The Retiree’s Guide to Starting a Side Hustle

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The road to retirement isn’t an easy one. Today, the average couple needs nearly $740,000 to survive in retirement, according to a Merrill Lynch study. Perhaps even more surprising is how much families haven’t prepared: households aged 50 to 55 have only saved $124,831, and households aged 56 to 61 are only slightly ahead with $163,577.

Despite these dismal numbers, the gig economy spells good news for seniors. A Prudential study found that older Americans are embracing the freelance lifestyle, and the statistics are encouraging:

  • 31 percent of gig-only workers are Baby Boomers
  • 34 percent identify as retired
  • 86 percent say they get a lot of enjoyment and pleasure from their work
  • Despite needing gig employment to make ends meet in retirement (46 percent), only 32 percent say they are struggling financially.

If you’re tired of the 9-to-5 life, but still need to bulk up your savings, follow these steps to take your place in the side hustling market.  

Coordinate With Your Social Security Benefits

If you’re currently drawing Social Security benefits, it’s important to consider how a side hustle will impact your income. If you reach the full retirement age of 66 in 2018, the limit on your earnings for the months beforehand is $45,360. Once you begin drawing Social Security, you can’t earn more than $17,040 a year without reducing your annual benefits. While this number may seem low, it translates to $1,417 a month, which could help you pay off remaining debts and rely less on your 401(k) and other retirement accounts for everyday living. You might even use your cash to travel or take up a new hobby. Identify the weak spots in your finances and consider how a side hustle could supplement your lifestyle.

Create an Online Presence

The internet is where you’ll find side hustling opportunities, and if you haven’t already, now is the time to create an online portfolio. A business website allows you to list your skills and availability, connect with new and existing clients, highlight client testimonials, and establish your professional credibility. Check out our guide to learn more, and don’t worry, you won’t need a background in web design to get started.

Use Your Skills

You’ve built a wealth of knowledge with all those years in the workforce, so why not put it to good use? Side hustles are available for nearly every industry and skill level.


If you’re interested in ongoing freelance work that utilizes your professional chops, these sites can connect you with reputable sources:

  • Clarity: If you’re a good teacher, consider offering coaching services through The one-on-one system connects you with students eager to learn from your experience, and you’ll earn a per-minute rate.
  • FlexJobs: As a well-known site, FlexJobs attracts employers who need remote and flexible staff within every career, from engineering to freelance writing. You’ll pay $49.95 for annual access to their job listings, but the site lets you browse the database before making a decision. If you don’t want to pay, head over to their free sister site,, which only lists freelance jobs that can be done from home.
  • Upwork: This freelance writing site allows you to bid for assignments that interest you, which is a great way to build samples for your online portfolio.
  • LinkedIn: LinkedIn has a job board, but there’s a better way to find freelancing gigs and connect directly with managers. Use the search box to type in the job you want, e.g., “freelance writer,” and filter the results to include Content only. This strategy will reveal individual users who are searching for candidates like you. Send them a direct message with a link to your portfolio. Personalization can help you stand out among your peers. 

Service/Micro Jobs

If you’d rather work on a limited basis, check out these sources for one-time gigs, also known as micro jobs:

  • Fiverr: This site is a place to provide individual services for a fixed price, from setting up websites to performing administrative tasks. 
  • TaskRabbit: If you’re skilled around the house, TaskRabbit can connect you with local folks who need help with yard work, home improvements, moving, furniture assembly, and more. 
  • Amazon Delivery: Amazon is a household name, and its two-hour Prime Now delivery service is popping up in cities all over the country. If grab-and-go is your style, check out their job openings in your area.

Use This Loophole

Your earning potential is endless as a freelancer, but as we learned, the rules are a little different if you’re collecting federal retirement benefits. The Social Security Administration deducts $3 for every $1 you earn over the $17,040 annual limit, which hinders your ability to close the gap between how much you’ve saved and how much you really need in your golden years. If this sounds familiar, there’s one loophole you shouldn’t overlook: investment income. Money earned through your investments—including property—is exempt from the SSA’s rules, which means that you can earn as much as possible without affecting your retirement benefits.

If you have a spare room or a second home, renting it out with Airbnb can significantly increase your income. According to a Priceonomics analysis, the average Airbnb host earns a whopping $924 a month, and payments are processed 24 hours after your guests check-in. If your retirement savings could use a boost, this option offers an immediate solution.

The gig economy isn’t going away, and there’s a sea of opportunity (and income!) available for those who search. Take advantage of flexibility in retirement and dive in. A side hustle can lessen the financial burdens of aging.