Khe Hy - Tales From The Pathless Path

[01:31] Paul: I'm here with Khe Hy Hy in what I'm calling Boundless Conversations. I've never done this before, but we are here to talk about— We're here to ostensibly talk about my book, but really, I want to talk about the book as an excuse to have deeper conversations in my continued fascination with trying to understand people's journeys. So Kay has been a huge inspiration on my journey. I quit my job in 2017, and I like to tell people I didn't have any friends except Seth Godin, which inspired me indirectly in books. And we'll start with 2017, about, I think it was 5 months after I quit my job. I walk into this conference, I'm really insecure.

I'm trying to land freelance projects. I'm trying to figure out my identity as a solopreneur. So I walk into this conference and Khe Hy is like interviewing, I think you were interviewing CEOs at the time for Quartz, but then I looked up your bio and I couldn't figure out what your angle was. And my first thought was just, oh wow, someone like me. I'd love to start there. You'll probably touch on your background, and if people don't know, you left a Wall Street career to eventually basically embrace what I call The Pathless Path, and we'll dive into more of the story there.

But yeah, to bring me to Khe then, like, what, what was your mindset at the time? I probably have more of an appreciation for what you're feeling then, but at the time I was like, oh, here's this person that has it figured out and knows what he's doing.

[03:15] Khe Hy: Wow. So first, thank you. And I see all of so many of our, our familiar friends in the chat. So it's so good to see everyone, Jill, Mary, and Nate, Chris, uh, and company. Um, and so are you referring to that moment in 2017 or the moment when I quit?

[03:33] Paul: Yeah, let's talk to me about 2017 and then we'll, we'll work our way back.

[03:38] Khe Hy: Mm, yes. So 2017, I would say that, um, so I quit in May of 2015, and I would say that there's like— I guess I'm pulling it back then— there's almost like different like stages of grieving, all right, like when you, when you leave a job, or there's different phases. And the first is, holy crap, I can do whatever I want. I remember I was like, I took my— I only had one kid then, and I took my wife and my daughter, like, let's go have lunch on a Tuesday as a family, and I'm gonna have two beers during lunch, and, and I'm gonna leave my phone at home. Uh, I was like, oh my God, this is so crazy, right? Um, and so, um, I started— so that was like that year, that first year was like really like excitement.

And we traveled, we lived in Canggu, Bali for a little while, right by, right off Rice Paddy Road by old man's. And you're kind of like, oh, I could do whatever the fuck I want. This is awesome. And like anything in life, any experience, that high kind of wears off. You know, our mutual friend Andrew calls them samskaras, which are like these like negative thought loops start to kick in and you're like, oh my God, what am I doing? What am I like, who am I?

What am I doing? Am I, have I made the right decision? So that was like, 2015 was like euphoria. Like I'm living like Julia Roberts style. Uh, 2016, I'm like, it's like the, oh crap moment. Uh, and it's the identity quake.

Your identity is smashed to smithereens, like blown to smithereens. Take like, imagine there's like a glass, like a picture of K in a frame and like every single person in your life is taking a sledgehammer and just smashing that thing. Not like violence towards you, but they're actually destroying the image and the conception that you had of yourself. And even if they're not doing it, it's what you feel. That was 2016, was the identity quake year. So bliss, first bliss, naive bliss, um, Julia Roberts bliss, then, um, smithereens, identity smashed into smithereens is 2016.

And 2017 begins the process of slowly, slowly rebuilding, um, the identity. And that lands us the moment where you and I met. Well, I guess I don't know, we didn't meet, but, um, our energies—

[06:22] Paul: he met after that on the— yeah, through your newsletter. Your newsletter was kind of an invitation to the fellow, fellow weirdos on The Path.

[06:30] Khe Hy: Yeah, exactly. Um, and so that was when we, um, that was— I started to have some, um, a renewed identity, right? In 2017, there had been 3 kind of identity markers that I had crossed. One was that there was the Rad Reads newsletter, which was kind of still a small thing, maybe like 2,000 subscribers back then. The second was I had gotten 2 press recognitions. So in my parents' eyes, I made it.

They're like, oh, you made it.

[07:01] Paul: He's in CNN.

[07:02] Khe Hy: He's in Bloomberg. He made it. Any creator here will know that just because your traffic spikes, if you don't have a business model, you don't have a business model. And then the third was a very important small but important, being an entrepreneur in residence at Quartz, which was an identity marker to cling to because I had embraced this new identity of being a writer. And Quartz was basically saying like, we validate this identity, not to mention the many dear friends that I have at Quartz and the mentors and so on. But that's the first 3 years, right?

[07:43] Paul: Yeah, that's fascinating. I think one thing that was shocking to me was when you're succeeding on a path that is familiar to everyone else, literally no one will ever ask, why are you doing this? Like, I guarantee when you were working in finance, nobody was like, hey, why would you continue to get promoted and do better? But as soon as you step off, there's a flurry of questions almost nonstop.

[08:09] Khe Hy: Why?

[08:09] Paul: What are you doing? What's your plan? Are you going to get clients? Are you going to, are you going to build a business? Are you going to hire people? And the reality is, in those first couple years, you have no idea what you're doing.

