Definitely build a project by learning a few of those technologies. It's ok to start out learning with a framework (Ruby on Rails is pretty acceptable as a fram

Definitely build a project by learning a few of those technologies. It's ok to start out learning with a framework (Ruby on Rails is pretty acceptable as a framework and easy enough to start with; same could be said with Django). I recommend this http://www.railstutorial.org/ http://www.railstutorial.org/ It's meant to be newbie friendly and it will teach you a lot of those things you mentioned above (Ruby, SQLite, Version control with git + github, Test Driven Development via RSpec, and cloud hosting via Heroku) while building a twitter clone. After that you should build your own projects and you will run into new questions and problems that will dictate your learning. Also don't worry about not knowing Ruby, the book will teach you. If you are too unmotivated but have 15 minutes to spend, try this completely: http://tryruby.org/ http://tryruby.org/ And don't fret too much about changing web technologies. Sometimes, you just have to keep your calm and focus on what matters - essential hacking skills and fundamentals.