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

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

Insights & moments

⚡Myth Buster· 1

The Trap of Growth Mindset: Hold It Loosely

◆Hot Take· 4