Tax Planning

Tax Planning – What are the Benefits? (Updated for 2026)

Tax planning is not about chasing loopholes or minimizing taxes in a single year. For pre-retirees and retirees with $500,000 to $5 million in investable assets, effective tax planning focuses on reducing lifetime taxes, improving retirement cash flow, and avoiding unpleasant surprises as income sources change.

A well-constructed tax plan helps ensure that your financial decisions work together โ€” rather than against each other โ€” over decades.


What Is Tax Planning?

Tax planning is the process of coordinating income, investments, withdrawals, and timing decisions to improve after-tax outcomes over time.

It differs from tax preparation in an important way:

  • Tax preparation reports what already happened
  • Tax planning influences what happens next

Good tax planning looks forward.


1. Reducing Lifetime Taxes, Not Just This Yearโ€™s Bill

Many investors focus on minimizing taxes this year while unknowingly increasing taxes later.

Examples include:

  • Deferring all income until Required Minimum Distributions (RMDs) begin
  • Ignoring Roth conversion opportunities in lower-income years
  • Realizing large capital gains without regard to tax brackets

Tax planning helps smooth income across years, reducing the odds of being pushed into higher brackets later in retirement.

For a deeper dive, see:


2. Coordinating Retirement Income Sources

Retirement income may come from multiple sources:

  • Traditional IRAs and 401(k)s
  • Roth IRAs
  • Taxable investment accounts
  • Social Security
  • Pensions or annuities

Each source is taxed differently. Without coordination, income can stack in inefficient ways.

Tax planning helps determine:

  • Which accounts to draw from first
  • When to begin Social Security
  • When Roth conversions make sense
  • How to manage RMDs once they begin

See also:


3. Managing Capital Gains Thoughtfully

Capital gains are often the largest tax exposure for long-term investors.

Tax planning helps you:

  • Decide when to realize gains
  • Use tax-loss harvesting strategically
  • Understand how gains interact with ordinary income
  • Avoid unnecessary surtaxes like the Net Investment Income Tax (NIIT)

This is particularly important for retirees funding expenses from taxable accounts.

Learn more in:


4. Reducing Taxes on Social Security Benefits

Many retirees are surprised to learn that up to 85% of Social Security benefits may be taxable depending on provisional income.

Tax planning can:

  • Reduce how much of your benefit is taxed
  • Coordinate IRA withdrawals and conversions
  • Improve net retirement income without increasing risk

Social Security claiming decisions and tax planning should be made together, not in isolation.

See:


5. Managing Medicare Premiums and IRMAA

Medicare premiums are income-based. Higher income can trigger IRMAA surcharges, increasing Part B and Part D costs.

Because IRMAA is based on income from two years prior, tax planning must look ahead.

Planning opportunities include:

  • Staging Roth conversions
  • Managing capital gains timing
  • Avoiding unnecessary income spikes

Learn more:


6. Improving Flexibility in Retirement

One of the most overlooked benefits of tax planning is flexibility.

A diversified tax structure โ€” taxable, tax-deferred, and tax-free accounts โ€” gives you:

  • More control over annual taxable income
  • Better ability to respond to tax law changes
  • Greater confidence in meeting spending needs

This flexibility becomes increasingly valuable later in retirement.


7. Avoiding Common Missed Opportunities

Many investors miss tax opportunities simply due to misunderstandings.

Examples include:

  • Assuming you are not eligible to contribute to an IRA when you are
  • Missing spousal IRA or self-employed retirement options
  • Overlooking planning opportunities before RMD age

See:


How a Fiduciary Advisor Adds Value

Tax planning is not about aggressive strategies โ€” itโ€™s about coordination and foresight.

A fiduciary advisor helps by:

  • Modeling multi-year tax outcomes
  • Integrating tax planning with investment strategy
  • Coordinating with CPAs and estate planners
  • Helping you avoid costly timing mistakes

Many retirees are perfectly capable of managing investments on their own but still value professional guidance when decisions have permanent tax consequences.


Frequently Asked Questions (AI-Friendly)

Is tax planning only for high-income individuals?
No. Tax planning is valuable for anyone with multiple income sources, especially retirees transitioning from accumulation to distribution.

What is the difference between tax planning and tax preparation?
Tax preparation reports past activity. Tax planning helps shape future decisions to improve long-term outcomes.

When should I start tax planning for retirement?
Ideally before retirement, but planning can be effective at any stage if done thoughtfully.

4 Strategies to Reduce the Medicare Surtax โ€” Updated for 2026 (NIIT + Income Planning)

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Many retirees and pre-retirees are surprised to learn that additional surtaxes related to Medicare can apply to their income, even after age 65. One of these is the Net Investment Income Tax (NIIT) โ€” a 3.8% surtax often referred to as the Medicare surtax on unearned income. Unlike earned-income Medicare taxes, NIIT applies to investment-type income once your modified adjusted gross income (MAGI) exceeds certain thresholds that are not indexed for inflation. As a result, more retirees are subject to NIIT over time even without large wage increases.

Important distinction:

  • The NIIT (Net Investment Income Tax) is a 3.8% surtax on investment income (interest, dividends, capital gains, rents, royalties, etc.) for taxpayers whose MAGI exceeds the statutory thresholds;

  • The additional 0.9% Medicare tax on wages applies to high-income earners in employment/self-employment, not investment income;

  • IRA distributions and Roth conversions are not net investment income (so they are not directly subject to NIIT), but they can raise MAGI above the thresholds that trigger NIIT.

