February 23, 2026

Review key 2026 Social Security updates and planning considerations for high-net-worth individuals, business owners, and multigenerational families.

Social Security is often viewed as a baseline retirement benefit. For high-net-worth individuals and business owners, however, it can still play a meaningful role—particularly in the context of tax planning, liquidity events, and legacy structuring.

As 2026 approaches, several structural and tax-related dynamics surrounding Social Security warrant attention. While many affluent families do not rely on Social Security as a primary income source, thoughtful coordination may support more efficient retirement income planning, Medicare premium management, and survivor income stability.

Below are several 2026 considerations worth reviewing within a broader wealth planning framework.

1. Wage Base Adjustments and Maximum Benefit Levels

Each year, the Social Security wage base adjusts for inflation. Higher earners will continue to see increases in the maximum amount of income subject to payroll taxes.

For business owners and executives, this creates two important planning considerations:

• Compensation structuring: Salary versus distribution decisions may affect long-term benefit calculations.
• Delayed retirement credits: Benefits increase for each year claiming is delayed beyond full retirement age, up to age 70.

Although Social Security may represent a modest portion of total retirement income for many high-net-worth households, evaluating claiming timing can be part of a broader income diversification strategy that includes guaranteed and market-based sources of income.

2. Taxation of Benefits: Managing Provisional Income

Up to 85% of Social Security benefits may be subject to federal income tax depending on “provisional income,” which includes:

• Adjusted gross income
• Tax-exempt interest
• 50% of Social Security benefits

For individuals with significant investment income, capital gains, Roth conversions, or business exit proceeds, the interaction between Social Security benefits and provisional income can affect after-tax cash flow.

Planning Considerations:

• Coordinating Roth conversion timing before claiming benefits
• Managing capital gains recognition in high-liquidity years
• Evaluating installment sales or deferred compensation structures
• Considering charitable strategies that may reduce taxable income

The objective is not simply minimizing taxes in a single year, but evaluating how various income sources interact over time under current tax law.

3. Medicare IRMAA Exposure

Income-related monthly adjustment amounts (IRMAA) can increase Medicare Part B and Part D premiums for higher-income retirees.

Because IRMAA calculations are based on prior-year modified adjusted gross income, liquidity events—such as selling a business, concentrated stock position, or real estate—can result in higher-than-expected premiums.

Planning discussions may include:

• Evaluating the timing of large transactions
• Assessing distribution strategies across taxable and tax-advantaged accounts
• Sequencing income sources in early retirement

For families navigating a business sale or major asset transition, modeling potential Medicare premium impacts can provide additional clarity around total retirement costs.

4. Spousal and Survivor Benefit Considerations

For married couples, Social Security can serve as a component of longevity planning.

The higher-earning spouse’s benefit amount may become particularly relevant, as the surviving spouse is generally entitled to the larger of the two benefits. Delaying the higher earner’s benefit may increase the survivor benefit, depending on individual circumstances.

Within multigenerational planning conversations, this may intersect with:

• Survivor income planning
• Trust distribution strategies
• Estate liquidity considerations

Social Security should be evaluated as one element of an integrated retirement income framework rather than in isolation.

5. Legislative and Funding Considerations

Social Security’s long-term funding continues to be discussed at the federal policy level. While benefits are expected to continue, future legislative adjustments—whether to payroll taxes, benefit formulas, or retirement age thresholds—remain possible.

Accordingly, planning discussions involving Social Security should incorporate flexibility. Strategies that rely on adaptable assumptions may be better positioned to adjust if legislative changes occur.

Integrating Social Security Into Broader Wealth Planning

For high-net-worth families, Social Security may function as:

• A government-backed income stream tied to inflation adjustments
• A tax-sensitive income source that interacts with other retirement distributions
• A survivor income component
• One variable within a coordinated retirement distribution strategy

When evaluated alongside tax planning, business transitions, estate structures, and philanthropic objectives, Social Security can be incorporated into a comprehensive planning review. Outcomes, however, will vary based on individual facts, assumptions, and future legislative developments.

While Social Security is often associated with foundational retirement planning, its implications can extend into tax strategy, Medicare planning, and survivor income considerations—particularly for business owners and affluent families navigating complex financial decisions.

At Omni 360 Advisors and Omni Legacy Law, Social Security discussions are typically integrated into broader wealth, tax, and estate planning conversations. If you are approaching retirement, evaluating a liquidity event, or reassessing your long-term income strategy, a coordinated review may help identify how Social Security fits within your overall financial framework.

This blog was developed with the assistance of AI-based tools for research, drafting and editing support (Chat GPT), and reviewed by OMNI 360 personnel for accuracy and relevance.