If You Have Millions Saved for Retirement, It’s Time to Start Worrying About These 5 Things

2026 Strategy Update: The retirement landscape has shifted considerably since 2024. Multi-millionaires spent years preparing for a looming “tax sunset” that never arrived. Legislation under the One Big Beautiful Bill Act (OBBBA) and new inflation indexing have rewritten the math for high-net-worth planning, and the strategy adjustments required are substantial. Here is what demands your attention now.

1. Estate Taxes and Legacy Planning

For those with significant assets, the federal estate tax now sits at its most manageable level in decades. The OBBBA, signed into law on July 4, 2025, permanently raised the federal estate and gift tax exemption to $15 million per individual, or $30 million for married couples, beginning January 1, 2026. That is a meaningful jump from the $13.99 million threshold in place through 2025, and a dramatic improvement over the approximately $7 million floor that would have applied without congressional action. Starting in 2027, the exemption adjusts annually for inflation. The 40% rate on amounts above the exemption remains unchanged.

Strategic gifting remains a powerful complement to the expanded lifetime exemption. The annual gift tax exclusion stands at $19,000 per recipient in 2026. Paired with Generation-Skipping Transfer (GST) strategies and Dynasty Trusts, wealthy retirees can shield assets from being taxed at each generational handoff. One important caveat: individuals who reside in one of the 17 states and jurisdictions that currently impose an estate or inheritance tax will still need to account for state-level liability, even when their estate falls well below the new federal threshold. Oregon taxes estates above just $1 million, while Massachusetts applies its tax from the very first dollar once an estate crosses its $2 million exemption.

What changed under the OBBBA

For most families with estates under $15 million, income tax planning now takes priority over transfer tax planning. Existing trust documents with formula clauses deserve a close review: many credit shelter or GST trusts may no longer provide any transfer tax benefit, and some could be actively disadvantageous by denying a basis step-up at the surviving spouse’s death. The environment has shifted from defensive urgency to long-range strategic opportunity. Estate plans built around a feared exemption reduction may need structural updates to reflect that reality.

2. Tax-Efficient Withdrawal Strategies

How you draw money out of your accounts matters as much as how you accumulated it. A structural change that took effect January 1, 2026 is the full implementation of the Roth Catch-up Mandate under SECURE 2.0. Workers age 50 and older who earned more than $145,000 in FICA wages in the prior year can no longer make pre-tax catch-up contributions to their 401(k). Those contributions must now be designated Roth. For the 2026 plan year, the IRS adjusted the lookback wage threshold to $150,000, meaning Roth treatment is required for anyone whose 2025 earnings exceeded that figure.

SECURE 2.0 also introduced an enhanced “super catch-up” limit for workers ages 60 through 63. Instead of the standard $8,000 catch-up, those participants can contribute up to $11,250 above the base elective deferral limit in 2026, provided their plan permits it. For high earners in this age range, the combination of the mandatory Roth treatment and the higher limit creates a real opportunity to shift more assets into a tax-free bucket before retirement begins.

The Roth structure helps eliminate the tax cascade that large pre-tax balances create in retirement. Traditional 401(k) balances trigger required minimum distributions beginning at age 73. Those RMDs count as ordinary income, which can cause up to 85% of Social Security benefits to become taxable and push modified adjusted gross income above the IRMAA thresholds that trigger Medicare Part B surcharges.

For retirees age 70 and a half or older who want to manage AGI and avoid higher Medicare tiers, Qualified Charitable Distributions (QCDs) have become more effective than ever under the 2026 rules. The annual QCD limit is $111,000 per individual. Married couples can direct up to $222,000 combined, provided each spouse has a separate IRA and each is at least 70.5 years old. A QCD routes money directly from a traditional IRA to a qualified charity, satisfying all or part of the RMD obligation without adding a dollar to taxable income. The OBBBA did not change the QCD rules themselves, but it did limit the deductibility of charitable donations for itemizers to amounts exceeding 0.5% of adjusted gross income. The law also introduced a separate non-itemizer charitable deduction of up to $1,000 for single filers (or $2,000 jointly) beginning in 2026. The QCD route bypasses both the new AGI floor and the itemization debate entirely, making it comparatively more attractive for philanthropically inclined retirees.

3. Asset Protection and Liability

High-net-worth individuals face a materially different litigation risk profile than the general population. Beyond standard homeowners’ insurance, millionaires should scrutinize whether their Umbrella Insurance limits actually reflect total net worth, not just home value. A $1 million umbrella policy on a $10 million estate leaves a significant unprotected gap, and insurers will not volunteer that observation at renewal.

Structural tools matter here as well. Holding real estate through Asset Protection Trusts or LLCs creates legal separation between personal wealth and potential claims arising from a specific property. This approach is especially important for retirees who hold multiple properties, since each one represents a distinct liability exposure. No structure is impenetrable, but layering these tools creates meaningful friction for plaintiffs and often encourages negotiated settlements rather than full judgments. The upfront cost of implementing these structures is typically a fraction of the cost of defending against an uncovered claim.

4. Health Care Costs and IRMAA

Healthcare is anything but a fixed expense for high-income retirees. The standard Part B premium for 2026 is $202.90 per person per month, up $17.90 from the 2025 rate. That figure is only the starting point for anyone with a six-figure income. The real cost driver is the Income-Related Monthly Adjustment Amount (IRMAA), a cliff surcharge: crossing a threshold by a single dollar triggers the full additional premium for the entire year. For 2026, IRMAA applies to beneficiaries with income exceeding $109,000 for single filers or $218,000 for joint filers, and total monthly Part B premiums for affected beneficiaries range from $284.10 to $689.90. A retiree who crosses the lowest IRMAA threshold by just $5,000 can face roughly $974 in additional annual Medicare costs. The surcharge is based on MAGI from two years prior, meaning 2026 IRMAA liability is determined by 2024 income. A large Roth conversion or a property sale in a prior year can produce a premium spike long after the triggering transaction is forgotten.

Long-term care costs also require a frank recalculation. The June 2026 national median for a private nursing home room is $11,294 per month, or roughly $135,528 annually, with semiprivate rooms running about $9,842 per month. Costs have risen every year and are projected to keep climbing, with estimates pointing to private-room medians approaching $14,000 per month by 2033. The decision between self-insuring and carrying specialized long-term care coverage should be measured against current liquid cash flow and projected longevity, using today’s actual figures rather than benchmarks from several years ago.

5. Advisory Fees and Value

As a portfolio grows, fee drag compounds in the same way returns do. On a $10 million portfolio, a 1% annual AUM fee translates to $100,000 per year regardless of market performance. That figure climbs to $150,000 on a $15 million portfolio. In 2026, a growing share of high-net-worth clients are shifting toward flat-fee models or family office structures, where the advisor’s incentive centers on comprehensive planning rather than on accumulating assets under management.

Two strategies that consistently justify their cost at scale are tax-loss harvesting and direct indexing. Both generate tax alpha that can offset advisory costs entirely in favorable years. The standard for evaluating any fee arrangement is straightforward: does the after-tax, after-fee outcome consistently exceed what a lower-cost alternative would deliver? If the answer is not a clear yes, the arrangement warrants renegotiation. At the net-worth levels this article addresses, even a modest improvement in after-tax return compounds into seven figures over a decade.

Editor’s note: This pass updated long-term care cost figures to June 2026 data from SeniorLiving.org, raising the private-room nursing home median to $11,294 per month ($135,528 annually) from the prior CareScout 2024 survey figures, and added context on the SECURE 2.0 “super catch-up” contribution limit of $11,250 available to workers ages 60 through 63 in 2026.

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