More employees are including side hustles in their retirement planning to make sure they will be able to stay ahead of a dipping economy.
getty
With prices skyrocketing, the economy dipping and uncertainty looming, more people are looking for side hustles. What started as a way for consumers to make additional cash from their passion projects, side hustles are now a financial necessity for 73% of Americans and a defining feature of the modern work culture in 2025. And it’s not just Gen Z or burnt-out millennials. Side hustles in retirement are becoming part of modern planning as retirees grapple with high costs of living.
Why Workers Are Planning Side Hustles In Retirement
One-third of Americans have a side hustle, collectively earning $83.1 billion extra per month, with 51% starting within the past year. I was curious if this was an artifact of the 2025 economic downturn or a permanent trend and sought out experts who shared six predictions on the future of side hustles.
And experts predict that in 2026 side hustles will become part of financial planning. Tim Fung, founder & CEO of Airtasker, told me that side businesses will become an integral part of household budgeting and that may professionals will increasingly monetize skills outside of their traditional nine-to-five roles, creating parallel income streams to support everyday expenses.
Tyler End, certified financial planner & CEO and co-founder of Retirable says he’s seeing a clear shift with 12.8% of users currently listing part-time work or a side gig in their retirement plan to stay engaged, supplement income and maintain purpose. And he considers it a positive shift when it’s done intentionally.
“For many retirees, a side business isn’t about going back to work,” he told me. “It’s about staying engaged, maintaining a sense of purpose and creating optional income on their own terms. People are retiring healthier and more energized than prior generations, and they want an outlet to use the skills and experience they’ve built over decades.”
End acknowledges that side businesses can reduce pressure on retirement accounts, plus provide fulfillment when tied to mentoring, consulting or helping others. “The most important thing is that these ventures stay flexible and low-stress,” he points out. “When retirees can control their time and easily step back if it stops being enjoyable, side businesses tend to enhance retirement rather than complicate it.”
End gave me some of the most common side hustles retirees are choosing:
- Retail: Often at places like Costco or CVS, assisting customers or handing out samples.
- Consulting: Taking on smaller roles in their current industries or firms.
- Handyman jobs: Small, cash-paying projects that fill time and provide social interaction.
- Hobby-based work: Monetizing personal interests such as arts, crafts or part-time roles at golf courses and similar venues.
- Dog walking and childcare: Flexible, community-based work with light physical activity.
- Driving/transport jobs: Shuttle driving or similar roles; less common for ride-share apps like Uber but still a popular option for steady, flexible work.
5 Tips To Get Side Hustles In Retirement Off The Ground
Jackie P. Taylor, CEO of Boost Strategy Group, says there’s a tectonic shift as side hustles permeate today’s job market. She asserts that side hustles aren’t rebellion—they’re risk management. Taylor told me that retirement today doesn’t have to look like previous generations imagined it, and she shared five strategies for you to consider.
1. Decide what kind of retirement you actually want. Before choosing a side hustle, Taylor advises that retirees be honest about their energy and desire. “Are you looking to build a true second career that requires a full-time commitment, or do you simply want to continue offering your expertise in the areas that energize you on a part-time basis? That decision should drive not only what you pursue, but how you structure this next chapter.”
That clarity informs whether you operate as an individual contractor or build a formal business, Taylor says. “If you’re offering expertise occasionally, working as a 1099 contractor may be sufficient. But if you’re creating recurring revenue, serving multiple clients or positioning this as a second career, forming an LLC or corporation provides clearer boundaries, increased credibility, better tax planning and flexibility to grow on your own terms.”
2. Taylor recommends considering fractional leadership–one of the most effective paths for experienced retirees. “Organizations increasingly seek seasoned leaders who can step in as fractional CXOs, advisors or operators without the cost of a full-time hire. This approach allows retirees to leverage decades of experience and judgment while maintaining flexibility and meaningful engagement.”
3. Taylor pinpoints scalable digital products as another option to package your expertise into scalable digital products or platforms. “Digital courses, toolkits, frameworks and thought leadership content allow retirees to monetize what they know without trading time for dollars. It’s an efficient way to extend your impact while protecting the freedom you worked hard to earn.”
4. Speaking engagements and paid event appearances reward credibility and experience, according to Taylor. “Companies, cities and organizations are actively seeking seasoned voices who can provide real-world insight, guide decision-making and help leaders avoid costly mistakes. For retirees, speaking engagements, panels and workshops offer meaningful income while preserving autonomy and allowing them to engage on a schedule that fits their lifestyle.”
5. Paid mentorship for small businesses offers impact with flexibility. Mentoring emerging entrepreneurs allows retirees to share hard-earned insight without the operational burden of running a business. “This work is especially impactful, and I know our Business Boost Society community would greatly benefit from experienced retirees who want to support founders on their entrepreneurial journey–whether that means committing five, ten or thirty hours a month,” Taylor states.
A Final Takeaway On Side Hustles In Retirement
The experts I consulted agree that the future of side hustles in the coming years is bright. They predict that side hustles will thrive as they morph into side stacking and become the new norm for workers–young and older–to keep up with the sliding economy in 2026 and beyond.
End told me he believes we will see more and more retirees embracing part time work or side hustles, especially as they become more accessible with digital engagement. “For everyday Americans, in jobs like teachers, nurses, mechanics, etc there is still an aspiration to transition to a new phase of life that isn’t as rigorous, ” he points out.
Taylor told me that if you’re energized by continuing to provide value after you retire, you deserve to be compensated for that expertise. She concludes that the beauty of this stage is you get to define any side hustles in retirement on your own terms.