Stay close to your audience
I just finished The 50th Law, by the incomparable Robert Greene, about the life and lessons of the drug-dealer-turned-rapper-turned-business-mogul, 50 Cent – a guy who continually finds ways to remain close to his audience.
On the street corners of Queens, while the other child drug dealers would look down on the users they sold to, 50 would actually talk to them, asking them about what they wanted. When he got a new batch of drugs to sell, he would give away a few free samples so the users could tell him if it was any good (and therefore needed to be cut), what was good about it, and also to spread the word that 50 had The Stuff.
When he transitioned into music, 50 would send out mixed tapes of his songs to the community, and later on his website, so he could learn what resonated. Only the most popular songs would make the album.
He admired the boxer Jack Johnson, who, without the benefit of a trainer, took on as many fights as he could, taking a lot of beatings and drawing out fights, even if he could put the opponent away quickly. Johnson learned and learned and learned, eventually becoming the greatest fighter of his era.
The book has many more examples of people who listened, people like Newton, Nietzsche, and Baldwin. Their success came in part by remaining close to their audience throughout their entire careers, no matter how successful they became.