<p>In this episode, Dave and Jamison answer these questions:</p> <ol> <li> <p>Hello gentlemen, long-time listener here, and I’d love your take on something that’s been keeping me up at night.</p> <p>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.</p> <p>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.</p> <p>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?</p> <p>Would really appreciate your wisdom on how to navigate this without losing more sleep.</p> <p>Thanks for everything you do!</p> </li> <li> <p>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.</p> <p>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.</p> <p>What would you do in my place? Brainstorm with me please 🥺</p> </li> </ol>
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