Jerry Colonna (CEO of Reboot, executive coach, former VC)08 May 2025

How have I been complicit in creating the conditions I say I don’t want?

6Frameworks

15Insights

Episode overview

Executive coach Jerry Colonna explains how asking, “How have I been complicit in creating the conditions I say I don’t want?” can restore agency without assigning total responsibility. He presents Reboot’s leadership equation—practical skills, radical self-inquiry, and shared experiences—and argues that its deepest purpose is resilience. The conversation applies these ideas to ambition, busyness, attachment, legacy, AI, and the unconscious family patterns that leaders reproduce inside teams.

Key ideas

Complicity differs from responsibility: examining one’s contribution to unwanted conditions can restore agency and expose self-delusion.
Reboot’s equation combines practical skills, radical self-inquiry, and shared experiences to strengthen leadership and resilience.
Powerful self-inquiry questions explore what is unsaid, unheard, avoided, or unconsciously recreated in relationships and organizations.
Attachment to growth, wealth, status, or praise turns achievement into a source of anxiety; worthwhile work can instead be approached as an intrinsically meaningful art project.
Shared experiences create confidential spaces where people can tell the truth without being fixed, judged, or forced to perform success.
AI can support reflection and pattern recognition, but Jerry hopes it elevates distinctly human capacities such as presence, connection, and strategic thinking.
Teams often reproduce their leaders’ unresolved childhood patterns, so people with greater organizational power carry greater responsibility for self-examination.
A growth mindset becomes counterproductive when treated as a rigid rule; useful mindsets should be held loosely and adapted to changing reality.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Self-Mastery4 steps

Breath-Taking Questions (Radical Self-Inquiry Prompts)

Journal on questions that scare you — that's where the gold is

Read →

Mindset4 steps

Detach Self-Worth From the Outcome (The Art-Project Reframe)

Pursue the work as a puzzle you enjoy, not as proof that you're somebody

Read →

Mindset4 steps

Hold the Mindset Loosely, Stay Attached to Growth

Keep the growth, hold the 'mindset' loosely — nailing it down turns growth into a fixed mindset

Read →

Leadership4 steps

Make the Unconscious Conscious to Fix a Team

Teams break on the leader's unsorted baggage, not on talent, strategy, or execution

Read →

Self-Mastery4 steps

The Complicity Question

Ask how you helped create the conditions you claim you don't want, to reclaim your agency

Read →

Leadership4 steps

The Reboot Leadership Equation

Practical skills + radical self-inquiry + shared experiences = better leadership and resilience

