Working While Retired

The Gig Economy and Retirees – Working while retired

Doing freelance work was once thought of a way to make money on the side while working a full-time job. That’s not always the case anymore. The draw of becoming your own boss and working on your own schedule is something most contract workers love. Past reports say that Millennials make up the brunt of the contract workforce. Now, college students and Millennials have a new competitor out there. Retirees are becoming more interested in side hustles and are definitely benefiting from working while retired.

Wait. Isn’t retirement supposed to be a life of leisure with tons of activities and vacations? Unfortunately that’s not always the case for everyone. People are living longer and retiring later in life. Retirees want and/or need something to keep them busy without feeling like they’re back working a tiresome 9-to-5 job. Surveys show that 70% to 80% of Americans want to work during their retirement.

working while retired
How you can prepare for work in the gig economy

Before you dive in and start signing up for every website available to freelancers, take the time to think about what it is that you want, and if you are an expert at something you can monetize, especially if you want to be on a site like UpWork. The number one mistake people make when they’re new to freelancing on UpWork is that they advertise themselves as a jack of all trades with the thought in mind that they’ll get more jobs. The problem with that is it gets confusing to those looking to hire you. For those types of freelance sites, the point is to pick one specialty and stick with it.

The proper way to be a jack of all trades is to do so across different platforms. You can sign up to be a rideshare driver while also selling items on Etsy and being a graphic designer on Fiverr. Many people choose to follow this type of side gig business model so they can both enjoy multiple gigs and maximize their opportunities. Interested in learning more about the best type of transcription jobs? Click here.

Think finding contract work is a chore? Thanks to technology and apps, freelancers say that finding work has never been easier. Sites like UpWork, Freelancer, and Fiverr make marketing yourself and your service a breeze. So as long as you have all the right documents, you can set up an account and start bidding on projects fairly quickly. With so many options to choose from, there is definitely a gig out there for you. You have to do your research and figure out which one is right for you.

working while retired


For retirees who don’t want to sit at a computer anymore, you can do something more interactive. Working for a rideshare company is popular among men who’ve retired and want to get out of the house. Forbes contributor Elaine Pofeldt reported, “One Uber driver I met recently told me he was a retiree who had lost his wife. He enjoyed chatting with customers while shuttling them around. He could have made new friends while volunteering, too, but given that he needed a little extra retirement income, too, his new gig work was a great fit.” Having the app open on your phone at all times gives you the freedom to choose when you want to pick up a ride.

Rent your home to travelers

More travelers are turning to Airbnb as their home away from home. Airbnb has become more popular for travelers for a few reasons. People like the locations and flexibility in case they need to extend their length of stay. Plus, it is usually a lot cheaper than staying in a hotel. When a host is highly rated, it could mean a nice cash flow from them. AARP writes that hosts over the age of 65 report earning $8,350 per year. Not bad considering the amount of work that goes into maintaining a nice clean place to stay for your guests.

Selling crafts as a hobbypreneur

Turn your favorite hobby into a full-time gig! Not everyone can hand knit a blanket.  If you can’t, and need help, there’s a crafty retiree who can do it for you in time for your next baby shower. According to Business Insider, “Etsy provides a space for 1.7 million “Hobbypreneurs” to turn a hobby into a profit-making venture.” While you are enjoying retirement doing your favorite craft, you can start selling those items online and make a pretty decent living out of it.


Many companies want to drive traffic to their site with SEO tactics, and creating high-quality content is a great way to do so. In a survey by CMI, nearly half of marketers say that they fell short of success because of a lack of well-produced content. Not every business owner has the time to write high-quality web content or blog posts, which makes hiring a freelance writer a great option. Find a business owner in need of a writer that works in the same industry that you recently retired from. With the right match, your freelance writing career can take off in an instant.

How do you know which is right for you?

If you don’t have an idea of what gig you would like to do, try a few of them out. You can always do a gig that relates to what you did as a career. Say, for instance, that you were a receptionist in an office for years. Virtual assistant and call center jobs allow you to work from home and apply the skills and expertise that you already have.

working while retired
Starting out in the gig economy

Finding work in the gig economy is a whole other ball game than when you were looking for a career. Unlike applying for a 9-to-5 job, getting into the gig economy is simple. In an interview with Forbes, Michael Ting, senior vice president at Hyperwallet explains how easy finding a job in the gig economy is. “ ‘You’ve now got these tech platforms and marketplaces where you can take a more passive approach—list your profile and talk about what it is you are skilled at and they will connect you with people who will pay you for those services.’ ” All it takes is finding the right site for the service you wish to be a part of.

Tips on how to thrive in the gig economy

It can be easy to get lost in the sea of contractors that now consumes most of the workforce in the United States. The demand for contract workers is going up and will continue to do so. In order to thrive and succeed in the gig economy, you’ll need to market yourself appropriately and have confidence.

Treat your side gig as a business

Want to make serious cash working a gig? Then you’ll need to treat it like a business. Even if you’re not tech savvy, you should consider creating a website and printing up some business cards. This is the perfect opportunity to make yourself look professional. Gigs need some sort of marketing plan in addition to registering on websites or apps. Do your marketing and customer service right and you’ll have repeat clientele and more referrals than you can handle.  

Give yourself credit and price accordingly

Now that you are your own boss, you need to determine your going rate. It’s true that you’ll get more jobs on sites if you have a cheap rate. The downside to that is that people could easily take advantage of you and abuse your services. You’ll find yourself working twice as hard for little income. Instead, write a profile that shows your years of experience and relate it to the gigs you want to work. Explain yourself in a well-written cover letter to “justify” your rate. It will surprise you that more often than not people will want to pay a higher rate to an expert so they can sleep easy knowing that they are hiring the best.

Side gig reviews

You probably had a few yearly reviews while working a typical 9-to-5 job. Yearly is typical in the corporate world, and not so much in the new side gig economy. Anytime you complete a job in the gig economy, clients can give you a review. Kimberly Palmer, author of The Economy of You: Discover Your Inner Entrepreneur and Recession-Proof Your Life, advises to not let criticism get in the way. Palmer says, “I feel terrible every time someone leaves a negative review or unsubscribes from my newsletter, but those kinds of disappointments are a necessary part of the entrepreneurial life. I try to just accept that, and move on.” The more positive reviews you get, the higher you’ll come up when people search for your service. They’ll also be more inclined to pay a higher fee to work with you because of your reviews.

What about transcription?

If you are a fast typist and have a good ear for listening, transcription can be right up your alley. Legal transcription can be the perfect gig for someone who used to work in the legal field maybe as a paralegal before. Think about it. You already know the legal industry, so that gives you a leg up when applying for jobs. Word to the wise: study up on how to properly transcribe and format a document. Legal transcription requires a high attention to detail of specific formatting you may not know about. Most transcription jobs can be worked remotely and on a flexible schedule.

So what do you say? Working a side gig in retirement means that you can be your own boss and work whatever job you’d like. As a freelancer, you are now in charge of your schedule so there will still be time to enjoy a day off. It can’t get any better than that!

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