Harvest Season: Year-End Planning

by Shala Walker 

I’ll admit it: I love spooky season! Every October, I look forward to watching scary movies, drinking hot cider, and seeing the creative costumes of tiny trick-or-treaters. When I was younger, I was most excited to visit haunted houses each season even though I’d scream louder than anyone else the second something jumped out of the shadows. In reality, the fright lasted only a few seconds, and in the end, whatever seemed unbearable moments earlier was usually just a person in a mask and some very good fog machines. 

From tax planning and investment strategies to budgeting and retirement savings, the “scary” parts of wealth planning all usually feel much bigger in the dark than they are once you walk through them. Most of what makes clients put off planning isn’t the complexity of the decisions. It’s the thought that the experience would be more uncomfortable than it actually is. 

So, as we enter the last quarter of 2026, it is crucial to take stock of your financial situation early and consider the following list of year-end planning opportunities.  

Did I Experience Any Life Changes This Year? 

If so, you may want to review beneficiary designations and trust structures for any potential updates resulting from a change in marital status, liquidity, births, business transitions, or interstate relocations.  

Do I Need to Review My Medicare Advantage or Prescription Drug Plans? 

Medicare Annual Enrollment Period runs from October 15 to December 7. This is your annual opportunity to re-evaluate and compare Medicare Advantage plans (Part C) or Prescription Drug plans in the market. 

Am I Prepared for Open Enrollment Period with My Employer? 

For companies offering group benefits, open enrollment typically occurs between early October and mid-November. During this time, individuals can make changes to employer-sponsored benefits, including contributions to health savings accounts (HSAs), dependent care flexible spending accounts (DCFSAs), flexible spending accounts (FSAs), or life and disability insurance coverage. Make sure to review your benefit options and note that some open enrollment periods require you to actively renew coverage; it is not always automatic. 

Have I Contributed to Retirement Plans? 

Be sure to make necessary adjustments to take full advantage of employer matching contributions and, if possible, max out your contribution to your employer-sponsored retirement plan for 2026. Also, work with your Wealth Advisor or CPA to determine whether an additional contribution to a traditional IRA or Roth IRA makes sense for you. 

Are There Any Significant Changes to My Income This Year That Affect My Tax Liability? 

If you have an increase in income, such as a significant bonus paid at the end of the year, you may want to adjust your withholding to align with the IRS safe harbor rules, which require individuals to pay 90% or 100% to 110% of their prior-year income tax liability. Check your income tax withholding and/or estimated quarterly tax payments to verify that you will not be subject to underpayment penalties for 2026. 

In contrast, if you find yourself in a low-income tax bracket, there may be some planning opportunities to take advantage of this year, like IRA distributions or conversions. 

Are There Gifts I Would Like to Make Before Year-End? 

In 2026, individuals can give up to $19,000 ($38,000 per married couple) to as many people as they want without incurring federal gift tax or using a portion of their lifetime gift tax exemption. If you are charitably inclined, you may want to evaluate gifting strategies such as gifts of appreciated securities, funding Donor Advised Funds (DAFs), or Qualified Charitable Distributions (QCDs) for IRA owners age 70.5 or older. Cash gifts are simple, but these strategies may further maximize tax benefits.  

Have I Taken Required Minimum Distributions (RMDs) for an IRA I Funded or Inherited? 

If you have reached RMD age or recently inherited an IRA, this may be the first year you must withdraw from these retirement accounts. Once you reach RMD age, you are generally required to withdraw a minimum amount each year to avoid a penalty. Currently, RMDs begin at age 73, but the rules can be more complex for inherited IRAs. Who you inherited the account from can determine your withdrawal requirements. Be sure to speak with your Wealth Advisor or CPA to finalize your plan to take your 2026 Required Minimum Distribution before the end of the year. 

Are There Underperforming Positions in My Portfolio That Can Lower My Tax Burden? 

Market volatility throughout the year sometimes leaves unrealized losses that can be strategically paired against capital gains. Harvesting these positions before the end of the year allows you to neutralize a potential tax drag while maintaining your target allocation. Tax loss harvesting, locking in portfolio gains, and rebalancing often require coordination between your portfolio manager and CPA. Engage in these conversations early to give your advisory team the runway to turn complex moving parts into an intentional outcome. 

As always, it’s important to weigh the pros and cons of all planning and tax-related items given your unique situation. Contact your Wealth Advisor if you have any questions or concerns regarding the strategies mentioned above. 

We hope you find this helpful. We welcome your feedback, and please don’t hesitate to contact your Wealth Advisor if you have any questions.