Episode 495: What to do when my boss quits and moving to Romania?

28 snips

Jan 12, 2026

Discover how to handle the anxiety of a potentially departing manager and the career implications it might bring. The hosts discuss strategies for positioning yourself for a promotion without undermining your boss. They also tackle the myth that job security is tied to management stability, encouraging a broader perspective on worries. Plus, hear insights from a former tech manager weighing a move to a smaller company versus a role at Google in Bucharest, exploring the perks of each and the importance of building a social life as an expat.

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ADVICE

Don't Rush Into Job Hunting

Don't immediately start a job hunt solely because your manager mentioned leaving.
Treat the manager's possible exit as low-probability unless you have other evidence.

INSIGHT

Reporting Does Not Equal Promotion

Reporting to a leader doesn't make you the natural successor, especially in engineering.
Management roles often require different skills and experience than IC work.

ANECDOTE

Manager Thought About Leaving Then Stayed

Dave shares a personal case where a manager considered leaving then stayed, leaving reports anxious for months.
The listener learned to follow up later instead of stewing in uncertainty.

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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 🥺