For several years now I have strongly considered one day being a full-time freelance writer. At times, it sounds so appealing — the freedom! But at other times it sounds like a horrible way to make a living. Lately, due to IBS flares and some burnout from working full-time in an office, I’ve been thinking about it more seriously. Here are the pros and cons I’ve come up with:

Pros of a freelance life:

• Flexible work schedule — that means sleeping in when I want to and long lunches with friends without watching the clock.
• No distracting or annoying coworkers.
• No need to use gasoline.
• Can work in your pajamas on the couch with the dog on your lap.
• If you are sick, you don’t have to use a sick day. If you need to leave town, you don’t have to use a vacation day. In other words, no limits on how much time you take off.
• There’s nobody watching over you — you’re your own boss.
• You choose the assignments you want.
• Low-stress work environment.

Cons of a freelance life:

• Unless you have some steady contract gigs, you’re constantly having to hustle for work.
• It’s extremely hard to break into freelance writing for big magazines.
• You work by yourself, and if you are a social creature, you can get lonely — or worse, cabin fever.
• You sometimes have to wait months for a paycheck.
• The pay can vary greatly month-to-month.
• You need a lot of motivation to keep the work coming in.
• NO HEALTH INSURANCE.
• No company-paid benefits, such as a 401(k) matching plan, life insurance, gym membership, free snacks and drinks, free Internet, etc.
• You do your own taxes…and taxes scare me.

I think I could handle the cabin fever/social aspect of it — I would just need to bring my laptop to coffee shops from time to time, and get out for lunch with friends frequently. I’d love the comfort of working from home and I’d be thrilled to spend most of the day with my precious pup. I think I could handle the lifestyle if I had one or two steady contract gigs, that way if the other freelance work slowed down a bit, I wasn’t screwed.

But here’s the big booger: health insurance. This is one of my biggest frustrations with America — that so many people must make job decisions based on health insurance. Last month I was in Europe for two weeks, and while their health care systems there are far from perfect, they are much more progressive than ours. Your job does not determine your health insurance, and you can live a freelance life without the burden of paying several hundred a month so that visiting a doctor doesn’t cost an arm and a leg. I honestly didn’t want to come back home after that trip. I love that Barack wants universal health care, but that is such an ambitious endeavor, I don’t have faith that it will ever be fully implemented in my lifetime.

So what do I do? If I go freelance, my options are to either purchase health insurance myself or to get a part-time job that has health care.

First, the purchase-it-myself option. Not too interested in that one. One of my best girlfriends does that but can only afford that catastrophic-type insurance. She pays $140 a month, but it still costs $90 to see most doctors, and prescription meds are very expensive. She puts off seeing doctors to avoid the costs. Another friend has no health insurance at all, and has had to forgo birth control pills and refuses to visit a doctor at all costs. Having a sleep disorder and a digestive disorder and a buttload of prescription meds, there’s no way I could do without. I’d have to have a plan that has reasonable co-pays and medicine costs, but that would run several hundred a month. Would I be making enough money to cover that? Not sure.

The part-time job option. This wouldn’t be too bad — I’d have an excuse to get out of the house several hours a week, would have some face-to-face human interaction, and would make some extra cash. The only problem is that very few companies offer health insurance to part-timers. Whole Foods and Barnes and Noble do, but those are the only two big ones I’ve heard of, and I’m sure they’re in high demand because of it. I looked on Craigslist the other day and found two or three part-time administrative jobs that have it, and that would be doable. Then again, I’m sure the competition is very stiff.

MediaBistro has a program, AvantGuild, that offers discounted health insurance to freelancers. I checked it out and while the discount prescription drug program does offer medicine at somewhat reasonable costs, the premium still looks like it may be a little high. I haven’t had a personal quote yet, but the examples given looked costly. It’s worth looking further into, but may not be enough help. If I was married to a guy with health insurance at his office, I’d be set.

It deeply frustrates me that America’s system is this crappy and causes us to be this reliant on our employers. It really shouldn’t be that way. People are forced to stay in jobs they would otherwise leave if it weren’t for the insurance. That penalizes people who want to stay home to raise their children, or are too ill to hold down an office job, or just can’t afford the premium. I have a feeling this may be the determining factor for why I may never walk down the full-time freelance aisle. I won’t be making a decision anytime soon, I don’t think, but I’m definitely going to keep pondering it.

Are any of you full-time freelancers? If so, how do you play the insurance game?