Part of me is the cautious, risk-averse type. 

Part of me is the sensation-seeking, risk-taking type.

Founded a start-up, contractors didn't do what they were paid to do, then litigation which is now over.

Interviewed with a few FAANG companies, now a similar type of company might hire me. 

I hired a SQL and java programmer to complete the coding challenges in the initial interview, so I now advanced to the next round.

Plan is to pay the programmer - after I get hired - to do the work while I get up to speed. I know python and am comfortable with ML. 

Thing is: I support my family with the income from my current risk-free, mind-numbing, soul-crushing job in the public sector. 

I don't want to quit Big Brother and I think I can balance both, despite the fact that I might get fired for doing job 2 during duty hours of job 1. 

I want job 2 to compensate for hte start-up failure and to leverage it into a senior mngt position at a FAANG company.