Pay off your debts, if only because they're one less thing to distract from whatever you're working on at the time, and because reducing your monthly living cos

Pay off your debts, if only because they're one less thing to distract from whatever you're working on at the time, and because reducing your monthly living costs will be a huge win when you start your company and/or consulting. Don't quit your job to start looking for independent contracts. Take on a small side gig or two while you're at your current job to work in your off hours. This will give you a taste of what independent consulting is like and the challenges involved. Also, in independent consulting people don't care about certification, they care about you solving their problems. Also, your questions of "Who wants to hire someone for less than a year?" makes it sounds like you're a good candidate for third party agency consulting. That's where Company A doesn't want to commit to a full time employees, so they hire a consultant from Company B. You're considered a temporary employee for Company B while working at Company A. Contract terms are usually fixed, but will often go month to month once the initial term is up. Some are often contact-to-hire. Certification will help you negotiate your rate with Company B, but isn't necessary, and there's a HUGE number of .NET jobs that use this kind of consulting. The downside is the consulting firm (Company B) takes a chunk of money before passing you a check. The counter-point is these firms often get contracts that would never be handed out on an independent consultant, and the upside for you is 40/hours a week of stable employment for a period of time, and a loose commitment that makes it easier to do side work and/or plan for your future. If you want to find a few of these consulting firms just search Dice for job listings.