Unfortunately I'm not having this dilemma, but it seems easy to maintain lifelong friendships after becoming wealthy in the stock market. Let's look at two scenarios: In one scenario we have four life long friends. One becomes an accountant, one an electrician, a grocery store manager while the fourth becomes a neurosurgeon. In this case there's an obvious socioeconomic gap. Being a neurosurgeon is more than how much you can make and what you can afford. It's part of who you are and how people see you. In this scenario I think the neurosurgeon will have a very hard time maintaining his friendship with his lifelong buddies. In the second scenario, let's keep everything the same except the fourth member of our posse is a school teacher. This school teacher happened to see the Tesla vision early and put everything he had into the stock as early as 50 bucks a share. Say he had 50 grand in cash and 200 grand in a retirement account. Now he's got 1.5 & 4.5M. He's 50 years old so 1.5 million isn't enough to carry him to retirement but he pays off his house and stops adding to his retirement funds so he has a lot more cash on hand. Buys a Tesla, adds onto the house, goes on more vacations with his wife. None of this is enough to cause a rift with his 3 buddies. When they comment about the fancy vacations he jokes with them "Hey, I told you teaching was a great gig. Three months vacation in the summer and a month in the winter, what do you expect me to do, sit at home and watch tv?". He's living the good life, enjoys the peace of mind of financial security and gets to keep his lifelong pals. Suppose our guy did even better than I described above and did well enough to retire. All he'd have to do is make his hobby his career. Instead of being a teacher, he's now a track coach or a hunting guide or a dance instructor. His buddies don't need to know if he doesn't make any money doing those things.