Jerry Colonna isn’t afraid to ask questions that make even the most senior executives uncomfortable.
You could say that it’s just part of his job. Jerry is the CEO and co-founder of Reboot.IO, an executive coaching and leadership development firm for some of today’s top CEOs and entrepreneurs, and the author of Reboot: Leadership and the Art of Growing Up.
However, it goes deeper. For Jerry, it’s also personal.
Before he was renowned for his innovative coaching techniques, he was—at least on paper—nothing short of an extraordinary success story.
In the 1990s, he won big by investing early in the internet with his venture capital firm, Flatiron Partners. Later, he moved over to the private equity arm of JP Morgan Chase.
But deep inside, Jerry wasn’t just miserable. He was thinking about ending it all.
Instead, Jerry chose to seek help and search within for what mattered in his own life. During this process, he learned to thrive in business and beyond through self-inquiry, embracing a mindful life, and connecting with himself as a human—flaws and all.
Now, he’s inviting other leaders to do the same.
A New Kind of Success
It was the early 2000s and Jerry Colonna appeared to be on top of the world. He was pivotal in funding some of Silicon Valley’s first major success stories. He was the founder of New York City’s first “Internet-specific” venture firms. He was named to the Forbes ASAP’s list of the Best VCs.
At just 38 years old, most would assume life couldn’t get much better for Jerry. However, despite the praise and growing wealth, he felt like he’d hit bottom.
“The irony was that I was at the peak of my external affirmation,” he says. “I was financially successful. I was well-regarded. Yet, inside, I felt hollow, empty, and hurting. I was lost and confused.”
Despite attaining a lifestyle most only dream about, Jerry felt hopeless. If he couldn’t be happy now, why even go on?
“I remember contemplating leaping in front of the subway at the Wall Street station in downtown Manhattan in February 2002,” he continues. “It was just after 9/11, and that part of Manhattan was still a wreck. The ghosts of those who had been killed still seemed to walk the ground.”
Thankfully, something inside stopped him from following his darkest impulses. Instead of ending his life, Jerry chose to take a more in-depth look at it. At his therapist’s urging, he left New York and sought treatment at Canyon Ranch in Arizona. It was a decision that would change everything.
The Human Behind Us All
Ready to embark on a new chapter, Jerry’s journey towards a new, enlightened life began before his treatment officially began.
On the way to Arizona, he dove into books about discovering your higher purpose, including When Things Fall Apart by Pema Chodron, and Let Your Life Speak by Parker Palmer. Inspired and energized, Jerry quickly immersed in figuring what made him who he was.
He also began exploring Buddhism on an intellectual level. “I became what I lovingly refer to as a nightstand Buddhist,” Jerry says. “I was reading all the good books, but I wasn’t actually living it.” That changed two years later when he officially took his refuge vows and dedicated himself to Buddhism.
So, how does this story of struggle, success, and spirituality have to do with high-level leadership? At least for Jerry, almost everything.
He realized that hiding behind the job title, net worth, and LinkedIn profile was a human with complicated hopes, dreams, and fears. For people to lead authentically and effectively, he realized that leaders had to open up, get to the root of their motivations, and answer some of life’s hardest questions.
It led him to radical self-inquiry.
The Power of Self-Inquiry
There’s nothing easy about self-inquiry. It forces you to be vulnerable and confront truths you’ve possibly spent a lifetime pushing away. However, if you truly want to become an authentic, resilient, and effective leader—not to mention live a life you enjoy—Jerry believes this practice is vital.
So, what exactly is self-inquiry? It’s all about digging into the core of who you are and deciphering what made you that way. It’s asking yourself the hard questions and doing your best to answer honestly.
“It’s to be done with skillfulness and compassion,” says Jerry. “When we start unpacking the wiring and the routines that define our lives, the first impulse is often to say, ‘What an idiot I am,’ or, ‘How can I be doing that?”
These thoughts are natural. Still, Jerry encourages leaders not to judge themselves too harshly. Instead, acknowledge these thoughts and continue to unpack them further.
It might feel like you’re digging yourself into a rabbit hole. But, in actuality, you’re getting closer to understanding the motivations that make you the person—and the leader—that you are.
Discover What Drives You
Why are you doing what you’re doing?
If you’re ready to begin practicing self-inquiry, then asking yourself that question is the perfect place to start.
Many answers could describe a leader’s motivation behind their philosophies, methodologies, visions, trajectories, and more. However, that’s only the beginning. Jerry pushes people to dig much deeper.
He wants leaders to follow their path in reverse, analyze it, and decipher if they’re currently where they want to be. “If you can’t understand how you’re wired and what’s motivating you,” says Jerry, “then how can you discern the right intention? It’s impossible.”
Jerry has consistently found that the more toxic, complex, or challenging motivations stem from an often deep-seated desire for love, safety, or belonging. This includes Jerry as well.
Growing up in poverty, he found his obsession with making money all went back to his childhood. “No amount of money would ever make me feel safe,” he says. “When I realized that, I understood that I didn’t need to pay attention to the money. I needed to pay attention to the things that would make me feel safe.”
That’s when he left a high-paying job he’d grown out of to find one he loved. “Just because I was good at it,” Jerry says, “doesn’t mean I was meant to do it.”
Whether self-inquiry unveils an entirely new path or reinforces the one you’ve been on for years, it’s a powerful way to ensure that you’re going the right direction.
“To me [self-inquiry] is an expression of agency,” says Jerry. “It’s a reminder that you have power. It’s a reminder that you have the capacity to choose much of your experience. Not all of it, but much of it.”
So this is the situation. What will you do?”
You’ll learn more about his mindful leadership advice, how meditation helps him through depression, why Jerry finds silent retreats incredibly important, and so much more.
Also, I’d love to connect with you on Twitter and LinkedIn, as well as have you keep up with my company imageOne. Learn about my mission to show business leaders how mindfulness can transform you and your business in my book donothing. Visit www.donothingbook.com for more information.