Five Worst Things About Being a Freelancer

I love my job--and I wouldn't trade it for any others on the planet (well, okay, if someone were to offer me Natalie Portman's job or Jodi Picoult's job, I wouldn't turn it down). But freelance writing isn't all skittles and rainbows, either. Over at Bob Bly's blog there's a discussion going on about the downside of freelancing, and some of them are biggies. Here are the biggest problems with being a freelancer--things that may make some people think twice about leaving their regular day jobs.

The benefit situation. This is probably one of the worst parts of going it alone--you're responsible for your own health care, retirement account, life insurance, and all those other perks you get with a regular job. The biggest problem (at least for me) is health insurance. It's painfully expensive for everybody, and if you have kids or a medical condition, forget about it.

Taxes. This is also a downside of freelancing: nobody is withholding your taxes. You have to have the willpower to withhold a portion of each check (and that's really tough when you need all of it one month). It's also on you to find the right tax professional and figure out the right structure for your business. I've been wrestling with this topic since February, and let me tell you: no English major should be forced to withstand such torture.

The many hats of freelance writing. If I had my way, all I would ever worry about would be sentence structure and appropriate word choice. I would never, ever think about marketing, bill collection, building a new website, or why my printer keeps jamming up. As a freelancer, some of the hats you have to wear aren't so bad--I like coming up with ideas for new ways to make money, for example. But the actual marketing....not so fun, especially if I have to use the phone to do it. I also can't stand chasing down late-paying clients or dealing with technical problems of any kind. If I could, I would hire flunkies to do all of that--but right now I fly solo, so I'm stuck with it.

Cash flow issues. It's a feast-or-famine game. One minute you've got so much work you're turning it away; the next minute your bank account is running low and no jobs are on the horizon. The unpredictability is something I love--you never know when your next windfall will be--but it can be nerve-wracking, too. It can take nerves of steel to stick with this business, especially when you're just starting out and don't have a long list of contacts.

Setting boundaries. I love talking about my job to others--but it can be a peeve when people hear "work from home" and think "oh, so that means you can pick up my brother from the airport next week!" Being a freelancer requires being firm about setting boundaries--and not only with clients, but also with loved ones. I have several freelancer friends who had to put their foot down when spouses and partners expected the house to be spotless and dinner to be on the table, since they were "home all day."

I love my job, but nothing's perfect--and these peeves are enough to make anyone want to tear some hair out. What are your biggest freelancing peeves?