[colanderman]

Even financial peers may nonetheless view your position as privileged, because they may not be able to give up whatever it is you did to be able to leave their job. Perhaps they are burdened with debt, or have a family to support, or may simply lead an expensive lifestyle that is not socially tenable for them to curtail. It could even just be that their partner – or potential partners if they are unattached – would be uncomfortable with them taking a two-year unpaid sabbatical, so even if they wanted to, they couldn't do so in good conscience.

To put it another way – who wouldn't take a two year sabbatical if they could? The fact that it's rare, even among well-paid tech workers, is a good indicator that it's not within the realm of relatability for most.

I also don't think it's necessarily a judgement of privilege. Consider the reverse scenario: a party of people enjoying their sabbaticals, and one person with a desk job. No-one's going to hold a conversation for long with that person, simply because their day-to-day experiences are not relatable. The sabbatical crowd will want to talk about long-term travel, how to stave off boredom, and the interesting startup ideas they're working on. No-one wants to hear this one guy's stories about scrum drama, getting a promotion, and taking their kids to the recent company outing. His stories may be positive or negative, boring or interesting, but no-one else can commiserate with their own current experience. For anything topical you're left with sports and the weather.

[txcwpalpha]

Your point is well taken, but when I mentioned people that "I know for a fact are better off financially", I was taking all of those things (debt, family, lifestyle) into account. Again, I'm sure for some interactions, those things apply, but I've had similar interactions with people that have no debt and have no family to support (and in fact, actually receive monetary support from their family/parents).

>To put it another way – who wouldn't take a two year sabbatical if they could?

It seems a lot of people, actually. Again, I can't speak for everyone, but even many of my close friends, who I know a lot about their financial situations and have actually had this conversation with, have even said that they could take time off just as I did and have no financial issues at all, but still would not do it because they feel too pressured by societal expectations to always have a job.

>I also don't think it's necessarily a judgement of privilege. Consider the reverse scenario: a party of people enjoying their sabbaticals, and one person with a desk job. No-one's going to hold a conversation for long with that person, simply because their day-to-day experiences are not relatable. The sabbatical crowd will want to talk about long-term travel, how to stave off boredom, and the interesting startup ideas they're working on. No-one wants to hear this one guy's stories about scrum drama, getting a promotion, and taking their kids to the recent company outing. His stories may be positive or negative, boring or interesting, but no-one else can commiserate with their own current experience. For anything topical you're left with sports and the weather.

There is far more to talk about than just sports/weather and work-related stuff. Even when I was employed, most of my friend group was not in the same industry and we were still able to have lengthy conversations even though most of the group didn't even know what "scrum" is, or never had to worry about a promotion, or never considered startups.

My experience has been that the topics of conversation or ability to commiserate isn't the issue. I've been in situations where I have had lengthy, wonderful conversations with a person where we clearly connect and can relate to each other, but as soon as I drop the "I am currently unemployed" bomb, their entire attitude toward me will change for the worse. (FWIW, I've also been in situations where their attitude has changed for the better, but I find those to be rarer)