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Jerry Colonna

@jerrycolonna.bsky.social
662 followers 595 following 76 posts

Cofounder and CEO of Reboot. Author of two bestsellers, Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong. More than two decades as a coach. Dang!

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Reposted by Jerry Colonna
Reboot @reboothq.bsky.social · 21/08/2026
There's a big difference between hands-off leadership and avoiding the hard stuff. @jerrycolonna.bsky.social explores how to facilitate tough conversations without owning problems that aren't yours. www.inc.com/jerry-colonn...
inc.com
https://www.inc.com/jerry-colonna/when-leaders-should-intervene-in-office-conflict/91225048
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Reposted by Jerry Colonna
Reboot @reboothq.bsky.social · 19/08/2026
When money comes up, what happens in your body? A tightness, a wish to talk about something else. Whatever arrives, it makes sense. It came from somewhere, and it was trying to keep you safe. Michelle Masters joins @jerrycolonna.bsky.social on the Reboot Podcast: buff.ly/J56wxYe
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Reboot @reboothq.bsky.social · 09/08/2026
Radical self-inquiry is not navel-gazing. It's the difficult practice of asking: What am I feeling? What am I avoiding? What truth am I withholding? And what is the cost of my silence? @jerrycolonna.bsky.social
buff.ly
Speaking Up as Radical Self-Inquiry
Radical self-inquiry is the deep, often difficult practice of turning inward and asking: What’s really going on with me?
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Reboot @reboothq.bsky.social · 07/08/2026
Kinship isn't only what's written in family Bibles or rendered in DNA. It's the felt sense of belonging with those whose values, heartbreaks, and hopes rhyme with our own. @jerrycolonna.bsky.social on finding your kinfolk:
reboot.io
Finding Kinfolk
In his essay, Jerry Colonna shares his reflections on finding kinfolk—those who feel like family, even if they aren’t.
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Reboot @reboothq.bsky.social · 24/07/2026
Transformation doesn't happen through transaction. In this Wisdom for Work conversation, @jerrycolonna.bsky.social and Angela McKenna discuss what it takes to build workplaces where accountability feels like respect, not humiliation.
reboot.io
Wisdom for Work #32 - Beyond the Review: Rethinking How We Talk About Performance at Work
Why does performance management feel transactional? Jerry Colonna and Angela McKenna examine why performance management is so challenging.
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Reboot @reboothq.bsky.social · 25/06/2026
Sabbatical isn't a pause from action; it's the action itself. The essential work of listening deeply. @jerrycolonna.bsky.social reminds us that the answers you seek don't come from the hustle. They whisper from the quiet spaces you create.
linkedin.com
LinkedIn Pulse
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Reboot @reboothq.bsky.social · 18/06/2026
Great leaders aren't the ones making headlines. They're the ones creating workplaces where people actually love to work. @jerrycolonna.bsky.social's piece on redemptive leadership reminds us that clarity comes from looking inward first.
inc.com
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Reboot @reboothq.bsky.social · 12/06/2026
"The best leaders don't let bad calls define their worth or paralyze their next move." How can you separate your self-worth from your leadership decisions? What decision are you avoiding because you're afraid of being wrong?
inc.com
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Reboot @reboothq.bsky.social · 31/05/2026
The question that cuts through all the noise: What is truly yours to do? @jerrycolonna.bsky.social's reflection on sabbatical reminds us that sometimes the most radical act is stopping long enough to listen.
linkedin.com
LinkedIn Pulse
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Reboot @reboothq.bsky.social · 24/05/2026
Jung said ignoring your shadow is like cutting off your head to get rid of a migraine. Most leaders do exactly that. Stay busy. Keep moving. But the parts of yourself you refuse to face have a way of forcing their way back in. @jerrycolonna.bsky.social
forbes.com
When Leadership Regret Becomes A Path To Redemption
To look back on all the mistakes you’ve made and be filled with regret is to be a leader.
