There was a recent article on nymag.com titled “I Love the Freelance Life, But It’s Taking a Toll on My Mental Health,” that got a few of us here at Billy talking. Not only do we work with hundreds of freelancers, providing them with accounting software and support, we employ a bunch as well.

The article highlights the anxieties and depression that can come with choosing to freelance as your career. It also cites a couple surprising studies that backs up these feelings, along with others such as “chronic strain and a reduced ability to relax” as well as “sleep disturbances, depressive symptoms, a high prevalence of antidepressant drug use, and ‘presenteeism.‘”

But then how does this jibe with surveys like Freelancing in America showing that 53% of freelancers began “by choice, not necessity,” and one by reportlinker showing that 70% of those surveyed agreed that “freelance workers are happier than traditional workers?” How can we reconcile what these studies and surveys say?

Do Worry, Be Happy

The truth of the matter is that freelancing can be (and almost always is) a stressful career choice. Being your own boss is stressful. Keeping a work-life balance isn’t easy. Finding new clients is hard. From taxes to insurance to expenses, the freelancer life certainly comes with a host of worries that a typical 9-to-5 employee doesn’t have.

This is why we have these now.

But if you ask most freelancers who have been doing it for a while, they’ll all probably say the same thing: yes, it’s stressful, but it’s worth it. The “Freelancing in America” survey showed that 68% started freelancing to earn extra money, and 42% cited more flexibility in their schedule as another main reason. What this means is that many freelancers feel that the time and money they are seeing from their choice outweighs the cases of anxiety, stress, and even depression.

This isn’t a contradiction. After all, people can still be happy even with clinical depression. All freelancers have days, even weeks where they want to throw their laptops out of the window in frustration. They’re humans, after all. But the benefits always seem to win over in the end. Our freelancers have this conversation plenty of times:

“I $%!$# hate this right now.”

“You going back to 9 to 5?”

“Oh hell no.”

Maybe You’re Born With It?

As the first article cites from an Intuit and Emergent Research study, there’s no sign of stopping the “gig economy” which will be over 9 million freelancers by 2021. The question is whether these people have the right temperament to live that freelancer life from the start, or whether that temperament can be developed.

The freelancers that seem to thrive are the ones who are OK with uncertainty, and deeply desire autonomy, control, and flexibility. If you’re the type that needs job (and paycheck) security, then freelancing may not be for you. This seems to be the conventional way of looking at it: that some people are just cut out to live that lifestyle, and some are not.

But the truth is a little murkier than you’d think.

On one hand, many experts point to the rise of the freelancing Millennial as evidence that if a group is conditioned to be more transient and unwilling to settle, they are more likely to have that right personality to freelance. On the other hand, many think that Millennials aren’t that into freelancing at all, and would prefer more stable careers but they face a changing economy. Again, we’ve run into a seeming contradiction. How do we resolve this?

Per usual, Baby Boomers have all the answers.

We All Want to be Free

It might come as a surprise, but Baby Boomers are more into freelancing than Millennials are. Why? Because at the end of the day, almost everyone (anxious or not) desires to be his/her own boss. Given the option, who wouldn’t choose this life? That’s why Baby Boomers, who have more professional connections, savings, experience, and desire to be free are more into finding ways to freelance: they just have the means to do so.

Yeah, but what about the other wrist?

Again, that’s not to say they’re any more equipped to deal with stress, anxiety, and depression; only that Baby Boomers are best poised to give it a shot.

So, are you cut out to be a freelancer? Is anyone? The answer is that you probably want it, but it’s “risky” to do it. All these surveys seem to indicate that if people can find ways to mitigate that risk, the natural human desire to fly free will always try to assert itself. Perhaps in a future post, we’ll talk about how to lower the risk before and during your freelance journey.

When did you realize you could become a freelancer? Let us know!

This article first appeared on Business 2 Community on August 28, 2017.

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