Self-liberation for sensitive overthinkers.
Welcome!
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Who am I?
I’m Tom Asacker. And the answer to that question depends entirely on when you ask it.
I’ve written ten books, spoken to audiences around the world—including a paradoxical TEDx talk— and consulted with everyone from scrappy startups to global non-profits and Fortune 500 companies. I’ve collected titles that sound impressive on paper, but the real story is messier, more human, and probably more interesting.
I went to university to study art and somehow left with an economics degree—my first lesson that life rarely follows the script we write for ourselves. I started as a professional magician, which turned out to be perfect training for everything that followed. Magic taught me that what people see isn’t always what’s really happening, and that transformation requires a willingness to embrace uncertainty.
From there, I climbed into executive roles, stumbled through corporate buyouts, and became a CEO who learned more from mistakes than victories. I invented medical devices, launched companies, won design awards—perhaps because I never stopped painting—and yes, also failed spectacularly at ventures I’d rather not mention (like that internet thing I launched and quickly shuttered). Each misstep taught me something I couldn’t have learned from success alone.
People call me a catalyst and non-conformist, which sounds nice but really means I have trouble sitting still when things don’t make sense. I rattle cages not because I’m rebellious, but because I’m genuinely curious about why we do what we do—and whether there might be a better way.
I’ve spent most of my career fascinated by a simple question: Why do people believe what they believe and do what they do? It’s a question that’s shaped how I see everything from running companies to raising kids to understanding myself.
I don’t have all the answers, but what I have discovered through all this stumbling around is a unique philosophy, a mental model that’s both simple and powerful. It isn’t self-help—it’s self-liberation. When you stop buying into various mental illusions, you can finally relax without guilt, play without fear, and be yourself without anxiety. It’s a shift that changes everything, especially for anyone ready to break free from their own self-deceptive thinking and reclaim freedom and joy.
Oh… and why am I doing this? I’m doing it because it is the truth. I want to share what I’ve learned about breaking free from the mental traps that keep us stuck, get to know you and hear your story, and help you discover the same sense of psychological freedom that transformed my own life.
The biggest lie we tell ourselves is that we should be able to handle everything on our own. But psychological freedom isn’t a solo journey—it’s something we discover together, with people who can see what we can’t see and help us think differently about what feels impossible.
You can contact me here.
What is The Age of Unknowing?
The Age of Unknowing is more than a newsletter. It’s provocative inquiries, live experiences, podcasts, multimedia, and community learning—all designed to deepen our understanding of ourselves and the world in ways that transform how we see who we are and how we might live.
We stand at a remarkable threshold. The old certainties are dissolving, the maps we’ve relied on no longer match the territory, and the pace of change has outstripped our ability to create new ones. This might sound alarming, but I believe it’s cause for celebration.
As Tom Stoppard wrote in Arcadia, “It’s the best possible time to be alive, when almost everything you thought you knew is wrong.” When the external scaffolding of assumed knowledge and a shared reality crumbles, we’re freed from its constraints. We can stop being hypnotized by inherited wisdom and start living from the inside out—trusting our inner compass rather than outdated maps.
The tension you feel? That uncomfortable friction between what you were taught and what you're experiencing? That’s not a bug—it’s a feature. It’s the growing pains of consciousness expanding beyond the boundaries others set for it. We’re caught between worlds: the wisdom passed down by those who love us, and the raw reality streaming through our senses every day. When these don’t align—and increasingly, they don’t—something has to give.
But here’s what I see in this moment: an unprecedented opportunity. The Age of Unknowing belongs to those willing to embrace uncertainty as teacher rather than enemy. Together, we’ll explore what it means to live skillfully and with a sense of aliveness when solid ground gives way—not by grasping for false certainties, but by learning to navigate the questions themselves with curiosity, courage, and grace.
Here are some recent posts as examples of the kinds of topics we’ll be getting into.
Why subscribe?
Why not? As a free subscriber you’ll receive several full essays per month, as well as notifications to both recommend topics/questions and participate in group Zoom discussions.
I’m also toying with launching a paid subscription tier, where you’ll be able to:
Access all recorded Zoom discussions and podcasts
Join the comments and conversations
Read the full archives of all past articles
Receive invitations and discounts to in-person retreats
Access my transformation video program “How to Be Alive!” (a $199 value), because survival is not the same as aliveness.
Schedule a free, 1-hour coaching call with me (a $400 value, first come, first served)*
What can we explore together? Having navigated these paths myself, I can offer guidance whether you want to write a book or screenplay, launch a podcast, start a business, give compelling talks, patent an idea, build a speaking career, grow your brand, become a consultant or coach, develop stronger leadership skills, or even learn closeup magic. I've done it all—the successes, the failures, and everything in between.
*Pro tip: This type of subscription can often be expensed as a professional development or business expense.
Welcome to the adventure!
