Would You Trade In the Freelance Life?

Besides the deadlines I’ve been scrambling to meet and the papers I’ve been frantically trying to finish, I’ve been doing a lot of thinking over the past few weeks and I’m in a real period of transition—perhaps the biggest of my adult life. I think it’s finally time to claim what I truly want to do, and stop making apologies for it. More on that in the next few posts.

So it’s gotten me thinking—with all of the instability that comes with the freelancing life, have you ever regretted your decision to pursue it, whether full time or part time? It seems to be one of the few career paths that’s virtually recession-proof…there will always be some kind of writing work somewhere if you’re willing to search for it (and put enough “feelers” out there). But do you ever regret giving up stability (whatever that looked like for you) for the admittedly unpredictable freelance life?

I can definitely see where the benefits would far outweigh the bummers—flexibility, the chance to work on a variety of projects that challenge you (rather than leave you feeling burned out, overworked, and generally stuck in a rut), not to mention saying “no” to those persnickety clients that often turn out to be more trouble than they’re worth. So why are so many of us reluctant to claim the life that we’ve dreamed of?

I guess fear is the biggest motivator to just stick it out, wherever you are. Fear of not having regular income. Fear of never finding work again. Fear of giving up the safety net (benefits, etc.) But think about it—wouldn’t you regret the fact that you didn’t take the chance to see if you really could do it? That maybe you could live life on your own terms? It would probably be the most terrifying—and exhilarating, satisfying—thing you would ever do. It’s good to really scare yourself once in awhile. It shows what you’re truly made of.

So, fellow freelancers, I ask you—would you ever trade in the freelance life for something a little more predictable?

Any Freelancing Regrets?

Everyone, no matter the profession, has days at the job where they feel like throwing in the towel and pursuing a totally different career. It wouldn’t seem as if freelancers have those days, since the freelance life is ripe with the promise of flexible hours, setting your own price, taking on a variety of different clients and projects, and basically living it up.

Right? Isn’t that all we freelancers do? (Sense the sarcasm?)

There are frustrating and non-productive days in the freelancing world, just as with a regular office job. Of course, it’s nice to not have to deal with clashing personalities and the never-ending office politics, but that doesn’t mean it’s all hunky dory all the time, either. It’s basically like job hunting all the time—sending out pitches, following up, trying to secure clients, following up again, and then trying to understand the nature of the work so you know the best way to proceed. It’s an endless cycle, and to the untrained eye, it may not seem very rewarding, either.

So let me ask you—are there any freelancers out there who have regretted their decision to pursue this crazy unpredictable life? It’s definitely a commitment, whether writing is extra income or your main job. Pitching editors, tracking down sources, doing interviews at their convenience (anytime, anywhere—Walmart, anyone? I’ve done it!), finding story ideas, hoping to get paid on time—and that’s when things are going well! Down times can seem like endless stretches of nothingness—it’s enough to make you want to ditch it all, buy a business suit, and head back to the office. And yet for all of the frustration, there are few things in life I find more satisfying. I just love it. I wish I would’ve known more about all of the opportunities available and how to go after some of what’s out there a bit sooner.

Have you ever regretted your decision to pursue freelancing? What were some of your darkest moments? What changed your mind?