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

Author: Jamison Dance and Dave Smith July 20, 2026 Duration: 28:41

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?


The weekly advice Soft Skills Engineering podcast, hosted by Jamison Dance and Dave Smith, operates on a simple but profound premise: writing excellent code is only one part of a successful career. The real challenges-and opportunities-often lie in everything else. This is a show dedicated entirely to the human side of software development. Each episode tackles the messy, complicated, and frequently unspoken questions that developers face daily. You’ll hear thoughtful discussions and practical advice on navigating office politics, having difficult conversations with managers, negotiating salaries, managing time and energy, collaborating effectively on a team, and building a sustainable, long-term career without burning out. It’s the crucial curriculum that most computer science degrees never cover. Jamison and Dave bring a blend of experience, empathy, and humor to these topics, offering perspectives that are both actionable and relatable. For anyone who has ever wondered how to handle a toxic coworker, get promoted, or simply find more fulfillment in their work, this podcast provides a much-needed forum. It’s a consistent source of guidance for the parts of the job that don’t involve a compiler, reminding listeners that their growth as a professional is inextricably linked to their growth as a communicator, a colleague, and a person. Tune in for honest conversations that go beyond the technical screen.
Author: Language: English Episodes: 50

Soft Skills Engineering
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