2025 End of Year Planning Checklist.

Year-end planning goes beyond retirement. As we move into 2025, evolving regulations, contribution limits, and coverage rules across multiple areas can affect your cash flow, taxes, and protection. This comprehensive checklist covers a wide range of year-end items across retirement planning, Health, Life, Medicare, and Property & Casualty insurance, so you can review the essentials before year-end.

Designed for individuals, families, and business owners, it's a practical, step-by-step guide to help you make confident year-end decisions with FSI Financial. Use it to prioritize what matters for your situation, coordinate actions across accounts and policies, and be sure important deadlines don't slip through the cracks.

Social Security Review and Optimization

Annual Benefit Assessment

• Review your Social Security Statement online at ssa.gov to verify your earnings record and projected benefits

• Check for errors in your work history that could reduce your future benefits, incorrect or missing earnings can cost you thousands over time

• Calculate your break-even point for different claiming strategies if you haven't filed yet

• Consider spousal benefit optimization if married, sometimes the lower-earning spouse should file first

• Evaluate working in retirement impacts, understand how earned income affects your benefits if you're under full retirement age

2025 Cost-of-Living Adjustment (COLA)

• Factor the 2025 COLA increase into your income planning and budget projections

• Adjust your tax withholding if necessary, COLA increases can push you into higher tax brackets

• Review Medicare premium impacts, higher Social Security payments may increase your Medicare Part B premiums through IRMAA

Be sure to remember that Social Security timing decisions are among the most important financial choices you'll make. The difference between claiming at 62 versus waiting until 70 can mean hundreds of thousands of dollars over your lifetime.

Medicare Annual Review Period

Open Enrollment Tasks (October 15 - December 7)

• Compare Medicare Advantage plans in your area, networks, formularies, and costs change annually

• Review Part D prescription drug coverage, ensure your medications are still covered at the best price

• Check provider networks, confirm your doctors and specialists remain in-network

• Evaluate supplemental insurance (Medigap) options if you have Original Medicare

• Consider Health Savings Account strategies if you have a high-deductible health plan and are still working

Healthcare Cost Planning

• Project out-of-pocket medical expenses for the coming year based on your health status

• Budget for premium increases, both Medicare and supplemental insurance premiums typically rise annually

• Plan for long-term care costs, consider whether long-term care insurance still makes sense for your situation

• Review beneficiary designations on all health-related accounts

Ask yourself: Are you prepared for healthcare costs to consume 15% or more of your retirement income? This percentage often increases with age, making accurate planning essential.

Under 65 Health Insurance (ACA/Marketplace)

If you’re under 65 and not enrolled in Medicare, be sure to review your Marketplace options and updates ahead of Open Enrollment. Rules and timelines can vary by state, so confirm details on HealthCare.gov or your state-based Marketplace.

2026 Highlights to Review

• Mark Open Enrollment: November 1, 2025 – January 15, 2026 (note: the federal window is scheduled to shorten in future years; state deadlines may differ)

• Double-check if your premium tax credits are changing: 2025 is the last year for expanded advance premium tax credits (APTCs), which may affect 2026 premiums

• Be aware of the new $5/month minimum premium rule for many plans—review and renew your application details to avoid surprises

• Watch for requests for income/personal information verification—respond within 90 days to help keep coverage and savings in place

• If low-income: be aware year-round enrollment ends; use Open Enrollment or see if you qualify for a Special Enrollment Period

• Ask about new HSA-eligible Marketplace plans for 2026—see if a Health Savings Account is right for you

For the most current information and eligibility details, visit HealthCare.gov or your state Marketplace.

Tax Strategy and Income Planning

Retirement Account Management

• Maximize 2025 contribution limits, IRA contributions increased to $8,000 ($9,000 if 50+)

• Take advantage of "super catch-up" contributions if you're ages 60-63 in employer plans

• Plan Required Minimum Distributions (RMDs) if you're 73 or older

• Consider Roth conversions, evaluate whether converting traditional IRA funds makes sense at current tax rates

• Review asset allocation across all accounts to maintain appropriate risk levels

Income Withdrawal Strategy

• Implement a systematic withdrawal approach, consider the 4% rule as a starting point, but adjust for your circumstances

• Coordinate multiple income sources, balance Social Security, pensions, and portfolio withdrawals for tax efficiency

• Plan for irregular expenses, set aside funds for home maintenance, travel, and unexpected costs

• Consider tax-location strategies, hold tax-inefficient investments in tax-advantaged accounts

This is your financial future at stake, a well-planned withdrawal strategy can add years to your portfolio's longevity while minimizing your lifetime tax burden.

