Brooklyn - thanks, both of those resonate with me.
Tyler - fear is definitely an issue for me, but I kinda know it is false one so it will solve itself money wise - the ego part is self induced not so much external, I don't give a shit what people think of me (outside of DW and kids) but I struggle internally. I have thought a lot about what you said and I think ultimately I am the type that will need to dive in, be removed to decompress/reinvigurate, and then it will be figured out.
ARS/FV - that is probably more what I talking about (not what but who)....I am jack of all trades type and like to do a lot so "what" won't be too hard.....except when the mastery of the "what" comes into play and turns into work again :). The "who" is much harder because it doesn't mesh well with typical conforming BS job/venture....think of a type A persone that like a bee also likes to float flower to flower whenever he so chooses.....I have no doubt I can fill time.
I know, I know that part of the answer is your FIRE who cares.....you can do it for free...etc..etc. Sorry, but my mind doesn't work that way....if I am doing something productive that benefits someone else making some sort of revenue then I expect to share in such revenue regarless of whether or not I need it. This sentiment of course exludes volunteering, helping the neighbors (unless it becomes regular and the expect it), and what not.
Good stuff, thanks.