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?