This is a transcript excerpt from the YouTube video "Win or Lose: TRYING Is The Purpose Of Life" (uploaded by Josh Trent). In this section Jason Pickard describes leaving Wall Street after managing "over a billion dollars," meeting with Paul Tudor Jones, and experiencing an identity "death" and grief cycle after stepping away from his role. He explains that becoming a coach reconnected him to a core gift—rhythm, ritual, and presence—which brought meaning and purpose. Josh Trent contrasts surface-level questions about wealth with deeper questions about how to live.
Questions this video answers
Over a billion dollars.
Paul Tudor Jones.
Chapters
So I then had this big death where I then said, okay, I'm leaving Wall Street. I had a meeting with Paul Tudor Jones, and I said, I'm just. I want to try something new. You know, I've done this now for 20 years, and I've had some success. I've just gone through some personal struggles, and I just want to see if I could reinvent myself. And he looked at me and said, you're the. You're the man in the arena. Kind of that Roosevelt quote about, you know, I don't. I'm gonna butcher the quote.
I know, exactly.
Yeah. But it's about, like, ultimately, like, it's not about winning. It's about the one who goes out and tries and goes through the blood and sweat and tears and. Yeah, win or lose, trying is the purpose of life. Standing in the arena, standing in there, being. Being willing to risk it all and try something new and be brave. And so, you know, I had a really big kind of death moment after that, because I was this important person. I was managing over a billion dollars, and I had a lot of people that were working for me that were emailing me that wanted to take me out to dinner, ask me questions. Clients, risk managers and executives and brokers. And also, I mean, you can imagine the whole thing. Multiple screens and phones and, you know, emails and text messages and research and all. And then it was, like, black. And all I'm doing is just driving my kids to school, back and forth like a taxi driver and, like, waiting in the pickup line for them to come out and then, like, going home and sitting, like. And I. You know, I had to go through, like, a really big grief cycle. Like, I had, like, a lot of shock and, like, anger and disbelief and regret and, like, confusion. Did I do the right thing? I just. I just left this job. And, you know, ultimately, I realized that as I started getting into coaching, that the thing that made me a good coach was tapping into the rhythm of my clients. And when I would give them some piece of knowledge that opened up their eyes and changed their life, I had that same feeling of magic. And so what I recognize is that what we're calling these roles is the ice cream, the consensus reality, the drummer, the magician, the trader, the coach, and now the abundance, archetype, creator. But really, underneath all of that was pulsing through me this gift that I was born with of rhythm and ritual and beat and heart and magic and wonder and curiosity. And that anytime I was on that line, no matter what role you put in front of it, when I was on that line. I was happy, purposeful, and successful. And so ultimately, that's what I realized is that I never actually left. Anything that was with me from the day I was born that'll be with me to the day I die is my unique gift, skills, and talents of those two things that you don't even. It's hard to even put words on there. It really is. It's below on that bottom of the cone level. It's an energy. It's a feeling of like when you're in the dance. Or the feeling of surprise. Right.
Even the question itself. How do I get wealthy? How do I be rich? How do I have this much money? That is a. On the top of the ice cream cone question. That's consensus reality question. A deeper, more soulful question would be, how can I live my life?
Well, yeah.
Which is really, like. That has been my question ever since I was a little boy.
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