Which retirement account should you withdraw from first: your taxable brokerage account, traditional IRA, 401(k), or Roth IRA?

The order in which you withdraw your retirement savings can have a major impact on how much you pay in taxes over the course of retirement.

For years, the conventional advice has been simple: spend your taxable accounts first, your tax-deferred accounts second, and save your Roth accounts for last.

But what if following that rule actually causes you to pay more taxes later?

In this episode of Divorce the IRS, Jimmy explains why there isn't one perfect retirement withdrawal order and how a more flexible, tax-conscious strategy can help retirees manage their income, investments, and long-term tax exposure.

In this episode, you'll learn:

• How the three retirement tax buckets work: taxable, tax-deferred, and tax-free
• Why the traditional taxable-first withdrawal strategy isn't always ideal
• How the IRA snowball can create larger required minimum distributions (RMDs)
• Why the years between retirement and Social Security may offer valuable tax planning opportunities
• How Roth conversions can help manage future taxable income
• Why IRA withdrawals can increase the taxable portion of Social Security benefits
• How large withdrawals can trigger higher Medicare premiums through IRMAA
• Why Roth accounts can serve as a tax shock absorber
• How retirement withdrawals can affect ACA health insurance subsidies before Medicare
• Why inherited taxable investments and traditional IRAs can have different tax consequences
• How the widow's tax penalty can affect a surviving spouse
• Why a proportional withdrawal strategy may help preserve flexibility
• How to create an annual retirement tax budget instead of following a rigid withdrawal order

Jimmy also discusses why retirement planning isn't just about finding the mathematically perfect strategy.

Watching an entire investment account slowly disappear can be emotionally difficult, even when your overall retirement plan remains financially sound.

Maintaining a combination of taxable, traditional IRA, and Roth assets may help retirees manage both their tax exposure and their confidence in the plan.

The biggest takeaway?

Instead of asking, "Which account should I spend first?" ask, "How much taxable income should I intentionally create this year?"

Some years, withdrawing from a traditional IRA may make sense. Other years, using taxable investments or qualified Roth withdrawals may help manage tax brackets, Social Security taxation, healthcare costs, and Medicare premiums.

The right strategy can change as your income, investments, tax laws, and personal circumstances change.

Retirement isn't just about making your money last. It's about making informed decisions about how and when that money is taxed.

Subscribe to Divorce the IRS for more retirement tax planning strategies, Roth conversion discussions, Social Security insights, and ways to manage taxes throughout retirement.

This content is for educational purposes only and does not constitute individualized tax, legal, or investment advice.

#RetirementPlanning #RetirementTaxes #RetirementWithdrawals #RothIRA #TraditionalIRA #401k #RothConversions #RequiredMinimumDistributions #SocialSecurity #IRMAA #TaxPlanning #DivorceTheIRS

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What if one of the best retirement accounts in America isn't a Roth IRA or 401(k), but a Health Savings Account (HSA)?

In Episode 37 of the Divorce the IRS Podcast, Jimmy explains why an HSA may be one of the most overlooked tax-advantaged retirement planning tools available.

Unlike a Roth IRA, an HSA can offer three separate federal tax advantages: tax-deductible contributions, tax-free investment growth, and tax-free withdrawals for qualified medical expenses.

But many people are missing the opportunity by treating their HSA like a checking account instead of a long-term investment account.

Jimmy explains how paying current medical expenses out of pocket, investing HSA contributions, and saving medical receipts could help you build a valuable source of tax-free money for retirement.

In this episode:

• Why HSAs can offer better tax advantages than Roth IRAs
• How the HSA triple tax advantage works
• Who qualifies to contribute to an HSA
• 2026 HSA contribution limits and catch-up contributions
• Why you may want to invest your HSA instead of spending it
• How to reimburse yourself for medical expenses years later
• Why saving medical receipts is so important
• Using HSA funds for COBRA premiums before Medicare
• How HSAs can fit into an early retirement strategy
• Using an HSA for Medicare premiums after age 65
• What happens when you withdraw HSA money for non-medical expenses
• Whether to prioritize your HSA, Roth IRA, or 401(k)
• Why leaving your HSA invested in cash could limit its potential

An HSA isn't just a way to pay for doctor visits and prescriptions. For the right person, it can become a powerful part of a tax-efficient retirement strategy.

The key is understanding how to use it, investing for the appropriate time horizon, and taking advantage of the tax benefits while you're eligible.

Subscribe to the Divorce the IRS Podcast for more conversations about retirement planning, Roth conversions, tax-efficient investing, and strategies designed to help you keep more of your money.

This podcast is for educational purposes only and does not constitute individualized tax, legal, investment, or insurance advice. Tax laws and HSA rules can change, and individual circumstances vary.

#HSA #HealthSavingsAccount #RothIRA #RetirementPlanning #TaxPlanning #TaxFreeRetirement #EarlyRetirement #RetirementIncome #RothConversion #FinancialPlanning #DivorceTheIRS

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Moving to the United States for work can create financial opportunities, but it can also introduce tax and investment rules you may have never encountered before.

In Episode 36 of the Divorce the IRS Podcast, Jimmy explains some of the financial issues foreign nationals should understand when living and working in America, including reporting foreign accounts, FBAR requirements, PFIC investments, U.S. retirement plans, Social Security, and international tax treaties.

You’ll learn why investments you owned before moving to America may create unexpected U.S. tax consequences, why foreign mutual funds and UCITS funds can become particularly complicated, and how choosing between a traditional and Roth 401(k) can affect someone who eventually plans to leave the United States.

Jimmy also walks through an example comparing two expats who make different 401(k) choices and discusses Social Security, totalization agreements, and how tax treaties may affect foreign nationals investing in the United States.

FREE GUIDE FOR EXPATS LIVING IN AMERICA:
https://baobabwealth.com/foreigners-in-america/?guide=foreigners-guide-download

LISTEN TO THE ABROAD IN AMERICA PODCAST:
https://baobabwealth.com/abroad-in-america/

BAOBAB WEALTH ABROAD:
https://baobabwealthabroad.com

This episode is for educational purposes only and should not be considered individualized tax, legal, or investment advice. Cross-border tax and financial rules can be complex, so consider consulting appropriately qualified professionals regarding your individual circumstances.

A few clarifications to the discussion in this episode: Roth 401(k) employer matching contributions are only treated as Roth if the employer plan offers that option and the employee elects it; otherwise, employer matching contributions are generally pre-tax. Social Security Totalization Agreements do not “transfer” benefits between countries, but can allow U.S. and foreign coverage to be combined for eligibility purposes, with each country paying its own benefit. Finally, tax treatment of investment gains depends on tax residency, account type, and applicable treaty rules, not nationality alone.

#ExpatsInAmerica #ExpatFinance #USExpat #CrossBorderPlanning #ExpatTaxes #FBAR #PFIC #401k #Roth401k #FinancialPlanning #BaobabWealth #DivorceTheIRS

• Visit Divorce-the-IRS.com
• Visit Baobab Wealth
• Visit Baobab Wealth Abroad
• Buy a copy of Jimmy's book, Divorce the IRS
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