And first couple, and that, that's why I've kind of realized the most important thing is probably not to— like, there's an initial phase where you almost have to like make money and like try a bunch of stuff to build confidence, but Even more important is probably finding other people who are similar, uh, to you such that you can just have normal conversations without those, why are you doing this? What are you doing? Did you find similar?

[08:48] Khe Hy: Yeah, I, I think, you know, and I see some people that are in different, um, phases of this journey in the chat. Um, I think that when you leave a known path, It's by definition of it being known and very few people doing it, you think that you're the only person that's actually done that. And I think that, you know, I could zoom out a step further and just talk about the, like, the Radar Reads newsletter and the post. It's like, you know, I'm like confused, you know, am I being, you know, am I being a good dad? Or I'm confused, am I a workaholic? Or I'm not sure if I'm being indulgent by pursuing things that I love, or I'm not sure of what it means to truly be happy.

And I think that you think that you're the only person who has those questions, right? And that's going through those ranges of emotions. And I actually, I felt that in the early days and the newsletter is actually the vessel or the vehicle that helped me connect to all these other people like you. Because people would just see that, they're like, oh, then what they would say is they're like, oh, I'm not alone in feeling that thing. And then they would kind of reflect back to me and then be like, oh, someone else feels this? Like, so we're in this together, right?

And then I think what it kind of grew into is like, Really, like, really what happened is like people bought— we could talk about like, yeah, you're a creator, you're a digital nomad, or you're a freelancer and we found each other. But what you could— but what really happened is you bonded over with this group of people over the human condition.

[10:37] Paul: It's so true.

[10:38] Khe Hy: And that's what it was like. Solo creatorship is just a vessel for these bigger questions of like What is the meaning of life? Why am I here? Why am I doing this work? Who am I doing it with? Am I loved?

Am I safe? Like, am I recognized? Am I relevant? Right? Solo creatorship is just one vessel for those questions, but Wall Street is actually another vessel for those questions. So to answer your question, we, I did feel alone, but very quickly by putting myself out there, I got so much feedback.

Back. And also very practically, I would say that so many of those relationships were enhanced by Twitter. Oh yeah, because it's just so easy to have these like hybrid conversations that are part partially private, partially like kind of like a bunch of weirdos sitting in the corner of the classroom talking, and public like broadcast. And I think Twitter really, uh, was a beautiful accelerant to finding that tribe.

[11:45] Paul: I think many people mistake people with platforms or following as like businesses. So they think, okay, has thousands of followers, is running a business, right? And I think you were really helpful in setting— like, you had a huge impact on me. Like, you, your generous spirit was something new and different and was a direct almost attack on our former ways of life. And I wanted that same spirit. It's like, I want to do things that don't make sense, that are generous in spirit for the sake of being generous, because they might actually make my life better.

So you just started introducing me to friends, even though we had never met in person. We didn't even meet until 2020. You just introduced me to friends. I've visited my friend Quinn in Vietnam and stayed with him all week, all through you. I've landed a client project in Boston through you and like, I've hung out with new friends in Taiwan because of you.

[12:48] Khe Hy: Taiwan. Yeah. And, uh, but remember, let me just add there, remember, uh, when I once shared your like PowerPoint templates in some random. Blog post and then you're like, oh my God, I haven't updated this in, in like 2 years.

[13:06] Paul: Yeah, I started getting all these, uh, these inbound requests and it's like, oh crap, people are buying this and it's not actually the thing anymore. It's like broken. And I, I basically like refunded a bunch of people and like sent it to them. But yeah, it's, it's fun how these things— and it's It's become a really cool, broader community. It's almost like we're like coworkers, but we have none of the downsides of being coworkers. 'Cause when I look at you, I see somebody building a different kind of business and I don't get jealous or envious.

All I'm thinking is, oh, Kay is opting into a game that is uniquely his. Like you're hiring employees right now. And like, I don't wanna do that, especially not right now, but I know, given how long you've been on the path, you probably know how far is too far. You know your constraints, you know how to do it on your terms. So it's really cool to see those different models, and that broader ecosystem is really inspiring right now.

[14:10] Khe Hy: Well, first of all, thank you for, thank you for, uh, those, those kind words. And I'll say it like when people respond, I think people, you know, I see people on the chat that have all different size newsletters. When someone responds to a newsletter with a thoughtful response, it actually, it really means a lot to the creator because you have these people, these creators that are sitting in their garages or in their spare bedrooms in front of their laptops for years with not like a ton of social interaction, especially during COVID And then someone has this like thoughtful thing to say that's like not like some throwaway compliment, but something really genuine. And it's really, you know, I always, I think whenever I get those, I reply, I'm like, you know, emails like this are the jet fuel that keep me going much more than, you know, course sales or things like that.

[15:14] Paul: That's interesting. So I call this the creative engine, and you can't create with the goal of just an outcome. It might drive some people, but most people need something else. So for me, it's like my writing actually inspires those emails and conversations, and those conversations inspire ideas that lead me down rabbit holes, and it kind of just keeps working. And I just want to keep doing it. Is that how you think about things too?

