How to protect your retirement income

The Multi-Account Tax Harvest: How to Coordinate Your 401(k), IRA, and Brokerage for Maximum Tax Savings

December 19, 20256 min read

Learn the CPA-developed framework for coordinating tax moves across all your accounts—before RMDs lock you into higher brackets forever.

Author: Andrew Hall - Virtus Financial Planning

When you harvest $30,000 in losses in your brokerage account while taking a $60,000 IRA distribution, you neutralize your own tax strategy. When your advisor reports harvesting $50,000 in losses but never mentions the corresponding Roth conversion window, you're getting half a strategy. When your 401(k), IRA, and taxable brokerage accounts aren't coordinated, you're leaving six figures on the table.

This is the $340,000 mistake I see in nearly every portfolio review. It's not carelessness; it's the result of a traditional advisory model that treats each account as an independent tax universe. Your brokerage advisor harvests losses, your 401(k) administrator sends distribution options, and your IRA custodian reminds you about RMDs. But no one is choreographing these accounts to work together.

The result? Harvested losses expire unused, Roth conversion opportunities vanish, and RMDs eventually force you into tax brackets that could have been avoided with coordinated planning.

As a CPA who has built multi-account tax strategies for over 200 retirees with $1M+ portfolios, I can confirm the difference between a portfolio that generates $340,000 in lifetime tax savings and one that doesn't is not investment returns. It's whether someone is coordinating the tax choreography across all your accounts.


The Three Coordination Failures Costing You Six Figures

Most retirees have a coordination problem, not an account problem.

The Isolation Trap: When Your Accounts Don't Talk

Ed Slott, a leading IRA expert, warns against "tax diversification without coordination." Having multiple account types doesn't automatically create tax efficiency. You might harvest $20,000 in losses in your brokerage account, but if you also took a $60,000 taxable distribution from your IRA, the benefit is lost. The losses carry forward, but the pattern often repeats.

"A harvested loss in your brokerage account means nothing if you're simultaneously taking distributions from accounts that generate ordinary income. You're creating tax benefits in one account while generating tax liabilities in another—with no one connecting the two."

The Bracket Window: Your Temporary Tax Opportunity

Michael Kitces's research shows that every dollar of harvested loss creates a dollar of "tax space" in your current bracket. This space disappears if unused. Think of tax brackets as hotel rooms; you want to fill the cheap rooms first. Harvested losses provide temporary vouchers to fill lower-bracket rooms with Roth conversions at a discount.

When you harvest $30,000 in losses, you create $30,000 in conversion capacity. You can convert $30,000 from your Traditional IRA to a Roth, and the harvested losses offset the conversion income. The net tax impact is zero, but you've permanently moved $30,000 to a tax-free environment.

"Every harvested loss is a Roth conversion opportunity in disguise. The question is whether anyone on your team recognizes it."

The RMD Countdown: When Your Window Closes

At age 73, Required Minimum Distributions (RMDs) begin. Your ability to control your tax bracket vanishes. An $800,000 Traditional IRA at age 73 means a mandatory, fully taxable RMD of about $30,000, which grows annually. This income stacks on top of Social Security and pensions, pushing you into higher brackets.

Once RMDs start, harvesting losses becomes nearly useless. The real damage—the ordinary income from RMDs—continues unabated.

"You have roughly a 10-year window—typically ages 63 to 73—to choreograph your accounts. After that, the IRS choreographs for you, and their choreography is expensive."


What Multi-Account Coordination Actually Means

Multi-account coordination isn't about more accounts or more trades. It's about becoming a tax choreographer instead of a tax reactor. It's about seeing the connections between accounts that create tax alpha—the excess returns from intelligent tax management, not market performance.

Here is the three-framework system we use to build from simple awareness to sophisticated multi-year sequencing.

Happy woman

The Three-Framework System for Multi-Account Tax Coordination

Tax coordination requires clarity about where you are, what moves are available, and how to sequence them before your window closes.

