Short answer: many retirees assume taxes get simple once they stop working — and that assumption is exactly what costs them. Retirement brings its own tax traps: giant required distributions, Social Security taxation, Medicare surcharges, and poorly timed withdrawals. The good news is that almost all of them are avoidable with a few years of planning before and during retirement.
Mistake 1: ignoring the RMD time bomb
A career of diligently funding 401(k)s and IRAs builds a large tax-deferred balance — and a large future tax bill. Required minimum distributions eventually force big withdrawals, taxed as ordinary income, whether you need the money or not. Retirees who never draw down or convert during their lower-income years can get hit with outsized RMDs that push them into higher brackets for the rest of their lives.
Mistake 2: wasting the low-income years
Mistake 3: triggering hidden surcharges
In retirement, a spike in income doesn’t just raise your tax bracket — it can increase how much of your Social Security is taxed and trigger Medicare premium surcharges (IRMAA). A poorly timed large withdrawal, capital gain, or Roth conversion can quietly cost you on several fronts at once. Smooth, planned income avoids these cliffs.
Mistake 4: poor withdrawal sequencing
Draining one account type at a time, or pulling large sums in some years and little in others, tends to waste low brackets and create spikes. A blended withdrawal strategy across taxable, tax-deferred, and Roth accounts usually produces a lower lifetime tax bill than any “default” order.
Mistake 5: forgetting to plan for the survivor
When one spouse passes, the survivor often files as single — with lower brackets and a lower standard deduction — so the same income is taxed more heavily. Failing to plan for this “widow’s penalty,” and for how assets and estate pieces pass, is a commonly overlooked tax mistake that good planning addresses in advance.
Frequently asked questions
Common ones include ignoring the future tax hit of large required minimum distributions, wasting the low-income years before Social Security and RMDs for Roth conversions, triggering Social Security taxation and Medicare (IRMAA) surcharges with poorly timed income, inefficient withdrawal sequencing, and failing to plan for the higher taxes a surviving spouse faces. Most are avoidable with proactive planning.
Yes — taxes continue in retirement, they just change form. Withdrawals from tax-deferred accounts, a portion of Social Security, capital gains, and required minimum distributions can all be taxable. Because income timing affects brackets, Social Security taxation, and Medicare premiums, retirement is actually a rich area for tax planning.
Sources
Founder & Financial Planner · Investment Adviser Representative · Series 63 & 65
Ian McGinnis is the founder of Dental Wealth Partners and a fee-only financial planner dedicated to dentists. As an investment adviser representative (Series 63 and 65), he built the firm to give dentists coordinated, fiduciary advice across their practice, taxes, investments, retirement plans, and long-term goals — the whole picture in one strategy. A graduate of Belhaven University, Ian previously worked at Davis Private Wealth, MML Investors Services, and Northwestern Mutual, and is based in the Jackson, Mississippi area. He is the author of The Wealthy Dentist and hosts the Smiles & Cents podcast.
Keep reading
- Retirement withdrawal strategy: which accounts to tap, and whenThe order you withdraw from taxable, tax-deferred, and Roth accounts can save years of taxes. Why your withdrawals look different before and after Social Security.
- Building your retirement paycheck: turning savings into incomeRetirement flips the problem from saving to spending. How dentists can turn a portfolio and practice-sale proceeds into a reliable, tax-smart paycheck.
- When should a dentist claim Social Security?Claiming Social Security early, at full retirement age, or at 70 changes your benefit for life. How dentists should think through the timing decision.