A Business Owner Paid Himself a Low Salary for Decades to Save on Taxes. The Trade-Off Shows Up Now, in a Smaller Social Security Check, and Selling the Company Won’t Fix It.

The post A Business Owner Paid Himself a Low Salary for Decades to Save on Taxes. The Trade-Off Shows Up Now, in a Smaller Social Security Check, and Selling the Company Won’t Fix It. appeared first on 24/7 Wall St..

A 66-year-old business owner running an S-corporation for decades is planning his exit. A buyer is circling, and he expects the sale to fund retirement. When it came time for him to request his Social Security statement, the projected monthly benefit was lower than expected. Friends with W-2 careers and similar lifestyles were getting noticeably bigger checks. He is now part of a wave of small-business owners reaching retirement age and discovering the same surprise.

On a small-business forum, an owner in a similar position asked why his estimated benefit looked modest after decades of running a profitable shop. The answer sits inside how Social Security counts earnings.

Why a Low Reported Salary Capped His Benefit

Social Security retirement benefits are calculated from a worker’s top 35 years of FICA-covered earnings. Those earnings feed the Average Indexed Monthly Earnings, which then feeds the Primary Insurance Amount (PIA), the monthly benefit at full retirement age (FRA). Only wages that ran through payroll taxes count. Distributions from an S-corp do not.

For decades, his accountant did what good accountants do: paid him a modest, defensible W-2 salary and routed the rest of profit out as distributions, which legally avoided the 15.3% combined Social Security and Medicare tax on that portion. Year after year, that strategy saved real money. It also meant the figure on his Social Security earnings record each year was the smaller salary, not the larger total he actually earned.

Picture it in round numbers. If his business produced $200,000 of profit in a typical year and he paid himself a $60,000 salary, only the $60,000 landed on his Social Security record. A neighbor pulling a straight $150,000 W-2 had more than twice as much credited every year. Stretch that across 35 years and the gap in Average Indexed Monthly Earnings is substantial. The benefit formula is progressive, so the gap in monthly checks is smaller than the gap in lifetime earnings, but it remains meaningful: potentially several hundred dollars a month, every month, growing each January with the annual cost-of-living adjustment (COLA), which for 2026 came in at 2.8%.

The Sale Won’t Backfill the Record

The check from selling the business is a capital gain on the sale of an asset. It is not earned income. It does not run through FICA. It does not get added to his Social Security earnings history and cannot lift his PIA. The transaction that funds the rest of his life cannot repair the benefit calculation behind it.

Waiting to claim still helps. Delayed retirement credits keep accruing until age 70, and those credits still apply to a smaller base. But the base itself is locked in by work history, and a one-time sale will not budge it.

What the Sale Year Can Still Do to His Taxes

A large gain in the year of sale raises provisional income, the figure Social Security uses to decide how much of the benefit is taxable. Once that number climbs past the upper thresholds, up to 85% of his benefit becomes taxable. That share is exposed to ordinary income tax rates; the benefit itself does not face a separate tax rate.

The same spike in modified adjusted gross income (MAGI) can trigger the Income-Related Monthly Adjustment Amount (IRMAA) on Medicare Part B and Part D premiums two years later. A 2027 sale shows up in 2029 premiums. Both effects are temporary, tied to the sale year, but worth modeling before signing closing documents.

What to Take Away Before the Closing Table

A few things are worth sitting with before the deal closes:

1. The trade-off was real on both sides. Years of lower payroll tax kept more cash in the business and in his pocket. The cost shows up now as a smaller monthly check. Understanding it as a trade-off is clarifying.
2. Timing the claim and timing the sale are separate decisions. Delaying benefits past FRA still grows the check. Spreading the sale across tax years or structuring it as an installment can soften the provisional income and IRMAA hit without touching the benefit math.

Every owner’s earnings history is different, and the gap depends on how low the reported salary ran relative to the Social Security wage base in each of those 35 years. A conversation with a planner who can pull the actual record is worth more than any rule of thumb.

The post A Business Owner Paid Himself a Low Salary for Decades to Save on Taxes. The Trade-Off Shows Up Now, in a Smaller Social Security Check, and Selling the Company Won’t Fix It. appeared first on 24/7 Wall St..