Strategize Now to Avoid a Nasty Tax Surprise in Retirement
If you did most of your retirement saving in 401(k)s and IRAs, unless you have a plan, you may end up paying a lot more in taxes than you bargained for.
Americans worry a lot about saving enough money for a long and happy retirement. What they don’t seem to spend as much time figuring out is how to keep more of what they have managed to save while working so hard.
No one can prepare for every expense that might crop up in what could be a 20-, 30- or even 40-year retirement. No matter the timeline, you can always plan for taxes … and should. Whether your savings are mighty or meager, Uncle Sam is going to want his share and will take as much as you’re willing to hand over, so it’s up to you to be sure the amount is fair.
To do that, you’ll have to think beyond the basics — beyond today and your tax-deferred IRA or 401(k). Your goal should be to get yourself into the lowest tax bracket possible every year in retirement. That means divvying up your nest egg into different tax “buckets”:
From just $107.88 $24.99 for Kiplinger Personal Finance
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
The taxable bucket
This includes the investments and savings you pay taxes on upfront and annually on the growth, including your bank accounts, non-qualified brokerage accounts, certificates of deposit, interest on bonds, etc.
The tax-deferred bucket
This holds your IRA and 401(k) accounts. You don’t pay taxes when you deposit the money or while the money is growing. However, you will pay taxes on 100% of the money you withdraw from this bucket. Once you turn 70½, you are forced to withdraw according to an IRS calculation through RMDs (required minimum distributions), whether you need the money or not.
You will pay taxes according to your tax rate at the time of withdrawal. This could be a higher rate in the future, meaning you could pay more in taxes than you saved when you initially deposited the funds. Therefore, if you’re highly invested in this bucket, you’ll have more taxable income on your 1040, which could push you into a higher tax bracket in retirement and cause your Social Security to be taxed accordingly.
The tax-free bucket
This includes Roth IRAs and Roth 401(k)s, along with specially designed life insurance policies and municipal bonds, where you pay the taxes upfront and accumulate the growth tax-free. For older savers who have contributed for years to the popular workplace 401(k), getting those buckets balanced usually includes converting some tax-deferred dollars into a Roth, which has tax-free earnings and withdrawals.
One client’s tax-saving strategy
Other strategies can further diversify your income streams and add even more tax efficiency to your retirement plan. Here’s how one of my clients recently cut her future tax bill down to size:
Michelle is in her mid-50s and plans to retire at 65. At that time, she’ll turn on three income streams: an $18,000-per-year pension benefit, a $30,000-per-year Social Security benefit, and $32,000 from an overfunded permanent life insurance policy. (She’ll do the latter through a strategy known as max funding, which allows the owner to withdraw the policy’s excess cash tax-free through loans that will be repaid with the owner’s death benefit.)
That’s $80,000 in income — but her adjusted gross income will only be $33,000 ($18,000 + half of her Social Security benefit). Assuming a standard deduction of $12,000, that leaves $21,000 of her $33,000 that will be taxed.
She also has a 401(k), which should be worth about $800,000 when she retires. She doesn’t need the income, but if she does, she should have a bit of a cushion before she hits the next tax bracket. She also can work on converting some of that money to a Roth account before she’s hit with required minimum distributions at age 70½.
The bottom line
Michelle’s money should last much longer than it would if it were all being taxed. She’d be taking out at least another $10,000 to $12,000 a year to get to the same net amount — the amount she’s decided she needs to live the lifestyle she wants in retirement.
Tax-deferred investment accounts can be a beautiful thing for savers. But they’re not the only way to go. The earlier you start, the easier it will be to find the balance you need with those three tax buckets.
Do your homework and preserve every dollar you can. The next time you meet with your CPA or financial adviser, talk about strategies that could help you avoid a nest-egg-nibbling tax burden in retirement.
Kim Franke-Folstad contributed to this article.
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Gregory Ricks, is the founder and CEO of Gregory Ricks & Associates and is a licensed insurance professional. He is also the founder of Total Wealth Authority, a team of outside financial, tax and estate planning professionals, and is the host of radio show Winning at Life on News Talk 99.5 WRNO (10 a.m. to 1 p.m. on Saturdays and 7 p.m. to 8 p.m. on weeknights).
-
It's Beginning to Look a Lot Like a Santa Rally: Stock Market TodayInvestors, traders and speculators are beginning to like the looks of a potential year-end rally.
-
The 2026 Retirement Catch-Up Curveball: What High Earners Over 50 Need to Know NowUnlock the secrets of the 2026 retirement catch-up provisions: A must-read for high earners aged 50 and above.
-
How Much a $100K Jumbo CD Earns YouYou might be surprised at how fast a jumbo CD helps you reach your goals.
-
A Financial Planner Takes a Deep Dive Into How Charitable Trusts Benefit You and Your Favorite CharitiesThese dual-purpose tools let affluent families combine philanthropic goals with advanced tax planning to generate income, reduce estate taxes and preserve wealth.
-
A 5-Step Plan for Parents of Children With Special Needs, From a Financial PlannerGuidance to help ensure your child's needs are supported now and in the future – while protecting your own financial well-being.
-
How Financial Advisers Can Best Help Widowed and Divorced WomenApproaching conversations with empathy and compassion is key to helping them find clarity and confidence and take control of their financial futures.
-
A Wealth Adviser Explains: 4 Times I'd Give the Green Light for a Roth Conversion (and 4 Times I'd Say It's a No-Go)Roth conversions should never be done on a whim — they're a product of careful timing and long-term tax considerations. So how can you tell whether to go ahead?
-
A 4-Step Anxiety-Reducing Retirement Road Map, From a Financial AdviserThis helpful process covers everything from assessing your current finances and risks to implementing and managing your personalized retirement income plan.
-
The $183,000 RMD Shock: Why Roth Conversions in Your 70s Can Be RiskyConverting retirement funds to a Roth is a smart strategy for many, but the older you are, the less time you have to recover the tax bite from the conversion.
-
A Financial Pro Breaks Retirement Planning Into 5 Manageable PiecesThis retirement plan focuses on five key areas — income generation, tax management, asset withdrawals, planning for big expenses and health care, and legacy.
-
4 Financial To-Dos to Finish 2025 Strong and Start 2026 on Solid GroundDon't overlook these important year-end check-ins. Missed opportunities and avoidable mistakes could end up costing you if you're not paying attention.