Coordinate taxes with the retirement decisions creating them

Tax Planning in Retirement

Retirement can create new control over when and where income appears. A coordinated tax plan can help you evaluate withdrawals, Roth conversions, capital gains, Social Security and Medicare costs across multiple years.

Fairchild Capital incorporates tax considerations into financial planning and coordinates with qualified tax professionals when appropriate.

Designed for adults 50+Before and throughout retirement
Multi-year perspectiveToday’s tax bill considered with future years
Coordinated planningIncome, investments and taxes considered together

Taxes become part of the retirement strategy

What is tax planning in retirement?

Tax planning in retirement evaluates how the timing and character of your income may affect taxes, healthcare costs and the resources available for future years.

During your working years, much of your taxable income may arrive automatically through a paycheck. Retirement can be different. You may have some control over when to use a taxable brokerage account, take money from a traditional retirement account, complete a Roth conversion or begin Social Security.

Those choices interact. A larger traditional IRA withdrawal may increase ordinary income. Selling appreciated investments may create capital gains. Additional income may cause more Social Security benefits to become taxable or affect income-related Medicare premiums. Waiting too long to address tax-deferred balances may reduce flexibility once required minimum distributions begin.

The short answer

Good retirement tax planning does not chase the smallest possible tax bill in a single year. It compares reasonable choices across multiple years while protecting cash flow, investment discipline and the flexibility to respond when laws or circumstances change.

The decisions worth coordinating

Seven areas a retirement tax plan may evaluate

Withdrawal order

Decide how cash, taxable investments, traditional retirement accounts and Roth accounts may work together. A fixed “taxable first” rule can miss opportunities created by lower-income years, gains, losses or future required distributions.

Roth conversions

A conversion generally moves money from a pre-tax retirement account to a Roth account and creates taxable income in the year completed. The analysis should compare the current cost with potential future benefits, while considering brackets, Medicare premiums and available cash for taxes.

Capital gains

Realizing gains can fund spending, rebalance a portfolio or diversify concentrated holdings. Cost basis, capital losses, charitable goals and the rest of the tax return can affect the timing and size of a sale.

Social Security

The taxable portion of Social Security depends on benefits and other income. Withdrawals, conversions, interest and gains may therefore change how much of a benefit is included in federal taxable income.

Required distributions

Traditional IRAs and many workplace plans eventually require distributions. Planning before they begin may create options, but a decision should not be made solely to reduce a projected future account balance.

Medicare premiums

Higher modified adjusted gross income can result in income-related adjustments to Medicare Part B and Part D premiums. Because the determination generally uses an earlier tax return, a tax decision can affect healthcare costs later.

Charitable giving

Households with charitable goals may compare gifts of cash, appreciated securities and—when eligible—qualified charitable distributions. The appropriate method depends on eligibility, documentation and the overall plan.

A tax return records what happened. Tax planning asks what should happen next.

Fairchild Capital can help evaluate tax-sensitive retirement decisions before they become irreversible.

Look for planning windows

Why the years around retirement may matter

The period after a final paycheck but before Social Security and required distributions can produce a different income picture from the years before and after it. That does not automatically make every low-income year a Roth-conversion year, but it may create a window worth evaluating.

Before retirement

Prepare the transition

Review deferred compensation, stock awards, retirement-plan contributions, appreciated holdings and the tax effects of the final working year.

Early retirement

Use available flexibility

Coordinate portfolio withdrawals, gains, Social Security timing and possible conversions while taxable income may be more controllable.

Medicare years

Watch income interactions

Consider how withdrawals, gains and conversions may affect both taxes and income-related Medicare premiums.

RMD years

Coordinate required income

Integrate required distributions with spending, withholding, charitable giving and portfolio decisions rather than treating them as a year-end task.

Brackets are not the whole calculation.

A decision can affect ordinary income, capital gains, the taxable portion of Social Security, Medicare premiums, deductions, credits and state taxes. Useful analysis considers the combined effect and the household’s actual goals.

Different accounts, different tax treatment

Building tax flexibility into retirement income

Retirees often hold money across taxable, tax-deferred and Roth accounts. That variety can create flexibility, but only when the accounts are coordinated with spending and investments.

Taxable accounts

Manage gains and basis

Withdrawals are not automatically taxable in full. Sales may create gains or losses based on cost basis, and interest or dividends can create income even without a sale.

Tax-deferred accounts

Plan ordinary income

Traditional IRA and many workplace-plan withdrawals are generally taxed as ordinary income, subject to individual circumstances and any after-tax basis.

