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10 Questions to Ask Before Taking a Job in Retirement

Working after retiring isn't always about the money. Before you commit, it's worth thinking through what really fits your goals, lifestyle, and future.

Kendall Blythe

Kendall Blythe

Over two decades making money matters clear, practical and relatable.

June 9, 2025 • Advertising Disclosure

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More Americans are working after retirement, whether for financial stability, social connection, or personal fulfillment. About 19% of adults 65 and older are still employed, according to a 2024 Pew Research Center analysis.

But before you take on a new role, it’s important to think through how it fits into your retirement plans. These ten questions can help you make a decision that supports your well-being and long-term goals.

1. Do I want or need to work?

Start by clarifying your motivation. Are you looking for extra income, a reason to get out of the house, or something to structure your days?

A 2023 Federal Reserve report found that many retirees who return to work cite purpose and engagement as major factors, not just money.

2. Will it affect my Social Security or pension?

If you’re collecting Social Security before full retirement age (currently 66 or 67, depending on your birth year), your benefits may be reduced if your earnings exceed certain limits.

In 2025, the earnings limit is $22,320. Pension income generally isn’t affected, but always check your specific plan.

3. Is the schedule flexible enough?

Part-time, seasonal, or contract work may suit your lifestyle better than a rigid schedule. According to AARP, many retirees prefer jobs that allow for travel, caregiving, or volunteering without conflict.

4. Can I physically and mentally manage the work?

Consider your energy levels and any health concerns. The CDC reports that about 78% of adults 60 and older have at least one chronic condition, so it’s wise to choose a role that fits your capabilities.

5. Does the job interest me?

You’ve earned the right to be selective. Many retirees find fulfillment in work that aligns with personal values, hobbies, or long-held passions. This can make the difference between joy and burnout.

6. Am I prepared to face age bias?

Although illegal, age discrimination persists. A 2023 AARP survey found that 78% of older workers had seen or experienced age-related bias in the workplace. Prepare yourself by focusing on your strengths and update your skills.

7. Will it interfere with other retirement plans?

Ensure the job doesn’t sideline things you value — like family time, travel, or volunteer work. Think about whether this is a temporary role or something long-term.

8. Does it offer meaningful benefits?

Some part-time jobs include access to health insurance, 401(k) plans, or wellness perks. This could be especially valuable if you’re too young for Medicare or want to supplement your current coverage.

9. How will it affect my taxes?

Earning income in retirement could raise your tax bracket or increase how much of your Social Security is taxable. The IRS notes that up to 85% of Social Security benefits may be taxable depending on your total income.

10. Is this a job I’m choosing or settling for?

The most important question may be the one that brings everything into focus. Make sure you’re pursuing this opportunity because it aligns with what you want, not because you feel pressured or uncertain.

Retirement redefined

Working in retirement can be rewarding, but it should fit your life, not the other way around.

Take the time to reflect, ask questions, and choose a path that supports the retirement you imagined.

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