Well I discussed my existential dilemmas and recurring vacillation regarding my academic career with both of my therapists a lot. My second T made that leap himself: he started out as an academic, then moved into business, then became a therapist. To be honest, I did not find them too useful that way. I personally found more understanding and support among my colleagues who are familiar with the current, ongoing challenges. Some did make me feel almost ashamed that I even questioned the whole thing but I think those were not the people to listen to really, they were far too simple-minded or short-sighted and not thinking holistically. I stayed in academia and am happy with it now, pretty much settled and not questioning my choice, but it took many years to get to this contentment. I resolved it with doing other things in parallel. I never wanted kids so for me that was not one of the issues, more feeling limited and forced into a structure that felt uncomfortable for me when I was younger, and the rat race associated with maintaining it. Anyway, I'm past that phase but have found many academic colleagues who really understand and know these dilemmas first hand, intellectually, practically and emotionally. Perhaps it also depends on the specific field.