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 18

Jerry ColonnaMentionsJerry is one of the most well-known and respected executive coaches in the world. He's co-founder and CEO of Reboot
“Today my guest is Jerry Colona. Jerry is one of the most well-known and respected executive coaches in the world.”
▶ Watch at ~0:30approx.
Fred WilsonMentionsJerry co-founded Flat Iron Partners with Fred Wilson
“Prior to coaching, Jerry co-founded Flat Iron Partners with Fred Wilson”
▶ Watch at ~1:00approx.
Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“Well, thanks for having me, Lenny. It's it's really a delight to meet you and to be with you today.”
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Chris FrickMentionsmy conversation partner a guy named Chris Frick who was at was one of the co-founders at first round
“my conversation partner a guy named Chris Frick who was at was one of the co-founders at first round”
▶ Watch at ~11:00approx.
Bruce SpringsteenMentionsmentioned
“One of my favorite books is uh uh Bruce Springsteen's autobiography.”
▶ Watch at ~20:00approx.
Ally SchultzMentionsmy co-founder Ally Schulz and I the roots of Reboot the Company began with me designing or Ally and I designing these boot camps
“my co-founder Ally Schulz and I the roots of Reboot the Company began with me designing or Ally and I designing these boot camps.”
▶ Watch at ~27:00approx.
Will SmithMentionsmentioned
“there's a quote that will Will Will Smith shared once that I think you'll like.”
▶ Watch at ~31:00approx.
Seth GodinMentionsSeth is an absolute Legend he's published 21 books including 18 International bestsellers
“Seth Goden, who's a dear, dear friend of mine, talks about art projects.”
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Andrew LuoMentionsAndrew is CEO of One Schkeema, one of our longtime podcast sponsors.
“I'm excited to have Andrew Luo joining us today. Andrew is CEO of One Schkeema, one of our longtime podcast sponsors.”
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Dan HarrisMentionsmentioned
“When when my first book came out, Dan Harris, who's a really good friend and client”
▶ Watch at ~44:00approx.
Simon SinekMentionsAuthor of Start with Why
“you can go back to what Simon Synynic would say is your why.”
▶ Watch at ~47:00approx.
Mike TysonMentionsmentioned
“there there's this viral video of Mike Tyson.”
▶ Watch at ~49:00approx.
Shel SilversteinMentionsmentioned
“Oh, yes. Yes. Shell Silverstein”
▶ Watch at ~55:30approx.
Dan ShipperMentionsDan is the co-founder and CEO of Every which is a company that is at the very bleeding edge of what is possible with AI.
“There's a really interesting use case I saw today uh that Dan Shipper shared that I think you'd love”
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Peter SengeMentionsthe great uh business writer Peter Sang
“the great uh business writer Peter Sang says it is uh virtually impossible to challenge the assumptions that made you rich”
▶ Watch at ~1:06:30approx.
Carl JungMentionsmentioned
“Carl Jung once said, "Until you make the unconscious conscious, it will direct your life and you will call it fate."”
▶ Watch at ~1:13:30approx.
SocratesMentionsmentioned
“I think it was Socrates who said the unexamined life is not worth living”
▶ Watch at ~1:15:00approx.
Parker PalmerMentionsone of my favorite teachers and dear friends is Parker Palmer
“one of my favorite teachers and dear friends is Parker Palmer”
▶ Watch at ~1:15:00approx.

