In this episode, Dave and Jamison answer these questions:

Hello gentlemen, long-time listener here, and I’d love your take on something that’s been keeping me up at night.

The high powered boss that I report to is someone I genuinely like and respect.This manager is smart, kind, honest, and overall great to work with. We have a solid relationship. I also come from big tech, so I sometimes feel I have better experience around managing projects and keeping teams organized. However she recently shared in confidence that there’s a chance of resigning in the next few months. and when I asked what keeps her up at night, the headache did not seem so big of a deal to me.

But ever since hearing this news, I’ve been catastrophizing the next few months. I’m not ready to job-hunt. At the same time, if this manager does leave, it could be a really good opportunity for me to step up.

So here’s what I’m struggling with: 1.How do I position myself for a potential promotion without making it seem like I’m going behind my manager’s back or trying to undermine them? 2.Should I quietly start looking for an job anyways, just in case? 3.And how do I stay sane when this might all be for nothing and the manager might actually stay?

Would really appreciate your wisdom on how to navigate this without losing more sleep.

Thanks for everything you do!
I’ve worked as an engineering manager in a few big companies in Berlin, but after too much corporate politics bs, I flipped the fingers and quit. In the 2025 economy, that wasn’t the smartest move — finding a new job has been harder than ever.

I’ve been focusing on smaller companies, ideally under 100 people. Ideally less politics, more autonomy. But now I’ve got an offer from Google in Bucharest — nearly double the compensation what I could get in Germany. The catch? I’d have to leave my strong circle of friends in Berlin and start over in a new city, new country.

What would you do in my place? Brainstorm with me please 🥺