How a portfolio career can help you make money and find success at work after age 50

Stepping off the treadmill doesn’t have to mean retiring. It doesn’t mean sitting in your living room, watching daytime TV and doing crossword puzzles, trying to find semi-productive ways to fill the long hours in the day. Nor does it mean retiring the knowledge and skills you’ve worked so hard to build. It simply means reevaluating whether you want to keep chasing the same goals you single-mindedly pursued in your twenties and thirties, and exploring new ways to repurpose all that you have learned.

There are so many options for how to design your portfolio career once you’ve unshackled yourself from a single full-time job. You might become a consultant, a coach, or professional mentor, a board member, a student back at school, or some combination of these. For many boomers, the sunset of their career is when they become an entrepreneur. According to a recent Census Bureau’s Annual Business Survey, 30% of American business owners are between 55 and 64, and another 20% are over 65. Wow, who knew that half of American entrepreneurs are 55-plus?

Here are a few tips for how you might create a portfolio career:

1. Talk with your boss. Determine if your current employer is open to an extended semiretirement plan for you. Phasing out of your current job could free up the time to develop other pieces of your portfolio while also providing a stable income.
2. Become a consultant. Consider whether your career expertise might be transferable into a consulting career in your industry (though if you are still a part-time employee, you need to be careful that you’re not competing with your current employer). You’d be surprised how many people want to know everything you know, especially if you’ve been working in the same industry for 10, 20, or 30 years.
3. Follow your passion. Assess your hobbies and interests and ask yourself if you could make money as a photographer, a writer, or a coach. When you have multiple streams of income, you have the luxury of earning just $10,000 or $20,000 annually from one of these activities as a piece of your portfolio puzzle.
4. Monetize your space. We often have larger living quarters or second homes as we get older. Maybe it’s time to consider earning some extra money by becoming a landlord or Airbnb host so that your extra space earns you extra money.

Paula Pretlow had a very active, fruitful career busting through glass ceilings as an African American woman whose single mother decided that her five children would voluntarily desegregate the Oklahoma City public schools during the stormy civil rights era of the late 1960s.

Armed with intelligence and the learned ability to navigate different and sometimes difficult environments, and with her fearless mother as a role model, Paula built a career in the finance and investment management world at a time where there were very few women, much less women of color. As a divorced single mother and natural community builder, on top of her demanding job, she had a very full life. Until she began to feel burned out and exhausted.

Feeling the need to change course, take a rest, and figure out how to spend the next phase of her life, she decided at age 55 to step away from the company at which she was a partner. Having given her company nearly a year’s notice to help prepare for a smooth transition, she was diagnosed with a very serious and aggressive form of breast cancer—one month before her planned exit date. Suddenly, the need for serious reflection became very urgent.

After bilateral mastectomies and successful treatment in an experimental medical trial, Paula decided not to return to corporate life. Instead, she has created a portfolio life to include the things she is most passionate about: making a difference in the lives of people often overlooked and underappreciated AND utilizing all that she learned from her many years in corporate America.

Today, she serves on multiple public and private corporate boards, including one at a Fortune 500 company, and national philanthropic boards, including one whose mission is expanding opportunities in America’s cities and another that focuses on meeting basic human needs in priority communities in the United States and Israel.

Paula says, “I’ve created a portfolio life that allows the precious time I cherish with my family and fulfills my need to make a difference in the world—by bringing a distinctly different voice and lived experience into corporate and philanthropic boardrooms. I’m alive and I’m having a tremendous amount of fun!”

Science has shown that around age 40 or 50, our sense of taste begins to dull. Perhaps variety is just the spice we need to reinvigorate our atrophying taste buds. A portfolio career may spice up your relationship with your work and enhance your life in ways you never imagined.