The biggest difference between managing taxes throughout your career versus during retirement is that when you are retired, you are responsible for calculating how much you owe and paying it on a timely basis. Retirees normally have several different income sources, and not all automatically withhold taxes from distributions.

Retirement Income Sources

Having multiple sources of income during retirement is a good strategy, as it helps protect you from market declines, tax legislation changes, and potential defaults or cutbacks in pensions or entitlement programs. However, be aware that the more income sources you have, the more effort it takes to determine how much you owe in taxes for the year.

As a general rule, retirement income is taxed as either ordinary income or long-term capital gains. Ordinary income includes:

• Employer wages
• Taxable interest payments
• Ordinary dividends
• Short-term capital gains (on assets held a year or less)
• Taxable withdrawals from retirement accounts
• Taxable Social Security benefits
• Withdrawals from health savings accounts (HSAs) for nonqualified expenses
• Annuity payouts
• Rental income
• Pension payouts

Income subject to long-term capital gains is taxed at 0 percent, 15 percent, or 20 percent, depending on your total taxable income. This type of income is generated from:

• Profits from the sale of a business (assuming you started and sold the business over more than 1 year)
• Real estate (excluding rental income)
• Securities
• Most other investments held for over a year
• Qualified dividends

Additional Investment Tax

Single taxpayers may be subject to an additional 3.8 percent net investment income tax (NIIT) on income generated from invested assets – if their modified adjusted gross income (MAGI) is $200,000 or more ($250,000 or more if a married couple filing jointly). Examples of investment assets include interest, dividends, long- and short-term capital gains, rental income, royalty income, and nonqualified annuities.

Automate Tax Withholding

One way to make tax planning easier in retirement is to have taxes automatically withheld whenever you take income distributions. Much like having payroll taxes withheld from your paycheck, when you file year-end taxes, you reconcile the amount owed by either paying more or receiving a refund.

There are certain income sources on which taxes are automatically withheld, but be aware that a fixed percentage (e.g., 10 percent) may not be the appropriate amount for all taxpayers. The fixed percentage withheld may vary by investment type, and in many cases, the account holder can change the default withholding. The following shows how taxes are handled for different retirement income sources.

• 401(k), 403(b), and other qualified workplace retirement plans – Basic distributions are typically subject to 20 percent withholding. However, required minimum distributions (RMDs) are subject to a 10 percent withholding. Note that if the plan balance is high enough for the RMD to place the taxpayer in a higher tax bracket, a 10 percent withholding may be too low. Set up or change the withholding percentage by submitting Form W-4R to the plan administrator.
• IRA (Traditional, SEP, and SIMPLE) – Unless the retiree specifies otherwise, non-Roth IRAs typically withhold 10 percent of distributions. Set up or change the withholding percentage by submitting Form W-4R to the custodian.
• Annuity – Annuities are taxed as ordinary income, thus subject to a tax rate based on the total amount of income the retiree receives throughout the year. Note that a non-qualified annuity is usually comprised of already taxed income plus earnings. When a retiree starts receiving distributions, only the earnings portion is taxed. Set up or change the withholding percentage by submitting Form W-4P to the issuer.
• Pension – Pensions are taxed as ordinary income, thus subject to the total amount of taxable income received throughout the year. Set up or change the withholding percentage by submitting Form W-4P to the payer.
• Social Security – If Social Security benefits and all other income totals less than $25,000 per year, the beneficiary generally does not have to pay income taxes. However, if a retiree earns a higher amount through a combination of income sources, including tax-exempt income, up to 85 percent of Social Security benefits may be taxable. In this scenario, the retiree can request that the government withhold a fixed percentage (7 percent, 10 percent, 12 percent, or 22 percent) from his Social Security paychecks. Set up or change the withholding percentage by submitting Form W-4V to the local SSA office.
• Taxable bank or brokerage accounts – These accounts may give you the option to have a percentage of taxes (10 percent or choose your own percentage) withheld from investments with realized capital gains, dividends, or other asset-based income. Retirees who withdraw regular income or periodic high distributions may want to elect a percentage of taxes withheld to reduce their tax liability at the end of the year. You can make this election at the time you set up your withdrawal.

Develop a Tax Payment Plan

One of the best ways to enjoy retirement is to automate your tax payment plan. You can do this by actively selecting a withholding percentage for each income source you own and varying it based on the amount and frequency you tend to draw down each year.

Another option is to pay estimated quarterly taxes (due Jan. 15, April 15, June 15, and Sept. 15 every year). This is how most independent business owners and contractors self-pay their taxes in order to avoid an underpayment penalty. This strategy works best if you receive unexpected income throughout the year, earn self-employment income, or receive rental or taxable investment income.