Resources · 33

RebootCoinedbook · Jerry Colonna and Ally Schultz
“He's co-founder and CEO of Reboot, an executive and leadership development firm”
▶ Watch at ~0:30approx.
ReunionMentionsbook · Jerry Colonna
“He's also partner at JP Morgan Chase and is the author of two books, Reboot and Reunion.”
▶ Watch at ~1:00approx.
Flatiron PartnersCoinedcompany · Jerry Colonna and Fred Wilson
“Prior to coaching, Jerry co-founded Flat Iron Partners with Fred Wilson”
▶ Watch at ~1:00approx.
JPMorgan ChaseMentionscompany
“He's also partner at JP Morgan Chase and is the author of two books, Reboot and Reunion.”
▶ Watch at ~1:00approx.
LinearRecommendssoftware · Linear
“you now get a year free of linear superhuman, notion, perplexity, and granola.”
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Lenny's NewsletterCoinednewsletter · Lenny Rachitsky
“if you become an annual subscriber of my newsletter, you now get a year free of linear superhuman, notion, perplexity, and granola.”
▶ Watch at ~1:30approx.
YouTubeRecommendswebsite · Google
“don't forget to subscribe and follow it in your favorite podcasting app or YouTube.”
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GranolaRecommendssoftware · Granola
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PerplexityRecommendssoftware · Perplexity AI
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NotionRecommendssoftware · Notion Labs
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SuperhumanRecommendssoftware · Superhuman
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SnowflakeMentionscompany · Snowflake Inc.
“EPO is a next generation AB testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams.”
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AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk
“EPO is a next generation AB testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams.”
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EppoRecommendssoftware · Eppo
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ContentsquareRecommendssoftware · Contentsquare
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Naropa UniversityMentionscompany
“I was doing a talk I think here in Boulder at Nuropa University where I used to be on the board of trustees.”
▶ Watch at ~7:00approx.
Fitler ClubMentionsplace
“I was at uh I think it's called the Fitzer Club in Philadelphia doing a fireside chat”
▶ Watch at ~10:30approx.
First RoundMentionscompany
“Chris Frick who was at was one of the co-founders at first round really really good guy”
▶ Watch at ~11:00approx.
RebootCoinedbook · Jerry Colonna and Ally Schultz
“in re in reboot, my first book, I tell the story of what I refer to as my pursuit of lemon drops.”
▶ Watch at ~13:00approx.
CEO Boot CampCoinedcourse · Jerry Colonna and Ally Schultz
“And the original iteration of the boot camp we used to call CEO boot camp”
▶ Watch at ~27:30approx.
OneSchemaMentionssoftware · Christina Gilbert
“Andrew is CEO of One Schkeema, one of our longtime podcast sponsors.”
▶ Watch at ~39:00approx.
OneSchema FileFeeds 2.0Coinedsoftware · OneSchema
“So, we just launched the 2.0 of one schema file feeds. We've rebuilt it from the ground up with AI.”
▶ Watch at ~39:30approx.
SubstackMentionswebsite · Substack Inc.
“Oh my god, what if all of those people who have signed up to my Substack suddenly disappear?”
▶ Watch at ~43:30approx.
AmazonMentionscompany · Jeff Bezos
“don't read the Amazon reviews.”
▶ Watch at ~44:00approx.
Soldiers and KingsRecommendsbook
“I'm reading a book called Soldiers and Kings, which I highly recommend, which is about human smuggling from Central America into the United States.”
▶ Watch at ~50:30approx.
The Giving TreeMentionsbook · Shel Silverstein
“it sounds like the giving tree to me.”
▶ Watch at ~55:30approx.
RiversideUsessoftware
“We're using this platform, Riverside, to record this”
▶ Watch at ~1:00:00approx.
EvernoteUsessoftware
“he kept all of his journal entries I think over 10 years journal entries from Evernote”
▶ Watch at ~1:02:00approx.
ClaudeUsessoftware · Anthropic
“he uploaded that I think he uses Claude and he's asked Claude to highlight things”
▶ Watch at ~1:02:00approx.
ChatGPTUsessoftware · OpenAI
“I I'm using Chat GPT really as a writing and thinking partner in a way that I did not have before.”
▶ Watch at ~1:02:30approx.
Apple PodcastsRecommendssoftware · Apple Inc.
“you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.”
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SpotifyRecommendssoftware · Spotify
“you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.”
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Lenny's Podcast websiteRecommendswebsite · Lenny Rachitsky
“You can find all past episodes or learn more about the show at lennispodcast.com.”
▶ Watch at ~1:22:30approx.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster1:05:00

The Trap of Growth Mindset: Hold It Loosely

Colonna's issue isn't with growth mindset itself — it's helpful — but with how the ego turns it into a fixed mindset, labeling things good/bad and nailing down 'the proper way to do things.' Buddhism taught him everything is falling apart all the time, even a growth mindset; getting too fixed on the right way sets you up for attachment and suffering. Citing Peter Senge — it's nearly impossible to challenge the assumptions that made you rich — he advises staying attached to growth while holding the mindset loosely.

Growth mindset is helpful, but the ego weaponizes it into a fixed mindset
Getting fixed on 'the proper way' creates attachment and suffering
Everything is falling apart all the time, even your growth mindset
Peter Senge: it's near-impossible to challenge the assumptions that made you rich
Stay attached to the growth; hold the mindset loosely

“even our growth mindset. When we get too fixed on the proper way to do things, we're setting ourselves up for attachment and therefore suffering.”
Jerry Colonna · 1:06:00

“So the question is, how do you hold a growth mindset? loosely knowing that you ought to stay present to the world as it is,…”
Jerry Colonna · 1:07:30

#growth-mindset#ego#buddhism#business

Hot Take· 4

Hot Take10:30

The Big Lie: Success Won't Make You Happy

The belief that reaching a certain level of money, a house, or status will make you happy is, per Colonna, the big lie we're socialized with since childhood. He recounts his own late-30s reality — outwardly successful yet suicidal — and a 19-year-old at a talk who summed up his whole philosophy: you don't have to be a jerk, or miserable, to be successful.

