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Paul Millerd

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71
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2023-11-19
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2023-11-19
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  1. Are you trying to be a good person? Do you see a good person as somebody that works every day? Maybe. These are a lot of scripts people grow up with, right? Or like people that don't have a full-time job. Are they bad people? And so you're really just creating this space to get in touch with how do I actually feel about work? How do I get to know myself more? Are there things that I've lost touch with that really bring me alive?

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. Take three hours during a workday has to be during a workday. Block off your schedule, sneak out. People can pull this off. Go for a walk without a destination. Or do something from your childhood that you used to do all the time? Did you used to play basketball? Did you use to paint? Did you used to play an instrument? Do one of those two things, even better if you do both? And just pay attention. It's a sort of form of like work mindfulness. What is emerging? Do you feel bad for sneaking out of work? Where does that bad feeling come from? What does that mean about your definition of work and what work means to you? A lot of people have never really thought about like why do you work? People say money, okay, that's fine. But like, what else? Like, why? Why do you work?

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. Yeah. And so you have smart listeners, and smart people are great at excuses. So they'll say, oh, I can't do it because of this, this, this, this, this. I always think these things are much more possible if they really are the main priority. So what I tell people is fine. Don't take a sabbatical. Take an afternoon.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. After a long career in product management, thought he would return to work. But by the end of the break it was crystal clear to me that I was ready to move on to a new adventure. And then you said Several weeks into your sabbatical, you stop checking your email. My heart was no longer in the work. I didn't yet know what I wanted to do next, but I knew it was time to shake things up, right? And you probably weren't in that state when you were still at Airbnb.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. Try to find three months of that where you can create space and reconnect with yourself, explore things, just see what emerges, see how you feel. I think this is so vital for people in their 30s or 40s who have worked for 10 years just to reconnect with themselves. And three months in a total of five hundred months, like people accomplish much more impressive things than that, like saving for their dream home. That is such a powerful thing people aim for that they make it happen, right? Even people that don't have a ton are able to make that happen because it is such an important priority. And for me, I think creating this space was more important than owning house, getting married. Like it was the most important thing for me. And I actually quoted your piece. I pulled up the quote, said Lenny Richitsky took us back.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. Three month sabbatical is much more attainable than people think. Companies are desperate to keep people and are much more open to things like this these days. And the way I frame it is if you're assuming you're going to work continuously in adulthood, that's about 500 months

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. And so I sort of think about protecting them. And yeah, a lot of people are looking for meaning through work in a job shape container. And I think that's just really hard to find. You can find it for short bursts, but maybe after seven or ten years, it's just not doing it anymore.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. The hidden assumption I had around work for the first 32, 33 years of my life was work sucks. You have to figure out how to tolerate it, right? And within that frame, try to do your best to enjoy some of it. But ultimately, it's a trade-off of your time. You have to suffer through it. A lot of it is going to suck and you have to put up with that. I'm very protective of what I do and don't do. This is why it was very easy for me to say no to Penguin. I didn't want to write a second book for them. I want to write a second book the way I did, which was super fun process. Writing a book was the one of the most fun things I've ever done in my life.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. The big shift there, the big shift for me actually, when I left my job, I wanted to run away. I wanted to escape work. I wanted to not work. And I just more or less accomplished that. Like I basically lowered my cost of living in Asia to about a thousand per month. But then I started developing this relationship with writing and creating and all these things I actually like really enjoyed. And I wasn't doing them to be famous or grow a following. I was just, I just really liked them. And I like doing it in public because I was meeting others that were engaging on these ideas. So the big aha for me was, oh, you can design around liking work.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. But they've lost that sense of aliveness. And they're looking to reinject that. And they need maps of how to approach that, how to think about that. What are the models, things like that. So, yeah, it's a pretty big umbrella. It's a nice way to like claim everyone's path. Yeah, I think. The shared ethic is really a sense of possibility and opportunity and optimism.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. Yeah, so I think it ranges from a short sabbatical. And I to someone like you or me, who are sort of like on this path and committed to this creator path. Things like that, there's a huge component of their creator economy. Not the creator economy from a VC perspective of all these startups that are going to save creators, but creators that are actually betting on themselves, finding some deeper satisfaction and better relationship with work and committing to it. But it also encompasses people that are independent freelancers, that have sort of a stable path, more predictable income than like creator economy stuff. And it also includes people that are jumping from job to job. I also have examples of people that are older. I talk to a lot of people in their 50s. They've solved their financial problems.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. Because a lot of what my book is an exploration of like why does it feel so weird to do your own thing? Why does it actually feel shameful to leave a full time job, which is an aberration in the history of the world?

