Thanksgiving Financial Checklist

As the holidays approach, it’s easy to get swept up in travel plans, year-end deadlines, and gift lists. But November isn’t just a time for reflection—it’s a window of opportunity. Before you carve the turkey and kick off the holiday season, take a moment to check in on your financial strategy.

This Thanksgiving financial checklist includes seven smart moves you can still make before year-end. They’ll help reduce your tax burden, increase clarity, and set you up for a more successful 2026. When April rolls around, these are the decisions you’ll be thankful you made today.

✅ 1. Revisit Your Tax Withholding and Estimated Payments

If you’ve had a strong income year, expanded your business, or received unexpected gains, now is the time to review your withholding and quarterly tax payments. Underpaying could lead to IRS penalties, while overpaying ties up cash that could be working for you.

Use November to:

• Adjust your W-4 if you’re an employee with supplemental income
• Recalculate Q4 estimated taxes (due in January)
• Confirm payments align with new income or capital gains

A quick check-in now can prevent a tax-time scramble later.

✅ 2. Lock in Year-End Deductions and Business Expenses

If you’re a business owner, self-employed professional, or contractor, November is a great month to make strategic business purchases that count toward this year’s deductions.

Consider:

• Buying necessary equipment or software
• Prepaying for services, subscriptions, or rent
• Accelerating professional development expenses
• If retired, take your RMD Distribution

Just make sure the purchase is made and the service is received—or the item placed in use—by December 31 to qualify.

✅ 3. Maximize Retirement Contributions

There’s still time to increase contributions to retirement accounts before the end of the year. These pre-tax contributions reduce your taxable income and grow your long-term wealth.

Make sure you’re taking full advantage of:

• 401(k) plans – Up to $23,500 for those under 50, and for those 50 or older have a $7,500 “catch-up” contribution for a total contribution for $31,000. For those 60-63, there is an $11,250 “super catch-up” contribution for a total contribution of $34,750.
• Traditional IRAs – Contributions may be deductible depending on your income
• SEP IRAs or Solo 401(k)s – For business owners or freelancers

Check your year-to-date totals and, if possible, bump up contributions in your remaining pay periods.

✅ 4. Evaluate Charitable Giving Strategies

Giving Tuesday isn’t the only reason to support nonprofits in November. Charitable donations can also reduce your taxable income if you itemize deductions.

Smart giving strategies include:

• Donating appreciated securities instead of cash
• Setting up or funding a Donor-Advised Fund (DAF)
• Making Qualified Charitable Distributions (QCDs) from IRAs if over 70½

Not only do these strategies help causes you care about—they can reduce your tax liability while making a real difference.

✅ 5. Review Capital Gains and Harvest Losses

Have you sold investments for a profit this year? If so, November is a key time to review your portfolio and offset those gains with any potential losses.

Tax-loss harvesting can:

• Offset up to $3,000 of ordinary income
• Reduce net capital gains
• Allow you to reposition your portfolio for 2026

Just be mindful of the wash-sale rule—you can’t repurchase the same or substantially identical investment within 30 days of selling it for a loss.

✅ 6. Schedule Your Year-End Tax Planning Meeting

If you haven’t already, now is the time to book a year-end planning session with your JV Rizzo & Co. These meetings can uncover final opportunities to:

• Adjust income or expense timing
• Take advantage of credits or deductions
• Plan distributions, bonuses, or buyouts
• Maximize your annual gift-giving of $19,000 tax-free to family members

Waiting until late December can mean rushed decisions and missed chances. November offers enough runway to make deliberate, strategic choices.

✅ 7. Reflect on What Worked—and What Didn’t

Thanksgiving is a time to pause and reflect. Before the new year arrives, take stock of your financial wins and lessons learned in 2025.

Ask yourself:

• Did I hit my savings or business profit goals?
• Were there financial surprises I can plan for better next year?
• Am I making progress on my long-term wealth or retirement plan?

A moment of honest reflection now can lead to a sharper, more focused 2026.

Final Thoughts: Gratitude for Proactive Planning

Financial clarity isn’t about scrambling at tax time. It’s about creating rhythms of review, action, and alignment throughout the year—especially in the final stretch. By checking off the items on this list, you ensure your financial decisions this year support your success in the next.

Take a deep breath, enjoy the season, and know that you’ve taken intentional steps toward your financial goals. Now that’s something to be thankful for.

Need help finishing the year strong? Schedule your year-end financial strategy session with James V. Rizzo & Company today—and head into the holidays with clarity and confidence.