The idea that milestones deliver happiness is a lie taught since childhood
Colonna was outwardly successful but suicidal and lost in his late 30s
You don't have to be miserable to build a career
You don't have to be cruel to succeed

“It's not only not the case, it's the big lie that we're socialized with since childhood.”
Jerry Colonna · 10:30

“So what you're telling me is you don't have to be an [ __ ] to be successful.”
11:30

#happiness#success#socialization#mental-health

Hot Take32:30

Attachment Is the Source of Suffering — Treat Your Work as an Art Project

When Lenny admits his self-esteem tracks his newsletter's growth curve and quiets an imposter-syndrome voice, Colonna reframes it: what if you enjoyed the puzzle of creating something from nothing without your self-esteem being attached to whether it succeeds? Borrowing Seth Godin's language, treat the work as an art project. The deeper attachment isn't the money — it's proving 'I'm a somebody,' and that attachment is the source of the suffering.

Busyness and growth can be ways to quiet an imposter-syndrome voice
Alternative: enjoy the creative puzzle without pinning self-esteem to the outcome
Seth Godin's 'art project' framing detaches ego from results
The real attachment is proving you're 'a somebody,' not the income
Attachment to the outcome fuels your own suffering

“What if you could enjoy the puzzle of trying to create something new, trying to create magic, something out of nothing?”
Jerry Colonna · 33:00

“But really the deeper attachment is see I'm not nothing. See I'm not a nobody. I'm a somebody.”
Jerry Colonna · 35:30

#attachment#imposter-syndrome#self-esteem#creativity

Hot Take44:00

Don't Read the Reviews — Write for Yourself First

When Colonna's first book came out, friend Dan Harris told him not to read the Amazon reviews; he read two in the first hour and none since, because he can't experience them without becoming attached to how people feel. He wants to sell books and move readers, but the person who gets the most out of his writing is himself — he writes to answer his own questions, and whether it becomes a book people buy is secondary.

Dan Harris advised him not to read the Amazon reviews
He read two reviews ever — to avoid attachment to others' feelings
The person who gets the most from his writing is himself
He writes to answer his own questions; sales are secondary

“said to me, uh, don't read the Amazon reviews.”
Jerry Colonna · 44:00

“But you know who gets the most out of my writing? Me.”
Jerry Colonna · 45:00

#writing#attachment#creativity#detachment

Hot Take57:30

AI Will Burn Away What Doesn't Matter in Being Human

On AI anxiety, Colonna — old enough to remember installing an IP stack and 1,200-baud modems — says a year ago he thought it was a similar transition, but now sees it as genuinely different, like putting on sharp, unsettling glasses that challenge our role as humans. His hope: AI takes care of what doesn't matter, while presence, human connection, and strategic thinking get elevated so we spend more time on what matters. He notes he uses ChatGPT and Claude as thinking partners while keeping his live human writing buddies.

AI feels different from prior tech transitions — not just a faster modem
It's like sharp, unsettling glasses that challenge the human role
Optimistic view: AI handles what doesn't matter; presence and connection get elevated
A colleague fed 10 years of journals to Claude to reflect back what he isn't saying
He uses AI as a writing/thinking partner alongside human writing buddies

“what I am hopeful about is that that which does not matter in the experience of being human kind of gets burned away and is…”
Jerry Colonna · 1:00:30

“Where does this all end up? I have no idea. You know, it is unsettling. It's uncanny and it's also enlivening and exciting.”
Jerry Colonna · 1:03:00

#ai#future-of-work#human-connection#technology

Explainer· 4

Explainer20:00

Unsorted Baggage: You'll Pay the Price in Tears

Colonna cites Bruce Springsteen's autobiography — 25 years in psychoanalysis — and Springsteen's point that we all carry unsorted baggage from childhood and will eventually pay the price of not sorting it, usually in tears. We're socialized to develop bypassing skills instead of consciousness skills, and the bill comes due later, sometimes as depression or entrepreneurs sabotaging their own successful businesses. Waiting only makes the tears more intense.