Roth accounts

Preserve optionality

Qualified Roth withdrawals are generally federal-income-tax-free. Roth assets may provide flexibility in years when additional taxable income would be especially costly.

Cash reserves

Fund decisions deliberately

Cash can cover spending or conversion taxes without forcing an investment sale, but holding excess cash can have opportunity costs.

The account used for spending can also affect the investment allocation that remains. Tax planning should therefore be connected to a complete retirement income plan.

One retirement decision can affect several future tax years.

Compare the tradeoffs before moving money, realizing gains or beginning a new income source.

A coordinated planning process

How Fairchild Capital approaches retirement tax planning

Start with your retirement plan

Clarify expected spending, income sources, investments, family priorities and the decisions that require action.

Build the multi-year picture

Identify expected changes in wages, pensions, Social Security, required distributions, gains and other taxable income.

Compare reasonable strategies

Evaluate the potential benefits, costs and limitations of different withdrawal, conversion, gain-recognition or charitable-giving choices.

Coordinate implementation

Work with your qualified tax professional when tax advice, return preparation or confirmation of individual tax treatment is needed.

Review as conditions change

Update the analysis when laws, income, markets, spending, healthcare or family circumstances materially change.

Important distinction

Financial planning can identify tax considerations and compare scenarios. It does not replace individualized tax advice from a qualified tax professional, and projected tax results are not guaranteed.

Related Fairchild Capital resources

Explore the broader retirement planning overview, retirement income planning and planning for Oregon PERS members.

Common questions

Tax planning in retirement FAQs

What is retirement tax planning?

Retirement tax planning evaluates how withdrawals, Roth conversions, capital gains, Social Security, required distributions, charitable giving and other income may affect taxes and the broader retirement plan across multiple years.

When should I begin tax planning for retirement?

Planning before retirement can help identify upcoming income changes and decisions. The years between a final paycheck and the start of Social Security or required distributions may offer additional flexibility, but the appropriate timing depends on individual circumstances.

Should I withdraw from taxable accounts before my IRA?

Not automatically. The appropriate order can depend on current and future brackets, capital gains, required distributions, Medicare premiums, estate goals, charitable plans and the assets held in each account. A flexible multi-year strategy may be more useful than a universal rule.

Will my Social Security benefits be taxable?

They may be. Federal taxation depends on filing status, benefits and other income, including tax-exempt interest. State treatment can differ. Use current IRS and state guidance and consult a qualified tax professional for your circumstances.

Does a Roth conversion reduce taxes?

A Roth conversion generally creates taxable income now in exchange for moving assets into a Roth account. It may improve future flexibility in some situations, but it can also increase current taxes and Medicare premiums. Results depend on future tax rates, investment performance, time horizon and individual circumstances.

How do required minimum distributions affect taxes?

Required distributions from traditional retirement accounts are generally included in taxable income except for applicable basis or other exceptions. They can affect tax brackets and other income-related calculations. Under current federal rules, many account owners begin at age 73, but exceptions and future changes may apply.

Can retirement income affect Medicare premiums?

Yes. Medicare Part B and Part D can include income-related monthly adjustment amounts based on modified adjusted gross income reported on an earlier federal tax return. Certain life-changing events may allow a new determination.

Does Fairchild Capital prepare tax returns?

This page describes incorporating tax considerations into financial planning. Individualized tax advice and tax-return preparation should be handled or confirmed by a qualified tax professional. Ask Fairchild Capital how coordination would work for your engagement.

Tax rules change. Confirm current information through the IRS required-distribution guidance, IRS Social Security tax guidance and Medicare cost information.

Take the next step

Make tax decisions part of the retirement plan.

Schedule an introductory conversation about the decisions ahead and whether Fairchild Capital may be the right fit.

Fairchild Capital, LLC5603 SW Hood Ave
Portland, OR 97239
503.828.3796info@fairchild-capital.com

This material is provided for general informational and educational purposes only. It is not individualized investment, tax or legal advice and should not be relied upon as a recommendation to take or refrain from any action. Tax laws, government-benefit rules and retirement-plan provisions can change, and their application depends on individual circumstances. Consult qualified financial, tax and legal professionals before implementing a strategy.

Fairchild Capital, LLC is an SEC-registered investment adviser. Registration does not imply a particular level of skill or training. Advisory services are offered only where Fairchild Capital is appropriately registered or exempt from registration. Investing involves risk, including possible loss of principal. Financial and tax projections rely on assumptions, actual results will vary and no strategy can guarantee a particular tax or investment outcome. Review Fairchild Capital’s Form CRS and website disclosures.

Information reviewed September 2026. © Fairchild Capital, LLC.