After figuring out what would fulfill him, he should consider starting his own venture doing exactly that. A venture is my material representation of freedom, his may differ -- the take away is that freedom is what enables you to get unstuck. I used to be in a similar position, making good money as a tech exec and feeling stuck. The freedom to impact the world, in my chosen fashion, was the cure and my only regret was that I didn't figure that out sooner. The most surprising thing to me was that the money side of things accompanied the impact I was able to achieve, without making it a focus.