[15:45] Khe Hy: I think, um, one of my, my mantras is follow the fun. And, and so I think there's a few ways that I approach creativity, right? I think one of the questions that we ask in our course is, what if this were easy? And so we're kind of like looking for the path of least resistance or looking for that flow or that ease in your daily activities. And so my creativity, and to, to a much broader extent, my life writ large, is motivated by this guiding question, which is actually very different than how I grew up, where it's like everything had to be a struggle, like CrossFit and all-nighters and red eyes and, you know, perfectionism. And like, all these things used to be It's like, if there wasn't a struggle, it wasn't worth it.

And so a lot of my creativity, and even like the, you know, building a business and so on, is still very much driven by like this ease. And so I would say that in writing specifically, so that's why things that are not easy for me. Um, you like highly produced things, not easy. Um, podcasting, not particularly easy, more like the editing side of it and the logistics. Writing, super easy, uh, for me. Live events, super easy.

I could, you know, probably do 2 live events a week for a year now. Uh, and people will look at our boot camps like, oh my God, crazy production. Like, that was actually easy because I like conversations. I like— I think I do well live. I don't do well, like, in the, like, YouTube world of, like, ah, like, I don't know where to put my hands and, like, things like that. So I think that my creative process is very much, like, driven by this ease.

Writing in particular, and you'll see a lot of writers will say this, is that, you know, it might sound selfish, but I often— I'm writing for myself. And it's a way of like hashing out some thoughts or some like, you know, some scars, which are these like thought loops or some kind of suffering. I'm just like, like the only way for me to kind of actually cope with them and understand them is through writing. And so I would say that writing particularly is driven by that. You know, I think Oprah has called it public confessional in the form of therapy. Therapy in the form of a public confession.

So there's like a therapeutic side of like all these things that you hold in and finally just having a place to share them, even if it's semi, not anonymous, but semi impersonal, that I have found with, with writing. And, you know, Nate Cadlack's on the line here is I really I really gravitate towards design. I love design. I'm very consistent with colors and patterns and what I wear and all that. There's an overarching design philosophy and it's easy for me. I love being on the weekends, I'm on Figma and I'm sharing these wireframes with Nate.

I'm like, what do you think of the grid box here? Is this color work? And all that, like it comes very naturally to me. I'm not going to be a designer. I'm not striving to be a designer, but it's a, it's a method of creative expression that really makes me come alive and I lean into it. And then as a result, as the person on the other side, the customer, I would suspect that the Rad Reads customers or Rad Reads fans, they're like, there's a very specific design aesthetic that K has that kind of brings it all together.

It brings together the surfing, it brings together the beach, the playfulness, you know, like the culture of the moment. I mean, I'm wearing a Dave sweatshirt, right? It doesn't get more like culture, pop culture than that. And so I would say like that ease— oh, it's so good. That ease is much of a guide for my creative pursuits.

[20:24] Paul: When I wanted to quit my job, I had this impulse of basically wanting to escape work. And what I've since discovered is that that's kind of a flawed— I had a broken model of what work was. I only thought of work as like a full-time job, constraints, not being able to really do what I'm doing, suffering some of that script you talked about. And my journey over the last 5 years and writing the book has really been realizing, uh, it's a shift from seeing work as things you have to do for a paycheck to actually the things you would choose to do and continue to do. I kind of call it the real work of your life, um, is finding the things you want to do and commit to it. And when you do that with enough experimentation, I found you actually can find like the lightness and the ease and the playfulness.

This has really opened up for me in the last year, and it's kind of mind-blowing. If I—

[21:22] Khe Hy: like, it's like a cheat code.

[21:25] Paul: If I told myself 10 years ago that, like, you can just not work a job and figure out stuff to do and you'll be light and happy and playful, I don't know if I would have believed it. Did you go through that shift? Was there any moment when you're like, Oh, it's not about escaping or working less. It's about finding the things worth doing.

[21:47] Khe Hy: I, I, so absolutely. I think that there is, um, so Ali Abdaal has this, um, exercise, which I think he got from someone else who I won't be able to attribute, but he calls it the, what's your ideal ordinary week? And so in this hypothetical scenario, you know, love while you're your expenses are paid for, your living expenses are paid for, for 2 decades or something, but you're still subject— I think I added this part— but you're still subject to life's constraints, right? If, if you have high blood pressure, you still have high blood pressure. If your parents are aging, your parents, you know, are still aging. If you don't get along with your cousin, you still don't get along with your cousin, right?

So you have like And by the way, like if all your friends live in New York and you can't like move them to Bali with you, right? So you have kind of like the constraints of life. So what's your ideal ordinary week? And so you could take this and you could say, well, okay, I'll sleep for 8 hours. I'll meditate for 2. I'll read for 1.

I'll exercise for 1. I'll hang out with my kids for 3. And you kind of list all these things. You've kind of hit, I don't know, 14 hours. You still have 10 hours to allocate. And by the way, in this hypothetical world, there's no concept of a weekend other than the fact that the weekend is when your friends are available to hang out because they're, you know, they're subject to the constraint of work.

So you have 70 hours to allocate. By the way, like That's like a job, right? So you kind of have to start to think about like, well, what could I do for 70 hours a week? And let me tell you, if you're listening to this and you're grinding at a desk job that's soulless with a schmuck of a boss, and you're like, oh, I could fill my days up. Like, let me tell you, like, You can only watch so many movies. You can only surf for so many hours.

