There’s a moment, somewhere past the hour mark, when Trinidad James leans back and drops it without drama: “I’m not fighting for my life. 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 Q&A, the episode settles into something slower and more lived-in, like two old friends comparing notes in the middle of the smoke.
Early on, they slide into the emotional weather report of the times: anger, frustration, this feeling that everything is at a boil. James cuts through it: “Anger is really just aggravation,” he says. “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. He talks about his grandfather, shot three times fighting Nazis, once in the head, and how he came home without hate, even going back after the war to visit the people who had once been “the enemy.” Then he quotes his grandmother: “There are no good people. There are no bad people. There’s just people.” It doesn’t need 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. But not as a brand deck or a flex; more like a tool that can help or hurt depending on how you hold it. James is clear: “Do not be dependent on cannabis… let it enhance your life experience. 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 talks about taking tolerance breaks just to feel like his “raw kid” self again for a day or two, and how that version of him still designs whole collections and albums in one inspired stretch.
Josh counters with pandemic flashbacks, when the whole world was locked inside and he turned his feeds into rolling school. “You’re running out of tips?” he says, remembering those days. “Let me show you how to an index card and fold it the right way… If you fold it the wrong way, it’ll square up. No, you got to go with the fibers. You can see them. Hold on to the light, maybe you can see the fibers.”
At first, it sounds like a stoner how-to. 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. They crack open vulnerability: how it works, how long people avoid it, and the strange triggers that finally kick those doors down. James doesn’t overcomplicate it. “Sometimes trauma breaks down walls,” he says. Simple. Heavy. True.
From there, they get deep into craft. Josh walks through the discipline behind things most people never think about: microphones, rolling papers, all the objects that quietly hold up a culture. He talks about studying the history of papers, the old mills, the forgotten brands, the people who came before. “Don’t be scared to study the step that you skipped,” he says. It’s half advice, half confession.
James brings it back to people and places. If you don’t study the culture or the community you’re trying to speak to, he says, your work might still sound good, but it won’t hit the same. Without that grounding, “you only hear the talent but you don’t feel the soul.”
That back-and-forth — materials and music, factories and feelings — is where the episode really breathes. It’s not about being perfect. It’s about being honest with the path.
The Scale Of Life
Late in the episode, Josh reaches for one of his favorite artifacts: an old pack of rolling papers printed with a chart of life, from childhood to old age. He explains how, after turning 50, he decided to smoke one sheet from that pack every birthday. “There will come a time when I’m either going to run out of sheets, the sheets beat you, or the sheets are going to run out of me.”
It’s a metaphor you can hold in your hand. A countdown you can actually taste. James lets the moment sit. You can almost hear the pause in the room before they move on.
Living Your Life Is Your Job
Again and again, the conversation comes back to how to live: not online, not on paper, but in real time. James says it in one of the episode’s most grounded lines: “Living your life is your job. That’s what you’re obligated to do.” You’re not a saint or a villain, he reminds people. “You’re not a good human. You’re not a bad human. You’re human. The things you do are good. The things you do are bad.”
Josh echoes it with his own angle on responsibility and legacy: not trying to be remembered as rich, but as someone who actually tried to help, someone who didn’t “subscribe to hate” even when life gave him every excuse to.
Why This Conversation Matters
The strength of Episode 3 lies in its pace. It doesn’t chase clips or controversy. It lets ideas arrive the way they do in real life: slowly, with detours, jokes, tangents and sudden clarity. It’s a long, smoke-filled talk between two people who actually care about craft and spirit: about anger, memory, mastery, cannabis, survival and what it takes to feel fully alive in a time that keeps asking you to shrink.
High Times has always been at its best when it makes room for those conversations. 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 now available on the High Times YouTube channel.
