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Jerry Colonna: observation

8 May 2025 Lenny's Podcast How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

“seen this a thousand times Lenny, entrepreneurs sabotaging their successful businesses because the belief system from their childhood goes something like, I don't deserve success so let me blow it up.”

— Jerry Colonna

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Everything needed to verify it.

Speaker
Jerry Colonna
Attribution
Verified speaker
Claim type
observation
Recorded
8 May 2025
Publisher
Lenny's Podcast

Transcript context

…Thank you for giving me more of that answer. And trust me, your listeners are going to appreciate you being fully there in just the way you were. So let's take a step back. The fear is, if I can reflect back to your original question, the fear is if I go there, I don't know what's going to happen as a consequence of that. If I pause and ask myself, is this relationship working out for me? I might end up leaving this relationship. If I pause and ask myself if this career isn't working for me, I might leave my career. And the good news bad news is that's true. That is absolutely true. And if we look at some of the other observations we were making before like anxiety and depression, we have this belief system that if I pay no attention to the thing that I'm afraid of, it's somehow going to magically go away. If we pay no attention to the source of discomfort, it's somehow going to go away. And that's not actually how life works. More often than not, what we do is we respond to the source of challenge, whether it's a discomfort in our relationship, whether it's a discomfort in the way my life has unfolded. We respond to it by plasting over band-aids and sometimes they're relatively healthy, we become obsessed with working out, or sometimes they're unhealthy. We become obsessed with work or substance abuse or that kind of thing. Or sometimes, and this is super popular right now, we lean into what I would call as a spiritual bypassing where we go to Peru and we go do ayahuasca or we spend the weekend doing mushrooms with friends... And what we're really not doing, Lenny, is confronting the parts of ourselves that need some tending to because we're afraid of the consequences. But I'll tell you a quick quote. One of my favorite books is Bruce Springsteen's autobiography, and about in the middle of the book, he has this passage where he talks about having spent 25 years in psychoanalysis. So let me just let that statement land. Bruce fucking Springsteen, 25 years in psychoanalysis. And he has this passage where he talks about the unsorted baggage of our childhood. And what he rightly asserts is that 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 than not is in tears. Now, this is Bruce Springsteen talking about this. This is not some airy-fairy transpersonal Jerry Colonna coach. And the reason I draw that out is we as children are socialized not to develop these consciousness skills. We are socialized to develop what I would call bypassing skills. And as he correctly points out, if you continue to bypass sorting out your baggage, there's going to come a day where you're going to have to pay that price. It could be in your own depression, it could be in, I've seen this a thousand times Lenny, entrepreneurs sabotaging their successful businesses because the belief system from their childhood goes something like, I don't deserve success so let me blow it up. seen this a thousand times Lenny, entrepreneurs sabotaging their successful businesses because the belief system from their childhood goes something like, I don't deserve success so let me blow it up. We put this all under the rubric of midlife, but I don't know, when does midlife begin, 35? When does it end, 70? What I do know is it's the bulk of our adulthood. Okay, I think you've done an excellent job convincing me and others to spend time on this now, and I think there's an assumption of it gets harder, the tears get more intense as you wait longer. There's this ticking time bomb that better some amount of tears now than 10 times more tears later. Is that right?…

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