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Reboot @reboothq.bsky.social · 16/05/2026
How have you been complicit in creating the conditions you say you don't want?" @jerrycolonna.bsky.social's signature question isn't about shame, it's an invitation to lifelong curiosity and a call to embrace radical self-inquiry with courage, not criticism.
inc.com
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Reposted by Jerry Colonna
Reboot @reboothq.bsky.social · 08/05/2026
Sometimes the life you built becomes the cage you need to escape. @jerrycolonna.bsky.social sits down with Chip Conley on Midlife Chrysalis to talk about the moment he almost gave up, and how that breakdown became his breakthrough.
meawisdom.com
The Emotional Journey of Jerry Colonna - MEA Wisdom
What if the life you built is no longer the one that fulfills you? In this powerful episode, former venture capitalist turned CEO coach Jerry Colonna shares
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Reboot @reboothq.bsky.social · 03/05/2026
The longing to belong is not just about finding our place; it's about remembering we were never meant to do any of this alone. @jerrycolonna.bsky.social explores finding true kinfolk in his latest newsletter:
linkedin.com
LinkedIn Pulse
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Reposted by Jerry Colonna
Reboot @reboothq.bsky.social · 27/04/2026
When is staying silent actually a failure of leadership? @jerrycolonna.bsky.social reminds us that true leadership means speaking up when it matters most, even when it's uncomfortable. The gritty work of leadership requires courage that few are willing to summon.
inc.com
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Reboot @reboothq.bsky.social · 22/04/2026
There's a difference between leading and simply managing. @jerrycolonna.bsky.social reminds us that true leadership means addressing the heaviness in the room that everyone feels. The climate at work shifts dramatically when people feel seen in their whole humanity.
inc.com
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Reboot @reboothq.bsky.social · 17/04/2026
The leader who commands respect rarely receives it. @jerrycolonna.bsky.social shares how authentic leadership creates the influence that force never could.
inc.com
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Reposted by Jerry Colonna
Reboot @reboothq.bsky.social · 10/04/2026
True leadership begins when you stop chasing the illusion of safety that money promises and start confronting the emotions driving your decisions. @jerrycolonna.bsky.social asks: Are you leading with empathy, or are you micromanaging out of fear?
inc.com
How Your Relationship With Money Shapes Your Leadership
Your relationship with money has the power to shape your leadership. Here is how to ask hard questions, confront emotions and move forward.
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Reboot @reboothq.bsky.social · 02/04/2026
All leaders face tough decisions, but how you handle them defines your legacy. @jerrycolonna.bsky.social offers essential reflection questions for mindful leadership:
inc.com
Legacy Isn't Just About Impact. It's Also About People
Legacy isn't solely for people you engage with daily. Read on to understand how your legacy extends beyond your internal circle.
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Reboot @reboothq.bsky.social · 29/03/2026
In his latest Inc. Magazine column, @jerrycolonna.bsky.social challenges leaders to look beyond the headlines and political pressures to examine what truly matters: building organizations where inclusion isn't just policy, but identity.
inc.com
Beyond the Trend: What Is the Future of DEI in Leadership?
Businesses implemented DEI in response to public pressure. Is it better to have an inclusion policy than not having one at all?
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Benjamin Dreyer @bcdreyer.social · 22/03/2026
Happy Chico Marx's birthday!
Groucho, Zeppo, Harpo, and Chico Marx.
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Reposted by Jerry Colonna
Reboot @reboothq.bsky.social · 20/03/2026
Our life experiences directly shape our business values. The courage to speak hard truths, to admit when things aren't working or when change is needed, comes from embracing our personal stories rather than hiding from them. @jerrycolonna.bsky.social
inc.com
How Your Story Can Shape or Break the Type of Entrepreneur You Become
Your story will shape or break the type of leader you are and the legacy you ultimately leave behind. You get to choose which it will be.
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Reboot @reboothq.bsky.social · 17/03/2026
Leaders draw closer to what truly matters with each return to self, purpose, and love. @jerrycolonna.bsky.social explores this cycle of renewal with Nucao's founders in a conversation on why personal transformation leads to organizational clarity.
reboot.io
#176 - Balancing Growth & Inner Purpose - with Christian Fenner, Mathias Tholey, & Sebastian Ross
Christian Fenner, Mathias Tholey, and Sebastian Ross discuss the transformative power of learning from failure with Jerry Colonna.
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Letters from A Psychotherapist @jemoyer.bsky.social · 28/02/2026
Shitty therapists
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Reboot @reboothq.bsky.social · 26/02/2026
Crisis leadership primer from @jerrycolonna.bsky.social: Put solutions on pause Listen deeply Honor your team's pain Stand on your values When navigating disaster, true leadership requires compassionate presence, not perfect responses:
inc.com
How to Lead Through Disaster
When disaster hits home, the only and best thing you can do as a leader is to stay present. Here is how to face grief in the workplace.
