You should make yourself financially bulletproof first, and have some investments. You'll have to do real work, which might not be something you're used to doing. Don't delude yourself that it'll be easy, your current job is undoubtedly easier than teaching.
But that said, yes you should, if it's not stupid for you to do it. You can't help change the system by helping capitalists, the best thing a leftist can do is either join a union or become a teacher. Pick a job to make money, or to help society. The middle ground exists purely to make losers feel better about existing inside capitalism.