In this episode, Dave and Jamison answer these questions:

1. I work for a small software company on a team of about 7 or 8 engineers. I like working here. I like the people, the autonomy, the pay, my boss, and the stack among other things. I try to remind myself of this regularly so I don’t take it for granted. I’ve been here for about 2.5 years and would love to continue working here.

   Our CTO, like many, has become a big AI cowboy coder. Every few months, he vibe codes a new project and then decides to interrupt the full workloads that we have a limited number of engineers to do to hand his project off to be cleaned up, worked into the product, and solve all of the problems that remain once actually put into practice. This usually ends up going to a different engineer per project, who is then tied up with the CTO’s whims and is no longer available to do the work planned by product. Our EM knows this and knows the frustration and lost velocity, but what can he do? (rhetorical, not the question)

   Most recently, I was tasked with implementing some reporting dashboards he did into the product, but he specifically asked me to make it in such a way that he can continue to work on and add to because he can’t be bothered to run the actual product. This is very concerning to several of us. He has no clue what he’s writing or how bad it is. We’ve talked about perhaps making him do PRs, but a) who can make him, he’s the CTO, and b) he’ll have no clue what to do with PR pushback given that he has no clue what he wrote. And again, who can make him actually fix it if he asks us to rubber stamp it? (rhetorical, not the question)

   I’ve been listening to the show for years and I’ve talked to friends at other companies, so I know this is everywhere. Is it as everywhere as it seems? Is it worth finding a new place to work where the CTO isn’t running so rampant? As I stated before, I’d rather not leave, but if I talked about that as a concern, I don’t want it to sound like an ultimatum, even if maybe it is at some level. Is this just the new reality for us, or is there something that can be done?

2. I am a senior software engineer at a big tech company. I live in central Europe but my team is in the US and I’m 9 hours ahead. I have 7:30 pm meetings and sometimes take an hour before and/or after this meeting to prep or follow up. Previously I slept in later and started later to deal with these meetings. However, now my daughter is starting kindergarten and I wake up early (5-6AM) to be with her, drop her off, etc. Now in the evening meetings my brain is fried and I can’t even articulate myself well. The next day I think about so many things I wish I had said in those meetings.

   I can’t quit as I make 160K right now and I would only be making 60-80K tops in my country and have some financial commitments. Relocation to the US is also not an option because I have kids and don’t want them to move.

   So far I have been skipping meetings and my manager has not expressed concern but I feel so detached from my team. I don’t even know what most of my peers are working on.

   It feels like I am out of ideas to make this better. Please share your space wisdom with me :)

This is a rerun of episode 331.

In this episode, Dave and Jamison answer these questions:

1. Listener ninjamonkey says,

   I am a new grad who is half a year into the role now at a very large company. Recently, a senior engineer on my team asked me to create a ticket for an infra team for a problem with a service. I provided logs and steps to reproduce the issue and did a health check before submitting.

   Right after, the manager of the team put me into a group chat with their team, asked why I created the ticket and told me to start doing my job and they can’t debug for me.

   From these interactions and comments on the ticket, it feels the infra team will likely not work on the tickets I report or de-prioritize them. This has left me discouraged and hesitant.

   I will have to do lots of this kind of infrastructure work in the future. Additionally, one of the goals my manager set for me is to work with more external teams for the upcoming year.

   What do I do here? Do I tell my manager about these interactions? Do I tell my team lead, staff/seniors to swap out for different kind of story?

2. I work for a small startup. I was the first employee other than the 2 founders.

   Being the first developer hired, naturally means I have the most knowledge about our application. I also have good organisational skills, which has led to me becoming and being referred to as the “Lead Developer”.

   I have recruited 2 of the 3 new developers, and have trained both of them and got them up to speed.

   At first I was pleased with the progression and was keen to grow into the position, and told the founders so.

   Since then, I have changed my mind, I don’t want to be the lead - due to the following:

   • The communication is absolutely pitiful. Any questions we ask of the founders we get about a 30% reply rate no matter the form of communication.
   • We get poorly defined tasks and requirements
   • The CTO will just blast through some of our features over the weekend and say here I fixed it for you

   I don’t want to quit my job (just yet… its a comin though).

   I have actually discussed the above points with them, but I know these 2 founders will never change their ways.

   How do I tell them I just want to go back to being an Individual Contributor like my Employment contract states?

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?