Sometimes in long running posts you need to go back to the beginning.
M Ridzon said:
My main question is whether this is wise or not, considering my age, my comfy engineering position, and the severity of the pivot in my life. I'm curious if anyone else here can relate or has a story to share about a similar experience.
"Wise" is an interesting word and invites a level of judgement from others which I think you've got here.
I think from what you've said your wife though is a very wise woman and knows you more perhaps than you do yourself.
Clearly the answer "No, Are you insane? Have you been drinking??" wouldn't work with you so she's going the more analytical route.
Realistically the challenges you face are substantial being:
Age - we're just not as able to do things as we get on in life as easy as we did.
Family situation - the little buggers cost you MORE as they get older not less
Cost of the tuition
Uncertain outcome - the market may have moved on by the time you get there, you cannot gain sufficient clients, you won't get to do what you want
Desire to change - Only you know how bright this flame is, but maybe its intensity will diminish as time goes on?
Or is this just a mega mid life crisis?
I think most of us have been there on the latter one. For me it presaged moving out from my comfortable, but increasingly managerial role into a start up consultancy which failed, but then I got to do what I'm actually good at which is technical engineering on a contract / consultancy basis and not all the managerial and selling stuff which I realised I'm not actually very good at.
Perhaps take a closer look at your current role / company / career track and decide to make a change there.
Probably better than deciding to be a plastic surgeon / astronaut / deep sea diver / racing driver or whatever else your itch turns to??
[Apologies for the slight sarcasm there....]
So "Wise?" It's not for me to say, but this is a judgement call only you can end up making with those around you who will be impacted by that decision.
Its been fun on this thread for sure and I do wish you all the best. I think I'm done now.
Remember - More details = better answers
Also: If you get a response it's polite to respond to it.