When it comes to retirement, “the best-laid plans of mice and men often go astray.”
Many older adults find that sometimes the most fastidious retirement can’t account for the unexpected. When you consider inflation alone, planning for future finances can be challenging. But when you add in unexpected medical costs, automotive repair and home expenses, it can be close to impossible to put away an accurate percentage of income.
This is one reason why “side hustles” are becoming increasingly appealing to older adults.
What is a “side hustle”?
Contrary to popular belief, the term “side hustle” did not spring forth from the Millennial generation. It was originally used to describe both scams and legitimate jobs in the 1950s,
However, its definition has since evolved. Over the past two decades “side hustle” has been legitimized into the umbrella term for any activity that helps you make more money, regardless of whether you’re retired or employed full-time.

Do older adults really “hustle”?
The short answer is absolutely.
In fact, Baby Boomers hustle more than Millennials.
The gig platform Wonolu conducted a survey that found one in three Boomers completes at least three gigs a week on its platform, compared to only one in five Millennials. Another survey from Bankrate found that Baby Boomers make up 28% of all side hustlers.
Benefits of side gigs for older adults
Most seniors are positioned perfectly to benefit from side hustles; they need to augment their income as opposed to replace it entirely. Side hustle expert Kevin Ha explains, “[Seniors] just need to make a little bit of income to supplement what’s already coming in. And side hustles are a great way to do that.”
Side hustles bring the same benefits to seniors they bring to all generations, including:
- A renewed sense of purpose: Having deadlines and projects to focus on gives seniors a sense of purpose to their day-to-day routine.
- A social outlet: Side gigs often require collaboration on projects and communication with colleagues and clients, all of which can provide a great social outlet for an older adult.
- Mental engagement: The mind is a muscle, and side gigs are an excellent way for older adults to stay mentally acute and engaged well into their sunset years.
Plus, no commutes or professional wardrobe requirements!
Are there risks to side hustles?
As with all endeavors, side hustling is not perfect. It’s important for older adults to be aware of common pitfalls involved in starting and running a side hustle. Examples include:
- Indemnification clauses: These types of clauses are common in side gig agreements. They leave the worker liable for legal and other costs in cases where a customer sues. This article provides helpful tips for how to negotiate the removal of an indemnification clause from a contract.
- Hefty tax implications: Most companies and platforms issue a 1099 form and thus do not withhold taxes. It’s important your loved one pays estimates of these taxes on a quarterly basis to avoid expensive penalties and interest. Also, keep in mind that a side gig is a great way to make money—and thus launch your senior into a higher tax bracket without them realizing. So, help them stay vigilant of their finances.
- Avoid multi-level marketing gigs: Although they seem enticingly simple, these schemes often result in a person paying more than they actually earn.
The website sidehusl.com is a helpful resource to vet side hustle opportunities. The site reviews earning potential, agreements and other important aspects of gig work in three categories: work, rent and sell.

Best side hustles for seniors
- Rent your space: Airbnb is a well-established way to earn side money. Your loved one can rent a space in their house, the mother-in-law cottage, or even the whole home. Silvernest, Peerspace and Giggster offer additional opportunities to rent a space on a temporary basis.
- Sell your hard-earned caretaking experience: Rent-a-grandma is a family-founded business specializing in placing “…caring women, possessing deep life experience with families as Nannies, Baby Sitters, and in-home Care Providers, as well as chefs, cooks and highly experienced domestic staff.” Sites offering similar opportunities include Care.com, Sittercity and UrbanSitter.
- Be an online mock juror: Similar to focus groups for forthcoming trials, online mock trials provide lawyers with an important sense of how jurors might vote on their cases. To learn more about how your senior can be a virtual juror, visit Online Verdict, Virtual Jury or eJury.
- Review books: Publishers are always looking for educated and seasoned individuals to review books. If your older adult loves to read, sites like OnlineBookClub offer the perfect opportunity to make extra cash.
- Be an expert: JustAnswer is always looking for subject matter experts in a wide variety of topics.
- Share your language: Does your loved one know a second language? Transcribing is big business. They can sign up to translate documents on sites like Translate or Bunny Studio.
- Sell stock photos: If your loved one is skilled with the lens, then stock photography is a perfect side gig. View the complete guide here.
- View more than 50 other opportunities for side hustles oriented to older adults here.
Older adults can also take advantage of gig platforms, online platforms designed to connect freelance individuals with paying customers. For example, WAHVE is designed for seniors with accounting experience as well as experience in insurance and human resources. Also, review FlexProfessionals, Onward Search, SkipTheDrive and FreeeUp for senior-oriented options.
In short, side gigs offer a refreshing and stimulating change to many older adults. And it’s never too late to start.
Just remember the words of C.S. Lewis, “You are never too old to set another goal or to dream a new dream.”