The best time to try is now while you are still relatively fresh out of school. It's not hard to sell a career story like "I took the job I could get out of school but what I really want to do is software engineering." My perspective is the market still sucks but is getting a little better. I'm getting more recruiters in my inbox and finally scored a couple recruiter screens from applications. A master's degree will help you for certain "old school" engineering shops - think aerospace/defense, automotive, medical devices, etc. Additionally, some SV shops like Nvidia value master's degrees because of the unique demands of their product (GPU drivers need performance and a certain level of academic rigor is beneficial when thinking through problems in that space). But it's not a panacea and likely won't help for most web dev shops. tl;dr just try. Don't let fear of failure hold you back.

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