Martha Stewart Says Work-Life Balance Is a Myth: 7 Money Rules That Shift After 65

Working beyond 65 can change how Social Security, Medicare, health savings accounts and 401(k)s work — and not all of those changes are helpful.

Martha Stewart, now 85, says she does not buy into the idea that career and personal life can be neatly balanced.

In a conversation on the “Richer Lives by SoFi” podcast with host Vivian Tu, Stewart said there is no such thing as work-life balance, according to Hola!.

Many Americans her age and younger are still employed. Bureau of Labor Statistics data show that in 2025, 19.1% of people age 65 and older were in the labor force.

A Pew Research Center analysis also found that workers age 75 and older are the fastest-growing segment of the workforce.

Earning a paycheck after 65 can change how federal rules handle your money, from Medicare enrollment to retirement withdrawals. Most of those shifts are favorable, but one can lead to a higher bill later.

1. Employer size determines when Medicare pays first

If you have coverage through your own job or a spouse’s current job, the employer’s size matters. For employers with 20 or more workers, the group plan generally pays first and Medicare pays second, according to the Centers for Medicare & Medicaid Services. If the employer has fewer than 20 employees, Medicare pays first.

That distinction affects whether you can safely delay enrolling in Part B. If your coverage comes from a current job, you can usually wait and later use a special enrollment period that lasts until eight months after the job or job-based coverage ends, whichever happens first.

COBRA does not count as job-based coverage for this rule. At smaller employers, however, Medicare is primary, so skipping Part B can leave you exposed to coverage gaps.

2. Medicare can shut off HSA contributions, sometimes retroactively

People with high-deductible health plans often continue contributing to a health savings account, or HSA, after 65. That ends once Medicare begins.

“Beginning with the first month you are enrolled in Medicare, your contribution limit is zero,” the IRS says.

The issue is timing. If you enroll in premium-free Part A after 65, Social Security can backdate that coverage by up to six months, though never before your 65th birthday, Iowa’s state health insurance counseling program explains.

Contributions made during that period may count as excess contributions.

Because applying for Social Security also automatically enrolls you in Part A, Iowa’s program recommends stopping HSA contributions six months before you enroll.

3. Delaying Social Security can still increase benefits until 70

For people born in 1943 or later, each year you wait past full retirement age adds 8% to your benefit, up to age 70. Continuing to work can make that delay easier to manage financially.

Once you reach full retirement age, the earnings test no longer applies. Starting that month, your pay no longer reduces your benefit, no matter how much you earn, Social Security says.

Before that point, however, earnings can trigger temporary withholding, which matters for anyone moving to part-time work before full retirement age.

4. Working longer can still boost your benefit

Your Social Security check is based on your highest-earning years. If you have a strong earnings year after you begin collecting, it can replace a lower-earning year in the calculation.

Social Security reviews the records of working beneficiaries every year. If higher earnings increase your monthly amount, the agency recalculates your benefit and applies the increase retroactively to January of the following year. No extra paperwork is required for that review.

5. Your current 401(k) may delay required withdrawals

Required minimum distributions, or RMDs, usually start at 73, or 75 for people born in 1960 or later. Workers who remain employed may be able to postpone RMDs from their current employer’s plan until the year they retire, as long as they do not own more than 5% of the company, the IRS says.

Be sure to check the plan documents to see whether the delay is allowed.

This exception does not apply to traditional IRAs, which must begin distributions at RMD age even if you are still working, or to 401(k)s left at former employers. Those accounts follow the standard withdrawal rules, including the first-year deadline that can create two withdrawals in the same tax year.

6. You can still contribute to an IRA at any age

The old age cutoff for traditional IRA contributions is gone. “For 2020 and later, there is no age limit on making regular contributions to traditional or Roth IRAs,” according to the IRS.

The key requirement is taxable compensation, such as wages or self-employment income.

For 2026, savers age 50 and older can contribute up to $8,600, including a $1,100 catch-up contribution. A working spouse’s income can also support contributions for a spouse who is not employed.

7. A larger paycheck can push up Medicare premiums later

Medicare premiums for higher earners are based on income from two years earlier. For 2026, Social Security generally looks at 2024 tax returns, the agency says.

People with modified adjusted gross income above $109,000, or married couples filing jointly above $218,000, pay at least $81.20 more per month for Part B than the standard $202.90, along with at least $14.50 more per month for prescription drug coverage.

That delay can be painful in the first years after retirement, when the bill is tied to a salary you no longer receive.

Social Security allows you to request a lower amount using Form SSA-44 after a life-changing event, including retirement or reduced work hours. You will need supporting documents, such as a letter from your employer confirming retirement.

These rules overlap, and the timing rarely works out neatly on its own.

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No balance, but a calendar

Stewart may be right that work and life never truly balance. What the rules above reward is something more practical: knowing the timing. The best moment to sort it out is the year before you leave your job, while your paycheck, employer health plan and 401(k) are still active.