The Year-End Financial Planning Checklist: Strategies Designed to Support the Life You're Building
How we help you turn moments of reflection into real financial momentum, together.
By Abigail McCloskey, CFP®, CLU®, Affinity Wealth Management
Year-end planning isn’t about racing the clock or checking boxes. It’s about pausing, reflecting, and taking small, intentional steps that bring you closer to the life you want to live.
At Affinity, we help you balance what’s in your control (taxes, investments, and planning decisions) with the bigger picture: what makes life feel rich. Whether you’re helping your kids with college costs, planning charitable gifts, or preparing for retirement, our year-end financial planning checklist gives you an inside look at how we walk you through key opportunities to consider before December 31st.
The Year-End Financial Planning Checklist
☐ Review Your 2024 Tax Return
If there's one thing we prioritize before the year wraps up, it's taking a fresh look at last year's tax return together. It’s a simple step that can uncover real opportunities to save and give you a clearer picture heading into the new year.
What we look for:
✔︎ Your effective tax rate and which bracket you're in
✔︎ Opportunities to fill lower tax brackets with Roth conversions
✔︎ Whether charitable giving strategies could benefit you
✔︎ Capital loss carryforwards from previous years we might be able to use
For many clients, tax planning has become a game-changer in financial planning. The strategies we explore together—gifting, charitable giving, Roth conversions, tax loss harvesting—all become clearer and more actionable when we understand your complete tax picture.
☐ Explore Gifting Strategies That Fit Your Family and Your Goals
As one client beautifully put it, they’d rather give with a warm hand than a cold one. There’s something so meaningful about seeing your generosity in action, whether it’s helping your kids buy their first home or sending your grandkids off to camp.
Here are a few year-end moves we may consider, depending on your specific situation and goals.
✔︎ Annual exclusion gifts
In 2025, you can gift up to $19,000 to as many people as you want without filing a gift tax form. If you're married, both you and your spouse can each give $19,000 to the same person, effectively doubling the gift to $38,000 per recipient.
If you're in your late 40s and 50s, we often explore this as a way to start transferring wealth out of your estate while helping your children in real time. It can reduce your tax bill while helping the next generation cover wedding costs, contribute to a down payment, or simply provide breathing room as they navigate their own financial lives.
✔︎ Front-loading 529s
If you're sitting on significant wealth and want to make a substantial investment in your children's or grandchildren's education, you can contribute up to $95,000 to a 529 plan in a single year. This represents five years' worth of annual gift exclusions, and it's a powerful way to fund education in one move.
For a one-year-old grandchild, a properly invested $95,000 contribution can potentially cover undergraduate and graduate education. The money grows tax-free, comes out tax-free for qualified education expenses, and if circumstances change, you can adjust beneficiaries or even roll the funds forward to the next generation.
✔︎ Targeted gifts for specific family needs
Not everyone is comfortable writing large checks to their adult children, and not every financial plan supports it. That's okay—there are other ways you can provide financial support without giving cash outright.
Maybe your daughter wants to send your grandkids to summer camp. Maybe your son is trying to upgrade the windows in his house. We help you think through gifts that often feel more personal than cash and can make a real difference in your children's day-to-day lives.
☐ Align Your Generosity with a Tax-Smart Plan
Giving back is one of the most rewarding parts of financial planning, and year-end is the perfect time to align your generosity with your goals. With a few thoughtful moves, we can help you make a bigger impact for the causes you love and be smart about your taxes.
✔︎ Donate appreciated stock instead of cash
Have appreciated stock? We often recommend gifting shares directly to charity instead of selling first. You’ll skip capital gains and still get the deduction. Here’s how it works:
→ The charity can sell the stock without paying capital gains tax
→ You get a deduction for the full fair market value
→ You've removed an overweighted position from your portfolio
✔︎ Use Qualified Charitable Distributions
If you’re retired and over 70½, you can direct up to about $108,000 ($115,000 in 2026) from your IRA straight to qualified charities through a qualified charitable distribution (QCD). Once you reach 73, the amount counts toward your required minimum distribution (RMD), and because it’s sent directly to the charity, it reduces your taxable income. While new OBBBA rules taking effect in 2026 will tighten some itemized charitable deductions, QCDs are unaffected and continue to offer one of the most tax-efficient ways to give.