Everyone carries unsorted baggage from childhood
Bypassing it doesn't make it disappear — the price is paid later, in tears
Common band-aids: overwork, substance abuse, spiritual bypassing (ayahuasca, mushrooms)
Entrepreneurs sabotage success from a belief they don't deserve it
The longer you wait, the more intense the reckoning

“So, let me just let that statement land. Bruce [ __ ] Springsteen, 25 years in psychoanalysis.”
Jerry Colonna · 20:30

“we all have unsorted baggage. And at some point we're going to pay the price of not sorting that baggage. And the price more often…”
Jerry Colonna · 21:00

#therapy#childhood#self-sabotage#avoidance

Explainer27:00

Shared Experiences: A Circle That Holds Space Without Fixing You

Reboot grew out of CEO boot camps where Colonna would bait-and-switch first-time CEOs — promising practical skills, then asking questions like "Who would you be without the story of who you are?" The value came from doing that work inside a circle of people who have your back and can hold space without fixing you or judging you. In an entrepreneurial culture trained to pretend everything is 'up and to the right,' the power of shared experience is being able to just tell the truth.

Reboot began as CEO boot camps that swapped tactics for deep questions
'Who would you be without the story of who you are?' is a core prompt
Shared experience = a group that holds space without fixing or judging
Entrepreneurs are socialized to pretend everything is working
The point is a relationship where you can tell the truth

“And imagine sitting in a group of people who can just hold that space without fixing you, without telling you what you're doing right or…”
Jerry Colonna · 28:30

“Imagine having the capacity to be in relationship with people where you can just tell the truth. That's what shared experiences are about.”
Jerry Colonna · 29:00

#community#vulnerability#leadership#reboot

Explainer41:00

The Second Noble Truth: Pushing Away Suffering Increases It

Colonna uses the Buddha's four noble truths to answer the fear of losing income and comforts. The key one is the second: that which we do to push away suffering increases suffering. Buying the nice couch or house to enjoy it is fine; buying it to push away the deeper question — am I good enough to be loved, safe, and to belong — only tightens the tenuous hold on your okayness. It all comes down to why you're doing what you're doing.

The four noble truths: suffering exists; pushing it away increases it; there's an end; the eightfold path
Buying things to enjoy them is fine; buying them to escape a fear is the trap
The underlying fear: am I good enough to be loved, safe, and belong
Motivation matters more than the purchase itself

“And the four noble truths are life is filled with suffering. That which we do to push away suffering increases suffering.”
Jerry Colonna · 42:00

“That which we do to push away suffering will increase suffering.”
Jerry Colonna · 43:00

#buddhism#suffering#money#consumption

Explainer1:11:30

What Really Breaks Teams Isn't Talent — It's Unsorted Baggage

Teams rarely fail from lack of talent, strategy, or execution, Colonna argues, but from the unresolved demons and unsorted baggage of their members. Groups fall into dynamics — a scapegoat, a truth-teller — and without individual self-inquiry they repeat the patterns of their family of origin. He tells of a CEO who realized his team dodged painful topics with jokes 'just like my family,' and invokes Jung: until you make the unconscious conscious, it directs your life and you call it fate.

