When you think of side hustles, you probably picture millennials or Gen Zers selling handmade crafts on Etsy or driving for Uber. But here’s a plot twist: baby boomers are absolutely crushing the side hustle game. That’s right—retirees and near-retirees are out here turning their skills and passions into extra cash, and they’re doing it better than anyone expected.
First, let’s talk about why boomers are so good at this. They’ve got decades of experience under their belts, and that’s a huge advantage. Whether it’s consulting in their former industry, teaching a skill they’ve mastered, or even starting a small business, boomers know how to get things done. They’re not just dipping their toes in the water—they’re diving in headfirst. According to a study by Side Hustle Nation, 24% of baby boomers (age 59-77) reported having a side hustle in 2025.
Take freelancing, for example. Platforms like Upwork and Fiverr are full of boomers offering everything from graphic design to financial planning. They’re leveraging their expertise to command higher rates than younger competitors. And because they’ve spent years building professional networks, they often land gigs through word-of-mouth referrals. According to research from Wonolo, baby boomers are earning an average of $573.55 per month from their side hustles, which is 39% more than the average retiree’s Social Security benefit in 2019.
Then there’s the gig economy. While Gen Z might be delivering food or driving rideshares, boomers are taking on higher-paying gigs like pet sitting, tutoring, or even renting out spare rooms on Airbnb. They’re choosing side hustles that align with their interests and lifestyles, which makes the work feel less like a chore and more like a fun way to stay active. According to a report by Upwork, baby boomers account for around 30% of the country’s freelancers, making them the generation most likely to start freelancing.
But here’s the real secret to their success: boomers aren’t afraid to invest in themselves. They’re taking online courses, attending workshops, and learning new skills to stay competitive. Want to start a blog? There’s a course for that. Interested in selling handmade goods? YouTube is full of tutorials. Boomers are proving that it’s never too late to learn something new.
Another advantage? They’re not doing it out of desperation. For many boomers, side hustles are about staying engaged, pursuing passions, and padding their retirement savings—not scraping by to pay rent. That mindset allows them to be more selective and strategic about the gigs they take on.
And let’s not forget the power of time. Many boomers are retired or semi-retired, which means they have more flexibility to dedicate to their side hustles. They’re not juggling full-time jobs or young kids, so they can focus on building something meaningful.
Of course, it’s not all smooth sailing. Boomers face challenges too, like navigating technology or competing with younger, tech-savvy entrepreneurs. But here’s the thing: they’re not letting those obstacles stop them. They’re asking for help, learning from their mistakes, and adapting to the changing landscape.
So, what can we learn from boomers? First, experience is valuable—don’t underestimate it. Second, it’s never too late to start something new. And finally, a side hustle doesn’t have to feel like work. When you’re doing something you love, it can be incredibly rewarding, both financially and personally.
Whether you’re a boomer looking for inspiration or a Gen Zer wondering how to up your game, take a page from their playbook. With the right mindset and a little hustle, you can turn your skills into success.
