Many people decide to work instead of taking a traditional retirement to have more disposable income or to stay involved in a passion project. You can achieve the lifestyle you desire by working during retirement or using your skills and wisdom to pursue a former hobby more seriously. Depending on your skill set and interests, consider these flexible gigs during your active retirement.

Substitute Teacher


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Most school districts welcome teachers with unique life experience who are willing to spend a day in the classroom. You can generally self-select a shift at schools near you or a certain age range that you are willing to teach. Then you can scan the available slots each morning to decide if you are willing to work that day. Substitutes aren’t always given clear teaching plans or are instructed to allow study time or project work. One of the most interesting substitute teachers I’ve encountered was a WWII survivor who shared his story with the class. Share your wisdom or life experiences with a group of impressionable kids for a day with a short-term teaching assignment.

Tour Guide


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If you’re a longtime resident of the area in which you’re retiring, your experience can translate into an interesting cultural experience for tourists. Consider the changes you’ve seen over the decades, locations of interest, and stories you can share. Create a unique itinerary with educational stops and determine how to handle transportation. With a website and social media, you can create a unique walking tour of a nearby cemetery, the architecture of a particular neighborhood, or even a gastronomical tour.

Board Member or CAM


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If you have a background in real estate, consider a paid position as a board member or a Community Association Manager for your homeowners’ association. This type of position offers flexible scheduling and doesn’t tie you down to a desk all day. Add community management experience to your toolbox of real estate knowledge and obtain your CAM license online when it’s convenient for you. You can turn your retirement into a lucrative job that leverages your skills and abilities with a professional status as a licensed practitioner.


Domestic and creative arts education in schools is practically non-existent. Because Home Economics and Shop classes weren’t available for an entire generation, it created a massive movement of makers who missed out on the opportunity to nurture their creative side in school. Many millennia’s who had two working parents never got the chance to learn these skills at home, and they’re seeking out classes, websites, and apps to learn the cooking, crafting, and making skills they missed out on in their youth. Share your expertise in woodworking, fusing glass, sewing, or cooking with a generation desperate for your advice. You can offer classes, start a blog, or set up a small business that caters to scout badge fulfillment in a myriad of skills.

Dog Walker

If you love four-legged pals of all kinds, consider becoming a dog walker. This gig is perfect for people who need a little extra prodding to get outside each day, but could still use a little cash on the side. Advertise on your neighborhood Facebook or Nextdoor page that you are available, or for more flexibility and earning potential, you can sign up as a professional dog walker on Wag. Passionate animal lovers can earn money working with dogs in every major city.

Flexible gigs keep you engaged and earning

If full retirement isn’t for you, consider expanding a passion project into a side gig. Having a part-time job will keep you engaged in your community, allow you to share your life experience with others, and provide a small income to offset expenses or fund adventures.