Opportunities for Aging Freelancers

Many believe that freelance working in the gig economy is the “future of work”.

But what about the future of workers?

Many freelance workers find success and fulfillment, though all freelancers need to hustle to find enough good gigs.  It’s definitely a game for young workers with the latest skills.

In my mind, one intensely important question is whether freelancing can be sustained over a lifetime. If freelance working is like video gaming, something that requires sharp eyes, twitchy reflexes, and no outside responsibilities, then how can aging workers or workers with families hope to compete for gigs?

Can older workers successfully freelance, other than as a hobby?

With these questions in mind, I was interested to read Scarlett Gibson’s post, “Top 5 remote jobs for freelancers over 50” in the Freelancers Union.” [1]  What sort of freelance work is especially good for geezers like me?

Gibson’s list of five.

Spoiler alert:  there are no surprises here.

Customer Service Agent

Live chat replaces the phone, so you can work from home. “Anyone can handle customer service jobs with light training”, she says.  Hmm.  Maybe this low bar is why customer service sucks so bad?

Freelance writing

Freelance writing does not require any technical skill.”  I’m not so sure about that.  But it is plausible that experience of a lifetime can be a big plus in fulfilling writing assignments.  There is nothing like actually knowing something about the topic, and older workers can win on that point.

Email Marketer

This seems to be a digital version of the perennial “marketing from home” scam business, which has always been a favorite side gig for older workers.  Sure, there is no heavy lifting, but I’m not seeing how older workers would be better at this than anyone else.


At first glance, this doesn’t seem like the ideal match for aging ears.  (Have you ever tried to transcribe random speech out of context?  It’s really hard.)

Even if this is a viable thing now, given the rapidly improving quality of digital speech processing, it won’t be for long.


For the multilingual, there may be gigs translating languages.  I guess that older workers may have more years of immersion in the languages, which could be a huge plus.

However, digital translation is already pretty darn good, so I wouldn’t expect there to be a ton of work for humans in the future.

Looking at this list, the opportunities are all common freelancing gigs.  The main theme is “no heavy lifting”,  (“Most of them don’t require special skills and are less physically demanding.”)

I will note that, like most gig work, there is an implicit premium on speed.  For example, transcription or translation services usually require 24 hour or otherwise quick turn around.  And even if there isn’t a hard deadline, these gigs likely pay piece work, so you have to work fast or starve.

The point is, working fast for long hours is not so easy for older folks, and so kids are likely to outcompete us geezers on that front, even if their work isn’t quite as good otherwise.

I’ll note that there are some perennial favorite gigs not on this list.

Notably, software development is not listed, though it is a common freelance gig.

This omission makes a certain sense.  Contrary to what some tell you, there is quite a bit of technical skill needed to create, test, fix, or even document software.  If you have experience with software, you can probably get a gig doing it, and I bet you won’t be reading about “Top 5” opportunities.

On the other hand, software development skills have a half life of only a few years, so older workers (and everyone else) have to top up skills and keep current.  There is no coasting on the glories of great projects you did at the turn of the 21st century!  Odds are that stuff is long gone and no one even remembers.

There are also many “trendy” gigs, such as YouTube video production, “coaching”, and social media support.  I guess these gigs are so youth oriented that geezers can’t really do it.  Would you want your band’s cool video produced by your mother or your grandmother, however technically competent?  I don’t think so.

I was a little surprised to not see copy editing and related gigs (i.e., reviewing and preparing digital materials) on the list. There have always been plenty of freelance editors that practice their whole life. Of course, like software, you need to actually know how to do it.

Overall, it is clear that Gibson was mainly focused on side-hustles, or something to take up as a second job when you are over fifty.  Obviously, if you have actual professional experience, you can try to go freelance doing it at any age.

With the focus on gigs that she thinks don’t require much training or experience, the resulting list is both generic and low paying.  Sure, anyone can compete for these pennies-per-hour gigs, including older workers.  But is it even worth the time?

I’ll note that in conventional jobs, older workers typically not only accrue experience but also shift into leadership roles.  This includes taking up a variety of high skill, high paying roles such as team leadership, project management, strategic planning, and technical consulting.  In these roles, deep experience gives the older worker the advantage over those youngsters, however clever.

Of course, leadership is something that really benefits from face-to-face contact.  So these kinds of gigs are not ideal for remote work.  (But see Scott Berkunm, The Year Without Pants [2].)


Overall, Gibson’s list isn’t especially helpful, except for the overall message that, “yes, you can do it”.

Whether “it” is worth doing is a different story.

  1. Scarlett Gibson, Top 5 remote jobs for freelancers over 50, in Freelancers Union Blog. 2018. https://blog.freelancersunion.org/2018/03/12/top-5-remote-jobs-for-freelancers-over-50/
  2. Berkun, Scott. 2013. The Year Without Pants: WordPress.com and the Future of Work. San Francisco: Jossey-Bass.


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