Every fall, busy families and professionals tend to overlook three financial decisions that have lasting impact into the new year. Open enrollment, charitable giving, and tax withholding rarely receive the attention they should. Why is that? For many families, it’s a busy time of the year as Thanksgiving and holiday shopping capture our attention. By the time you’re catching your breath, it’s the first week of January!

Our brains love to take the path of least resistance. “Let’s stick with what we have”. This is default bias at work keeping families from examining their options. Our brains are overworked in this busy season. The easier path of sticking with last year’s choices allows us to move on to the next decision, large or small. Here’s how to be more intentional with your choices this year:

Open Enrollment

• Compare both medical plans side by side. In my experience, dual-income families often pay for overlapping coverage. Doing a side-by-side comparison allows mom and dad to do their homework and select the best plan for their family’s current needs.

• Investing in your HSA. It’s the only account that’s tax-free going in, accumulating, and tax free at distribution time for medical costs. Many of my clients treat it like a retirement account, choosing to invest the proceeds much like their 401(k). Other clients treat their HSA as a checking account covering current year’s medical expenses. No right or wrong answers here; your financial plan will tell you what’s best for your family.
• Recheck your dependent care FSA contributions. This is a cash flow question with increased contribution levels of $7,500 in 2026. Higher income families WILL NOT be phased out based on AGI.     

• Review your employer life and disability coverage. Who gets what, when, if it’s necessary? While you’re at it, review your beneficiaries as well too. Are you just listing a spouse or do you have a revocable family trust that would be more beneficial to your surviving spouse and children?

Annual Giving

Families taking the standard deduction can now deduct up to $2,000 in cash gifts to a qualified charity if married filing jointly. Chances are many families are already giving but not keeping the receipts. Historically, taking the standard deduction hasn’t been integrated for tax purposes with deductible charitable cash gifts. That changes in 2026.   

• 2026 standard deduction of $32,200 can now be increased to $34,200 with a $2,000 cash gift to a qualified charity.
• Save your receipts. Better to remember this now than in April as you’re preparing your taxes.
• What doesn’t count? Gifts of stuff you bag up and haul to the curb for a nonprofit to pick up doesn’t count towards the $2,000 gift. Why? It’s qualified cash gifts only.

Families that itemize must be aware of the new limitations on charitable contributions in effect for 2026 and beyond. 

• The first 0.5% of your AGI in charitable gifts generates no tax deduction. At $500,000 of AGI, a couple filing jointly can’t count the first $2,500 of charitable giving. So if they have typically given $10,000 each year to qualified charities, in 2026 tax year only $7,500 will be allowed for itemizing purposes.
• What’s the solution? Options include lumping your gifts to a particular year and/or revisiting your formal giving plan. Giving more is a good thing that may be possible too. Best to integrate this into your financial plan to gauge sustainability.
• What about donor advised funds? Also limited, so the first to 0.5% of charitable giving generates no tax deduction.

Tax Withholding

Are you withholding enough federal taxes from your income this year? That’s a critically important question families need to ask and figure out. This trips up taxpayers, especially those who have an AGI over $400,000 married filing jointly. Here’s the best way to figure out where you stand now.

• Review year-to-date paystubs and federal tax withholding and compare them to your 2025 return.
• Q4 stock vesting such as RSUs will further inflate your math and likely tax withholding; make sure you add this in.
• Changes to open enrollment elections such as HSA contributions, your charitable giving, and itemizing or taking the standard deduction all need to be factored in.
• A quarterly estimated tax payment by January 15, 2027, for the 2026 tax year is possible. It’s not too late.

None of the above is very difficult to figure out. It takes time and an integration with your financial plan. Creating structure around how you manage open enrollment, giving, and tax withholding decisions is exactly what we do for our clients. Want a second set of eyes to review your work? Schedule a free consultation before it’s necessary.