It really depends on the situation. Once, on my first day at a new job in a very open working environment, my new boss came by to talk to me. He had run my background check, and I guess he thought I was a victim of identity theft, b/c my name had popped up on all these addresses in other cities and states. I confirmed that the information was correct, and just said I own some rental properties on the side. Well, one of my new co-workers caught wind of the conversation and demanded to know what my husband did for a living. I hadn't connected the two, so I told her. I guess in her mind, there was no way our two average jobs could result in such a side business. I knew early on that this was just a bridge job on my way to something better, but she made her disdain for me well known and told everyone else about my personal business. The day I quit that toxic place, I was so happy, and it reminded me to think twice before sharing anything, even though it was clearly my boss' fault for not having that conversation in his office!
I went out w/some friend a few weeks ago, and they know that we are close to FIRE - they ask a lot of questions, but are limited by fear (husband) and consumerism (wife). I mentioned something about our desire to move into a smaller home and not have a mortgage, and said that it would mean we could retire in 2-3 years instead of five, and the wife couldn't help herself but snort loudly. I smiled inwardly, she'll get it when we actually achieve the goal, right around the time she's looking to replace her new SUV w/another one. She works from home and barely knows how to get out of the neighborhood!
We were visiting family a few months ago, and the topic of $$ came up, as everyone is complaining about how much the neighborhood has changed, the cost of living is impossible, etc. My father in law (retired & penniless) made the comment that "the more $$ you have, the more you spend". I watched as everyone w/in earshot of this comment just shook their heads in agreement. I kept my mouth shut, hubby & I are proof that you can make better choices instead of accepting a stupid platitude as fact...