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Jobs to Consider When Coming Out of Retirement

June 22, 2021

Older Woman

Older women working in retail

By Steve Milano

If you’re coming out of retirement for financial reasons, or just to get back into a more intellectually stimulating atmosphere, you’ll need to consider a variety of actors before you pick the right job for you. Some jobs might requirer training, physical stress, or a  full-time commitment. More flexible, enjoyable jobs might not offer high pay and full benefits. Create a list of the parameters any job should offer before you begin looking at specific post-retirement job options.

Financial Considerations

If you’ve retired and are receiving Social Security, Medicare, Medicaid or Veterans Administration benefits, you might be limited as to how much income you can earn without losing some or all of your benefits. Check with the administering agency or a financial advisor to determine if a new paycheck will affect your current benefits or taxes.


As you look at post-retirement jobs, consider how much training you’ll need. Even a secretarial job might require you to have a thorough understanding of computer programs such as Microsoft Office, a common suite of word processing, spreadsheet and presentation software. If you enjoy tennis or animals, you can learn to teach tennis with a weekend certification workshop or start work as a pet sitter with simple on-the-job training as an assistant sitter. If you don’t mind going back to school for a few weeks, you can become certified as a school teacher.

Employee or Freelance?

Many seniors can turn their skills into a home-based business, either providing a service or consulting. You don’t have to start your own full-blow retail business if you supply goods or services to an established business, such as providing baked goods to a restaurant or editorial services to a local newspaper, magazine, or website. Decide if you’d like to be your own boss and the tax obligations and benefits that come with that type of work. Look for opportunities to work for others, but on your own terms, if that appeals to you more. If you’re just looking for a paycheck and interesting work without too much responsibility, working as an employee is your best option.

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