Six Year-End Moves That Can Decide Your Financial Season
Most people treat the last quarter of the year as a coasting period. They are booking holiday travel, closing out work projects, and thinking about anything other than their tax return. Meanwhile the clock is running on decisions worth real money. December 31 is a hard deadline for most tax planning opportunities, and once it passes, the options that were available in October are simply gone, the way a play call becomes irrelevant the moment the clock hits zero.
Here are the six areas worth putting on your fourth quarter checklist.
1. Tax Strategy
Start with the accounts you control directly. For 2026, the employee deferral limit for 401(k), 403(b), governmental 457, and TSP plans is $24,500.¹ The standard catch-up for participants 50 and older rose to $8,000, which puts the combined ceiling at $32,500.¹ If you are 60, 61, 62, or 63 this year, your enhanced catch-up is $11,250 instead.¹ IRA contributions max out at $7,500 with an additional $1,100 catch-up at 50 and over.¹
One change catches high earners off guard. Beginning in 2026, participants whose prior-year wages with the same employer exceeded $150,000 must make their catch-up contributions to a Roth account inside the plan.² If your plan does not offer a Roth component, that catch-up may not be available to you at all.³
Then there is tax loss harvesting. Selling positions at a loss to offset realized gains is standard practice, and up to $3,000 of excess loss can offset ordinary income with the remainder carrying forward. Just respect the wash sale window and avoid repurchasing a substantially identical security within 30 days on either side of the sale.
Roth conversions deserve a look in any year where income dips, whether from a sabbatical, a business loss, a job transition, or the gap years between retirement and the start of Social Security and required distributions. Conversions must be completed by December 31 to count for the tax year, and unlike an IRA contribution, there is no April grace period.
2. Investment Decisions
After a strong run in any asset class, portfolios drift, the same way a lineup that wins early in the season can quietly drift out of balance if nobody adjusts it. The allocation you signed off on three years ago may now carry meaningfully more equity risk than you intended, purely because the winners grew. Rebalancing is unglamorous and it is exactly the sort of discipline that separates a plan from a collection of holdings.
Concentration risk deserves specific attention for executives. If restricted stock units have been vesting for years and you never sold, your household balance sheet, your income, and your career may all be tied to one employer. That is three bets on the same outcome.
Required minimum distributions are a hard deadline. RMDs generally begin at age 73 and must be taken by December 31 each year, with the exception of your very first distribution, which can be delayed to April 1 of the following year. Delaying that first one means two taxable distributions land in the same year, which can push you into a higher bracket and affect Medicare premiums two years later.
Finally, watch mutual fund capital gains distributions, which typically post in November and December. Buying into a fund right before a large distribution means paying tax on a gain you did not participate in.
3. Charitable Giving
This is the area where 2026 looks genuinely different from prior years, and where a lot of donors are about to be surprised at filing time.
Three provisions took effect this year under the One Big Beautiful Bill Act. First, itemizers now face a 0.5% AGI floor, meaning only the portion of total giving above that threshold is deductible.⁴ On $500,000 of AGI, the first $2,500 of contributions produces no deduction.⁵ Second, taxpayers in the 37% bracket now see the benefit of charitable itemized deductions capped at 35%.⁶ Third, non-itemizers gained an above-the-line deduction of up to $1,000, or $2,000 for joint filers, though contributions to donor advised funds are specifically excluded from it.⁵
The floor makes bunching more attractive than it already was. Concentrating two or three years of intended giving into a single year clears the threshold once instead of losing it annually.
For anyone 70 and a half or older, qualified charitable distributions remain one of the most efficient tools available. The 2026 limit is $111,000 per person, up from $108,000.² A QCD is not deductible, but it never enters AGI in the first place, which quietly helps with the new 0.5% floor, the 35% cap, the SALT deduction phase-out, and the 3.8% net investment income tax.⁶ Making QCDs before age 73 also shrinks the balance that future RMDs are calculated against.⁶
Gifting long-term appreciated securities may be more tax-efficient than cash in some situations, but the best approach depends on your tax situation, AGI limits, and overall financial plan. Consider consulting a tax professional.
4. Legacy Planning
The federal estate and gift tax exemption reached $15 million per person for 2026, or $30 million for a married couple, and the One Big Beautiful Bill Act made that level permanent with annual inflation indexing.⁷ The annual gift exclusion holds at $19,000 per recipient.⁷
Those headline numbers convince many families they have nothing to plan for. In Maryland that conclusion is often wrong. The state estate tax exemption sits at $5 million per person and has not moved since 2019.⁸ That leaves a $10 million band where an estate owes nothing federally and still owes Maryland.⁹ Maryland is also the only state that levies both an estate tax and an inheritance tax, with a flat 10% rate on transfers to non-lineal heirs such as nieces, nephews, friends, and unmarried partners.¹⁰
Beneficiary designations are the piece most often neglected. They override your will. A retirement account still naming a former spouse pays that former spouse, no matter what your estate documents say. Pull the actual statements and read the names.
