Go all in Frank Reynolds style IASIP.
I've heard it said that there are 3 common ways wealthy people often get into trouble:
1. private air travel
2. boats
3. buying a restaurant
Obviously there are plenty of others...but those first two are not good financial company to be in.
It's great that you are thinking about making a change. Nowhere in your post did you really seem to address whether the actual work was something that you would want to do. It's good to analyze it in a dispassionate way, but you should really ask yourself if the passion will be there.
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