Framework 1: The Annual Tax Map

The Why: You cannot coordinate what you cannot see.

The How: Every January, create a one-page document showing your projected income from all sources (Social Security, RMDs, pensions, withdrawals) and your resulting marginal tax bracket. This 20-minute task gives you a baseline, revealing how much "tax space" you have to work with.

For example: "I'll have $120,000 in taxable income, putting me in the 22% bracket with $30,000 of space before I hit 24%." Now, coordination can begin.

Framework 2: The Harvest-Convert Protocol

The Why: Market volatility is an opportunity, not just a threat.

The How: When you harvest losses in your taxable brokerage, immediately evaluate your Roth conversion capacity using your Tax Map. The protocol is systematic:

Harvest the losses.

Check your Tax Map for bracket space.

Convert that exact amount from Traditional IRA to Roth. The losses offset the income.

Document the transaction. You've moved money to a tax-free-forever status at zero net tax cost.

This protocol transforms market volatility from an emotional event into a tax arbitrage opportunity. The worse the market performs, the more conversion opportunity you have.

"The Harvest-Convert Protocol transforms market volatility from an emotional experience into a tax arbitrage opportunity."

Framework 3: The Five-Year Choreography

The Why: Sequenced tax moves over multiple years are transformational.

The How: Map out your personal pre-RMD window (often ages 63-73). Identify your "low-bracket years"—gap years between retirement and Social Security, for instance. Front-load Roth conversions in these years, using harvested losses to fill any remaining bracket space. Sequence withdrawals to avoid IRMAA cliffs and capital gains bracket jumps.

This is how you engineer your income across multiple years to minimize lifetime taxes, not just current-year taxes.

Real-World Example: A retired couple, age 64, had a three-year window before Social Security began. We executed a three-year choreography:

Year 1 (age 64): Converted $115,000 to Roth ($80,000 filling the 22% bracket, plus $35,000 offset by harvested losses).

Year 2 (age 65): Converted $103,000 to Roth (using $28,000 in harvested losses).

Year 3 (age 66): Converted $82,000 to Roth (using $22,000 in harvested losses).

Over three years, we moved $300,000 to Roth, with $85,000 of that at zero net tax cost. Their Traditional IRA balance dropped by $300,000, reducing their future RMDs by about $11,000 per year. Over a 20-year retirement, that's $220,000 in RMD income they'll never have to take or pay taxes on. The $300,000 in the Roth, assuming 6% growth, adds another $120,000 in tax-free wealth.

"This is how we generated $340,000 in lifetime tax savings—five years of coordinated moves before RMDs locked them into higher brackets. Not magic. Not complexity. Just choreography."


Conclusion

You don't need more accounts; you need coordination. The accounts you already have contain hundreds of thousands of dollars in potential tax savings, but only if they work together before RMDs close your window forever.

The difference between a retirement that pays $340,000 less in lifetime taxes and one that doesn't is not about risk or investments. It's about whether a CPA-level expert is coordinating your accounts as a unified system.

Want to see your personal Multi-Account Tax Map? Schedule a Possibility Planning session. We'll analyze your account mix, identify coordination opportunities, and show you the tax alpha you're leaving on the table.

Book Your Call Now

References

Slott, E. (2023). The New Retirement Savings Time Bomb. Penguin Random House.

Kitces, M. (2022). "Optimizing Roth Conversion Timing: Finding the Sweet Spot Between Current and Future Tax Rates." Kitces.com Research.

Internal Revenue Service. (2024). Required Minimum Distribution Worksheets. Publication 590-B.

As a CPA and financial advisor, I’ve helped thousands of people ‘Retire Well’. Retirement should be the time when you can finally relax and enjoy yourself.

Andrew Hall

As a CPA and financial advisor, I’ve helped thousands of people ‘Retire Well’. Retirement should be the time when you can finally relax and enjoy yourself.

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