Teams fail from unsorted baggage, not lack of talent/strategy/execution
Groups reproduce family-of-origin patterns without self-inquiry
A CEO recognized his team's joke-deflection as 'just like my family'
Jung: make the unconscious conscious or it directs your life as 'fate'
If the most powerful person won't do their work, the group manifests their dysfunction

“Carl Jung once said, "Until you make the unconscious conscious, it will direct your life and you will call it fate."”
Jerry Colonna · 1:13:30

“If that person refuses to do their work, the entire group will become uh a manifestation of early dysfunction in the individual's lives.”
Jerry Colonna · 1:14:30

#teams#leadership#group-dynamics#psychology

Story· 2

Story13:30

The Pursuit of Lemon Drops

As a boy growing up amid chaos and financial insecurity, Colonna found stability at his immigrant grandparents' home, where his grandfather kept an endless supply of lemon drops in a green pantry — which he came to equate with wealth and safety. By his 30s he had the lemon drops (outward success) but didn't feel safe, which forced him to examine how his relationship to money shaped his career, school, and self-worth choices.

Childhood chaos and insecurity made his grandparents' home a source of stability
Lemon drops became a symbol of wealth and safety
By his 30s he had the symbols of success but still didn't feel safe
The gap drove him to examine how money shaped his life choices

“I had lemon drops, but I didn't feel safe, which was kind of a mind [ __ ]”
Jerry Colonna · 14:30

#money#childhood#self-worth#story

Story47:30

What Kind of Ancestor Will I Be? Legacy and the Toppled Oak Tree

With his children now adults, Colonna is animated by the question of what kind of ancestor he wants to be — what those who come after him will believe was true about him. He counters Mike Tyson's dismissal of legacy, saying he can't shake the thought that someone down his lineage will ask 'What did you do?' about a hard time in the world. He closes with the image from his book Reboot of a toppled oak tree — 'Here lies a good man' — wanting to dissolve into the earth having lived purposefully.

Colonna's guiding question: what kind of ancestor will I be?
Legacy = what descendants will believe was true about you
He rejects Mike Tyson's view that legacy is a made-up thing that doesn't matter
He wants the answer to 'What did you do?' to be 'I tried'
The oak tree image: 'Here lies a good man,' dissolving into the earth having been purposeful

“he's like, I don't give a I don't give a [ __ ] about my legacy. It's just a madeup thing that doesn't matter.”
49:00

“at the end of my days, I want to be like this tree, just slowly dissolving into the earth, having done the best job I…”
Jerry Colonna · 54:00

#legacy#meaning#mortality#purpose

Takeaway· 4

Takeaway04:30

The Complicit Question: The Coaching Prompt Jerry Colonna Is Known For

Colonna's signature question is "How have I been complicit in creating the conditions I say I don't want?" He is deliberate about the word complicit: it means accomplice, not responsible — you're driving the getaway car, not robbing the bank. The point isn't self-blame; it's to evoke your own agency and expose the ways you delude yourself, e.g. claiming you hate being busy while feeling unnerved when your calendar isn't jam-packed.

Complicit ≠ responsible — think accomplice, the getaway driver not the robber
The question's purpose is to evoke agency, not assign blame
It surfaces self-delusion: saying you don't want something you secretly seek
Example: 'I don't want to feel busy' while feeling disconcerted when the agenda isn't packed

“How have I been complicit in creating the conditions I say I don't want?”
Jerry Colonna · 00:00

“As I I will share, you are driving the getaway car. you're not sticking up the bank teller.”
Jerry Colonna · 05:00

#self-inquiry#coaching#agency#self-awareness

Takeaway24:00

Four Radical Self-Inquiry Questions to Journal On

For people who journal but don't know what to journal on, Colonna offers a set of questions designed to startle you: How have I been complicit in creating the conditions I say I don't want? What am I not saying that I need to say? What am I saying that's not being heard? What's being said that I'm not hearing? You don't have to share the answers with anyone but yourself — self-delusion and attachment are the biggest contributors to our own suffering.

