Why the hell would you want to do a “side hustle”? That’s a question I asked myself after I’d retired and I was always being asked what I was doing with myself now, and whether I was doing any consulting or side hustles. Early on I was settling into retirement with the last thing on my mind being how I’d come up with extra “work” I could do. But you know what? After a while, the quiet, the slowness, the inactivity of retirement began to catch up with me. And that led me to revisit this idea of the side hustle.
So I’m looking into it, and reading about how retirees with decades of professional experience are uniquely positioned to leverage their deep knowledge to tap into new online income streams. Instead of just a leisurely retirement, many are actually finding success by adapting their established skills to the digital marketplace, which allows for flexible work schedules while at the same time giving your brain some exercise. The challenge, though, is identifying how your existing expertise translates into an online service or product that people will actually pay money for.
While retirement was always expected to be my time to rest, relax and reap the rewards of years of hard work, I discovered that I was not quite ready to slow down and stop contributing entirely. And I found that that’s a growing trend among seniors, baby boomers and retirees. The pursuit of the side hustle. Roughly 25% of baby boomers said they have a side hustle, according to a 2023 Bankrate survey.
The financial landscape has shifted significantly for the baby boomer generation, and it’s led many to seek additional income streams beyond the regular retirement savings. The need to supplement retirement income is a reality for a growing number of seniors aiming to maintain their pre-retirement lifestyles and also meet future needs.
So here’s why I concluded that I Should Consider A Side Hustle as a retiree:
It isn’t just about money.
There Are Mental And Social Benefits. Working in a capacity that you enjoy and find stimulating can significantly boost your cognitive health and ward off feelings of isolation that some retirees might experience. A side hustle allows you to continue learning, solving problems, and interacting with others, all of which promote mental agility and well-being.
Of Course There’s Increased Financial Security
Even a modest increase in income from a side hustle can provide a buffer against unexpected expenses and help stretch your retirement savings further. It can also act as a financial safety net, giving you peace of mind and a measure of control over your financial future.
So What Are The Key Insights About Starting A Side Hustle?
- You Can Leverage Your Existing Expertise: The most successful online ventures for experienced individuals often stem directly from the skills and knowledge acquired over a long career, whether in accounting, engineering, project management, or any other field.
- You’ll Have Total Flexibility and Control: Online work offers the ability to set one’s own hours and choose projects, providing a better work-life balance than regular full-time employment.
- There’s Usually A High Demand: Companies often hire experienced consultants and freelancers for specific projects because they like not having the overhead of a full-time employee. So that creates demand for specialized knowledge.
- Most Important To Me Is You’ll Be Able To Stay Mentally Active: Engaging in consulting or teaching online can provide significant satisfaction and keep the mind sharp..
So What Are The Easiest Side Hustles That A Recent Retiree Could Start?
Here are five of the easiest side hustles for retirees to start earning extra money.
1. Rent out a space you already have
If you’re an empty nester or haven’t made the jump to downsizing yet, you probably have a spare room at your house. Renting out the room on a short-term basis through a site like Airbnb is an easy way to earn passive income.
Or, if you’re not comfortable mingling with a weekend guest, you could rent out your entire home when you’re out of town and make even more money.
To get the most rental income possible, you’ll want to read up on tips and advice from current hosts. There are many articles and YouTube videos on how to improve your listing, take better photos and get more bookings.
Keep in mind there are local and state restrictions on Airbnbs, so make sure you’re familiar with the laws in your area.
More traditional long-term rentals are another option that can offer more predictability, but you’ll be forced to lock in a rental rate for a longer period.
2. Provide child care
If you love children, providing much-needed child care to busy families can be an easy way to bring in extra cash.
Care.com and Sittercity are some of the more well-known services where child care workers can upload a profile with their credentials and experience to find babysitting gigs and nanny jobs.
Another site, Rent A Grandma, got its start as a failed Shark Tank pitch back in 2012, but went on to become a successful nationwide service. It connects families with older women who provide household services like child care, tutoring, home-cooked meals and pet sitting.
3. Substitute teacher or tutor
Have a passion for education or learning? Substitute teachers are in high demand across the country, and this side gig comes with few prerequisites and a flexible work schedule.
