A retirement side gig can emerge from boredom, isolation, or simply the desire to earn some extra spending cash. No matter the reason, it’s clear that senior side hustles will only grow as more baby boomers enter the retirement ranks.
A 2024 study showed that retirement side gigs generate nearly $6 billion in revenues nationwide. This number is likely to increase, as a recent survey indicated that 41% of respondents plan to rely on a side hustle during retirement.
Millennials no longer dominate the side hustle arena. Side gigs are becoming a serious option for retirees seeking a financial boost or a way to just have fun. Whether it’s inflation, longer lifespans, or simply a desire to socialize, more seniors are converting their hobby hustles into side hustles.
Like younger generations, seniors have discovered that technology can give them a competitive edge in launching and maintaining a side gig. AI tools like ChatGPT can help anyone create effective business and marketing strategies, even for first-timers.
Technology Redefines The Retirement Side Gig
The nature of the retiree side hustle has undergone a shift. Once, it was all about turning hobbies into businesses. Phased retirement lets people work fewer hours, leading to more specialized skills-based side gigs.
AI and other internet-based applications have transformed the way people start their small businesses. It doesn’t matter which industry you look at; retirees have uncovered new ways to pull from their decades of experience. AI platforms enable you to access a virtual assistant quickly without the typical costs associated with larger companies.
“Seniors are increasingly leveraging AI tools and remote platforms to offer specialized services like consulting, writing, or online tutoring,” says Ryan Elam, founder & CEO at LocalEyes Video Production in Los Angeles. “Technology is lowering barriers to entry and allowing retirees to monetize expertise without the physical demands or overhead of traditional work.”
What’s the experienced professional’s greatest fear? It’s staying relevant. Used properly, AI can keep you up to speed on the latest trends. It can help guide you to markets that value your specialized knowledge. It keeps you agile, no matter your age.
AI and Apps Power Retirement Side Gigs
Generative AI platforms offer a wide range of services useful for creating business documents. They can conduct research for you. They can suggest strategies or prioritize tasks. They can proof, edit, and comment on your drafts. If you’re really in a bind for something quick, they can even create the draft itself.
But be careful. Not all the kinks have been worked out yet. These tools have been designed to please. Too often, rather than saying they don’t know the answer, they make one up. This is called hallucinating. It’s one reason you can’t rely on AI to do your work for you. You need to constantly check it. (The key to success here is writing prompts correctly, but this subject goes beyond the scope of this article.)
Many traditional internet-based apps have incorporated AI into their processes. For example, Grammarly, a program that edits your writing, now includes an AI checker. Ironically, it also uses AI to suggest rephrasing. There’s one thing you should note about AI checkers: they identify sections of your draft that sound AI-generated. These programs often give incorrect results, especially if your writing is similar to their training data.
The video conferencing application Zoom now uses AI to summarize your conversation. It’s still not as good as the raw transcript, but it is a reasonable first draft.
Finally, you have your distribution apps (e.g., Teachable and LinkedIn Learning for online courses, and Amazon and Etsy for products). These utilities are great for freelancers and content creators.
The takeaway here is that technology isn’t just an add-on—it’s a key enabler that transforms experience into income.
“We’re seeing more seniors waking up to the fact that their wisdom is billable,” says Patrice Lindo, career pivot coach & CEO at Career Nomad in Atlanta. “Tech has cracked the gate wide open—whether it’s teaching on Teachable, advising on LinkedIn, or launching a consultancy from their kitchen table. They’re not retiring—they’re reclaiming. And this is an important point to call out because there’s a lot of knowledge in our retirees who are leaving the workplace.”
It turns out this reclaiming spirit has real implications for both income and personal fulfillment. Flexibility is often a key factor when seniors pick their gigs. Online apps like Instawork and Upwork nod to the retiree’s need for autonomy. You can vet the offers and only take the jobs that fit your preferences.
“We’re seeing more seniors turn to flexible, app-based work to stay active, earn supplemental income, and stay connected to their communities,” says Kira Caban, head of communications at Instawork in San Francisco. “Technology has made it easier than ever to find shifts that match their skills and schedules—on their terms.”
Freedom, both financial and personal, remains the hallmark of retirement side hustles. It’s the not-so-hidden value retirees most cherish.
Tips for Launching a Retirement Side Gig with AI and Online Apps
Here’s your checklist that provides practical guidance on how to get started:
- Start with a single clear service or offer.
- Test demand before scaling.
- Keep tech tools simple.
- Maintain separate business finances.
- Pull in insights from multiple experts.
In the words of Frank Sinatra, “Nice and easy does it every time.” You’re retired. You don’t have to swing for the fences. Relax. This isn’t rocket science. It’s something you’ve done your entire career. Let your muse guide you.
Of course, this doesn’t mean you should be flippant. You must be deliberate, but keep that cool confidence age has bestowed upon you.
“The most important step when seniors start a side gig is to start with one clear offer that solves a real problem,” says Sophie Musumeci, CEO & founder at Real Entrepreneur Women in Sydney, NSW, Australia. “Then test it before trying to scale. Too many get stuck trying to do everything perfectly, when the truth is: Clarity comes from action.”
You can search the internet and find many sites providing business start-up tips for those over 50, but “testing small” might be one of the best.
Oh, yeah, that and “using tech wisely” is the other.
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