How to Win the “Support Myself in Retirement” Battle

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Posted by The Savvy Retiree on October 5, 2020 in Save Money

I had planned to write a different column today…and then I was thinking about an article that appears in the October issue of The Savvy Retiree and, well, I just really wanted to write about it. I think it says so much about the real world of freelancing and the possibilities that exist there, particularly when you’re on the backside of retirement and you’ve not had an opportunity to save as religiously as you might have hoped for life’s third act.

I’m not going to give away the entire story because I want it to be fresh for you in case you haven’t read it yet. Instead, I’m going to just highlight a few items relative to my own experiences and those of other freelancers, digital nomads, and remote workers that I know. My hope is that they inspire you to think about what’s possible in your own life.

The story in question comes from 72-year-old Sharon O’Day, who received an email from freelance website, Upwork, congratulating her on her three-year anniversary on the site and noting that she has earned nearly $40,000 as a ghostwriter.

As Sharon proudly writes, that email “was proof that I had won a significant battle: the ‘how do I support myself in retirement’ battle.”

This is something I write about all the time—that freelancing websites such as Upwork, Fiverr, Guru, PeoplePerHour and so many others really do offer a legitimate shot at earning a meaningful amount of money. For some people, that’s well into six-figure territory annually. For others, such as Sharon, it’s a smaller amount but still plenty enough to change the trajectory of retirement and provide a greater sense of financial security. As Sharon writes, her freelancing success means “I know I’ll have ample income to cover my needs in the future.” 

I often get pushback on this idea of retirees turning to freelancing. When I pitched a story similar to Sharon’s to an editor at another publication, he shot me down, insisting that freelancing is too hard, too scary, and too technical for retirees, and that there’s no upside to encouraging them to pursue such an option because it will end in disappointment.

That was such a frustrating reply to receive because I knew he was thinking myopically. And I knew from my conversations and reporting—including chats with pooh-bahs at both Upwork and Fiverr—that retirees are a growing portion of the freelancing pie. A statistic I’ve reported before is relevant here: more than one-third of people 65+ who have done any work in the last year did so through freelancing. That’s from Upwork. And it tells me that freelancing is not too hard, not too scary, and not too technical for retirees.

But this isn’t to imply that freelancing is a money tree you can harvest at will. As Sharon notes, and as I have pointed out, success takes time and it requires a bit of strategy.

Her first assignment paid a whopping $27. But then it led to a long-term gig that saw her write scores of pieces, at higher prices, for this particular buyer.

That matches my own story. One of the very first gigs I landed on Upwork nearly two years ago was to edit and clean up another writer’s work for a travel-related credit card site. That one-time gig paid little, about $50, but it turned into an assignment to produce several stories a month, resulting in a substantial payday of thousands of dollars over the course of about 10 months.

As for the strategy: Sharon recognized, rightly, that “we all develop so many skills over our lives that have value to others, but that we take for granted because they seem so natural to us.” She knew she’d built up a particular set of skills over her long working career, so she fashioned her profile to highlight those, effectively “thin-slicing” her talents, as I have written about in the past. 

Ultimately, the big takeaway is that because she found freelancing—and because she put in the effort to succeed at freelancing—Sharon is earning as much as $3,000 a month in extra income and “best of all,” she said, “I can decide how much I write and when and where I do it, whether at my South Florida lakeside home or elsewhere.”

I’m not sure there’s a better summation of freelancing in retirement.

By Jeff D. Opdyke