Investment Portfolio Review

Asset Allocation Assessment

• Rebalance your portfolio to maintain your target allocation across stocks, bonds, and other assets

• Review international exposure, consider whether your global diversification remains appropriate

• Evaluate bond duration in the current interest rate environment

• Consider dividend-focused strategies for income generation in retirement

• Review fees and expenses, high costs can significantly erode long-term returns

Risk Management

• Assess sequence-of-returns risk, early retirement years are critical for portfolio preservation

• Consider bond ladders or CDs for guaranteed income

• Review emergency fund adequacy, retirees should maintain 6-12 months of expenses in liquid assets

• Evaluate whether annuities make sense for a portion of your portfolio

Estate Planning and Beneficiaries

Document Updates

• Review and update wills and trusts, ensure they reflect current wishes and tax law changes

• Update beneficiary designations on all retirement accounts, insurance policies, and investment accounts

• Consider power of attorney documents, both financial and healthcare directives should be current

• Review estate tax implications, understand how federal and state estate taxes might affect your heirs

Legacy Planning

• Evaluate life insurance needs, determine whether existing coverage still serves its intended purpose

• Consider gifting strategies, annual gift tax exclusions allow tax-free wealth transfer

• Plan for charitable giving, explore strategies like Qualified Charitable Distributions from IRAs

• Discuss plans with family members, communication can prevent future conflicts and ensure smooth transitions

Insurance Coverage Review

Health Insurance Assessment

• Compare Medicare supplement options if you have Original Medicare

• Review long-term care insurance policies and premiums

• Assess dental and vision coverage, Medicare doesn't cover these important areas

• Consider critical illness or accident insurance based on your health and family history

Property and Liability Protection

• Review homeowners or renters insurance, ensure coverage keeps pace with property values

• Assess auto insurance needs, retirees often qualify for discounts due to reduced driving

• Consider umbrella liability coverage, protect assets from potential lawsuits

• Evaluate disability insurance, determine whether coverage should continue into retirement

Action Timeline and Professional Guidance

Immediate Actions (Next 30 Days)

• Order your Social Security Statement if you haven't reviewed it this year

• Schedule your Medicare plan review before the December 7 deadline

• Gather financial statements for portfolio review

• Update beneficiary information on all accounts

Quarterly Reviews

• Monitor portfolio performance and rebalancing needs

• Review spending against budget projections

• Assess tax withholding and estimated payments

• Update emergency fund as needed

Make sure to consider working with qualified professionals for complex situations. Tax advisors, fee-only financial planners, and insurance specialists can provide personalized guidance that generic advice cannot match.

Your Next Steps

Retirement planning in 2025 requires attention to multiple moving parts, but approaching it systematically makes the process manageable. Start with the immediate action items, then work through the other categories at a comfortable pace.

Remember that these decisions compound over time, small improvements in your strategy today can lead to significantly better outcomes over the years ahead. Your specific situation will determine which items deserve the most attention, so be sure to prioritize based on your individual circumstances.

Take Your Next Step

Curious how these 2025 changes affect your retirement plan? Schedule a free, no-pressure consultation with a specialist today! Contact us at 727-623-4645 to discuss your specific situation or click here to download the 2025 End of Year Planning Checklist.

Want an easy reference for all these important tasks? Download our comprehensive 2025 Retirement Planning Checklist, it's designed for printing and includes space for notes and deadlines.

Contact Information: Lamont, Broker Director FSI Financial Visit our website or call for personalized assistance with your retirement planning needs.

This material is for informational purposes only and does not constitute tax, legal, or financial advice. Medicare benefits, eligibility requirements, premiums and/or copayments may change annually. We do not offer every plan available in your area. Currently we represent 8 organizations which offer 51 products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program (SHIP) to get information on all of your options.

This information is not intended as tax, legal, investment, or retirement advice or recommendations, and it may not be relied on for the purpose of avoiding any federal tax penalties. You are encouraged to seek guidance from an independent tax or legal professional. The content is derived from sources believed to be accurate. Neither the information presented nor any opinion expressed constitutes a solicitation for the purchase or sale of any security.