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Q&A: Is it better to take Social Security earlier and invest it?

June 29, 2026 By Liz Weston

Dear Liz: I’m 64 and retired. My wife is 54 and still working. Half the people I talk to say take Social Security and just invest it, as you’ll make more than waiting until you get older. Others say that the tax hit isn’t worth it because my wife still works. I’ve talked to a couple financial people, and still get mixed answers. What is your opinion?

Answer: Social Security can be surprisingly complicated and many people don’t understand the nuances that should guide claiming decisions. In other words, half the people you’re talking to likely don’t know what they’re talking about.

Let’s start with a few basics, starting with the “tax hit.” If you have income other than Social Security, up to 85% of your benefit may be subject to tax. That doesn’t mean 85% of your benefit is taxed away. It means up to 85% is included in your taxable income, and subject to your tax bracket. In 2026, federal tax brackets range from 10% to 37%.

The earnings test can have a dramatic impact if you start Social Security before your full retirement age. The earnings test reduces your benefit by $1 for every $2 you earn over a certain limit ($24,480 in 2026). If you’re retired and not earning money, though, the earnings test doesn’t apply regardless of what your spouse might earn.

What starting early does do is permanently reduce your benefit. If you’re the higher earner, it also reduces the survivor benefit that one of you will get when the other dies. At that point, the smaller of a couple’s two checks goes away and the survivor has to make do with a single benefit.

If you delay, on the other hand, your benefit gets larger. After full retirement age, delayed retirement credits add 8% each year until your benefit maxes out at age 70. This guaranteed return is about twice what you’d currently get from any other low-risk investment, such as one-year Treasuries. You might earn more in the stock market, but you also could suffer losses.

Copious research shows that most people are better off delaying. You can start by reading “How Much Lifetime Social Security Benefits Are Americans Leaving On the Table?” by David Altig, Laurence J. Kotlikoff & Victor Yifan Ye for the National Bureau of Economic Research at https://www.nber.org/papers/w30675.

Filed Under: Q&A, Social Security Tagged With: delayed retirement credits, should I take Social Security at 62, Social Security, Social Security claiming strategies, survivor benefits

Q&A: Living in your rental? The tax benefits aren’t so clear cut

June 29, 2026 By Liz Weston

Dear Liz: My husband and I have owned a rental property for 20 years. We’ve never lived in it. Now, we want to get out of the landlord business. We know we’ll have to recapture depreciation, but we always thought we could live in the property for a couple of years to save some on the capital gains taxes. Our accountant has told us that this is no longer true and we cannot save much by living in our rental. Federal and state taxes will take most of our profit. Is this true?

Answer: Congress dramatically shrank the loophole that once allowed people to reduce or eliminate capital gains on rental and vacation properties.

When selling a primary residence, homeowners can shelter up to $250,000 of home sale proceeds, or $500,000 for married couples, from capital gains tax if they’ve owned and lived in the home at least two of the previous five years. Those rules were established in the Taxpayer Relief Act of 1997.

Before the Housing Assistance Tax Act of 2008, landlords could move into their rentals for a couple of years, sell the properties and then invoke the home sale exclusion as if the property had been their primary residence all along.

Today most if not all of the gain on your property is considered “non-qualified use.” Only the appreciation you experienced before 2009, and after you move in, would qualify for the exemption.

The benefits of moving into a rental for a couple of years can vary greatly, depending on the specifics of your situation. Your tax pro can walk you through the math and advise you about some of your other tax-saving options, such as a 1031 exchange for another rental property or holding the real estate until death, when your heirs would benefit from a valuable step-up in basis. If you’re done with being a landlord, though, the cleanest solution might be to simply sell and pay the tax.

Filed Under: Q&A, Real Estate, Taxes Tagged With: capital gains, capital gains on a home sale, home rental, home sale exclusion, home sales, rental

Q&A: Don’t leave your finances on automatic

June 22, 2026 By Liz Weston

Dear Liz: During the 2024 open enrollment period for Medicare, your column mentioned that Part D enrollees’ out-of-pocket payments in 2025 would be limited to $2,000, but only for covered prescriptions. That spurred me to be sure my prescription drug plan covered the one brand name drug I take. It didn’t and I found the only plan in my area that does just in time before the open enrollment period ended.

More recently, I learned from your column that I can pay Medicare premiums from my health savings account. Like many HSA participants, I have been letting my contributions accumulate for later-in-life medical expenses. But now that my husband and I are investigating moving into a continuing care retirement community, it helps to know that we have the option of paying Medicare premiums this way and have more money left over each month after we pay the monthly fee.

Answer: Thanks for sharing those experiences!

It can be easy to leave our finances on automatic, but there are at least two areas where it’s important to shop every year: health insurance and auto insurance. Health insurers constantly change their formularies, or list of covered drugs, as well as what tier a drug might be assigned to. A prescription you get cheaply this year could be more expensive next year or not covered at all. Auto insurers, meanwhile, tend to raise rates on loyal customers because they know many people will stay put out of inertia.

It’s also important to have a plan to eventually spend HSA funds before you die. A spouse can inherit an HSA and retain its tax advantages, but the account becomes taxable if anyone else inherits it.

Filed Under: Medicare, Q&A Tagged With: health savings account, HSA, Medicare, Medicare Part D, Medicare prescription drug plan

Q&A: Will Taking Social Security at 62 Affect Your Spousal or Survivor Benefit?