The good news is that after your first full year of retirement, you will have set the bar for how much you owe in taxes – referred to as your safe harbor. Thereafter, you’re not subject to an underpayment penalty as long as you pay at least:

• 90 percent of the prior year’s full tax bill or
• 100 percent of the prior year’s full tax bill (if AGI is $150,000 or less;$75,000 or less if married filing separately), or
• 110 percent of the prior year’s full tax bill (if AGI is more than $150,000; more than $75,000 for individuals or married couples filing separately)

Remember that in addition to creating a retirement income plan, it’s important to develop a tax payment plan as well. This will help make tax season go a whole lot easier.

In one year’s time, the U.S. inflation rate dropped by more than half, from 8.2 percent in September 2022 to 3.7 percent in September of 2023.

If there is a downside to lower inflation, it’s a lower cost of living adjustment (COLA). This year, the inflation rate plummeted from 6.4 percent in January to the current 3.7 percent. While food prices, both grocery and dining out, continue to increase. Between February 2020 and September 2023, grocery store prices rose 25%. That was slightly above the 23% increase in menu prices during the same period. But a number of consumer goods prices had decreased by midsummer, such as:

• Gasoline (-26.5%)
• Airline fares (-18.9%)
• Car and truck rentals (-12.4%)
• Major appliances (-10.7%)
• Televisions (-9.9%)

The Problem with Inflation Data

Inflation data can be misleading for a number of reasons. First, while inflation statistics are quoted annually, these are compounded figures. The annual inflation figures for the past three years are as follows:

• January 2022: 5.9%
• January 2023: 8.7%
• January 2024: 3.2%

If you add each year’s annual inflation, it comes to 17.8 percent; however, compounded prices rose by 18.8 percent over the three-year period. Now, imagine the compounding effect of inflation over many more years.

Second, when you hear that there is a decrease in inflation, it is not that prices are lowering; instead, it’s that prices are increasing but at a slower rate. For prices to drop, we would need actual deflation and not just lower inflation.

Finally, you need to remember that whether it is from a Social Security COLA increase or a raise at your job, an increase in income equal to inflation does not keep up with the actual cost of inflation. This is because of taxes. If you get a raise equal to inflation, you take home that amount less taxes, so your wages or Social Security is really not keeping up with inflation.

Take all three of these factors together, and that’s why inflation feels much worse at the grocery store than it appears on paper.

Social Security Benefits

The fluctuating inflation rate doesn’t just impact the prices of consumer goods, it also affects income. Specifically, Social Security benefits are adjusted each year based on changes in the cost of living.

More than 71 million Americans currently receive Social Security and Supplemental Security Income (SSI) benefits. One in four households of people age 65 and older depend on their Social Security check for at least 90 percent of their family income. Therefore, it is very important that COLA adjustments keep up with inflation.

Given that the inflation rate fluctuated between 7.1 percent and 9.1 percent last year, Social Security benefits increased by 8.7 percent in 2023. However, since inflation has dropped significantly in 2023, Social Security benefits will increase by only 3.2 percent in 2024.

To find out how much individual Social Security paychecks will increase, beneficiaries can check the Message Center of their my Social Security account. In early December, recipients will receive notification of their increased payment by mail.

How the Increase is Determined

Be aware that if there is no year-to-year increase in inflation, there is no cost-of-living adjustment for Social Security income. While inflation rates vary, it is pretty uncommon not to have some sort of increase.

Effective January 2024, the average monthly Social Security benefit for a retired worker is $1,907; for a married couple, the combined average is $3,033. The maximum amount of earnings subject to the Social Security tax is scheduled to increase from $160,200 in 2023 to $168,600 in 2024.

Health Savings Accounts

Starting in 2024, the annual contribution limit for an HSA linked to a high-deductible healthcare plan will be $4,150 for individual coverage; $8,300 for a family plan.

2025: Catch-up Contribution

Starting in 2025, people ages 60 to 63 will be able to significantly increase catch-up contributions to certain employer-sponsored retirement plans. The limit will increase to $10,000 – or 50 percent more than the regular catch-up amount – whichever is greater.

2026: Catch-up Contribution Twist

Starting in 2026, catch-up contributions made by people earning more than $145,000 will have to be contributed to an after-tax Roth account. Note that the Roth account requirement applies only to workers whose wages are subject to FICA taxes, so it does not apply to partners, the self-employed, or state and local government employees.

As of this writing, the IRS has not yet released changes to contribution limits for qualified retirement plans in 2024.