Show Notes
Adam “Smiley” Poswolsky is a workplace belonging expert, internationally recognized keynote speaker, and bestselling author whose work explores friendship, loneliness, human connection, and the ways technology is reshaping our relationships with one another. In this conversation, Sam and Smiley trace a line from the early digital-detox movement and Camp Grounded to the present moment of AI, hybrid work, and widespread social disconnection.
Smiley speaks about the loneliness crisis, the particular struggles facing young people and men, and why belonging and friendship have become increasingly important both inside and outside the workplace, arguing that organizations need to design intentionally for human connection, and that belonging cannot simply be handed off to an HR department - instead, it has to become part of the everyday culture of a workplace.
The conversation also turns to artificial intelligence and the temptation to automate increasingly large parts of our creative and professional lives. Smiley makes the case for using AI thoughtfully while preserving the kinds of distinctly human practices—conversation, presence, intuition, personal storytelling, friendship, and simply spending time thinking—that technology can easily crowd out.
Along the way, Sam and Smiley explore the value of “weak ties,” the difference between belonging and mattering, the difficulty of genuinely listening to another person, and why our most personal stories may become increasingly valuable in an age of machine-generated content. They close with Smiley’s practice of moving from comparison toward care: when ambition, social media, or creative anxiety starts to take over, turn toward friendship, community, and service.
About Adam “Smiley” Poswolsky
Adam “Smiley” Poswolsky is an internationally recognized keynote speaker, workplace belonging expert, and bestselling author of The Quarter-Life Breakthrough, The Breakthrough Speaker, and Friendship in the Age of Loneliness. He has spoken for organizations including Apple, Google, Verizon, JPMorgan Chase, and the U.S. Navy, and his work has appeared in publications including Harvard Business Review, The Wall Street Journal, Fast Company, The New York Times, and The New Yorker.
Learn more about Smiley at smileyposwolsky.com, through his Substack newsletter Friends with Smiley, on LinkedIn as Adam Smiley Poswolsky, and on Instagram at @whatsupsmiley.
More from Voices of Esalen
Today, we return to that stack of dusty reel to reels, discovered a couple of years ago, as a part of the storied Esalen archives. This one turns out to be a gem: a conversation that was recorded in 1976, not at Esalen, but at the Bel Aire School in Tiburon, California, likely recorded and preserved by Esalen archival legend Paul Herbert. This talk features two famous thinkers - psychologist Rollo May and author of the pentagon papers, Daniel Ellsberg. Their subject is good and evil. Rollo May was a pioneering figure in American existential psychology as well being as an early teacher at Esalen institute. Earlier in life, May had been a Protestant minister and had studied with the prominent theologian Paul Tillich. By the time of this recording, he had published some of his pivotal books, including Love and Will, Power and Innocence, and The Courage to Create. In those texts he explored human beings creative possibilities and their capacity for destruction. Daniel Ellsberg was a former Marine as well as a Harvard-trained economist who worked as a strategic analyst at the RAND Corporation and served in the Defense Department, where he helped shape nuclear war planning and American policy in Vietnam. He rose to great prominence in 1971 when he provided the Pentagon Papers to the press, where he exploded the classified history of American involvement in the war. He faced charges carrying a possible sentence of 115 years; the case was dismissed in 1973 because of government misconduct. So when these two men met in 1976 at the time of this talk, the Vietnam war had only been over for one year. Ellsberg’s prosecution was only a few years behind him. Rollo May had recently published a book on creative courage. Listening today, we might keep those lives in mind as we encounter a world that remains as difficult, and full of urgent moral themes, as ever.
When Ellen Watson first arrived at Esalen in the summer of 1984, she expected to stay for a few months. Instead, she remained onsite for more than two decades, engaging in an immersion in the practices, teachers, and experiments that helped define Esalen during one of its most fertile eras. She has remained associated with Esalen, teaching programs and training bodyworkers and teachers of bodywork.
Artificial intelligence has become deeply embedded in everyday life, and way too nuanced to describe as a single phenomenon. In this third installment of How We’re Really Using AI, Sam attempts to create clarity through specificity, speaking with people whose work and lives reveal distinct corners of the emerging AI landscape.
In this live conversation recorded at Esalen in the spring of 2026, author Robert Moor joins Andrew Castle, weaver of Esalen’s Treenet, to explore the ideas at the heart of Moor’s new book, In Trees. Moor describes trees as a way of being: branching outward into curiosity and experimentation, pruning what no longer works, adapting around difficulty, and remaining deeply rooted in place and relationship.
In this episode, Sam speaks with Jet Eveleth, a clown teacher, performer, writer, and integrative medicine practitioner who lives at the fertile crossroads of medicine and mischief. Jet has studied integrative medicine, Traditional Chinese Medicine, meditation, and psychotherapy at Harvard Medical School, while also training with legendary clown teacher Philippe Gaulier, touring with Second City, and performing in the spectacular Las Vegas show Absinthe.