Improvisation, freestyle, and re-learning how to share space

Toni Blackman shares how she used the “wisdom of the cypher” to help communities connect, listen, and build trust where it was lost.

2 min readMar 31, 2022

When we tell you watching Toni Blackman speak feels like looking in a spiritual mirror, we get the feeling we’re not the only ones. Our DNA is eerily similar: FLS+, a joint improvisational entity focused on public speaking, freestyle rap, and organizational dynamics; she, an emcee-turned-competitive-debater-turned-hip-hop-organizer.

We rarely see our experience so directly reflected — yet, we get the sense she could make anyone feel seen and heard; the kind of person who talks to you when you don’t know anyone at the party; who catches you up on the all inside jokes.

Are we projecting? Maybe…

She certainly doesn’t need our blessing; when the first “Hip Hop Cultural Envoy” to travel with the State Department speaks on the power of freestyle rap to build trust and connection, you listen. Her 2019 talk, “The Wisdom of the Cypher,” feels particularly prescient today. So many of us are craving connection with each other, but finding that, when the moment we’ve been waiting for finally arrives (that in-person happy hour, or first day back in the office), it doesn’t come as naturally as it once did.

We have to re-learn how to share space.

Improvising in a cypher may be the key to bridging that gap. Cyphers — circles of people extemporaneously exchanging information, ideas, or even food — dates back centuries to African traditions of eating, dancing, drumming, singing, and, more recently, to hip hop culture. Most importantly, the cypher is a shared space: “If you’re not listening to each other, looking at each other… if there’s no exchange of energy, information, and ideas, it’s not a cypher” says Blackman.

The bottom line: we have to start with ourselves

In order to start feeling comfortable around each other, we have to realize that failure and vulnerability are part of the process. Maybe a joke doesn’t land like you thought it would, or you’re self-conscious about how little you “did” over the pandemic, or you farted in Whole Foods — freeing ourselves of the need to be “prepared” is ironically what makes us most relatable. Making it up as we go along is the point. “When we improvise,” says Blackman, “it gives us access to vulnerability on a whole other level.”




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