Starting in 2026, taxpayers who take the standard deduction will also be able to claim an above-the-line deduction for cash gifts to qualifying charities, which is up to $1,000 for single filers and $2,000 for married couples filing jointly.
In turn, that lower taxable income can potentially reduce Medicare premiums and the taxation of Social Security benefits, allowing you to support organizations you care about while saving money.
☐ Find the Right Roth Strategy for Your Future
If you’re approaching retirement or earning at a high level, year-end can be an ideal time to consider a Roth conversion. For many, this move creates valuable long-term flexibility, helping you manage taxes now while building more freedom later.
The sweet spot often comes during the years between retirement and required minimum distributions (RMDs), when your income may be lower and tax rates more favorable. Converting IRA dollars to Roth during that window allows your money to grow and come out tax-free in the future.
High earners can benefit too, even if income limits block direct Roth contributions. The “backdoor Roth” strategy—funding a traditional IRA and then converting it—can achieve similar results. It’s simple in concept but easy to misstep without guidance, especially around tax timing and Medicare implications, so it’s important to consult a professional before diving in.
These are the kinds of opportunities we review together each fall to help you make the most of your year-end planning window.
☐ Revisit Past Losses to Strengthen Future Gains
Tax loss harvesting involves selling investments that have declined in value to offset gains elsewhere in your portfolio. In strong market years like 2025, there may not be many losses to use.
However, if you have capital loss carryforwards from previous years, we'll explore whether this could be the perfect time to use them. When your portfolio has delivered strong returns and becomes overweighted in certain positions, those old losses can offset the gains, providing a great opportunity to rebalance your portfolio.
The key? We make sure there's a reason for every move. We don't harvest losses just because we can; there should always be a clear purpose that fits your broader financial picture.
☐ Plan Your January Financial Reset
Your year-end financial planning checklist shouldn't end on December 31st. January is a great time to connect and reflect on what did and didn’t work financially in the past year.
✔︎ Review What Worked (and What Didn't)
Questions we help you consider:
Did I save enough in my retirement accounts?
Should I shift from pre-tax to Roth contributions?
Were there financial hurdles I wish I'd addressed sooner?
These aren't just retrospective questions; they're planning opportunities for making the new year more successful.
✔︎ Strengthen Your Financial Foundation
Whether you need six to twelve months of expenses in cash reserves, January is often when we create a plan for getting there. If the past few years have taught us anything, it's that having liquid reserves often helps to provide both financial security and confidence for the future.
Related: What High Achievers Should Be Doing Differently in Wealth Management
Start the New Year with Confidence
Year-end financial planning works best when it's tailored to your specific situation: your tax bracket, your family goals, your retirement timeline, and what makes life feel rich for you.
At Affinity Wealth Management, we walk clients through these strategies every year, not just to check boxes, but to ensure every decision aligns with the life you're building. No surprises, no missed opportunities—just a plan that fits who you are and where you’re headed
You’re likely familiar with many of these strategies from our past conversations, but if anything here sparks new questions about your situation, we’re always here to talk it through and offer additional insight.
If you're not yet a client and you're ready to take a more strategic approach to year-end planning and beyond, we invite you to learn more about how Affinity Wealth can help you align your financial decisions with what truly matters to you. Click here to learn about the Connect Meeting.
Key Takeaways:
What's one of the biggest year-end financial planning opportunities? Reviewing your 2024 tax return to reveal your effective rate, potential Roth conversion windows, and capital loss carryforwards you may be able to leverage
How can gifting potentially reduce taxes? Strategic family gifts (up to $19,000 per person annually) and donating appreciated stock instead of cash let you transfer wealth tax-efficiently while avoiding capital gains.
What financial steps should I prioritize after the new year? Use January to assess whether you saved enough in retirement accounts, evaluate shifting from pre-tax to Roth contributions, and build 6-12 months of liquid reserves to strengthen your financial foundation.