Your Fall Financial Checklist: 10 Key Moves Before Year-End

Summer in New England is ebbing quickly: less daylight, cooler nights, leaves flying from the trees, and fewer social engagements.  It’s also the perfect time to shift focus from relaxation to preparation. The final quarter of the year brings several important financial decisions – especially with the newly-enacted One Big Beautiful Bill Act (OBBBA) in play.  Here’s a quick guide to 10 key action items to consider and address before year-end:

1. Employer-Sponsored Benefits Enrollment (usually October-November):

The annual enrollment period gives employees an opportunity to choose workplace benefits for the coming year.  Health, dental, vision, disability, and life insurance elections are important (and enviable!) perks for those still working, as are elections for Flexible Spending Accounts (FSAs) and Health Savings Accounts (HSAs).      

2. Medicare Open Enrollment (October 15 through December 7):

Medicare beneficiaries can switch between Original Medicare and Medicare Advantage plans or update prescription drug coverage.  It’s important to resist the temptation to automatically renew your elections from prior years, as premiums, formularies, and provider networks can change annually.  Take particular care if this is your initial enrollment year for Original Medicare, as Medigap policy selections can be difficult to change in subsequent years.  

3. Year-end Tax Planning (October through December):

This is your annual opportunity to optimize taxable income and deductions before year-end.  Key considerations include accelerating or deferring income and deductions, maximizing retirement contributions, harvesting capital losses to offset gains, and reviewing charitable giving strategies.

4. Open Enrollment for Health Insurance Marketplaces (typically early November through mid-December):

Individuals and families will be able to select, renew, or change Affordable Care Act (ACA) marketplace plans for 2026.  Action items here include reviewing coverage changes and premium updates, assessing eligibility for subsidies, and evaluating the compatibility of HSAs with your chosen health insurance plan.

5. Required Minimum Distributions (by December 31):

This applies to most retirees over age 73, as the IRS requires withdrawals from traditional IRAs, 401(k)s, and other qualified accounts.  Failure to withdraw the required amount may trigger steep penalties.  

6. Tax Withholding and Estimated Payments (final adjustments in Q4):

Ensure sufficient withholding and/or estimated tax payments to avoid underpayment penalties.  OBBBA may substantially change your tax perspective, as the standard deduction is made permanent at a higher level than before and is enhanced with an additional temporary deduction for seniors.  The much-discussed limit on the SALT (State and Local Tax) deduction has also been substantially increased this year.  This may provide an opportunity to bunch itemized deductions into 2025 and to prepay charitable donations before year-end to lock in benefits under current rules.  Review detailed calculations with your tax accountant and adjust the final quarterly estimate payment due in January.

7. Investment Portfolio Rebalancing (throughout Q4):

Restore target asset allocations after a year of market fluctuations.  Sell outperforming assets and reinvest in underweighted areas.  

8. Tax-Loss Harvesting (by mid-December):

Where possible, realize investment losses to offset capital gains and reduce taxable income.  The ripple effect of this can be significant, as income spikes not only increase tax payments but may also trigger higher health insurance premiums. 

9. Year-End Retirement Contributions Deadlines (December 31):

Contributions generally must be completed by December 31.  IRA contributions can extend into April of the following year, but workplace retirement contributions must be completed by year-end.

10. Charitable Moves (Q4):

The fourth quarter of the year is often optimal for strategic giving, and that is particularly true this year because of OBBBA due to pending changes for 2026.  Take advantage of the opportunity to reduce your current year tax liability by gifting appreciated securities, making contributions to Donor-Advised Funds, or making Qualified Charitable Distributions (QCDs) from IRAs for those 70 ½ or older. 

The Utlimate Takeaway

Proactive planning in these final months of the year can help to lock in benefits and set the stage for optimal outcomes in 2026 and beyond.  And as always, it’s important to review these provisions and any potential changes with your professional advisors. Contact The Howe Team today with any questions and to assist you with any of these action items.