5. Insurance Checkup
Policies purchased fifteen years ago were built around a life you may no longer be living. Request in force illustrations on permanent policies, particularly older universal life contracts priced when interest rate assumptions looked very different. Confirm that disability coverage still reflects current income, since group coverage capped at a percentage of base salary may ignore the bonus and equity compensation that make up most of an executive's pay.
Umbrella liability coverage is often relatively low cost compared with the coverage it can provide, but premiums vary by carrier and individual circumstances.
On the smaller end, health FSA balances are use it or lose it. The 2026 contribution limit is $3,400 and plans that permit carryover allow up to $680 to roll forward.⁷
6. Long-Term Care
Roughly 70% of adults age 65 and over will need some form of long-term care services during their later years.¹¹ Very few plans account for it.
The tax code offers partial help. For 2026, deductible premium limits on tax-qualified policies run from $500 at age 40 and under, to $1,860 for ages 51 through 60, $4,960 for ages 61 through 70, and $6,200 above age 70.¹² Those limits apply per person, so both spouses can use their own age band.³ Benefits from indemnity-style policies are tax free up to the greater of actual qualified costs or $430 per day for 2026.¹³
The premium deduction usually requires clearing the 7.5% AGI medical expense threshold and itemizing, so treat it as a secondary consideration. The primary question is whether the coverage protects the right amount of assets and preserves flexibility for your family.
The Common Thread
Every item above rewards the same behavior: deciding on purpose, early, rather than reacting in late December when the useful options have already expired. A team that waits until the fourth quarter to start planning its next possession is already behind. Intentional beats reactive, in either arena.
If you want the full conversation on these strategies, including where they tend to break down in practice, Ken and I covered all six on a recent episode of the Overtime Earnings podcast. We walk through the tradeoffs, the mistakes we see most often, and how these decisions fit together for business owners, executives, and pre-retirees. Search Overtime Earnings wherever you get your podcasts.
To discuss how any of this applies to your situation, reach out to Greg Foster, Director of Marketing and Client Engagement at Phoenix Private Wealth.
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**References**
1. IRS, "401(k) limit increases to $24,500 for 2026, IRA limit increases to $7,500" (IR-2025-111) — https://www.irs.gov/newsroom/401k-limit-increases-to-24500-for-2026-ira-limit-increases-to-7500
2. IRS, Notice 2025-67, retirement plan cost-of-living adjustments for 2026 — https://www.irs.gov/newsroom/401k-limit-increases-to-24500-for-2026-ira-limit-increases-to-7500
3. LegalClarity, "Long-Term Care Insurance Premiums: Tax Deduction Limits" — https://legalclarity.org/long-term-care-insurance-premiums-tax-deduction-limits/
4. Taft Law, "Charitable Giving After the OBBBA: The 2026 Outlook" — https://www.taftlaw.com/news-events/law-bulletins/charitable-giving-after-the-obbba-the-2026-outlook/
5. REN, "What Every Advisor Needs to Know About Charitable Deductions in 2026" — https://www.reninc.com/blog/what-every-advisor-needs-to-know-about-charitable-deductions-in-2026/
6. Keiter, "How Will the OBBBA Impact Your Charitable Giving Strategy?" — https://keitercpa.com/blog/how-will-the-obbba-impact-your-charitable-giving-strategy/
7. IRS, "IRS releases tax inflation adjustments for tax year 2026" (IR-2025-124) — https://www.irs.gov/newsroom/irs-releases-tax-inflation-adjustments-for-tax-year-2026-including-amendments-from-the-one-big-beautiful-bill
8. Scheuerman Law LLC, "Maryland Estate Tax 2026: Exemptions, Planning, and Key Considerations" — https://www.scheuermanlaw.com/blog/maryland-estate-tax-2026/
9. Frame & Frame, "Maryland Estate Tax vs. Federal Estate Tax [2026]" — https://frameandframe.com/blog/maryland-estate-tax-vs-federal-estate-tax/
10. Maryland Reporter, "A Guide to Inheritance Tax Laws in Maryland for 2026" — https://marylandreporter.com/2026/03/03/a-guide-to-inheritance-tax-laws-in-maryland-for-2026/
11. ElderLawAnswers, "New Long-Term Care Insurance Premium Deductions for 2026" — https://www.elderlawanswers.com/new-long-term-care-insurance-premium-deductions-for-2026-21356
12. American Association for Long-Term Care Insurance, "2026 Tax Deductible Limits For Long-Term Care Insurance Increase" — https://www.aaltci.org/news/long-term-care-insurance-association-news/2026-tax-deductible-limits-for-long-term-care-insurance-increase-3-percent
13. IRS Revenue Procedure 2025-32, cited via CompareLongTermCare.org, "Tax Advantages of Long-Term Care Insurance" — https://www.comparelongtermcare.org/tax-advantages