you can contribute pretax dollars to an investment account that can grow and be withdrawn tax-free to be used for eligible healthcare expenses over the rest of your life.

Does your employer offer a Flexible Spending Account?  If so, you have the benefit of setting aside a specific amount from each paycheck, pretax, to go into an account to be used for various healthcare expenses for that year. The trick with an FSA is that these dollars don’t roll over every year so you may need to adjust how much you contribute each year based on what you expect to spend on healthcare-related expenses for the upcoming year.

2. Disability Insurance
Check whether you have disability insurance through your employer. Some employers automatically provide this benefit, covering the premium and offering about 60-65% of your income if you need it. If your employer offers you the option to purchase additional coverage, remember that paying the premium yourself means your disability income will be tax-free. If your employer pays the premium, the income will be taxed, which can affect your take-home amount. Understanding your coverage and tax implications is crucial to ensuring you have adequate protection. Use open enrollment as a time to confirm you have disability insurance, review how much coverage you have, and consider whether you might need additional coverage through a private policy if what you have through work would not be sufficient for your family.

3. Life Insurance
Review your life insurance options during open enrollment. Employers often provide a base amount of life insurance, typically one to two times your salary. You may also have the option to purchase additional coverage for yourself or your spouse. Group policies offered through employers are usually more cost-effective, making this an opportune time to secure adequate life insurance, especially after significant life changes like marriage, home purchase, or childbirth.

4. Legal Benefits
I’ve seen a lot more employers starting to offer legal services to their employees. This could be useful to you if you need estate planning done, which could be at a free or reduced cost through your benefits. There are also legal plans you can sign up for that allow you a set number of hours of legal counsel as well. Be sure to check your full benefits package to see if this is available to you!

I hope this helps you in reviewing your employer benefits during this open enrollment season and if you have questions about whether you have the right coverages for you, reach out to us at MainStreetplanning.com and we would be happy to review your employee benefits with you as you decide what benefits are right for you this year.

The post 4 Things to Review During Open Enrollment appeared first on MainStreet Financial Planning.