There is a moment after the hour mark when Trinidad Kesselman drops it without drama. “I’m fighting for my flow state.” It’s quiet, almost offhand, but it lands like someone who has spent years stripping away noise until only the essentials remain. I’m fighting for my flow state.” It’s quiet, almost offhand, but it lands like someone who has spent years stripping away noise until only the essentials remain.
In the third episode of the High Times Podcast, Josh Kesselman sits across from the Trinidadian-American artist, songwriter and creative architect for a long, open conversation about smoke, discipline, vulnerability, work, and the strange ways people learn to live with themselves.
Watch the full podcast here.
A Conversation That Moves
James shows up the way he sounds on his best records: present, grounded, funny, observant. Josh opens the door, and instead of a question-and-answer session, the episode becomes more relaxed and lived in, like old friends exchanging notes amid the smoke. James gets to the heart of it, saying that anger is just a form of frustration. “If you’re not going to do nothing, you’re not fed up.” It’s a small line with big consequences, especially in a world where everyone feels pushed to pick a side and start swinging.
Josh responds with a family memory instead of theory. Josh responds with a family memory instead of a theory. There are no bad or good people. There are only people. It doesn’t require unpacking. It just sits there, like a joint in the ashtray, changing the air in the room.
Cannabis, Enhancement And The Limits We Imagine
Of course, they talk about weed. It’s not a brand or a flex, but a tool. It can be helpful or harmful depending on the way you use it. James is clear, “Do not become dependent on cannabis… Let it enhance your experience of life.” I don’t believe in dependency. I believe in enhancement.”
From there, the theme settles in: the difference between using something to run away and using it to come back — to yourself, to your work, to the people around you. James speaks about taking tolerance breaks to feel like his ‘raw kid’ self for a few days, and how he still designs entire collections and albums during that inspired stretch. He recalls those days and asks, “You’re out of tips?” Let me show you the correct way to fold an index card. If you fold it wrong, it will square up. You have to fold it with the fibers. You can see them. It sounds at first like a how-to for stoners. Then it lands as something else: a memory of improvising under pressure, of trying to keep people connected and uplifted when everything outside felt like a bad trip.
Vulnerability, Craft And The Long Road To Mastery
Midway through, the talk slows down and goes inward. The talk slows down and turns inward at the halfway point. James doesn’t overcomplicate it. He says that trauma can sometimes break down walls. Simple. Heavy. From there, they dive into the craft. Josh walks you through the disciplines behind the things that most people don’t think about. Microphones, rolling paper, and all the other objects that quietly support a culture. He speaks about the study of the history behind papers, old mills and forgotten brands. He says, “Don’t hesitate to go back and study what you missed.” It’s half advice, half confession.
James brings it back to people and places. He says that if you don’t research the culture and community of the people you are trying to reach, you may still have a good sound, but the impact will be different. You can only hear talent without that foundation. It’s about being honest, not perfect. The Scale Of Life
Towards the end of the episode, Josh pulls out one of his most prized possessions, an old package of rolling paper printed with a chart showing the progression of life from childhood through old age. He tells how, upon turning 50, he began to smoke a sheet of paper from the pack on each birthday. There will be a point when I run out sheets, you run out sheets, or you run out sheets. You can taste the countdown. James allows the moment to sit. Living Your Life is Your Job
The conversation keeps returning to the topic of how to live, not online or on paper but in real-time. James states it in the most realistic line of the episode: “Living is your job.” It’s your duty to live your life. You are not a hero or villain. “You are not a good person. You are not a bad person. You’re human. You’re human. The things you do is bad.” The strength of Episode 3 lies in its pace. It allows ideas to arrive as they would in real life, slowly, with tangents, detours and jokes. This is one of them. This is one of them.
Guest
Trinidad James
is a Trinidadian-American recording artist, songwriter and creative director whose work moves across music, fashion, storytelling and media.
Watch The Full Episode
Episode 3 of the High Times Podcast with Josh Kesselman, featuring Trinidad James, is
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