Congrats Tim! I appreciate your writing, your vulnerability and honesty, and your insights on concepts many people see as flat, 2-dimensional. I'm 59 and I've quit several jobs but also have been fired a couple of times too, so am hardened somewhat and feel less emotion around a job change. As a founder of a multimillion dollar CRM consulting company with a couple of dozen employees (when we were doing well, I felt wounded when a valued employee would hand in their resignation. I turned to the Four Agreements, and in particular #2 "it's not personal".
You're right about avoiding deathbed regrets: as Nike likes to say, "Just Do It".