"Keeping it real" as a notion is subjective. So subjective. It is, at times, a crutch used by both the noble and the malicious. It is simultaneously recognized as en vogue, and an ancient struggle.
How does a notion so seemingly simple cross the barrier of obscure subjectivity and become everyone's modus operandi? I. Have. No. Idea.
Actually, I do have an idea. Let's redefine what it means to keep it real. The short and simple truth about doing this is that it involves basically two things.
First, there must be a realization that someone, anyone, everyone else's experience is no less valid, valuable, or "real" than our own. Failure to start here, will inevitably leave us enhancing, puffing up, and attaching to our own story. In other words, we'd find ourselves stuck over-identifying with ego so much so, that true authenticity has no chance to rise up.
Secondly, we must be willing to speak from the heart. Sounds simple, but not entirely. Speaking from the heart means choosing truth over thought. It means choosing compassion over disregard. It means choosing freedom in lieu of guarding against feelings of vulnerability. It means letting go of fear.
A thug's tendency isn't to tell you that he misses his dad, or that he feels vulnerable out in these streets. Nor should it be. But at some point, it is his, as well as, all of our duty to the rest of society to examine our personal truths. Then, in an informed way, we each allow the insight into those personal truths to dictate how we are in the world.
Holla if you hear me.