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  13. Right, and a lot of us are in this situation. Now, if you're an accountant at an accounting firm in your early 20s, like maybe there is a track and you can sort of plan it and it's pretty legible, but even still, I would argue that developing a relationship with uncertainty, not knowing what's happening, experimenting a little more, it's all of these things in one. And it's sort of my attempt to come up with a better narrative around work. And it's been pretty cool because a lot of people are embracing this and now using the term like, oh, I'm on my pathless path. Right, and it allows people to sort of name it and gives them comfort. I've had people email me that have been on a path for seven years. And they're like, this is the first time I actually felt okay about my path.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. I really shied away from trying to define it super clearly, right? I think I have this passage at the beginning of the book that it's like the pathless path is basically a shift away from the default. It's a shift away from not knowing what you're doing as a problem to be solved toward an abrasive uncomfort, discomfort, and uncertainty. And it's sort of a personal journey of shifting away from operating around scarcity towards operating from a sense of abundance, having faith that things might be okay, right? And this, on a path like yours, this is a necessary condition. You have no idea what comes next because nobody has been on the Lenny path before.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. There aren't these comfortable middle class jobs that are growing and abundant. They're shrinking. Davidor, a economist from MIT, has pretty good research on this. And it's just making people a little more unsettled. It sucks, but this is the reality we're living in, especially places like the US becoming super tech heavy. And how do you navigate that? It's hard. Everyone's struggling with their relationship to work.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. Right, and so we're constantly needing to reinvent and reevaluate. And I think thinking of our lives as this smooth trajectory up this corporate ascent sort of limits the possibilities of our own life. So just acknowledging that we are being disrupted, we all have personal lives where we have relationship challenges, health challenges, external shocks, inflation, things like this that are changing our reality all the time. And it sort of sucks that

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. It's interesting. I did not think my book would resonate with people that were firmly in sort of the traditional work role, full-time jobs, big companies, things like that. The tightness between my identity and work reality and loosened it up a little bit and I'm able to like play with it a little more. I had one friend, he said, from your book, I made a list of the four priorities. Right now, I'm getting three of them. And it's helped me become more aware that, oh, I'm actually getting these three things that I prioritize. I'm missing the fourth. I'm probably going to have to make a change two years from now. Maybe another role because I do want to lean into that fourth thing. I think it's really just about like remixing your path. My hot take is that we're all on a pathless path.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. I think there's nothing wrong with the default path. The difference I would make is are you sort of conscious about what you're actually doing? What are the costs of your game? What are the trade-offs? What sort of implicit contracts are you creating with yourself? A lot of times when people quit their jobs, they forget to fire the manager in their head. They don't realize they can take the afternoon off to spend it with their kids. They've created this implicit contract that Monday through Friday eight to ten hours a week. You have to work, right? And that may work for people, but are you actually opting into that or are you just sort of accepting the default?

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. Like, people have a hard time even contemplating it. Like, you'll trigger insecurities in other people by just existing outside the frame of the default path. And it's the default path in their head of their conception of how the world should work and does work, right? And so a lot of what I explore is what is life beyond the default path? And what are the stories we can use to one at minimum feel better about what we're doing? And two, what are the stories we can adopt to thrive?

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. I think the default path is different for everyone and slightly different in every different culture. It's really the story in your head about what you should do. And most of us have some sort of script that we're living out. This is especially powerful when we're in our late teens and early twenties, right? We're trying to like execute a script. And it can be different in every country, like in the US, it's sort of like go to college, get good grades, get a good job. make a good salary, buy a house, get married, have a family, things like that. And when it comes to work, the default path is get a job and work continuously for all of adulthood. And when you opt out of the default path, there aren't really offerings.

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source

  21. Take three hours during a workday has to be during a workday. Block off your schedule, sneak out. People can pull this off. Go for a walk without destination or do something from your childhood that you used to do all the time. Did you used to play basketball? Did you used to paint? Did you used to play an instrument? And just pay attention. What is emerging? Do you feel bad for sneaking out of work? Where does that bad feeling come from? What does that mean about your definition of work and what work means to you? A lot of people have never really thought about like why do you work? People say money. Okay, that's fine. But like what else? Like why are you trying to be a good person? Do you see a good person as somebody that works every day? Maybe these are a lot of scripts people grow up with. You're really just creating this space to get in touch with like, how do I actually feel about work? How do I get to know myself more? Are there things that I've lost touch with that?

    2023-11-19 · Lenny's Podcast · Redefining success, money, and belonging | Paul Millerd (The Pathless Path) · IDENTIFIED FROM THE TRANSCRIPT · source