You can only go out to restaurants so much time. You will have a lot of time left. And so people come back at me and they're like, well, you know, you're a solopreneur and you worked on Wall Street, so you have the circumstances to make that happen for yourself, which is not totally true. But, but But sure. Okay. Well, uh, let's accept that that's true then.

Then I'll like, yeah, I still have to figure out what do I want to do? How do I want to spend my time for 70 hours a week? And guess what?

[24:30] Paul: That's a huge fear for people too. Mm-hmm. What will I do?

[24:34] Khe Hy: People cannot fill out that. They cannot fill out that spreadsheet beyond the 14 hours, you know, each day.

[24:42] Paul: I don't know if this was true for you, but The biggest challenge is kind of when you're in a job that you don't really like, there's this low-grade misery that is tolerable and can keep going forever. Hold on, then I'm gonna, I'm gonna do the quote from the book here. So we got the book. Kay calls this pebble in my shoe. So this is a really powerful metaphor for me. So I say a friend, Kay Hy, provides a a perfect description of this phase.

15 years into a successful career in finance, he walked away to find a new path. However, it took him a long time to make that decision. He reflected, it definitely wasn't a sudden realization. It's a little bit like having a pebble in your shoe where you're walking and something is off and it's mildly uncomfortable. I thought that was really powerful. And you say in that same interview, awesome interview on Zigzag, um, you kind of realized eventually you were a passive participant in your life.

So how do you, like, how do you get from that to— is it surprising to you, like, where you are now?

[25:55] Khe Hy: Yeah, I mean, I, I genuinely pinch myself and I'm like, is this my life? And again, I also, I also invite people. Like, if, um, you know, I, I say this to aspiring creators, like, if you want to see what— like, if you want to shadow me for a week, I'm not convinced you want my life. Uh, same. Like, I'm pretty sure— I mean, I'm on camera 5 hours a week. Like, um, I don't know if— I don't know if many— I've written an essay for 225 consecutive weeks.

You know, I don't think Angie always says to me, like, want that.

[26:36] Paul: I give you a lot of credit for never really knowing what's coming next.

[26:41] Khe Hy: Totally.

[26:43] Paul: So I can't, I think I can't tell you what's going to pay the bills beyond like next couple of months. I have no idea.

[26:49] Khe Hy: Like, some people hate that.

[26:51] Paul: I love it. I love not knowing. Yeah.

[26:55] Khe Hy: Well, so to answer your question, um, I mean, we can take a very, we can take a very simple example because I talk about it often, is surfing. So when I was on Wall Street, I was, I said to myself, I want to learn how to surf. I want to be a good surfer. I want to live by the beach. That was like my retirement dream is to be a surfer and live by, live by the beach. So you could say like in my ideal ordinary week, I would surf for a couple hours a day.

And so lo and behold, you know, through the divine grace of God, I was, you know, I was able, I'm able to surf every day. And at, you know, 30, 35, 37 years old. So, you know, 18 years earlier than expected. I didn't retire, but I had the freedom to do it. Okay. So I get to Manhattan Beach.

I live walk, you've been to my house. I live walking distance to the beach. And I can surf every day now. Okay, cool. This was a dream that I had for like 20 years. Okay.

Reality check. So you walk down to the beach. First of all, no one really tells you the water's freezing. It's 57 degrees, right? Okay. No one told you that.

Second of all, um, none of your friends can surf with you because they're all working. So you're by yourself in freezing water. Third of all, surfing is very dependent on Mother Nature. And there are weeks where there's no waves. You wait weeks for like a 6-second wave that you dream about for the rest of your life. Months sometimes.

All right. Next, it's really freaking hard, right? Like the vision that you have of a surfer, like a Kelly Slater or so on, like It doesn't look anything like that. The water is not blue, it's gray. When it rains, you can't surf for 3 days because sewage water drains into the ocean. The list goes on and on and on and on.

And then, and what I was lucky in that I was like, if that, can you imagine like you build up this vision for 20, like, Imagine you're waiting for retirement and you build that up as the thing that you want. You sell your soul to Goldman Sachs so that you can have that like 6 or 7 years early. And then you get it and you're like, this sucks. And in fact, many friends moved to Manhattan Beach from the East Coast. They don't surf anymore because it sucks.

[29:37] Paul: That's so funny.

[29:39] Khe Hy: What doesn't suck about it is you can embrace the entire lifestyle. It's not about this vision, this identity of being a surfer. It's about the routine act of putting wax on your board every morning. It's about seeing your casual homie in the water that you've actually never seen them in street clothes on, with street clothes on, and you're just like, hey man, catch any waves today? It's about watching the seagulls in the cold dark night. It's about the sun cracking at the break of dawn.

Those are the things that actually make it special. But that's not the conception that one had of surfing, right? It's very, very different. Uh, and so I— it's just an example of like, it's really hard to even know what you want and what makes you happy.

[30:29] Paul: Yeah, the— what I'm sensing there is just a sense of wonder and possibility, like just in awe for the world. This is one thing I notice over and over that kind of tips the scales. I call it, uh, people are able to deal with certain discomfort, um, and expected rewards for indefinite periods of time. And then like taking an uncertain path just doesn't make sense because it's trading certain discomfort for uncertain discomfort. But what tips the scales is this sense of I might find something out. This sense of awe, this wonder.

