These 5 major tax mistakes can lead to costly headaches after you retire. Learn how to avoid them now

These 5 major tax mistakes can lead to costly headaches after you retire. Learn how to avoid them now Rebecca Payne Sat, May 16, 2026 at 9:25 PM GMT+7 5 min read When it comes to drawing down your retirement savings, planning is everything — without it, you might face surprise tax bills that could put a dent in your hard-earned savings. Thanks to Jeff Bezos, you can now become a landlord for as little as $100 — and no, you don t have to deal with tenants or fix freezers. Here s how Robert Kiyosaki says this 1 asset will surge 400% in a year and begs investors not to miss this ‘explosion’ Dave Ramsey warns nearly 50% of Americans are making 1 big Social Security mistake — here’s how to fix it ASAP Here are five ways to ensure that you re prepared when it comes to how your retirement income is taxed. A survey in 2024 conducted by Nationwide Financial found that 50% of respondents believed that Social Security benefits were tax-free (1). If you re under the impression that you won t ever have to pay taxes on Social Security benefits, here s your wake-up call: Depending on your income, you may have to pay federal income taxes on a portion of your Social Security benefits. The IRS calculates what portion of Social Security benefits are taxable by adding one-half of your benefits, plus all of your other income, including tax-exempt interest (2). If this total, your "combined income," is greater than the base amount for your filing status, you may owe taxes on your benefits. The base amount for single people, heads of household or qualifying surviving spouses, is $25,000; the base amount for married couples filing jointly is $32,000. If you re over these thresholds, how much tax could you have to pay? Fifty percent of your benefits could be taxable if you re filing single, head of household or are a qualifying surviving spouse, and your combined income is between $25,000 to $34,000; for married couples filing jointly, it s $32,000 to $44,000 (3). And, up to 85% of your benefits could be taxable if you re filing single, head of household or are a qualifying surviving spouse, and your combined income is more than $34,000; for married couples filing jointly, it s $44,000 income. Read More: Non-millionaires can now hoard property like the 1% — how to start with as little as $100 Tax-deferred retirement accounts such as 401(k)s and IRAs demand that you take required minimum distributions (RMDs), which are minimum amounts you have to withdraw from your retirement accounts every year, beginning at age 73 (4). According to a report from Bloomberg, having a mix of account types allows for more flexibility, since Roth withdrawals are not subject to RMDs, and are tax-free as long as the account has been open at least five years (5). If your future RMDs are likely to inflate your tax bill, you could consider converting a portion of your 401(k) or traditional IRA to a Roth IRA, though you will have to pay tax on that portion in the tax year you re converting it. According to Bloomberg, waiting to make Roth conversions until after age 63 can have an unpleasant consequence: higher Medicare costs. Since Medicare Part B and D premiums are calculated based on income from two years prior, the Bloomberg report says, a substantial Roth conversion "could trigger an IRMAA (income-related monthly adjustment amount) surcharge on those premiums." Medicare premiums are calculated annually, however, and according to the report, for some retirees in low-income years, it can make sense to make larger conversions "despite the tax hit." "The long-term benefit of that conversion may outweigh the short-term pain of Medicare premiums, which are a one-year thing," Tim Steffen, director of advanced planning for Baird Private Wealth Management, told Bloomberg. If you have investments outside of tax-advantaged retirement accounts, a strategy to offset your capital gains, or possibly your taxable income, is tax-loss harvesting. If you sell an investment at a capital loss, you may be able to deduct this capital loss from your capital gains, reducing your capital gains taxes. If your capital losses in a year are greater than your capital gains, you can deduct up to $3,000 ($1,500 if married filing separately) from your annual income (6). If your capital losses are more than the limit, you can carry forward the loss and apply it to later years. With the tax-loss harvesting strategy, experts recommend replacing the investments you ve sold with similar assets, but not by repurchasing the same asset, which can trigger the IRS wash-sale rule. This rule says you cannot buy back the same or a "substantially identical" security soon after, while claiming a capital loss (7). Bloomberg notes that this strategy "may be less useful for investors expecting higher tax rates later or those already able to realize gains at a 0% rate." Finally, consider what the tax implications will be for your heirs if you are leaving them retirement savings acco

These 5 major tax mistakes can lead to costly headaches after you retire. Learn how to avoid them now

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