Episode 510: Old and behind and how do I hang on for the last few years until retirement?

Episode 510: Old and behind and how do I hang on for the last few years until retirement?

April 27, 2026 · 34 min

About this episode

Dave and Jamison discuss the challenges of socializing in a remote work environment, particularly for older employees feeling out of place among younger coworkers.

In this episode, Dave and Jamison answer these questions: I work at a large remote company. We meet up once or twice a year. I don’t really know much about my engineering coworkers aside from the 5 people on my team, so the in person meet ups seem like a good place for me to get to know people from the other teams. I am a career switcher, and am currently a mid level IC (borderline junior) in my late 30s and a youthful appearance. At these meetups, my position and appearance (and honestly, possibly my demeanour) makes me feel like I am expected to socialize with other ICs in their 20s. Although they are nice people I find it hard to relate to them when talking about non work related topics since I am much older and in a different stage in life than all of them, (married with a mortgage and kids). I want to socialize with coworkers closer to my age and stage in life but most of them are team leads or manager. I feel like socializizing with them would be seen as brown nosing. I’ve also heard that once someone is a manager, it is very hard for them to befriend ICs because they are now their boss, and that they mostly befriend other managers. My previous career had little…

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