You have set yourself a difficult challenge. But one that I very much identify with.
I have worked with the same group of people for 20 years across 2 different companies. 10 years ago, we climbed Kilimanjaro together. When you have peed behind a rock together, seen people laid low by altitude sickness, and generally shared the trials and tribulations of such a feat, you'd think you could be as authentic as it is possible to be.
But when I shared some of my thoughts about the corporate grind with my friend and CEO, I was hoisted by the petard of my own honesty. The CFO - the traditional voice of calm - was, meanwhile, close to tears identifying with me about how difficult it is to align what we genuinely want with what we have to deliver.
Did your what-if session help you to decide how to bridge the divide?