Somewhere around 37, give or take five years, a switch flips. The goals that drove you for two decades stop meaning anything, the achievements pile up and nobody cares, and the question quietly changes from how do I win to how do I die well. Dr. Drew Littlejohns has lived both sides of that line: multiple eight-figure brands, two bankruptcies, two divorces, seven and a half years sober, 25 years of mountaineering Colorado’s fourteeners with his kids, and a PhD in archetypal masculinity written under Doug Gillette, co-author of King, Warrior, Magician, Lover. This conversation is equal parts field guide and comedy hour.
In this conversation, you’ll learn:
What actually happens in a midlife crisis: the biological and psychological shift that turns external achievers inward, and why the new goals refuse to fit on a calendar
The three-step protocol for when you’re lost: stop moving, build two seconds of space between stimulus and response, and find a community that will love you until you can love yourself
Why playing for keeps is what men are starving for, told through 250 hours of hardcore World of Warcraft and a death one-third of a level from the finish line
The containment principle: why an uncontained area of your life (money, emotions, technology) tells your whole family that thing doesn’t matter
Sailing versus rowing to Catalina: the art of aligning with what is instead of grinding against it
Why the hardest question a man can be asked is “what do you want,” and the coaching method that traces a taboo fantasy back to the simple curiosity underneath it
The shadow shouts in taboo but whispers in curiosity. Listen to the whisper before it starts shouting.
BetterHelp: Get 10% Off Your First Month Of Therapy The ManKind Podcast has partnered with Betterhelp to make it easier for listeners to access licensed mental health therapists who can aid them in their mental health journey. Brandon and Boysen stand by this service as they use BetterHelp for their therapy needs. #Sponsorship #Ad
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