Originally published March 2025
I had the incredible honor of singing with the super-talented reggae band, Organically Good Trio, on the final day of VI Jam Fest. It didn’t go exactly as planned. I was supposed to hop up and drop in my own verse on an instrumental tune of theirs called “Beam Me Up.” I’d expanded on something I’d written previously and loved how it fit with their song. However some wires got crossed, and I was called to the stage as they started a completely different tune.
I don’t have a lot of experience with musical improv, and only had a quick couple of eight counts to lead me in to a song I was entirely unfamiliar with. At that point it would have been far more awkward to decline the invite than it was to just roll with it. I knew it was one of those moments when you just say a little prayer, dig deep, and do the best you can with what you’ve got.
In the moment it felt like a total blur. I knew I hadn’t completed bombed, but it was such a stark contrast from what I was anticipating that I couldn’t escape an intense awareness that it was not as good as I wanted it to be. It wasn’t what I’d practiced.
My amazing friend Angela filmed the whole thing for me. When I told her what happened she suggested I go watch the video because I’d probably feel better about it once I saw my performance. I was afraid it would have the opposite effect. When she texted the next day with a link for the HD download, she also sent along this encouragement, “I hope you can see it how everyone else did.”
What I realized through the course of the night and into that next morning, based on conversations and messages, was that everyone saw it as exactly what it was – improv (rather than a failed attempt at a rehearsed performance). The band told me how sorry they were for the mix up, but that I’d done a great job. Another friend who creates social media content for a rapper, ended an unrelated conversation by saying, “Hey, by the way, were you free-styling with that band earlier? You killed it!” The Windmill Bar posted their own short clip that looked and sounded good. But I have to be honest, despite all that, I still hadn’t watched the whole video until I added the captions to it for this post.
When all is said and done, I’m actually grateful that it happened the way it did. I want to improve at free-styling and impromptu drop-ins, and the only way to do that is to practice. From time to time, it’s good to perform through discomfort. Some of the most significant moments in my career thus far have been incredibly uncomfortable. (I was so nervous when I played for the 2018 Hitmakers & Rum Chasers in Nashville, I was afraid I’d drop my pick.) On a deeper level, I’m also learning to not only accept my humanness, but to embrace it. This was an excellent teaching moment. I grew as an artist, and as a person. I’m good with that.