Um, and I think that's often what keeps people going on the journey too. And I think what's really opened up for me is like, it's really exciting not knowing, because I know there might be bad stuff that happens, right? Like surfing might suck one day, but it might also be really interesting, might lead somewhere fascinating.

[31:27] Khe Hy: Yeah, I, I would absolutely too, you know, wonder and, and possibility, but I would even like pull that in one notch and just say, like, I think a big change between now, me now and me on Wall Street, is I am completely content in the present, right? So like, the present is beautiful, like always. And, you know, I, when I was at a job, I was always kind of— that is true, Jeff. I've been like staring at your eyes, like you have like incredible eyes. So, but the, you know, when I was on Wall Street, I was always like looking for, you know, to a future. I'm like, oh, this next vacation, or I was looking backwards.

I'm like, oh, remember that time when we did this or when I didn't have to do this? And the present moment always sucked. I was trying to escape the present moment through work, through alcohol, through just surfing the web and just being distracted, right? Through experiences even. And I think part of it comes with age. I will say that a big change is I'm an hour to 90-minute meditator a day for almost like 7 years now.

So, I just have this deep comfort in the present. But I think it's also just like an acceptance of this moment, which actually comes back to the ideal ordinary week, which is just like being content in what is happening in that moment, not clinging to something, not desiring something in the future, or not clinging to something in the past.

[33:14] Paul: Yeah, it's so powerful. And I think tying it back to your 2016-2017 experience, like the path to get there is not a straight line. It's kind of this like dip, right? And I think that's what I experienced. And people, people have these ideal visions of wanting to quit their job and live at the beach. I've actually done that and been around those people and nobody actually wants to do that full-time.

They're people, what I've found, want to be useful. They want to contribute to the world. They want to connect to themselves. They want to connect to the world. Um, but to get to a state where you can do that in a way that's connected to you, it often means taking a step back. So I always tell people, um, it might suck, but it might also be worth it if you're able to commit to the, the path.

[34:05] Khe Hy: Yeah, I mean, that's very Taoist of you, right? Um, but I, yeah, I, I absolutely agree. And the thing I would add too I've had— what I'm about to say, I've spoken to some of the people in the chat about this point. But there is just this, like, how do I best state it? It's like, okay, you like— there's like these like choppy, choppy waters, right? I like to use water analogies.

These like really choppy waters where The chop could come from people's expectations, or the chop can come from your own expectations, or the chop can come from some failed project that didn't go as well as you thought, or the chop could come from figuring out the American insurance healthcare system as an entrepreneur and how much that sucks. So the chop keeps coming in all these different ways, and I honestly believe that the thing that gave me the best advantage in doing what I've done is the ability to stay calm in all that choppiness. And so you could use an investing analogy here, right? Like, you know, you could take a stock like Amazon stock in the early days, right? It's like zig up and down, up and down, up and down, up and down. But if you look at it over 30, 20 years, it's just like a straight shot up.

Right? And so I think that— and I really— you mentioned, um, our shared friend Andrew Taggart, who was like my spiritual teacher, who I, I wouldn't be here without him. Uh, and I talk about him often because he, he completely changed my life. Uh, but what he did was he gave me the tools to look inside so that when the chop was happening I could just like, I don't know if I'd remove myself from it or shield myself from it, but it just didn't get to me. So when someone was like, you should be doing this, or you should be doing that, or my parents are like, why are you doing, you know, you're crazy, you're letting us down and we invested so much time and money for it. And when all those things were being thrown at you, that chop, you know, it's like the ability to kind of tap into some internal source of calmness and weather it, navigate it, stay alive to play another day.

I think that, you know, whatever success I've had as an entrepreneur is just because I've been in the game for 7 years now and I stayed in the game.

[36:50] Paul: It's so true. Yeah, yeah. I often think— I've found that I like writing, I like creating, I like connecting with people, and I'll pro— I want to do it for 25 years, so I don't get too caught up in like succeeding this month. I've taken, I call it the long, slow, dumb, and fun way. Um, I do it a little calmer, um, because I know I'll keep playing, but yeah, experience is very similar thing of just seeing the path itself and the benefits, um, of having to deal with these blows. Um, similar thing with like parents, like not really understanding your path and like their script is like, we struggle so that you can make money.

Right. And feeling like you're not good enough. And over time you do get, like I say, you turn these ambiguous worries into like tiny little existential crises along the way, but then you experience them so often that you can go into that observer mode and it's like, oh, I see you, money fear, you're showing up this week. Yeah, I can dance with this. I'm I've done this before. We'll be fine.

[37:59] Khe Hy: And you start to see, you know, in our course we ask people like, what's— why did you— why do you want to be more productive, right? It's a productivity course, or on its outset it's a productivity course. And so we ask them, why do you want to be more productive? And but we ask them to ask why 5 times. And the 5th why will really show that lingering hurt.

[38:23] Paul: Right.

[38:23] Khe Hy: It'll be things like, I am unlovable. So you're kind of like, if I'm more organized, if I produce more, I will be loved because I'm afraid of being unlovable. I am unlovable. I feel unsafe. I feel unworthy. I'm scared of rejecting rejection.