June 22, 2026 By Liz Weston

Dear Liz: I am a teacher, retiring this June. I have my teacher’s pension and will receive a small Social Security benefit as well. I am married and my husband’s Social Security benefits are far greater than mine. Should I start drawing on my Social Security benefits next year when I turn 62, assuming when my husband starts drawing on his when he turns 70 in seven years I will then get a higher benefit? Is there any downside to taking my Social Security benefits for seven years while I wait for him to start taking his?

Answer: Your early start would reduce the future spousal benefit you’ll be eligible for when your husband applies at age 70, says Mary Beth Franklin, a former Investment News columnist and author of “Maximizing Social Security Benefits.” The early start would not, however, reduce your future survivor benefit should your husband die first.

Spousal and survivor benefits are both based on your husband’s work record, but they’re calculated using different rules.

Spousal benefits can be up to 50% of your husband’s benefit at his full retirement age. If you’re already receiving your own benefit, the spousal “top off” adds an additional amount to your check once your husband applies and you’re eligible for a spousal benefit. The top off amount is calculated by subtracting your benefit at full retirement age (FRA) from 50% of your husband’s benefit at full retirement age.

A simplified example may help show the effect of an early start. Let’s suppose your own retirement benefit would be $1,000 a month at age 67 and your husband’s benefit at his full retirement age would be $3,000. Social Security subtracts your FRA benefit ($1,000) from half of his ($1,500) to determine the “top off” amount ($500). If you apply for your own unreduced benefit at age 67, the top off amount would be added once your husband applies for his benefit and triggers a spousal benefit for you.

If you start early, on the other hand, your own benefit would be permanently reduced. Starting at 62 means you’d receive $700 a month. Once your husband applies and the spousal benefit is triggered, you’d get the additional $500, but now you’d be receiving $1,200 a month instead of $1,500 you would get if you’d waited.

That doesn’t mean you should delay, Franklin notes. The additional cash could make it easier for your husband to put off filing. And, as noted above, an early start on your own benefit wouldn’t affect any future survivor benefit.

While spousal benefits are based on your husband’s benefit at full retirement age, survivor benefits are based on what he actually receives (or what he had earned, if he dies before starting benefits). If your husband waits to file until after his full retirement age, his benefit earns 8% annual delayed retirement credits until his benefit maxes out at age 70. As a survivor, you would be eligible to receive up to 100% of that benefit.

Filed Under: Q&A, Retirement, Social Security Tagged With: claiming strategies, Social Security, Social Security claiming strategies, spousal benefit, survivor benefit

Q&A: Timing matters with estimated tax payments

June 16, 2026 By Liz Weston

Dear Liz: Your recent column about how to distribute estimated tax payments over the year (equal versus backend loaded) may have missed an important nuance. Your answer regarding the Form 2220 safe harbor is correct and would apply if the taxpayer’s income were retirement fund distributions. As I read the query, however, it’s possible (perhaps likely?) that the year-end distributions are from a taxable brokerage account. In that case, even absent intra-year distributions to the taxpayer, the dividends appearing in the account are deemed constructively received when paid by the portfolio companies into the brokerage account.

I can understand how an IRS agent would simply argue for equal payments. And I similarly understand that a competent accountant would know the safe harbor rules. It’s impossible to know which of them is correct here from the letter as printed.

Answer: My answer relied on guidance from Mark Luscombe, principal analyst for Wolters Kluwer Tax & Accounting, and he says that you have a point.

The original writer stated that they received the majority of their income at the end of the year, and most of it was dividends from their brokerage account. The writer had been told by an IRS agent that estimated tax payments were due throughout the year, while the writer’s accountant contended that wasn’t necessary. The writer didn’t specify whether it was a taxable or retirement account or when the dividends were actually paid into the account.

Luscombe assumed that the dividends were received at the end of the year, but the writer could have meant that dividends were only withdrawn then.

If the account is a qualified retirement brokerage account, it wouldn’t matter when the dividends were paid, only when the withdrawal was made, Luscombe notes. If it’s a taxable account receiving dividends throughout the year, then the IRS agent would be correct that the dividends would be taxable based on when they were received into the account.

Filed Under: Q&A, Taxes Tagged With: estimated tax payments, IRS, safe harbor

Q&A: Should I consider Roth conversions now or after I retire?

June 16, 2026 By Liz Weston

Dear Liz: My husband and I both waited until age 70 to start Social Security. I will be 72 in September and am considering retirement. My husband is retired, 74, and taking required minimum distributions (RMDs). We have always tried to maximize contributions to our pre-tax retirement accounts and are now realizing the downside as we pay taxes on those mandatory withdrawals. Should I consider Roth conversions now or after I retire? I realize I will need to pay taxes on those conversions, but would it be best to do that when my income is lower? I am thinking about my kids and their future.

Answer: Late-in-life Roth conversions can be tricky. The amount you convert is removed from RMD calculations, lowering future tax bills. But the conversion is added to your current taxable income, potentially making more of your Social Security taxable and temporarily raising your Medicare premiums (thanks to income-related monthly adjustment amounts or IRMAA) in addition to generating a big tax bill.

Theoretically, a conversion could still make sense if your current tax rate is lower than the one you’ll have once you start required minimum distributions at 73. The case for conversion is strengthened if you want to pass this money to your kids. They likely would have to empty any inherited retirement account within 10 years, and they could be in their peak earning (and tax-paying) years when they do so. By converting now, you would in effect be paying the tax bill for them, perhaps at a lower rate than they might face, and allowing them to inherit the money tax-free.

A tax pro can help you with the calculations so you’ll understand the financial impact of a conversion. Then you can make an informed decision about whether to proceed.

Filed Under: Medicare, Q&A, Retirement, Retirement Savings, Taxes Tagged With: IRAs, IRMAA, Medicare, Roth conversions, Roths

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