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

In this episode, Dave and Jamison answer these questions:

1. 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 you do, cheers!

2. I have a non-CS engineering degree, and am looking to transition into Software Engineering. I have the option of pursuing a degree with Tuition Reimbursement from my job, but am in a bit of a strange situation deciding which degree. Basically, I’ve figured that with my current Engineering background I could pursue either a second Bachelor’s degree through Universities offering a “Post-Baccalaureate” program in Computer Science, or a Master’s degree, with maybe only a slightly longer program to get the Master’s as opposed to the Bachelor’s. Otherwise the total length/cost of the programs would be roughly the same.

   I have heard though that it might not be a great idea to go into a Master’s program unless you know what specifically you want to study.

   I am curious what you think would be more “hire-able” between the two options for someone pursuing the career change into Software Engineering?