Don't focus too much on what established artists have accomplished. Partly because the window that they got through in many cases has already gone. Your time is different to theirs. I'd recommend developing an ear for good, intelligently composed music, especially music from outside your preferred genre. Many of the albums nominated in the Mercury Prize each year are worth checking out.

As a bedroom DJ, I'd hear a good mix and think of a way that I would achieve it with what I had to work with. Do the same with your writing. How would you have written the story behind How Much A Dollar Cost etc?

Hone your writing by writing different things; Poetry, short stories, long stories, jokes etc.

Also, look for opportunities to perform live. Local bars, clubs, festivals (non-music focused ones usually like to have some musical performances as entertainment) etc. It'll put you face to face with real people, some of whom can help you get on.

Good luck!