Episode 522: I stayed too long at my first job and should I get a masters degree

Episode 522: I stayed too long at my first job and should I get a masters degree

July 20, 2026 · 29 min

About this episode

Dave and Jamison discuss career stagnation and the decision to pursue further education.

In this episode, Dave and Jamison answer these questions: I stayed too long at my first company and now my career is ruined? Hi both, long time listener. (Since I graduated university 4 years ago actually and felt I could never find a job but listening to you guys made me feel not like such an outcast in our field.) I graduated in 2022. Didn’t really apply around much and almost immediately accepted the full time offer from the company I did my internship with during my degree. And fast forward to middle of 2026… I am still here. I’ve long stopped growing as an engineer and have actually been stuck on a simple CLI tool for almost 4 years now with little to no cloud/backend/etcetera experience to show in my 5 year career. I don’t feel I am desirable in the job market at all due to this and waited way too long to look for a job because I was comfortable and happy. I feel paralyzed (no need to put on your space therapist hats BUT some career advice would be wonderful!) (Also did I mention I am in Canada and want to move to Europe and live the rest of my life there but visa sponsorship with my level of experience is impossible? Maybe that’ll be for my next question…) Thanks for all…

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