Journaling helps most when you have the right questions to sit with
The four questions center on complicity and on unspoken/unheard truths
You know you're in the zone when a question takes your breath away
The most important person to share the answers with is yourself
Self-delusion and attachment are the biggest sources of suffering

“So my famous questions include things like what am I not saying that I need to say?”
Jerry Colonna · 24:00

“Self delusion along with entachment are the biggest contributors to our own suffering.”
Jerry Colonna · 26:00

#journaling#self-inquiry#questions#buddhism

Takeaway37:00

The Spelling Test on the Fridge and Unconditional Love

When we stick a child's spelling test on the refrigerator out of pride, the unintended message can be that we only love them because they got an A. Colonna argues parents must do their own internal work to convey unconditional love — a human birthright — so a child learns to value the goal because solving a puzzle is fun and hard work is affirming, not because love depends on the result. That unshakable feeling is what you'd want for your own child, and for yourself.

Praising achievement can imply love is conditional on performance
Parents must do internal work to convey unconditional love
Unconditional love is a human birthright
Hold the goal because the work is affirming, not to earn love
The same unshakable regard you want for your kids applies to yourself

“When we take that test, that spelling test, and we stick it with magnets on the refrigerator, it's out of pride.”
Jerry Colonna · 37:30

“And so it's really critically important that we as parents do our own internal work to convey that unconditional love. That is our birthright as…”
Jerry Colonna · 38:00

#parenting#unconditional-love#self-worth#children

Takeaway1:16:30

More Power Means More Responsibility to Do Your Own Work

The more power you have, Colonna argues, the more moral responsibility you have to pause and examine how you're complicit in the conditions you say you don't want. He illustrates with a CEO of a 15-person company frustrated that no one makes a decision without her — yet she's furious when they decide something she disagrees with. To build a scaled leadership team you have to tolerate people making boneheaded decisions about things you care deeply about; that discomfort is your growth edge.

More power = more moral responsibility to do radical self-inquiry
A CEO wanted autonomous decisions but couldn't tolerate disagreement
You can't demand independent decisions you're unwilling to let stand
Scaling leadership means allowing 'boneheaded' decisions
That discomfort is the leader's growth edge

“I would argue that the more power you have, the more moral responsibility you have to actually pause and figure out what it is that…”
Jerry Colonna · 1:17:00

“You want to build a scaled leadership team, you have to be willing to have them make boneheaded decisions.”
Jerry Colonna · 1:18:30

#leadership#delegation#power#founder-mode

Key ideas

Frameworks in this episode

Breath-Taking Questions (Radical Self-Inquiry Prompts)

Detach Self-Worth From the Outcome (The Art-Project Reframe)

Hold the Mindset Loosely, Stay Attached to Growth

Make the Unconscious Conscious to Fix a Team

The Complicity Question

The Reboot Leadership Equation

People & resources mentioned

People · 18

Resources · 33

Insights & moments

⚡Myth Buster· 1

The Trap of Growth Mindset: Hold It Loosely

◆Hot Take· 4

The Big Lie: Success Won't Make You Happy

Attachment Is the Source of Suffering — Treat Your Work as an Art Project

Don't Read the Reviews — Write for Yourself First

AI Will Burn Away What Doesn't Matter in Being Human

✶Explainer· 4

Unsorted Baggage: You'll Pay the Price in Tears

Shared Experiences: A Circle That Holds Space Without Fixing You

The Second Noble Truth: Pushing Away Suffering Increases It

What Really Breaks Teams Isn't Talent — It's Unsorted Baggage

❝Story· 2

The Pursuit of Lemon Drops

What Kind of Ancestor Will I Be? Legacy and the Toppled Oak Tree

▲Takeaway· 4

The Complicit Question: The Coaching Prompt Jerry Colonna Is Known For

Four Radical Self-Inquiry Questions to Journal On

The Spelling Test on the Fridge and Unconditional Love

More Power Means More Responsibility to Do Your Own Work

Myth Buster· 1

Hot Take· 4

Explainer· 4

Story· 2

Takeaway· 4