Will you pay me for this?

Some aspects should be taken in to account.

1 People that desperately want to be good at something are delusional because thats is just a dream they see themselves already there but they do not have the key to unlock that door.

2 when people go and see someone to help them out in something they want someone to fix that for them otherwise they would be fixing that by themselves.

3 People like that are emotional strugglers they have mental blocks they do not follow up.

4. If a third part is going to make them to commit into something they will be blaming the third part for their failures.

So basically, coaching then?

Personally, I wouldn't pay you for that, simply because (as people have rightfully pointed out), I'd want a mentor to help me improve at things, not a human alarm clock. 90% of what you mention here could be automated with a free program, and the other 10% wouldn't be all that useful unless you had a decent amount of experience in the field I'm trying to learn.

No. If you're not good at this then you cannot provide any guidance or advice. At which point I can just use reminders, or build an app with random positive messages popping up as notifications every week or so.

I like this variation of this idea: Put up X dollars and commit to tasks. If you don't show proof that you did it, you don't get the money back. Maybe send the money to a black hole if tasks aren't accomplished... like burning ether-- your company shouldn't keep the money because otherwise there's misaligned incentives, but donating the money to charity seems like it might motivate you to work less (maybe not?), which wasn't your original goal. It's a bit harsher but it means... it actually matters to commit.

In this scenario no one is selling you knowledge--instead, you're forcing yourself to be more motivated. And you make money by taking a small cut when a task gets accomplished, so you have a financial interest in your customers succeeding.

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.

I 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.

Revealed preference (https://en.wikipedia.org/wiki/Revealed_preference) is often different from stated preference, particularly with “soft” purchases like this one. Put up a web page - or a few different pages - and find out.

Sounds like a great idea, partly because I don't know you and so I have less fear of failing in front of people/the world.

How much do you have in mind?

https://bossasaservice.life/

I think this is a desperately needed service but I can’t think of the right way to do it.

No, unless you’re good at it and willing to provide some guidance.