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Reboot @reboothq.bsky.social · 15/02/2026
The stories we carry with us shape our entrepreneurial journeys. @jerrycolonna.bsky.social explores how embracing your personal narrative (even the painful parts) impacts the people you lead and the legacy you leave behind. www.inc.com/jerry-colonn...
inc.com
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Reboot @reboothq.bsky.social · 10/02/2026
Elders aren't made by age. They're made by choosing to stay when it would be easier to disappear, by helping one more person make it through the night. @jerrycolonna.bsky.social on what it means to become an elder.
linkedin.com
LinkedIn Pulse
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Reboot @reboothq.bsky.social · 08/02/2026
"'Redemptive leadership is an act of waking up." @jerrycolonna.bsky.social examines how self-discernment enables leaders to retrieve what organizations have lost—whether that's vision, integrity, or the belief that renewal is possible:
linkedin.com
LinkedIn Pulse
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Reposted by Jerry Colonna
Reboot @reboothq.bsky.social · 06/02/2026
Ever wonder why leadership positions always seem to find you, even when you don't want them? It might go back further than you think. @jerrycolonna.bsky.social on parentification and the patterns that follow us into leadership.
inc.com
How Early Parentification Impacts Leadership Patterns
Early parentification leads to overachieving, boundary issues, and difficulty accepting praise and help. Here's how it impacts leaders.
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Reposted by Jerry Colonna
Reboot @reboothq.bsky.social · 04/02/2026
Grief is not something to be managed, but witnessed. In his latest Inc piece, @jerrycolonna.bsky.social reveals the unexpected truth about leading through disaster: true leadership is about presence, not quick fixes.
inc.com
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Reboot @reboothq.bsky.social · 30/01/2026
Ever feel like you're building something clear, only to watch the pieces shift right as you get close? You're not doing it wrong. @jerrycolonna.bsky.social on why trying to hold a fixed image of leadership might be what's holding you back.
inc.com
How to Figure Out the Puzzle Pieces of Your Leadership Journey
Leadership is like a puzzle that you desperately want to put all the pieces together. But the hard part is that you can’t.
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Reboot @reboothq.bsky.social · 29/01/2026
The expectations placed on leaders right now are brutal. Navigate every decision with perfect sensitivity. Don't upset anyone. Get it exactly right. @jerrycolonna.bsky.social shares advice for leading with courage when there's no clear right answer. buff.ly/RdIpIAY
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Metropolitan Community Churches @mccdenomination.bsky.social · 16/01/2026
Join the Council of Elders for an online Prayer Vigil for Peace. The virtual doors will be open for 6 continuous hours and you are welcome to join us for as short or as long a time as you wish. Just come along when you can and stay for as long as you want.
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Reboot @reboothq.bsky.social · 08/01/2026
Wellness routines help, but they're not enough on their own. Real transformation requires asking deeper questions about what drives you and why. @jerrycolonna.bsky.social on what radical self-inquiry actually looks like for leaders.
athyna.notion.site
How Self-Awareness Became The Ultimate Edge | Notion
Cover image 🎨
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Reboot @reboothq.bsky.social · 30/12/2025
Chatbots can predict the next character in a sequence. But they can't offer what @jerrycolonna.bsky.social calls "presence-based, heart-based empathy." In our latest podcast, psychiatrist Dr. Judson Brewer shares what AI therapy gets wrong—and right.
reboot.io
#182 - What AI Therapy Misses: The Power of Human Presence - with Dr. Judson Brewer
Jerry Colonna sits down with Dr. Judson Brewer to explore the hidden risks and surprising possibilities of AI-powered therapy.
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Reposted by Jerry Colonna
Reboot @reboothq.bsky.social · 29/12/2025
Your leadership legacy is shaped by how you navigate hard decisions. @jerrycolonna.bsky.social shares reflection questions to help you build a legacy you won't regret:
inc.com
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Reboot @reboothq.bsky.social · 23/12/2025
When leaders go first—when they honestly say “I’m yellow today, because I didn’t sleep last night”—they model something transformative: that it’s okay to be human. @jerrycolonna.bsky.social explores how vulnerability creates the foundation for trust & collaboration:
linkedin.com
LinkedIn Pulse
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Reposted by Jerry Colonna
Reboot @reboothq.bsky.social · 17/12/2025
Can algorithms replace human presence in therapy? Dr. Jud Brewer breaks down what AI actually is, prediction machines, and why that's fundamentally different from genuine connection.
reboot.io
#182 - What AI Therapy Misses: The Power of Human Presence - with Dr. Judson Brewer
Jerry Colonna sits down with Dr. Judson Brewer to explore the hidden risks and surprising possibilities of AI-powered therapy.
