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stfu

Only if it is really increasing my personal learning curve.

1. I want to try stuff my own.

2. Then I want an expert to step in.

3. The expert should teach me how to improve the stuff I already started.

4. And now the important part: I need to understand why/what makes it better.

5. Teach my how to "think" like a pro.

There is a gazillion of tutorials and stuff out, but what I am missing the most is fixing the gap between what is going on in my head vs. what is going on in the head of the teacher.

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This might help the OP come up with a hybrid approach. Create tutorial videos, blog posts, whatever that have lessons with exercises. Publish them for free. People pay for you to take time reviewing their work and then meeting with them over Skype for feedback and personal instruction. Hmmm. I guess that doesn't scale too well either. You would have to charge $100+ an hour to make any money. Maybe you charge a small monthly amount for access to all content. I dunno. Actually speaking to the person with experience is key, but their time is so valuable that it stops being affordable enough for people that need it.

Consider that the OP creates a marketplace for such services. He can funnel in enough customers that someone offering services in his marketplace can easily find $100/h gigs to fill their whole working day. He can scout out great talent who would be more than happy to make anything close to $800 a day, or half that much for that matter.

I like it. I know multiple people who would love to be able to pick up work like this on a light day. Everyone should be teaching their craft to some degree, too.

Totally agree. When I first started designing I went through hundreds of tutorials which made it very overwhelming.

I want to create a program that is organized and will help people actually learn how to create attractive and usable websites.

My main goal however is to not only help those learn design (and give them feedback), but to also help them put their skills to practice and either build a business or find contract work (if that is desired).

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