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From Heartbreak, Through Resilience, To Equanimity

“You stayed in your core with your core beliefs. Your humanity stayed there. It may have been easier in some ways to give up that, but I think you would have lost yourself.” – Jerry Colonna 

Looking back over the many client conversations and Bootcamp circles I’ve had the honor of being present for, so many have been around transitions. The arc of a leader’s journey in the role of CEO is nothing short of turbulent, with its ups and downs, twists and turns. At some point along the way, they wonder: Am I the right person for this role? Or, maybe I should move on, but to what, and when will I know if this is right? Some leaders arrive at the juncture of transition more abruptly, like Chad Dickerson, our podcast guest in this week’s conversation with Jerry around his transition out of Etsy.  

And, like anyone in transition, abrupt or otherwise, there’s heartbreak and grief to sit with while the heart muscle of resilience grows bigger to hold it all so that we can be at peace, in a new place, with what we’ve been through and where we find ourselves. If we’re lucky, we find ourselves having arrived with more congruency between our inner person and our outer person. 

With that, I want to leave you with an excerpt from Jerry’s book and how he witnessed Chad’s leadership in transition. It’s a great prelude to this podcast conversation. 

From Reboot: Leadership and the Art of Growing Up:

Of course, the night would be perfect; the stars crisp and achingly bright, the lulling cadence of cars crossing into Brooklyn from Manhattan over Colonel Roebling’s wondrous bridge, the ka-thump, ka-thump, ka-thump of tires hitting expansion joints.

I’m sitting on a picnic table while Chad Dickerson sips from a bottle of beer. Tomorrow, Chad will announce to the world that he’s been asked to step down as CEO of Etsy, the online marketplace for handcrafted goods he had led for the past six years.

I am here to listen, to bear witness to, and hold the story of this bittersweet moment. It’s painful to watch my client, my friend, confront this new reality. Although he’d done many things right, although he’d grown into a leader with heart and authenticity, he was being fired.

I’m startled. I see something familiar but new in Chad, something powerful, something even more important than success or failure as a CEO. Years before, I’d given him the metaphor I often use with clients: “Take your seat.” “Sit like royalty in your leadership seat,” I say. “Sit as if you’ve the right to be there.”

Over time, he’d done just that. He’d taken his seat, the company had grown, he’d built a powerful team, and the stomach-churning had subsided. He did this by looking at his own stuff, through radical self-inquiry.

Watching Chad, reassuring him, I realize he’s gone beyond taking his seat as a CEO. He’s grown into something calmer, steadier. He’d become not merely the man he’d always intended to be, the man he chose to be, but a gentle, brokenhearted warrior who leaned into his own pain to find the strength to do what is right.

The back of the warrior is strengthened by knowledge of knowing the right thing to do. The soft, open heart is made resilient by remembering who you are, what you have come through, and how those things combine to make you unique as a leader.

What standards of dignity do you hold yourself to, regardless of how things unfold? What do the people who have counted on you to lead them need from you at this moment?

These questions shaped our inquiry into how he should handle what had transpired. His desire for radical self-inquiry had enabled him to ask (and to answer), “What kind of leader am I?”

Looking ahead to how Chad would carry himself as the news became public—as he passed the baton to his successor; as he fielded questions from his team, his colleagues, his coworkers, his friends, and his family—I knew he’d sit regally, steady even in his shaky vulnerability. I knew he would be transparent about his pain, but I didn’t realize that the dignity with which he communicated would make him the epitome of grace.


Finding Yourself in Unaccustomed Earth Human nature will not flourish, any more than a potato, if it be planted and replanted, for too long a series of generations, in the same worn-out soil. My children…
Still Standing Still Years ago, I wrote that founding, running, and working in a startup can often feel as if you’re often feel as if you’re standing still while your hair’s on fire.…
Fresh Tracks Growing up in West Central Wisconsin, I know intimately the inhospitable season that is winter. Parker Palmer notes in Letting Your Life Speak, that these winters will drive you crazy…



The Reboot Podcast with Jerry Colonna, Team Reboot, and Startup Leaders

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