How do you upskill yourself?

So I took the Learning how to learn course on Coursera some time ago. The key point that the lecturer is trying to make is that when you start with an unknown subject, it is better to first uncover some key areas. They are calling them chunks. So imagine having a big dark terrain and slowly start shedding light in some areas until you uncover it all.

I'm doing that when I'm trying to learn something new. Take a new language for example. I will start by asking some key questions:

• Why was that language built in the first place?
• What key problem is trying to solve?
• What other languages are similar to this one?
• What does the syntax look like?
• What are some key differences from other languages?

Etc. Trying to answer these questions will shed light on half of the terrain.

After it, it's time to go deeper. Start a quick project, read other projects on GitHub, get involved in communities and discussions around the web. Follow some people that are working on that language for some time.

The first time I'm starting something new, I am not trying to be an expert. I'm trying to get my self familiar with the subject but also surround my self with experts. I will either be interested and will want to continue with it or will just back down.