Second Act Success: 4 Ways Retirees Can Succeed in Finding an Encore Career

While many people look forward to enjoying their golden years, others are delaying or coming out of retirement. According to the Department of Labor, there’s a growing trend of older adults participating in the labor force. The department expects the force growth rate of the 65- to 74-year-old age group to be about 55%, and 86% for the 75-and-older age group’s growth, compared with a 5% increase for the labor force as a whole.

There are many reasons why many older adults are “reverse retiring.” For some, it’s a matter of financial security or generating extra income to fund a comfortable retirement. But beyond financial peace of mind, returning to work allows one to explore passions and try a new path.

These so-called “encore careers” help older adults stay engaged, generate income and find a purpose. If you’re retired or close to retirement and considering changing careers or pursuing a passion that pays, check out these four tips that can set you up for success in your second act.

1. Look before you leap

Before you let the excitement of an encore career overtake you, you’ll need to prepare and create a plan. Take time to evaluate your motivations for an encore career: Is this for my financial security or fulfillment? What are my salary expectations? Is there market demand for my skills and services? Will going back to work affect my retirement plans and current benefits? These are all important factors to consider before starting your second act so you can succeed without the benefits a 9-to-5 may have provided previously.

2. Pick something that excites you

While many folks take on an encore career for financial security, it’s also an opportunity to do something you love and that excites you. Take the chance to test drive a new career or interest you’re passionate about.

For example, if you enjoy spending time with pets, become a professional pet sitter or dog walker. If you love weddings, get ordained and become an officiant. You can start with a few gigs, and with a little patience, you can soon build a reputation and clientele doing what you love.

3. Find support

Working for yourself can seem challenging and isolating, but it doesn’t have to be. In fact, if you plan to be self-employed, it’s important to build a support network. If this is your first time working for yourself and heading a business, find a mentor to guide you. Organizations like the Service Corps of Retired Executives (SCORE) can connect you with experienced mentors who can help you start and grow your small business.

You’ll also want to identify key players you’ll need to help you succeed in your encore career. If there are areas of your solo venture that are outside your wheelhouse, find freelancers or contractors who can fill the gaps. Sites like Upwork and Fiverr can help share the workload and provide expertise when needed.

4. Plan for your health

If you’re coming out of retirement or putting it off for an encore career, it may mean changing your health coverage. For example, if you’re a retiree on Medicare, you may have to pay higher premiums or choose to pay for private insurance to supplement your existing Medicare plan benefits. Also, some health insurance plans don’t offer important health care services like vision coverage for routine eye exams and eyeglasses or contacts.

Even if you don’t need glasses now, your vision will naturally decline as you age. According to the National Institutes of Health, older adults may have trouble seeing up close, distinguishing colors and adjusting to changing light. Also, your risk of certain eye diseases and conditions increases as you age and they seldom show symptoms. Left untreated, vision problems can impact your ability to work after retirement. That’s why it’s so important to have vision insurance that includes an annual eye exam.

If your health plan doesn’t include vision insurance or your coverage changes and you lose your vision insurance, you still have options. Insurance plans, such as VSP® Individual Vision Plans, are designed for those who work for themselves. Individual vision plans are simple, personalized benefits that start as low as $13 a month and provide an average savings of over $300 per year. To learn more, visit

Coming out of retirement and working for yourself can seem overwhelming, but with careful planning, you can secure extra income and pursue your passions. Using these four tips, you’ll be ready to start your encore career and succeed in your second act!

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