You know, a lot of these come down to like isolation and ultimately death, right? They're different, like manifestations of it. And so it's the same thing. It's like when you start to get these like moments of self-doubt, or, you know, you have this perfectionist tendency and you're afraid to hit send, or you can't actually, you know, ship that project, you keep procrastinating, chances are it's one of these kind of repetitive negative thought loops that are coming back to you that are saying like, no, you're— watch out, you might be unlovable, right? Watch out, you might be unsafe, right? Like the money thing.

And sure, I think many of us grew up with challenges around money, and our parents may have struggled in certain ways, or we never felt like we had the financial means that we wish we had at the time. And so, you know, when you— when these money fears come up, it's that, that same repetitive pattern. And so by being able to look inwards, uh, is super, um, you— hey, you start to— you just def— you notice it first of all, and you notice the way in which it drives you. Once you notice it, then you can like talk to it, right? And some people like actually will like put their hand on their body to like reassure that, that part of you that you're okay, you know, you're safe, you are loved.

And then you can work on healing it through different forms of therapy or coaching or meditation or, you know, different— I, I ask, like, there's a lot of ways to, to really heal those parts of you, uh, and everyone has their own ways of doing it.

[40:16] Paul: Yeah, so want to get to some questions. Yeah, people can drop—

[40:21] Khe Hy: what if this was easy question that keeps coming up.

[40:24] Paul: Yeah, I like that one too. What if this was easy? If people have questions, we can drop them in the chat. So one question I thought would be cool to talk about is like best tips for building friendships online. I know I think this is a hard one with people because they kind of like rush into things. I think the biggest thing you can do is just kind of give and be generous first to like all sorts of people, no matter what.

[40:55] Khe Hy: Yeah.

[40:56] Paul: And that kind of just makes you somebody that people want to be friends with. I don't know if you have a— you probably have a better answer to this.

[41:03] Khe Hy: I think there are a few ways. One is to Just be very, just like, again, now it's gotten, it's like, there's a lot of like fabricated vulnerability, but I think so much of it is just like, just like, shit, I don't know what I'm doing. Right. And like when people, people can see through the fabricated vulnerability, you know, people are quite good at the LinkedIn posting through, yeah, spotting through BS like that. But I think like being vulnerable, like, I don't feel like—

[41:36] Paul: is this—

[41:37] Khe Hy: am I being selfish for doing this? Am I being a good dad or a bad dad because I do X or Y around my kid? Am I being a good spouse because I did this? Or am I being selfish because I want to go on a surf trip, right? I think that just sharing like that, people, if they believe that you're genuine, being genuine, they immediately built this kinship with you without you even necessarily noticing it. And at that point, then they might go in and, you know, there might be some way to connect, right?

So that would be one. The second would be to just give and not expect anything in return. And again, it could be like kind of this very Adam Grant style, but, you know, going like micro acts of generosity, right? And I use the example often of, you know, Nate, who's on the line, he was on at one of the bootcamps. We had never met. And I made, you know, I always make some passing comment on design and he sends me this like 14-minute Loom video.

That's like basically like a full-on design critique of, of like the entire brand.

[42:49] Paul: This is big Nate Cadillac help right here.

[42:52] Khe Hy: Exactly.

[42:53] Paul: I got like 5 Loom videos from him.

[42:56] Khe Hy: There you go. And so, and, and that's the thing. And Nate's awesome and he's genuine and he's not doing it to try to get exposure on someone's channel or this or that. But guess what? That's the byproduct of it. Um, but that's the least important byproduct is that, you know, like him and I are friends.

Like we're going to have dinner or with our wives, uh, and our kids, uh, on March 5th. We're going to have pizzas in Silver Lake or Echo Park. And it just happens very organically. So look in— another person who's excellent at this is Justin Lai, who's on this, where he just goes in and just— it's like he's the number one helper. It's like he's a Twitter bot. He's like the Twitter love bot, and he just shares love and wisdom on Twitter.

And by the way, if you're any any private communities with Justin, he does the same thing in private communities. It's totally on brand. So again, these like little things and people are always like, oh, I have to like, you know, take like a 40-minute call and explain, like sit down with them for coffee. No, just like bump up the thing, promote the thing that they're sharing. If you know, if you believe in it or just celebrate a win publicly for them or just tell the world how awesome they are, right? You will, you'll find that the other thing is is to also just like be, just like not aggressive, but be direct.

Like there's so many people that we have all these conversations on Twitter and I'll just slide into the DMs and be like, hey, we should just, let's just jam. No agenda. I'm not asking for anything. I don't want to, I'm not asking to promote anything. Let's just jam. And you'd be surprised.

I, you know, pre-COVID, again, this is why I love Twitter so much. But pre-COVID, when someone would ask this, when I would go to a new city, 50% of the people that I would have coffee with were Twitter friends that I was meeting for the first time. And everyone like who's not on Twitter thinks that that's so strange. And everyone who's on Twitter is like, of course, that, that's like, makes perfect sense.

[45:05] Paul: This is why I'm in Austin. I mean, yeah, my like social network here is like Twitter people, like knowing—

[45:12] Khe Hy: totally.

