Oct 5, 2018
Cass Midgley interviews Andy Chaleff, author of "The Last Letter."
We interview people you don’t
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encourage people in the process of deconstructing their faith and
help curb the loneliness that accompanies it. We think the world is
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We taped this conversation on Sept 29th, 2018.
The intro music is by Dave Weckl called "Just Groove Me"
The segue music on this episode is "The Living Years" by Mike and the Mechanics. Thanks for listening and be a Yes-Sayer to what is.
Andy Chaleff is a private mentor
and advisor to a handful of high-profile business leaders. He has
been behind the scenes
of many of the disruptions in mindfulness and education today.
eMindful, InnerExplorer, SOLE and The Cleveland Municipality School
District are just a few of the clients that he has helped guide to
His approach is unconventional. He lives with clients for a week at a time and touches all aspects of their lives, from child rearing to office intrigue, childhood trauma to facing death. His clients see him less as a business coach and more as a guide and partner in a lifelong journey.
Andy’s work is a byproduct of his own life story. He left the U.S. at age twenty to escape the sadness of his mother’s death, traveling the world. After backpacking for years, he finally set roots in Austria, where he helped to take an IT company public in 1997. He has visited over sixty countries and lived in seven of them around the world.
In spite of his business
success, Andy felt empty inside. In 2005 he sold everything he
owned to embark on a radical life do-over. After experiencing
profound inner transformation, he founded a coaching business with
his dear friend and mentor, Cees de Bruin. Their company,
Meaningful Relations, helped thousands of people in more than
Andy is a walking paradox. He is as loving as he is provocative, and his mentoring style is equal parts unsettling and comforting, irreverent and compassionate. His mother affectionately called him, “My little shit-stirrer.”
Andy founded the non-profit, The Last Letter, which goes by the same name as the book that he published, inviting individuals to share their feelings in letters to loved ones. His life's work is helping people connect with themselves and others through vulnerability and self-awareness. He helps people transform their most feared and painful emotions into their greatest source of motivation and connection.
When he is not consulting clients, he serves as the Director at Amsterdam’s Welvaren Training Center. He enjoys Amsterdam and bores people with the history of the city whenever he has the chance. Andy lives between Amsterdam and London, with a few months of the year spent in the US.
My conversation with Andy made me think of two movies, both of which illustrate the beauty of naivete. Naivete is an ignorance of norms of some kind--cultural, social, religious, political, logical, etc. Naivete can be bad or good for us depending on that which we're ignoring AND the amount of agency that is intact while acting on our ignorances. In other words, whether they are chosen by us, or we've fallen prey to them. Andy is the former. He's fully aware of how the world works, the norms of culture, society, logic, etc. And has seemingly chosen to transcend them and live his own life, follow his own gut, march to his own drum. In this sense it can't really be called naivete, can it. So for lack of a better word, I call it Zen. He walks 6 inches off the ground the rest of walk on. Now I know some woo-woo people who think they don't live by the same natural laws that the rest of us do, but that can be self-delusional. But Andy's practice walks right along the edge of that cliff without going over.
As an ex-Christian, I cringe at how naive I was to believe as literally as I did. To be a fundamentalist Christian, one must check their skepticism at the door. So in a way, it is willful naivete but not coming from within, but pressures from without--peer pressure, everyone's doing it, the fear of Hell, the desire to please God and people, etc. So still no agency.
One of the movies is called Enchanted, with Amy Adams and Patrick Dempsey. It's about a young maiden named Gisele who lives in a land called Andalasia--a beautiful place, displayed in cartoon animation, reminiscent of Disney fairy tale films. Andalasia is a fantasy world with a lot less trouble or problems than the real world, and as a result, emotions such as anger and frustration are rarely experienced by its inhabitants. Gisele is cast into the real world by an evil witch and we, the viewers, are transported into live action filming. The beauty for me is Gisele doesn't let the real world bring her down the cynical pessimism that is prevalent. She stays naive and it's refreshing to see. In this clip, she believes a prince charming character is coming to get her because a squirrel told her. Dempsey's character, a real human, tries to talk sense into her. Here he models a healthy skepticism by our standards, but in this metaphor she calls him out for being a no-sayer. An argument ensues and Gisele experiences anger for the first time and it feels good. My guest today, Andy, grew up thinking anger was bad because his dad was a rager. He suppressed his own anger in fear that he would become like his father. As a part of his therapy, he learned to be honest with his feelings and his body and no be ashamed of being human. Gisele is not ashamed of being naive. In fact she chooses it, like Andy. That being said (and spoiler alert), she ends up staying a human, letter her cartoon prince return to Andalasia, and falls in love with Dempsey. Because in the spirit of the dialectic, they were both right--his realism and her willful naivete.
The second movie is The Man Who Knew Too Little with my hero, Bill Murray. Murray is a naive Blockbuster Video clerk, named Wallace Ritchie, who travels from Des Moines, Iowa, to London to celebrate his birthday with his wealthy younger brother, James. When Wallace turns up on the same night that James has plans to attend a high-profile client dinner party where he hopes to bring in millions from a German investment firm, James needs to keep Wallace away during the evening, so he gives Wallace a ticket to the participatory Theater of Life. The theater game requires Wallace to assume a character and interact with actors portraying people in dramatic situations. At the corner phone booth, where the game is to begin with instructions of his mission, should he choose to take it, an actual call intended for an actual assassin rings first, unbeknownst to the producers of the show and Wallace, and he's now a part of a scheme to kill some key figures and revive the Cold War. Wallace leaves the phone booth to begin his mission--oblivious to its criminal intent, and the real assassin gets the call from the Theater of Life. Blissfully unaware, Wallace walks without fear into a complex web of intrigue involving defense ministers, call girls, and Russian hitmen. For Wallace, all the world's a stage, and he's amazed at the skill of the actors, while his pursuers are mystified by their adversary's fearlessness in the face of threats, torture and bullets.
In this clip, Wallace, played by Murray, (did I mention that?) has started his quest, thinking he's being filmed for the show, The Theater of Life, when he's approached by two actual hooligans wielding real knives.
So, perhaps you can see how these two movies demonstrate a way, albeit fictional and metaphorical, for us in the real world to take everything less serious, especially ourselves. Andy got so depressed after his mother died that he wanted to die. Instead of killing himself, he killed the anxious, depressed, fearful Andy and resurrected as the fearless, transcendent Andy you're about to meet. I need people to model for me those characteristics I truly aspire to be--caged up within me, afraid to emerge. Gisele, Wallace, Bill Murray himself, and Andy Chaleff are examples that encourage, enable and empower me to step into a more authentic version of myself--fearless, naive, and yes-sayers.