My advice would be to figure out what your biggest strengths are and to emphasize and augment those with whatever IT stuff you try to learn. This will give you

My advice would be to figure out what your biggest strengths are and to emphasize and augment those with whatever IT stuff you try to learn. This will give you the biggest payoff for the least amount of effort. Then look at the trade offs for learning whatever tech you want to. For instance, the trade off probably doesn't make much sense to dive into machine learning if you have to (re)learn linear algebra, probability theory, and calculus before you ever open up a ML book. You'll spend years learning and hence foregoing a better salary just to get prepared to enter the market and be severely disadvantaged against the young and hungry mid 20 year olds whose heads are still chock full of theory and have their first couple of years of experience under their belts. You have experience building businesses, likely at least decent i.e. easily improvable financial skills, and probably lots of project management experience. A positive example of what I'm talking about is this. Read up on AGILE/Scrum/Kanban, take on some freelance jobs in a domain your comfortable with, apply the methods, and within a year or so you should be able to get a well paid management job. That's just a suggestion. Do the cost/benefit analysis for yourself, figure out your biggest strengths, and then just learn enough of the IT to bolster your strengths and pump up their monetary value on the market. Best of luck