Trey Anastasio is the guitarist and frontman for Phish—a jamband originally from Vermont that has been going strong since 1983. Phish’s trademark is its improvisational style and unique sound that ensures each show is different from the next. This approach has led to an adoring fan base that follows the band from city-to-city each tour. I’m one of them. My time with the band dates back to 1997 when I was still in high school. I believe that Phish is the greatest rock band in history and Trey is the greatest living guitarist. But my love of Trey and Phish is not what this post is about.
Earlier this month, reggae legend Toots Hibbert of Toots and the Maytals fame, passed away due to complications from COVID-19. He was 77 years old. I was saddened by this news. I love the music Toots and the Maytals created over the years. I frequently turn to it on sunny weekend afternoons when I’m outdoors. Toots will be missed by many.
What caught my attention that day was an Instagram post Trey wrote in memory of Toots. The backstory is that Trey’s Vermont recording studio—called “The Barn”—is a popular destination for other musicians to record. In 2003, Toots came to The Barn to record a new album, True Love. Trey recalls that day, fondly (emphasis mine):
When Toots and the band arrived for the session, I was nervous and basically speechless. Toots was a ray of light, so kind and welcoming. The guys in the band hovered in the corner, smoking more ganja than I had ever seen consumed. We decided to play Sweet and Dandy. I was a bit mortified and confused as to why such an iconic song should be re-released, but we recorded it, and it was was a thrill. What happened next I will never forget for as long as I live. Toots was supposed to do a song with Willie Nelson, but Willie was not there of course. Toots began searching, playing different Willie songs deafeningly loud through the giant speakers in the barn, while a bunch of us stood next to him by the soundboard. He said that he had to believe every single word in order to sing a song, a lesson I’ll never forget.
That last sentence deeply resonated with me. (On a separate note, Trey’s almost child-like reverence for another musician brings the story to life. Here’s a man at the very top of his game who is nonetheless grounded in humility and respect for the greatness of another—the mark of a true craftsman).
Like many people in public-facing roles who are looked upon as experts, I’m frequently asked to opine on things. I typically have a thoughtful response to offer, but sometimes I don’t. I’m a terrible bullshitter, so I’ve learned to get better at saying “I don’t know.”
More deeply, as executives, founders, leaders, and any number of roles we inhabit, we’re often expected to switch personas or fudge the truth. I have always felt uncomfortable doing this, which is why I work hard to build a conviction around what I’m doing.
The same goes for writing or building a new product or pretty much anything else that I feel requires conviction. I can’t fake it.
This topic surfaced in an interview I gave with my friend Gonz Sanchez on his Seedtable Podcast. I talked about trying to honor my desire to have one persona across all contexts of my life. It’s hard for me to switch masks so I want to minimize situations that require it. That approach won’t work for everyone, but it does for me.
If, like me, you have to believe every single word, sooner or later you’re going to have to build conviction around what you do and say. I still have some work to do—don’t we all?—but the more you do it, the more the momentum builds for it being the norm.
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