People always say thet you should not quit your job before you have the next job lined up, but what if you plan to do freelance? This is my dilemma.

A bit of context (rant).

My current job is my first official job. Small company, VERY HIGH staff turnover rate. I have been here for 2 and a half years. My commute on a good day is < 20 mins, and money is relatively good.

During the last 6 months, all devs above me resigned, which lead to the system maintenance being passed on to the few devs left. Our biggest system is a legacy system (Windows CE), and new clients are actively signed up and new features requested. The codebase is not even worthy of being called spaghetti, changes break every client, I need to wash my hands every couple of minutes. Seriously, I would rather maintain obfuscated code. It is like a bunch of highschoolers wrote the system, though I think they would have done a better job.

Management is nice and understanding, but the state of the codebase is killing the spirits.

I fill my nights and weekends moonlighting to keep my mind off of the 'daymares' at work. I have never been a team player, and thrive on my own. I have been thinking quiting and going full freelance/contract the last couple of months. Should things not work out, I can always go job hunting (see issue in par. 1)