Sage Reflections: Dr. Deena Shaffer

"Move In The Direction Of Aliveness"

I first met Dr. Deena Shaffer in the dimly lit basement of Toronto Metropolitan University, back when I had an office that smelled like old ambition and burnt coffee. She was a beam of light in that dreary space—radiant and magnanimous. And what struck me then still holds true today: how she appears is how she is in real life.

Over the years, I’ve followed her journey with admiration, watching her evolve from a brilliant academic-practitioner into a soulful entrepreneur and thought leader. She’s become, to me, a wise and loving older sister—a kindred spirit whose light feels both ancient and ahead of its time.

Going into our Sage Advice conversation, I expected wisdom. I expected warmth. What I didn’t expect was the pain behind it all—the origin story shaped by grief, by the unimaginable back-to-back loss of both parents in her youth. To witness someone so luminous trace their light back to such profound darkness was both humbling and transformative. What unlocked in real time was a new mirror—one in which I could see my wife Bailey and I more clearly. We pride ourselves on being both academics and entrepreneurs, and I believed that rare duality made us outliers. But Deena revealed a third way: that we’re not alone, that we’re part of a quiet but rising tribe of ambidextrous souls who heal through creation.

If there’s one message from Episode 2 I hope lands with you, it’s this:

Move in the direction of aliveness.

1. Enduring Wisdom

Deena said this with the ease of someone who has lived it, over and over again. And when she did, something in me both softened and sharpened. I’ve come to learn—sometimes the hard way—that nothing about my life is meant to be linear. Whenever I’ve tried to walk the path prescribed by others, I’ve ended up smaller, dimmer, more dissonant with myself.

This quote transported me back to the moment I left Toronto Metropolitan University to pursue entrepreneurship full time. My friends and mentors got it. So did my fellow innovators. But my boss didn’t. And in their disappointment, I saw the familiar face of conformity—the one that asks us to stay, to settle, to squeeze ourselves into legacy systems. That moment should have come sooner. All of them should have.

The truth is, I’m not meant to be employed. I’ve tried, sincerely. But I’m an entrepreneur, artist, activist, and creative at heart. Structure, when it’s not of my own making, chafes. I want to be me. Be free. Be weird. And that has always required going left—especially when everything else is going right.

2. Unsettled Wisdom

“Live life as though everything is rigged in your favour.” — Rumi

When Deena shared this, my first instinct was to nod. To agree. To believe. But then a quiet resistance flared up in me—a tension between the life I want to believe in and the one I’ve lived so far.

I’ve experienced more loss, heartache, failure, and disappointment than their opposites. There were seasons—long ones—where nothing felt rigged in my favour. When a previous engagement was broken off by people in pain, it shattered the illusion that I could manifest a life of light by simply believing in it. Up until that point, I had tried to live that way—like the universe was conspiring for me. But after that rupture, everything started to feel rigged against me. I kept showing up in hope, only to be met with more collapse.

And yet… something has shifted.

I find myself entering a new season. One where things—slowly, subtly—are beginning to go my way. Not all of them. But enough that I'm finally receiving evidence that the world might actually reward faith. And so I'm learning, day by day, to believe again—not naively, but courageously. To act as if things are rigged in my favour, even if I still need to squint to see it.

3. Legacy Wisdom

When Deena said those words, something ancient stirred in me. My eyes welled—not just because the phrase was beautiful, but because it named something I’ve been orbiting for years. I call it love. She calls it aliveness. But it’s the same thing.

For me, “lead with love” has always been a dual command: to lead others through love and to allow love itself to lead me—as if it were a future way of being, calling us forward. Deena’s framing made it more visceral. Aliveness is love with roots in the body. It’s a compass made of breath, of pulse, of presence. And in that, I found a new clarity.

This idea echoes through everything I do. It’s not just how I lead—it’s how I live. Love, in the Bell Hooks sense, is the will to nurture the spiritual growth of another. Sometimes that “other” is yourself. Sometimes it’s the world.

If more people lived this wisdom—if they truly chose aliveness over performance, love over fear—we’d see a radically different world. Safer. Softer. More compassionate. People wouldn’t be trapped in ignorance, because they’d have loving teachers. They wouldn’t be crushed by poverty, because they’d have loving governments. They wouldn’t be alone in their vulnerability, because they’d have loving communities.

It’s a simple idea. But like all great truths, it could change everything.

4. Quotable Wisdom

Some sage gems from Episode 2 worth revisiting:

• “Move in the direction of aliveness.” - Dr. Deena Shaffer

• “Loss is a barometer.” - Dr. Deena Shaffer

• “I leave it all on the dance floor—because we’re still here.” - Dr. Deena Shaffer

• “If everyone else is going right, go left.” - Tenniel Rock

• “The honest mess of a life can be cohered.” - Dr. Deena Shaffer

• “May my life be a contribution to another human’s ease.” - Dr. Deena Shaffer

• “There is no one type of learner. There is no one way to learn.” - Dr. Deena Shaffer

• “Beauty felt like a luxury… except that it makes someone feel something in the story, in the resource.” - Dr. Deena Shaffer

• “I’m unafraid to be in the presence of someone who is like sobbing their guts out with animal cries because of loss. I know that too.” - Dr. Deena Shaffer

• “Learning happens everywhere, all the time.” - Dr. Deena Shaffer

• “Be small. Be small. Be small… doesn’t compute.” - Dr. Deena Shaffer

• “There is something for me in this idea: ethical entrepreneurship.” - Dr. Deena Shaffer

• “There’s more in you than you think—if only you were made to realize it.” - Hamza Khan

• “How can you be a ‘yes’ in someone’s journey?” - Dr. Deena Shaffer

• “It is the greatest privilege to be alongside two humans through the journey of them being alive and then them not being alive.” - Dr. Deena Shaffer

5. Emerging Wisdom

“Beauty is unimportant—except that it makes someone feel something in the story.” - Dr. Deena Shaffer

That line struck a chord deep in me. I’ve often wrestled with the role of aesthetics in leadership—wondering whether beauty, elegance, and grace matter when the world is burning. But Deena reframed it. Beauty, when it stirs the heart, becomes essential. It softens the guard. It makes space for transformation. That’s a principle I’ll carry into my keynotes, my coaching frameworks, and the next chapters of my forthcoming book.

And then there was the image—startling, haunting, unforgettable—of someone sobbing with animal cries in front of her. A pure grief. A rawness that most of us flee. But not Deena. She stays. She holds. She doesn't flinch in the presence of suffering, because she’s befriended her own. That, too, is a kind of beauty.

This episode evolved my belief in hope as a strategy. It reminded me that even someone as luminous and accomplished as Deena feels the temptation to give up. And yet, through ingenuity, tenacity, creativity, community, and above all—a pure heart—she persists. She believes in the possibility of a better outcome. That’s hope. That’s leadership.

If you walk away with one thing, I hope it's this:

Move in the direction of aliveness.

Thank you for tuning in to Episode 2 of Sage Advice. If something moved you, share it. If something landed, leave a review. Your reflections mean more than you know.

New episodes drop every Sunday morning—until then, stay hopeful, and move in the direction of aliveness.