Leadership and the Longing to Belong With Jerry Colonna

On this episode of Redefining Work, I’m joined by Jerry Colonna, founder and CEO at Reboot.io, and author of “Reboot” and the upcoming “Reunion: Leadership and the Longing to Belong.” We discuss what it means to bring your whole self to work, how to become more self-aware, and why it’s everyone’s responsibility to dismantle negative social systems.

Jerry has led a rich and wide-ranging career, having worked as a reporter, a venture capitalist, a teacher, and now a writer and executive coach. That variety has shaped who he is today. 

“I think that the richest lives, the fullest lives, are often marked by these interesting inflection points, where we allow ourselves the liberty and the luxury of trying something new,” Jerry says. 

In this episode, I’m thrilled to share Jerry’s advice for helping people feel complete at work and in society. 

You can also listen/share the episode directly syndicated on any of these channels: Apple Podcasts | Spotify | Google Podcasts

Move Around, Not Just Up

Focusing too narrowly on career growth can restrict our potential. Many of us fall into the narrative of moving “up and to the right” in our careers, Jerry says, but experimenting with new possibilities allows us to build more complete identities — and bring that fullness to our work.

“One of the challenges that we have, as modern animals, is that we believe so firmly in climbing the rungs of a ladder, or moving up and to the right, that we fail to welcome in the various parts of ourselves,” Jerry says. “And then we create cultures where the fullness of our colleagues is not welcomed in, and we become droids. We become mechanistic expressions of work.”

Organizations can support innovation and people simultaneously. They do so by perceiving each person’s unique interests and passions “not as a distraction from your work, but as an enhancement, and as a supplement, to the way in which you operate and you do your work,” Jerry says.

He advises leaders to create spaces where everyone can come to work as whole people instead of having to build their identity around a particular role.

Embrace Learning and Self-Awareness

As an executive coach, Jerry has encountered many ambitious people with expertise, yet they struggle to build on their success. As a business leader, it’s tempting to tell people what to do, but the real value leaders provide is empowering people to navigate their next steps.

“Our real task is to work our way out of a job. Our real task is to unleash the potential of people that we work with,” he says. “And so if we tell them what to do in the moment, it may alleviate a certain amount of anxiety, and that's useful. But really, what we want to do is to teach them to fish.”

Getting an outside perspective from a leader or coach can help us be more mindful. We naturally go on “autopilot,” which isn’t necessarily a bad thing. But if we turn on autopilot instead of consciously speaking, interacting or making decisions, we can hurt ourselves or others. 

This can be a problem for individuals, organizations and our broader society. “We then find ourselves saying things like, ‘Well, why did I speak so aggressively to that person?’ … Why is it that we have an organization that is constantly avoiding conflict? Or, as is often the case right now, in our society? Why is it that we scapegoat various peoples?” he says.

We must turn off that autopilot and examine our behaviors “to create a certain kind of opportunity for the best of ourselves to emerge,” Jerry says. “And I think that's a radically important task for those of us who hold power, both within organizations and in our society.”

Take Responsibility for Creating Change

In 2020, Jerry realized he had to use his privilege to be more active in fighting systems of oppression. “We have a moral responsibility, especially those of us who hold power in some form or another,” Jerry says, “to see the ways our silence, our lack of engagement in the struggles of the world, implicitly support the oppression.” 

The more he came to terms with this responsibility, the more Jerry recognized that few institutions answered the call. “We see a connection between, say, anti-Black racism, anti-immigration feelings, the marginalization of trans people, that direct assault on civil and human rights — and the silence that I hear from business,” he says. 

In his latest book, “Reunion,” Jerry walks readers through a journey of radical self-inquiry, helping us understand how we can dismantle systems of oppression and relieve the pressure from those who have long fought these battles. “Too often the work of doing the work has fallen to the people who have borne the cost of systemic othering,” Jerry says. 

Taking on the work of dismantling systemic oppression is more than being an ally, he says, it’s becoming a “co-conspirator” in putting a stop to systemic othering — and the work has just begun. By looking inwardly first, each of us can contribute to creating a larger sense of belonging.

People in This Episode

Jerry Colonna: LinkedIn, X (Twitter), “Reunion: Leadership and the Longing to Belong”

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