Hey DragonCar - very interesting question in light of recent conversations I've had.
I'm an attorney - as are you. I originally started in a firm and had multiple co-workers/friends. One in particular is closer than the others. Well, I'm not retiring, but I am being very aggressive in getting rid of certain types of cases and streamlining my practice to only the most profitable, most enjoyable cases. I also just spent two months in Mexico. I've got zero debt and a pile of cash invested.
My friend worked with me at the other firm and left to open his own firm right next to me. In total we have 6 years of practicing right next to each other. An interesting twist in this situation is that my friend/co-worker is my former partner/boss and is actually 6 year older than me.
Anyway, I have been open with him. Maybe open in a way that is uncomfortable to him. Just a few days ago he told me he was jealous of me because he sees me rejecting cases I don't want and re-organizing my firm to work less but make more. He specifically commented on how he was jealous that I have no debt but he has student loans, car loans and a big mortgage. He wasn't being angry or weird but it was a tough comment because I had no idea what to say and, probably handled it badly because I was caught off guard, said "I'm sorry. I don't mean to be a dick. I'm not trying to put you down ever maybe view it as aspirational??" What a dumb comment (on my part).
Anyway, it is tough because who can you share your success with if not your friends? What does it feel like to always be hiding a part of you? I now understand the saying, "It's lonely at the top." If you can't talk about your success and you don't want to lie and commiserate in a way that is inauthentic then your only option is to remain silent. The silence will kill your relationships because sharing and mutual understanding is the basis of enjoyable relationships.
Anyway, a conundrum to be sure. I know some recommend being totally silent on the issue. So far, I do the opposite. I tell people the truth.*** I figure its better to have people around me that get it. That understand me, where I'm coming from and where I am going. If it makes them feel bad we will probably drift apart. But, what good is a relationship based on fundamental misunderstanding anyway? I feel like this approach has cost me some relationships but also attracted some other really awesome people into my life.
So, there you go. My two cents.
*** It's not like I go around saying, "My net worth is XXXX." But, I talk about MMM, the 4% rule, my business successes/failures, my worst financial mistakes, whatever is relevant to the conversation. When people ask questions, I answer.