My first time rapping on stage? Broadway. Times Square.
I had no plan. I agreed moments before.
The beat dropped. I stepped up. Froze. Took a breath—then let loose.
Freestyling about computer programming…
To a few hundred Laravel developers.
A few months later, I joined Lin-Manuel Miranda’s rap academy, training with pro rappers and beatboxers.
I’d freestyled for fun since childhood—but never trained.
We ran drills to find flow. Played games to spark creativity.
Battled to sharpen wit.
5 Lessons from Training to Freestyle:
🎤 Lesson 1: Routine unlocks flow.
The first few times you try something, you overthink it. Flow only comes with repetition and monotony. The magic of practice is that it frees you to experiment.
🎤 Lesson 2: Nonsense is liberating.
Ever done improv? The first 20 minutes is just weird, silly warmups to lower your inhibitions. It works.
🎤 Lesson 3: Turn practice into play.
We made up games to train skills. One focused on “portholes”—connecting unrelated ideas (e.g., aliens & bananas). Creativity thrives in constraints.
🎤 Lesson 4: Chemistry is real.
Some people just click. Freestyling with certain partners felt effortless—like we were reading each other’s minds. You can’t manufacture it. You just know when it’s there.
(Clem was my guy.)
🎤 Lesson 5: Adapt and thrive.
In freestyle and in life, there’s no script. You either roll with the chaos—or it rolls over you.
Thinking back, that first performance could’ve been a disaster. But the second I stopped thinking and just let it happen? Everything clicked.
Kinda wild how much that applies outside of rap, too.
Ever had a moment where you just had to wing it—and it worked out?
