To Free or Not to Free?

Like many people, I'm in a financial bind right now; I need more money to meet my obligations. I've cut just about everything I can reasonably cut, and I'm still coming up short! Yes, it sucks.

So, in an effort to try to earn some more money, I've been participating in "contests" on 99 Designs. They are a site that lets businesses post a graphics project, for which designers compete to win. Sounds good, right? Well, as with everything, it has it's ups and downs.

On the upside, you have a chance to show your work to get paid. Many sites, such as Guru, make you bid to get the job. If you have a strong enough portfolio, you may land a job, but it's difficult. I've only succeeded at getting 2 jobs through Guru in over 3 years. Yep, whatever I'm doing there, it's not working! With 99 Designs, it's not about your portfolio, it's about your interpretation of the clients requested design. Your work does the talking.

Now for the bad news. I've yet to win anything on 99 Designs. Not that it's a scam or anything, just that it's a very competitive marketplace. I've spent many, many hours working on a variety of projects, only to come up with nothing. At least in the financial sense. Arguably, you can say that I gained experience and possibly portfolio items, which is true, but the bill collectors don't accept that as payment!

So, here I am, in the financial bind, hoping to make more money, and taking the risk of doing a lot of work for free. It's pretty scary. So much so, that I wonder if I should be putting my time into something less risky, but what? I can work more hours at my "regular" job, but that won't get me to my goal of being a freelancer. I should be putting in more time in the digital design world. So, the question is, to work for (possibly) free, or to leave my path for something more sure? Is there a best of both worlds solution?