[45:13] Paul: Like, I met Chris Sparks. He messaged me when I was in Taiwan to learn about it, and we became friends. And a bunch of other people— it's always the personal stuff you connect over to. Totally. Let's see, what other questions do we have? How do you deal with it?

[45:30] Khe Hy: Can I address the 'what if it was easy' question? Yeah, people struggle with— so one of this question, 'what if it was easy,' and, and, um, Jill and forget who else was saying it. Their name starts with a T. It was inspired. It's a Tim Ferriss-inspired question. And so what if this was easy is as simple as it sounds, which is like, okay, I want to write a book.

Well, what if it was easy, right? Everything I've heard about a book is that it's not easy. I think people are like, you have to, you have to write for 4 hours every day. If you want to publish a book, the consistent narrative that I've heard is you have to write for 4 hours every day for like 12 to 18 months. Okay. And Paul is shaking his head.

So the what if it was easy question opens you up to possibility that that is a narrative, right? And maybe that's a narrative if you want a New York Times bestseller, maybe, but even then I would question that. Maybe it's a bestseller if you're writing about Maybe it's a condition if you're writing about a topic that you're not passionate about. Right? So for example, people always tell me, okay, you should write a book. You should write a book.

And a book would make perfect sense for everything we're doing, like a published book. And I think I could get a book deal, but it doesn't pass the what if it was easy test. It just, I, I, I, you know, I love 10K work. I don't love it enough to write a book just for my business. I'll be straight up with all of y'all. Uh, it could be a very good book.

And I could make a lot of money and do wonders for business, maybe it will tip to the point where it purely becomes something I do for the business because I have other stakeholders in the business now. But as of now, it just sounds way too much of a grind. And in fact, the book that I would want to write about is like some connection between productivity and mortality and like our finite time on earth and things like that. I don't think I'm ready to write that book. Yet. I don't think I have enough knowledge on the topic.

And so I do think I'll write a book one day. So that's the what if it was easy, and you can look at it in so many different ways. If you're struggling with that question, actually, one more point on that is a lot of times we equate struggle with worthiness. So we have a why, we have a script that says If it's easy, it can't be— the reward can't be good, can't be worthwhile. So some of that question might be unwiring that script. And then the last thing I'll say to Jill is an easier way to get at that question is where is there unnecessary struggle?

You could think of the thrashing, like, you know, whether you're learning how to swim or getting tossed by a wave, or, you know, you're doing something that you don't want to do, but because of someone else's expectation, the thrashing, the struggle, the— you could see, like, I'm just tensing up just thinking about that. Now, it doesn't mean don't do that thing, but it means inquire what's behind the struggle on that thing. I bet it comes back to those recurring thought loops, like, I'm unlovable, I'm scared of rejection, I don't want to be alone. And so then, you know, that's a much longer pathway, but again, recognize that the struggle, like you can opt out of that struggle. You might not see it right away, but you can always opt out of that struggle.

[48:58] Paul: Yeah. When I left my job, I intentionally designed to avoid that struggle. I didn't like the struggle and I wanted to escape it. So I was always searching for what are the hacks, what are the different ways to do things such that it might be fun. And in doing my book, I basically designed it the same way. It was like working with a publisher was off the table.

I don't want a boss. I don't want artificial— I want deadlines and timelines and emails and meetings. That would have destroyed it for me. So I basically just said it will take as long as it takes. I love writing, so I'll show up and write when I'm called to. Like, I would get stuck at certain points and just stop writing for a couple weeks and just say the, the words will come when they're meant to come.

And one quote in the book which I highlight is, uh, John Steinbeck in a letter to his son. He says, nothing good gets away. And yeah, I really believe that, right? If there is a good book in you, it's, it's gonna be written, right? But I kind of pair that with the idea like, yes, and as long as you create the space to let it emerge.

[50:11] Khe Hy: Yeah, right.

[50:11] Paul: So I'm always paying attention to like, when is— what does it feel the right time? When am I getting signals from people? So I had been writing consistently for 3 or 4 years, and 3 or 4 people said to me like, write this book. I read Amy McMillan's book, it made me feel amazing. I was like, there should be more of these. And I just crafted an experience that was on my terms.

It was super fun. I did two covers, two different covers, because I thought that'd be fun. I did block quotes even though 98% of books do indents. I was like, I don't care, I like that. And yeah, just did it on my own. Could I have— no, I know enough that I could have done something that was more successful, but I'm, I don't think it would've been fun.

Mm-hmm.

[51:00] Khe Hy: Yeah. And I think that goes to the point. Yeah. I think you can keep, like, just, you can opt out. I think you opted out of the traditional way.

[51:08] Paul: Journey going no matter, like over the long term. And like, I think from your journey and mine, like I wanna scream to people like it is actually possible to create a long game on your own terms that you can sustain.

[51:21] Khe Hy: Yeah.

[51:22] Paul: And I think it's more possible than ever.

[51:24] Khe Hy: And I just want to add, like, take Atomic Habits, right? We were just— I was with Dan Runcie yesterday. We were just reflecting that he outsold both Obamas. Like, think about that. His book on habits outsold both. Not if you add them together, but like they were 2 and 3.

Like in like last year's most read, most bought book. And then I asked James, how long did it take you to write Atomic Habits? He said writing plus marketing, 10,000 hours. So you could cut the math however you want on that. But that is a long, long time. There's, there's no way you can thrash through 10,000 hours.

