It’s not a scenario that most freelance writers want to consider, but it is a definite possibility for anyone who is in the business of freelancing. At what point would you feel inclined to throw in the towel, give up freelancing, and get yourself a “regular job” again? Can you convince yourself to work for the man again, commuting to an office every morning and working the 9-to-5 alongside everyone else? Can you give up the dot com lifestyle?

The Appeal of a Regular Job

I put a shoutout on Twitter a short while back to see if there were any freelancers who made the decision to go back to a regular job. Rob Blatt promptly replied in 140 characters or less, following it up with a more comprehensive email that described his situation.

In that email, Rob explained that he sort of fell into freelancing. He started with a “small handful of clients” who provided him with over 40 hours of work each week. He was happy, but he was “only making enough to get by on and put a little in the bank.” This is to be expected when you first start out with freelancing, but what bothered Rob the most was that he had “no insurance, no doctors visits and no vacations.” He was unable to step away from his work, because “the moment you step away, someone else is willing to take your job.” This is the nature of audio engineering, it seemed.

Eventually, Rob got started with podcasting, “because the world of audio engineering was starting to implode thanks to the record industry shooting itself in the foot repeatedly.” It was through this that Rob was able to find a job that would offer “more pay than freelancing, give me health, dental, and optical insurance, paid vacation time and would bring me into New York City.”

In this way, the appeal of a regular job for Rob was increased pay, significantly better benefits, and more stable source of income. Would that be enough for you to give up freelancing too?

Why Did You Freelance in the First Place?

Let’s go through some of Rob’s motivations one at a time. First, the “regular job” was able to offer him more money than what he was making as a freelancer. While a lower level of income can be expected for most starting freelancers, it is definitely possible to leverage your reputation over time to improve your income level. Guys like Chris Bibey can attest to that. I’m not as familiar with the audio engineering industry, but the right podcaster can make a pretty penny.

Freelancing is hard work, but so is a regular job. If you put in the effort and have a little luck on your side, it is possible to make enough additional income to cover the extras like proper medical and dental insurance, as well as “paid vacation.” If you can make 52 weeks of regular income in the span of 48 weeks, you can effectively give yourself four weeks of paid vacation.

Before you consider jumping back into the rat race and taking on a conventional job again, think about why you got into freelancing in the first place. It might be that you wanted work where you could largely dictate your own income level. Maybe you wanted a more flexible schedule. It could be that you liked the prospect of working from home. Whatever the case, these are the reasons why you chose to give up a regular job in the first place in favor of freelancing.

One Step Back, Two Steps Forward

I am not lambasting Rob Blatt for his decision to put his freelance career on hold as he pursues a more conventional career. Freelancing isn’t for everyone.

Going back to a regular job for a while might not be a bad idea for a lot of freelancers. The biggest hurdle that freelancers face early on their careers is finding legitimate (and consistent) work that pays well. This is because your prospective clients don’t know who you are and why they should turn to you instead of someone else. If you take on a regular job and build a name for itself, it is a lot easier to transition to freelancing. Prospective clients are more likely to already know who you are and, thus, it is easier for you to demand higher rates of pay.

Many of the best photographers and journalists in the world go through this career cycle: they start as freelancers, land a full-time job, build a name for themselves, and then charge a premium as an established freelancer. Rob feels the same way because he can use “my current position to build a name for myself and once I feel as if I can make the move back to freelancing without it impacting my lifestyle, I’ll go back.”

For all the freelancers and online entrepreneurs out there, how do you feel about the relationship between freelancing and regular work? Do the pros of self-employment outweigh the cons for you?