Tips for an 'expert beginner'

Recently a friend came to me with the problem that while he has been programming for about as long as I have (nearly 10 years) he is what would be considered an expert beginner. i.e., one who has mastered the basics but never pushed themselves beyond that. His degree is in business. He was always good at math in school, but never went beyond the basic requirements of his degree. Going back to school is no option for him, and he hoped I had advice for how he could move past this and begin moving to a career in computer programming.

Frankly, I didn't have much in the way of good advice. He's capable of picking up new languages fairly quickly, but struggles knowing what techniques are best suited for what problems. Debugging is also a challenge for him, as he hasn't much experience doing that beyond trivial problems.

So, I ask you all, what you would recommend someone in his situation?
He might check out Coursera. They have an impressive assortment of computer science related courses and specializations (sets of courses) that are free. And, if you're taking the free option, you can generally take as long as you like to work through the material, although there's an obvious disconnect from other folks working through the material at the prescribed pace - you don't get nearly the same level of support.

I think it's a good way to kick-start the motivation and start developing a portfolio to present to potential employers.
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