If I knew I couldn't fail, what would my next year actually look like?

Kris Kluver, in The Dysfunctional Family Office, asks UHNW families this exact question at the retreat. If you knew with absolute certainty that failure wasn't possible, what would AMAZING look like for you over the next year. The answers usually surprise the people giving them. They're bigger, more specific, and more honest than what people would have written without the prompt. The constraint of not failing forces you past the small, safe, defensible version of your goals into the actual version. Most people walk around with a public version of their ambitions and a much bigger private one they don't say out loud because failure feels too risky. The exercise lets the private version be visible. From there, the family or the individual can choose how much of it they actually want to pursue. The exercise is also useful annually, not just once. Kris Kluver uses this prompt with founders and rising generation members at thethirtyadvisors.com.