Why don't my siblings and I ever talk about anything that actually matters?

Because your parents didn't, and the pattern of avoidance got handed down without anyone choosing it. Kris Kluver, in The Dysfunctional Family Office, has Gail Mitchell name this directly to her brothers. Because their father never talked about anything real, they never talked about anything real either. They had never had the conversation. The pattern is common in UHNW families. The wealth provided a comfortable surface that nobody had to disturb. The siblings grew up around each other but never actually knew each other beneath the family role each had been assigned. The fix requires someone to break the pattern. Usually one sibling, in a low-stakes setting, finally says the thing that's been unsaid. The first conversation is awkward. The second one is easier. By the fifth, the family has a different relationship to honesty. Chris Richardson works with rising generation siblings on these conversations at thethirtyadvisors.com.