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Reposted by Jerry Colonna
Reboot @reboothq.bsky.social · 11/12/2025
When leaders avoid conflict, micromanage, or talk over their teams, it's often a symptom of deeper struggles. @jerrycolonna.bsky.social on how your unresolved patterns can distort your entire organization, and what to do about it. www.opensourceceo.com/p/jerry-colo...
opensourceceo.com
How Self-Awareness Became The Ultimate Edge
An interview with Jerry Colonna, Co-Founder & CEO at Reboot. 💘
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Reboot @reboothq.bsky.social · 09/12/2025
Winter has arrived, and with it, @jerrycolonna.bsky.social reflects on hummingbirds, paper cranes, and the deepest longing we carry: to belong. His newest piece weaves memory and wisdom into an invitation to live trembling but unbroken.
linkedin.com
LinkedIn Pulse
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Reboot @reboothq.bsky.social · 04/12/2025
We all wear masks. The question isn't whether we have them—it's what becomes possible when we set one down. @jerrycolonna.bsky.social on the cost of hiding and the work that redeems what we once feared most.
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Reboot @reboothq.bsky.social · 03/12/2025
Experience doesn't guarantee performance. Emotional intelligence does. Why @jerrycolonna.bsky.social believes you should stop filtering out entry-level talent who could transform your organization.
inc.com
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Reboot @reboothq.bsky.social · 01/12/2025
Behind every "how do I become a coach?" question is often a longing: to help, to serve, to be present to another human in their becoming. @jerrycolonna.bsky.social offers a compass for those who feel called to this work. Not a shortcut. A path.
linkedin.com
LinkedIn Pulse
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Reboot @reboothq.bsky.social · 26/11/2025
What does it mean to find strength in the midst of suffering? @jerrycolonna.bsky.social sits down with Chronicare CEO Oliver Ravn for a raw conversation about chronic illness, loneliness, stigma, resilience, and how our pain can become our greatest purpose.
reboot.io
#181 - Building The Company That 15-Year-Old You Needed - with Oliver Ravn
Jerry sits down with Oliver Ravn, CEO and founder of Chronicare, who's building peer communities for people living with chronic illness.
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Reboot @reboothq.bsky.social · 14/11/2025
"How do I become a coach?" Our CEO @jerrycolonna.bsky.social gets this question constantly. His answer might surprise you. It's not about certifications or scaling, it's about presence, discipline, and a lifetime's work.
linkedin.com
LinkedIn Pulse
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Reboot @reboothq.bsky.social · 18/11/2025
AI is putting leadership under unprecedented pressure. @jerrycolonna.bsky.social says this is NOT the time to lead quietly; it's time to be radically transparent with your teams about what's coming and how you'll navigate it together.
inc.com
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Reboot @reboothq.bsky.social · 11/11/2025
The pause that grounds you in your values? Essential. The indefinite freeze while waiting for certainty? Trust-destroying. @jerrycolonna.bsky.social breaks down the difference and shares his advice for leading when nothing feels clear.
inc.com
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Jerry Colonna @jerrycolonna.bsky.social · 27/11/2024
"These are the times that try men's souls. The summer soldier and the sunshine patriot will, in this crisis, shrink from the service of their country; but he that stands by it now, deserves the love and thanks of man and woman. Tyranny, like hell, is not easily conquered..." Thomas Paine
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Reboot @reboothq.bsky.social · 20/10/2025
Ever feel someone's nervousness become yours? Their fear of rejection pulling you to reject them? @jerrycolonna.bsky.social explores how to navigate these moments and stay in the truth of yourself. www.linkedin.com/pulse/wall-y...
linkedin.com
A Wall You Never Saw Before
"You will be walking some night / in the comfortable dark of your yard, / and suddenly a great light will shine / round about you, and behind you / will be a wall you never saw before. —Wendell Berry,...
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Reboot @reboothq.bsky.social · 14/10/2025
AI is transforming workforces, but the human element of leadership remains crucial. In his latest article for Inc. @jerrycolonna.bsky.social reveals how to build core values into your AI strategy while maintaining profitability.
inc.com
Lead the Machines: How Leaders Can Navigate AI's Impact on the Workforce
AI's impact on the workforce is increased profits and job cuts. Leaders can lead their teams with empathy in the face of rapid change.
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Bill Kristol @billkristolbulwark.bsky.social · 12/10/2025
Pope Leo quotes Hannah Arendt: “The ideal subject of totalitarian rule is not the convinced Nazi or the convinced Communist, but people for whom the distinction between fact and fiction and the distinction between true and false no longer exist." www.cbsnews.com/chicago/news...
cbsnews.com
Pope Leo calls for news agencies to stand as bulwark against "post-truths," lies and manipulation
Pope Leo XIV has encouraged international news agencies to stand firm as a bulwark against the "ancient art of lying" and manipulation.
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