Episode 386: Stuck with toil and how to get a dev job as a self-taught career-switcher in 2023


In this episode, Dave and Jamison answer these questions:

  1. I feel like I’m stuck. I’m in a senior/lead position technically called an SRE, but I find myself doing all kinds of cleanup work that should instead be spread across teams. My suggestions for automating toil and cleaning up tech debt fall on deaf ears until some principal engineer decides a couple of months down the line some problem is worth solving (then it’s urgent!!1).

    I’ve experienced this at a few companies now and see some patterns, but I’m not sure what the way out is yet. It seems I need to find the most respected person (and fight them! just kidding), gain their trust, and play politics to get basic problems solved and work properly distributed.

    I am exhausted. If you want me to lead, then give me the power I need to lead. If you want me to be a cog, then make it a decent work environment and pay enough. I feel like I’m stuck in some sort of purgatory. I’m considering going for a management job, but I think I’d hate it.

    How can I find a 9-5 that isn’t soul sucking and run by a few people who have the ear of the C-level?

  2. As two people who lead engineering teams, have conducting tons of interviews for developers and hired many, what are your opinions on the prospects of career changing self-taught developers landing a decent job in 2023 forward? I have a career in Product Marketing, working very closely with Product, Engineering, and Sales teams. I believe I bring a lot of the “soft skills” to the table and am teaching myself the “hard skills”. My concerns are that it will be incredibly difficult to actually find a job and, if I do, it’ll be an entry level role that effectively resets my existing 9-year career back to the starting blocks. In your experiences, would you hire folks looking to make a career move in anything other than junior positions, or would you be wary of them in favor of other candidates?

A speech bubble