Spend a good bit of time thinking about what the ideal way would be for you to spend 8+ hours a day (i.e. work), and how this would fit into your overall goals

Spend a good bit of time thinking about what the ideal way would be for you to spend 8+ hours a day (i.e. work), and how this would fit into your overall goals in life - beyond work/career. Do this by testing out all of the above hypothesis, e.g. speak to people (through linkedin for example) that have done that MS from an ivy-league mid-career (or whenever): get lots of experience data to give weight to these potential next steps. Ask lots of basic questions, why do you want money, what are you going to do with it. How much does reputation matter to you, and what does reputation mean. From the little info above, it appears that good company, is something important: (a) people that are at your level (and you need to think about what that means exactly), (b) people with whom you want to do projects that make a difference (and again, what does this mean) Could you have this out-with a work context?