Steer Your Retirement Tax Strategy Carefully

Are you nearing retirement and getting ready for tax season? Here are some retirement tax strategies to steer you in the right direction as the new year begins.
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Key Takeaways

  • Transitioning into retirement may mean changes in your employment status; make sure your retirement tax strategies keep pace
  • The near-retirement years can offer certain tax-advantaged savings alternatives
  • Downsizing your home? Consider the tax implications

The road to retirement is changing, and the best route isn't always clear. If you're approaching your retirement destination, don't forget to update your retirement tax strategies. For example, you might decide that it’s time to try out a new career, work part-time, or maybe add some volunteer work to your schedule. Does the house seem too big and cluttered now that the kids are gone? Maybe it’s time to downsize. 

Each of these changes may require a fresh look at your tax strategy as it relates to income, retirement savings, and allocating your assets. There may be plenty of changes in life as retirement comes into view. Just make sure your retirement tax planning isn’t overlooked on the road map.

Driving toward retirement? Check your tax strategy

Stay in the Driver’s Seat as You Transition

“Near-retirees need to think about what types of income they may or may not be getting in retirement,” said Lisa Greene-Lewis, a certified public accountant and TurboTax blog editor. “If someone is doing consulting work and a spouse gets Social Security, that may have tax implications.” According to the Social Security Administration, if you and your spouse have combined income of more than $35,280, you may have to pay taxes on some of the Social Security income.

More retirees may be jumping into the so-called “gig economy,” such as driving for Uber or Lyft, which means they’re subject to self-employment taxes, said Greene-Lewis. “But they’re also able to take deductions. For instance, if they are driving and purchase an SUV, they can get up to $26,200 in deductions for equipment, travel, and gifts for their business,” she said.

The Other RV—Retirement Vehicles

Managing retirement plans. As you push toward retirement, what should you do with your retirement plans? “Once you turn 50, you can step up your contribution limits with catch-up contributions: an additional $1,000 annually to your IRAs and an additional $7,500 in 2023 for 401(k)s or 403(b)s,” said Greene-Lewis. 

Leave it, roll it over, or cash it out? Have you made, or do you plan to make, any pre-retirement career moves? If so, what about those retirement plans? Provided you have more than $5,000 in assets, as a near-retiree, you may be able to keep your plan with a former employer until the plan’s normal retirement age. If the plan has good investment choices and low fees, this might be a good option.

You can also roll over a 401(k) to an IRA —but make sure the funds go straight to the rollover IRA account to avoid any money being withheld. Fees, taxes, and penalties can considerably reduce the amount of money you’ll receive from cashing out early. The amount you cash out will be subject to a mandatory 20% withholding for federal income tax, and there is an additional 10% early withdrawal penalty if you’re under age 59 1/2 for any amount not rolled over—even the withholding. You may also be responsible for ordinary income tax on the full amount of your distribution as well as state and local taxes, depending on where you live, on any amount you withdraw and do not roll over. 

If you’re weighing the decision to roll over into an IRA, it’s worth noting that charitable contributions (see more below) can be made directly from an IRA, but not from a 401(k). IRAs also tend to have more flexibility regarding beneficiaries. For example, 401(k)s and other qualified employer-sponsored retirement plans require spousal consent before you name anyone other than your spouse as beneficiary.

Health savings accounts (HSAs). For those with an HSA, any distributions from it to pay for medical expenses are tax free. At age 65, HSA distributions used to pay for non-medical expenses are subject to income taxes, but retirees can avoid the 20% penalty that applies to those under age 65 who use the money for non-medical reasons. Additionally, Greene-Lewis said those over 65 can deduct medical expenses if they amount to more than 7.5% of the person’s adjusted gross income.


As you approach retirement, you may want to reduce the physical drag of all those belongings. Changing your home and reducing your clutter can be an important part of your retirement tax strategy, too.

Home equity. If you choose to sell your house, keep an eye on the tax ramifications. You may have built up a lot of equity in your home, but if you’ve lived in it for at least two of the five years prior to selling it, you may not have to pay taxes on the capital gains. Greene-Lewis said tax laws allow a single filer to claim up to $250,000 in profit on a home sale with no taxes, and up to $500,000 for a married couple filing together. You should also consider any capital improvements made to the home (such as room additions, kitchen and bath upgrades, landscaping, etc.), and deduct the amount from the gross profit to determine what’s called your adjusted basis.

Charitable deductions. Your deduction for charitable contributions generally can’t be more than 60% of your adjusted gross income (AGI), but in some cases, 20%, 30%, or 50% limits may apply.

The drive toward retirement can be an exhilarating one, but it’s important to keep your hands on the wheel and steer toward the most efficient tax strategy.

TD Ameritrade does not provide tax advice. We suggest you consult with a tax-planning professional with regard to your personal circumstances.


Key Takeaways

  • Transitioning into retirement may mean changes in your employment status; make sure your retirement tax strategies keep pace
  • The near-retirement years can offer certain tax-advantaged savings alternatives
  • Downsizing your home? Consider the tax implications

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