July has been my busiest month all year, and the fruits of my labor have required me to work around the clock, which is why I’ve been MIA on Frugaltopia the last few weeks. It’s great that I’m getting new gigs, and I’m fine with the decision I made to take on so many projects to make up for the recession-induced lack of work earlier this year. But after a month of many 12 to 19 hour days spent writing, editing, and project managing – plus working through my “vacation” – I’m left contemplating the virtues of self-employment. What’s so great about it?

My Summer Office

Maybe it’s the mildly entrepreneurial aspect of it. I like making my own hours, choosing which projects I take on and how many. I enjoy not being confined to a cubicle, and instead working from my home office, which sometimes means spending the day with my computer on my deck, or telecommuting from another location. And of course, I’m happy to skip rush hour commutes. But beyond the surface stuff, I also find my freelance work to be more fulfilling than much of the work I’ve had as a full-time employee. If it weren’t for that, I’d still be in the office.

Perhaps it’s also the perceived sense of freedom I’m attracted to, but sometimes that seems like an illusion – especially when I consider the price I pay, quite literally, as a freelancer for social security, taxes, health insurance, and the unpaid time off for my own vacations. Not to mention the fact that there’s no severance, Cobra, or unemployment benefits for the self-employed. And in times like these, when freelancers are slaves to a feast or famine mentality, it can really throw your work and personal life out of balance.

“Freedom” is the word I always equate with my decision to be self-employed, but other than the formalities of the corporate structure that I’m not bound to (i.e., strict hours, limited vacation time, etc.), there really isn’t anything genuinely freeing about working for oneself. It puts you at greater risk of being temporarily unemployed; the hours are often longer; and you have to put extra time, effort, and work into keeping your employment consistent.

I felt lucky to have consistent work the first few years I was freelancing, but this year has been a roller coaster – too little work; then, too much work. Of course, too much work usually feels like a blessing. Who wouldn’t want the extra money or the luxury to choose among the most desirable projects being offered? But it’s also a curse because turning down work is painful when you don’t know if it’ll be there again when you want need it. And if you accept it all, as I did this past month, you’re going to be holed up, day and night, for as long as it takes to finish everything, even if that means letting everything else – your relationship, your friends, your vacation, your laundry, your usual standards of personal grooming – fall by the wayside. That’s when you start asking yourself (albeit rhetorically, and in this case, publicly) why the hell you’re doing this.

When it comes right down to it, I think it’s because I’ve always secretly wanted to torture myself by being a writer. Not an editor. Not a producer. And somehow the experience of being a writer feels more authentic when I’m working for myself – even if that, too, is just another kind of torture illusion, since let’s face it, I’m not really working for myself; I work for my clients.

I suppose a career is a work-in-progress, and there is something inherently stimulating and hopeful about that, even when the economy remains uncertain and you’re worried about the possibility of your livelihood suddenly evaporating. At this point, I’m just glad that I have work for the rest of the summer (and a few things lined up for the fall) as I continue to move forward, frugally, and hope for more good fortune.