Cash Rules Everything Around Me: Is Freelancing Viable for an Underemployed Academic?

I don’t usually post personal stuff here, but I think my situation might be shared by quite a few people towards the end of their graduate school work, and it seems relevant to academia in general, albeit somewhat tangentially.  This year, due to major budget cuts at the University of Iowa, I got much less funding than I was expecting, and have been pretty significantly underemployed for about eight months now as I put the finishing touches on my dissertation.  In the fall I was teaching just quarter-time at the UI and now I’m teaching two classes at the local community college.  Neither of these pays badly for the amount of work involved, and I love teaching, but they haven’t been quite enough to cover my expenses.   Even with some part-time work on the side, I’ve managed to rack up more student loans over the last six months than over the course of my entire undergraduate and graduate career before that.  It’s still far from crippling, but it’s really bothersome.  I've been able to do some amazing things in the past because of my lack of debt, and taking it on now feels like mortgaging my future freedom significantly.  Even worse, the low-wage jobs I picked up to (try to) fill in the gaps ended up distracting me from the job search somewhat, and it’s seeming increasingly unlikely that I’ll find a full-time teaching/research position by next fall.  I’ve since quit those side-engagements so that I can focus on the last few months of the job search – in fact, yesterday was my last day working as a cashier at the university’s parking garages.

I have enough loan cash that, combined with my income from teaching, I don’t need to worry about money for about four months.  I also have several thousand dollars in stocks which I can fall back on, though I think I might face a tax hit for cashing out.  And like many grad students, I have parents who can help me out if I absolutely need it.  Those last two don’t really appeal to me, though (particularly the parents part), and although I anticipate having to look for an office job starting in the summer, I’m really hoping to take advantage of the possibilities of this little interregnum of being under relatively few obligations for the first time in several years – my dissertation largely complete, only working about 20 hours a week, and suddenly casting about for a purpose in life. With that backdrop, I’ve decided to spend the next three months or so on a kind of experiment - making money doing freelance writing.

Before I came to grad school, I had some interest in freelance writing as a way of making a living.  Now, even more than then, I have a head full of esoteric interests and I’m an above-average (and perhaps as important, fast and prolific) writer.  I didn’t have any success as a freelancer in my early 20s because I just tried to pitch a few articles here and there, mostly focusing on things I 'wanted' to write about.   I had a romantic vision of the freelancing life – persuing high-concept stories, executing them beautifully, eventually compiling them into book-length collections.  But the reality is that volume and diversity are the survival tools of the average ‘lancer, facts that are becoming clearer as I try and learn the lay of the land.   A lot of the cash in freelance writing has obviously migrated to the Web, where Search Engine Optimization and slow drips of ad revenue over time seem to be the model that has prevailed over pay-per-piece.  Still, I have some serious ambitions as a Writer with a capital W, so I’m trying to conceive a strategy that, over the next three months to six months, will begin to produce a small income stream and will potentially allow me, in the coming year before I have to plunge headlong back into the academic ratrace, the freedom to pursue some non-academic writing projects I’m interested in for less financial reasons.  My strategy, as far as I’ve thought it through, breaks down to several parts:

1.   
       1- Quick and Dirty writing for ad- and referrer-revenue based sites like Squidoo and eHow.  These are very, very tiny drips of money, and it’s hard to say whether they’ll turn out to be worth it, but it’s clearly possible to make a living just writing about fitness, cooking, and etc. for sites like this. 
        
       2 - Pay-per-piece freelancing through sites like Guru.com and elancer.com.  These are sites where people looking to hire writers put up projects.  I have a pretty deep archive of work, so I should be able to get some unglamorous but paying work this way.

3.    
       3 - Putting together my own revenue-generating website.  My brother and I are collaborating at Haterade Gaming, which may end up becoming a small revenue stream if we can stick with it.


       4 -Conventional story concepts and cover letters for commercial magazines.  This market is dying, and maybe too competitive to be worth my while, but I have published in glossy magazines and have some real writing chops, so it would be crazy for me not to at least devote some effort to it.  My real goal here is to get someone to pay for me to go to India this summer and study Kerala martial arts.

My bigger goal is to try and make next year (assuming I don’t get an academic job) productive and fun, rather than just marking time.  I don’t want to move back in with my parents, but I also don’t particularly want to go out searching for a real job.  I’d rather figure out some combination of freelancing and part-time work to keep me afloat, but still free.  I see and hear about people living this lifestyle all the time, and it seems incredibly appealing.  Now’s when I have a chance to work towards having it for myself.