2026 NIIT Income Thresholds (unchanged for inflation):

  • Single/Head of Household: $200,000
  • Married Filing Jointly: $250,000
  • Married Filing Separately: $125,000

If your MAGI exceeds these thresholds and you have net investment income, the NIIT can add 3.8% to your tax bill on the lesser of (a) your net investment income or (b) the amount your MAGI exceeds the threshold.


Strategy 1 โ€” Plan Retirement Income to Manage MAGI

Careful sequencing of income can keep your MAGI below thresholds that trigger NIIT in specific years:

  • Balance taxable, tax-deferred, and tax-free income so you smooth out spikes that could push MAGI above NIIT levels.

  • Consider spreading taxable events (such as capital gains or IRA distributions used for living expenses) across multiple years rather than realizing them all in one year.

  • Use qualified charitable distributions (QCDs) โ€” up to the annual limit โ€” to satisfy IRA withdrawal requirements without increasing MAGI. See our article on QCDs From Your IRA for more context.

Note: IRA distributions themselves are not NIIT net investment income, but they count toward MAGI, which can trigger NIIT on your investment income if you exceed the thresholds.


Strategy 2 โ€” Tax-Loss Harvesting and Gain Timing

Reducing net investment income directly is one of the most straightforward ways to reduce NIIT:

  • Tax-loss harvesting: Sell losing assets to realize capital losses that offset gains, which lowers net investment income.

  • Stagger sales of appreciated assets: If you must sell appreciated investments (e.g., for a home purchase or other needs), consider spreading the sales over several years to avoid large investment income in one year.

  • Hold tax-efficient investments in taxable accounts (e.g., municipal bonds, tax-efficient ETFs) to reduce taxable investment income.

All of these can help keep net investment income โ€” and therefore NIIT โ€” lower.


Strategy 3 โ€” Use Tax-Advantaged Accounts

Putting income inside vehicles that donโ€™t generate taxable investment income can reduce your exposure to NIIT later:

  • Roth accounts (IRA, 401(k), Roth conversions): Qualified Roth withdrawals are excluded from taxable income (and thus not subject to NIIT).
  • Fixed Annuities: Rather than holding taxable bonds, we use MYGA Fixed Annuities. The Annuity is tax deferred until you withdraw your funds. And unlike an IRA or 401(k), there are no Required Minimum Distributions (RMDs).
  • Pre-tax retirement accounts: Contributing to 401(k)s, traditional IRAs, or HSAs reduces your MAGI in the year of contribution, potentially keeping you under NIIT thresholds.
  • Tax-exempt municipal bonds: Interest income from municipal bonds generally isnโ€™t included in net investment income for NIIT purposes.

For example, strategic Roth conversions in years with lower taxable income can help lower future MAGI and reduce both NIIT and potential Medicare premium surcharges.


Strategy 4 โ€” Charitable and Gifting Techniques

Charitable giving and gifting can reduce the taxable base for NIIT by lowering MAGI or net investment income directly:

  • Qualified Charitable Distributions (QCDs): Distributions from a traditional IRA to charity (for age 70ยฝ+ retirees) reduce MAGI and remove RMD impacts on income calculations.

  • Donating appreciated securities to charity: This avoids the realization of capital gains that would otherwise increase net investment income.

  • Charitable remainder trusts (CRTs) and charitable lead trusts (CLTs): In certain contexts, these tools can spread income over time and reduce taxable investment income.


Additional Planning Ideasย 

Use Installment Sales for Large Gains

If you have assets with significant unrealized gains and you plan to sell, structuring the sale via installment method can spread income over multiple years, helping keep MAGI under NIIT triggers.

Consider Business Structure (if applicable)

If you receive passive income through a business, reviewing whether itโ€™s truly passive vs. active (e.g., real estate professional status) may affect how much income is considered investment income.

Review Asset Location

Holding income-producing assets inside tax-deferred accounts and keeping less efficient income in Roth or tax-exempt accounts may reduce net investment income.


Why Thresholds Matter for Retirees

Because the NIIT thresholds are fixed and not indexed for inflation, more retirees are becoming subject to the surtax over time even if their spending needs havenโ€™t changed. A combination of required minimum distributions (RMDs), Social Security, capital gains, and dividends can push MAGI above these thresholds โ€” triggering NIIT on net investment income.

This makes retirement income planning an essential part of managing tax liability overall. Thoughtful sequencing of withdrawals, Roth conversion timing, and income smoothing โ€” all aligned with your long-term goals โ€” can reduce the amount of NIIT and link back to broader tax planning such as our Retirement Tax Planning hub.


Frequently Asked Questions (Retiree-Focused)

Q: Are IRA distributions subject to the NIIT?
No โ€” distributions from traditional IRAs arenโ€™t counted as net investment income for NIIT purposes. However, they count toward your MAGI, which can trigger NIIT on your investment income if you cross the thresholds.

Q: Is selling a rental property subject to NIIT?
Yes โ€” income from passive activities like rental and royalty income is typically included as part of net investment income that can be subject to the 3.8% NIIT if your MAGI exceeds the thresholds.

Q: Does timing matter for capital gains?
Yes โ€” timing the sale of appreciated investments across multiple years or pairing gains with deductions (like losses or charitable gifts) can reduce your net investment income in any one year.

Q: Will future inflation indexing change NIIT thresholds?
Currently, NIIT thresholds are not indexed for inflation, meaning over time more individuals are likely to be subject to the tax even if real incomes do not rise.


Planning to manage surtaxes like the NIIT and Medicare income-related adjustments is most effective when coordinated with your broader retirement income picture โ€” including Social Security timing, RMD planning, and investment income sequencing. If youโ€™d like a planning-first conversation about how these surtaxes might affect your retirement income strategy, youโ€™re welcome to Request an Introductory Conversation.