It's almost inevitable that traveling with your boss will lead to an uncomfortable situation. These unforeseen circumstances typically cannot be prevented, but at the end of the day, you're forced to navigate a cringeworthy dynamic with your employer that will make returning to the office after the work trip all the more bizarre and challenging. These cringe moments can include an odd quirk or eccentricity you learn about your boss or your boss learns about you. For instance, I once had a boss learn the hard way that I sleep with my mouth open on flights. This was obviously not the plan, and I wish my former employer could unsee that sight.
Another kind of uncomfortable interaction on a work trip can relate to toxic hierarchical structures. This Redditor shared their story of how their frequent traveling resulted in a seat upgrade to first class. However, somehow their boss thought that they should be entitled to the upgrade simply because she's the boss. She even requested that the two have a one-on-one conversation after the trip about "respecting protocol." Keep scrolling below to see how the original poster responded. For more stories like this, here is one about an interviewer who brought their kid to work.
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