When is it OK to talk about money?

[Nathan Gesner]

In 2005 my oldest brother asked me how my house sale was going. I mentioned it went under contract in three days and we were making $125,000 profit. I was in the military and would be considered lower middle-income at the time, so this profit was pure luck and a real blessing. I only answered his question, but later learned he felt I was "bragging" about it.

We grew up poor (I would pay good money for more of that government cheese if anyone has a source!) but all my siblings are now middle class. I've worked hard to grow a successful business, a strong investment portfolio, and am now part of the evil 1%. I try to keep it on the down-low with everyone, not just my family, but they do know I own investment property, that I travel quite a bit, etc. Even when they ask questions about how many properties/units I have, I try to play it down (without lying) and then change subjects quickly. I just learned my mom has been referring to me as her "millionaire son" even though I've never told any of them what I earn or what I'm worth. 

Anyway, I'm just throwing this question out for my own curiosity: when do you feel it's safe to discuss income or net worth with others? Do you feel it's better to lie about it so they never know anything?