What type of person do you picture when you come across the term “freelancer?” Is it a Millennial at your local coffee shop writing a thousand words on why 1999 was the best year for movies? Is it a post-Millennial (Generation Z? iGen?) picking you up in their Uber or Lyft? Maybe it’s a young professional who is picking apart your company’s SnapChat profile to show you why it’s not going viral.

Well, you might be picturing the freelancing landscape all wrong. According to a study by Mavenlink, “47% of executives state that they are looking to hire contractors to fill management and senior executive roles–even c-suite contractors.”

Yes, this survey by Mavenlink focused on corporate work, but it does give solid insight into what professional freelancing looks like. Namely, it’s skewed in favor of older workers. Baby Boomers are the best poised to benefit from the so-called “gig economy” and they’re getting the choicest of gigs. So what can young workers learn about becoming a career freelancer from this industry trend? For those considering the freelance lifestyle, here are some lessons learned from those who got there before us.

1. Expertise and flexibility are key.

To be clear, it’s not that there are more Baby Boomers freelancing than younger generations. According to studies from UpWork, 47% of workers ages 18-24 are freelancing versus 28% of Baby Boomers. But rather, it’s that the Boomers are increasingly choosing to go freelance and thus reshaping corporate America in their wake. And it’s because they can.

According to the Mavenlink study, corporations want “a wider, more specialized talent pool without a large financial investment.” In other words, they want cheap experts in their field, and Baby Boomers are the perfect group.

Their expertise obviously comes from years of work experience. Unfortunately, the younger generation can’t quite compete unless the positions involves recent technology. Likewise, it’s hard for Millennials to compete with the flexibility that Baby Boomers have in their lives. Be it a nest egg after decades of work, or a spouse to split expenses with, or a home that’s paid off, or cheap health insurance through Medicaid; older workers have more financial stability to weather not having the usual work benefits that can make freelancing tough for younger workers.

The Take-Away: Specialize quickly; embark while you have other means. If you’re a young worker looking to become a full-time freelancer, emulate the Baby Boomers. Specialize in something and become an expert. Then, launch your freelancing career while you have some benefits in place. Maybe you’re still on your parents’ health insurance. Or maybe you still live at home. At the very least, keep your day job while you start freelancing. Be the Boomer.

2. You’ll always want to do it.

Check out this slide from an UpWork presentation:

It shows that our youngest working generation wants to freelance, and so does our oldest. Furthermore, their 2016 study showed that 63% of those surveyed said they are freelancers by choice than by necessity, which is up from 53% in 2014. It seems as both our economy and technology allows for freelancing as a career, more people are choosing to do it even when they don’t have to.

The biggest reasons why are pretty obvious: flexibility and freedom. These surveys show that the desire to be your own boss and make your own hours will only intensify the older we get. It’s interesting that the desire dips during the middle period of our lives as the graph above shows. It’s almost like workers have to delude themselves into thinking a 9-to-5 is ok, until they rediscover their passion to be free once they get to a certain age.

The Take-Away: You’ll always want to freelance, so why not now? Don’t get us wrong, a lot of people are perfectly happy to be 9-to-5ers. And we’ve written before on how you need a strong stomach to be a freelancer. But the numbers tell us that if you have the itch now, in your early work career, you’ll probably always have it. 35% of the US workforce is freelancing, and growing year over year. If you feel the urge, there’s no better time than now to get started on the freelancer path.

3. It’s a beneficial lifestyle.

Let’s take a closer look at the reasons Boomers are freelancing more these days. From the Upwork survey, they do it: “…to share their expertise with others, to earn money to supplement their retirement savings, or for the pure joy of continuing involvement in their chosen profession.” So in short, a big reason is that it makes them happy.

Keep in mind, these Boomers could continue to work full-time jobs. They have the expertise, as mentioned above, and they’re set to dominate the workforce for the next decade. They don’t have to stop working a 9-to-5, and many won’t, but more and more are choosing to go freelance because it makes them happier.

And it’s healthy too! Data shows that working past traditional retirement age led to an 11% lower risk of death if healthy, and 9% even if they’re not particularly healthy. Boomers are happier, healthier, and wealthier by choosing to keep working, and freelancing is what they want to do the most.

The Take-Away: It’s never too late. Becoming a freelancer is not a choice you’ve already missed out on. The evidence shows that many are finding their side-hustle later than you’d expect. So don’t get down on yourself if you haven’t made the leap yet. You can make freelancing into an aspirational goal and something to work toward.


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