I think your idea could work. I did this last year. I helped my friends little brother transition from being a bartender to being front end developer (perfect timing with covid19) and a new friend transition from being lawyer to a QA engineer. We would chat and text message what we are working on, gotchas, hot topics etc. We then would meetup occasionally on Fridays for drinks and talk shop. It was a win/win situation, they got into a new lucrative career and I got a new friend to talk tech with. This all plays into my mantra I got from the movie Office Tigers on Netflix: On your way up, bring those around you with you.
Ask HN: Will you pay me for this?
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Re: Ask HN: Will you pay me for this?
#12I won't pay you, but I'm guessing somebody would.
I guess you would have to establish credibility.
e.g. If someone wants to be a great actor, but you have no acting experience.
I guess you could play the matchmaker role. I know there are coaching services out there, at least one that is 'startup-y', but prob plenty more room.