Requirements for becoming a substitute teacher are modest at most school districts. You generally only need a bachelor’s degree to get started, and no prior teaching experience required.
The pay isn’t bad either, especially for a side gig. Substitute teachers make an average of about $21 an hour, or roughly $43,500 a year, according to the Bureau of Labor Statistics.
If you have an advanced degree, you might be able to work part-time as an adjunct instructor at a community college and boost your earnings even more.
Or would you rather work one-on-one with students? Like subs, tutors are also in high demand. There are dozens of tutoring companies out there, like Tutor.com or Skooli, that can match you with work so you won’t need to market yourself to find new clients.
4. Sell things you already own
As they say, one man’s junk is another man’s treasure, especially when it comes to online selling.
Well-known online marketplaces like Facebook, eBay, Etsy and OfferUp can be gold mines if you’re looking to unload some unwanted things around the house.
Whether it’s furniture, old paintings, vintage clothes, classic cookery or jewelry, you can sell some of the stuff you no longer use for more money than you think.
To get the most money for your items, try some of these tips.
- Take high quality photos of the item in natural light from multiple angles: Consider creating a dedicated “staging area” in your home so you can take photos of multiple items at once.
- Write useful descriptions: Make sure your posting contains keywords people are likely searching for. Be as descriptive as possible, and try to answer questions buyers are likely to ask — it’ll save you time.
- Price competitively: Browse other listings similar to your item to get an idea of the going rate. Pay attention to the condition — if your item is newer or nicer than others listed online, you might be able to set a higher price. Or if similar items have been listed for a long time, you could undercut them slightly and make a quicker sale.
- Be flexible: Some people might offer to pay you a little extra if you can deliver the item to their home. Being flexible with availability and meetup locations can really pay off. Be willing to haggle on the price, too.
5. Drive for Lyft or Uber
If you’re a good driver with a reliable car, there are a slew of driving jobs out there. Driving for Lyft or Uber (the two largest rideshare apps in the country) is one way to earn extra money on a flexible schedule.
You earn money based on how many rides you take, and you’ll get paid each week (or more often, if you choose) through direct deposit.
You also get to choose when and how often you work. Don’t like driving at night? Then don’t! You don’t necessarily even need to drive other people around. You could sign up for Uber Eats or DoorDash and deliver food to customers instead of driving them around.
If you really love the idea of being your own boss and you don’t mind hustling, consider becoming an independent driver who builds their own client base. By passing out business cards at hotels, airports and local attractions, you could potentially work fewer hours and still earn more money since rideshare companies take 20 to 25 percent of your earnings.
Finding Side Hustle Opportunities
Second career seekers can find side hustle opportunities in various places. Online job platforms like Indeed and Upwork curate many freelance, part-time and project-based roles suitable for those looking to pivot into a new career without committing to a full-time job. Other platforms include:
- Companies like Tours by Locals and Airbnb Experiences offer ways to earn money by providing tours and activities.
- ServiceScape offers people the ability to market their editing, design and writing skills
- At PeoplePerHour, you can start freelancing your technology skills, video, photography, musical talent and business-savvy ideas.
- Wyzant is a massive community of tutors matched to people looking to learn what you know.
Bottom line
So retirement isn’t the end of the road, it’s like a fresh start filled with possibilities. A side hustle can be your ticket to staying active, financially secure and socially connected. By leveraging skills you acquired throughout your career and exploring your options, you can bring in extra money to help make your retirement that much better.
So I just went over what I consider to be the low hanging fruit when it comes to side hustles. Things that don’t require you to do any research and learn new skills, but rather just take advantage of your existing expertise. For some, myself included, the challenge of diving into something completely new may inspire their side hustle. Either way, I look at it as ongoing brain exercise, which is something I know I need as I grow older. If I make a little money along the way, that’ll just be icing on the cake.
In future posts, I’ll keep you up to date as to what kinds of side hustles I’m pursuing personally, including what’s working and what’s not. I’ll also show you how, if that’s of any interest at all. In any event, I hope your retirement is a thriving one. Be well, and be safe!
Peace,
Gus