[52:14] Paul: No way.

[52:17] Khe Hy: And so, you know, look for those signs of that ease. And again, it doesn't mean quit your job. It doesn't mean give up your project, but what it does mean is like have an antenna that's like, boop, boop, boop, boop, boop, boop. Oh, ease alert, ease alert. Look in, look in, look in. What's here?

What's behind this? What's the topic? Who's it with? What story am I telling myself? What story am I not telling myself? And then you can kind of like hone into those.

[52:41] Paul: Yeah, I, I was realizing somebody pointed out James Clear's tweet where he was writing about how long it took, and I realized I almost have the same journey. I started writing publicly in 2010 for a business school blog, and then I wrote after that about a health crisis. Then I wrote on Medium, and then— and I look back, I was like, oh my God, writing is the most consistent thing I've done for the past in years and what I published and I, it's been really shocking, like how well the book is doing. Like I didn't put any effort into the launch or anything and I'm just like tweeting about it, but people are starting to tell other people and it's really because I kind of validated it through like hundreds of conversations and it's really just an emergent product of like things people already were down with.

[53:37] Khe Hy: And I think the key point is that you had to— or one of the key points that I think a lot of people in the chat might still be wrestling with as you're talking is like you had to give yourself permission to not go after a published book deal, and you had to give yourself permission to know what— but it was easy for you because you have the self-awareness to know what you want and what you don't want. And I think that most people don't have that. It's actually a great metaphor for The Pathless Path. Think about how meta it is, right? Because you're like, sure, you could have gotten a published book deal if you want. You could have stayed in consulting, right?

It's that you knew your why, you knew your non-negotiables, and a published book would not clear that hurdle. I think a lot of people might not know their why, their how, their non-negotiable. Then, of course, you should go for the published book deal because that's what everyone else says you should do, and that's the thing your parents will high-five you for.

[54:46] Paul: Although, if you want approval as a solopreneur, the boomers are eating my book up. They are loving the author title. I am suddenly visible. After 5 years. I'm like, this thing is still net negative money. And I'm like, this has been— they're loving it.

It's, it's pretty funny. But yeah, so we're running up on time. Wanted to do 3 rapid-fire questions and then we can wrap up. Favorite book that has inspired you on this journey?

[55:23] Khe Hy: Oh man. I don't know, man. I don't read that much. Um, so, but I would probably say the book that I come back to the most is the Tao Te Ching, the Stephen Mitchell translation. Just kind of puts, you know, like, it puts the, the whole, um, like, the whole bigger picture of, like, this, like, dual world that we live in. Like, this is good, this is bad.

Like, you know, you're gonna die and you're alive. Like, it just really kind of changed the way that I think about a lot of the binary views that we have in Western society. Like, The Pathless Path, right? I mean, The Pathless Path is a Taoist phrasing— framing.

[56:11] Paul: Yeah, I'm just remixing. Yeah, I'd love to. Um, the—

[56:17] Khe Hy: you wouldn't be the first, you won't be the last.

[56:20] Paul: Favorite metric for success now?

[56:26] Khe Hy: Uh, presence, like true presence around loved ones.

[56:35] Paul: Love it.

[56:36] Khe Hy: Not, not doing great on that metric, by the way, right now.

[56:40] Paul: So you'll get it back.

[56:42] Khe Hy: Room for improvement.

[56:43] Paul: Take a step back, take a step forward. Um, Most interesting trade-off or thing you valued, you discovered that didn't know before you took your leap. Hmm.

[57:03] Khe Hy: Oh, doing, doing things that are like economically not that, that don't make sense. So like, like cleaning dishes. I used to hate cleaning dishes because it's like I wanted to like hire TaskRabbits to come into our house because that was, you know, that was my job. My wife cooked, I cleaned. And I'm like this, you know, calculating my hourly rate. I'm like, this is absurd.

Like I could pay someone to do this, like arbitrage it on this. And then Lisa's like, yeah, but then we'd have a stranger in our house cleaning our dishes. Now, like I find so much joy in like the— like I never understood why someone would garden. Um, and now I, I, you know, Manhattan Beach is not garden friendly. Um, but like, I have get so much joy in like in sweeping leaves and loading and unloading the dishwasher and cutting vegetables and things like that. So like, I think, um, seeing the beauty, like I would always have to be listening to a podcast while I was doing one of those things, and now I'm just like I'll be honest, I don't read that many books.

I barely listen to podcasts. I like to read long-form digital. That's kind of like my main source of reading. But yeah, I like quiet stillness and things that are non-economically producing activities.

[58:36] Paul: I love that. That's great. Yeah, I, early on in my journey, I was cutting costs to kind of extend my runway and I realized I was playing accountant. Uh, but I wrote in my book, like, I realized that playing accountant is not a personality and I needed to shift to actually like living life. Um, yeah, that's beautiful. Uh, where I, I'll throw up some of the links here to Kay's course.

Yeah.

[59:07] Khe Hy: His, uh, actually we have like a little goodie for— if you drop this link in. Oops. Oh, yeah.

[59:18] Paul: Is that on the YouTube?

[59:23] Khe Hy: So, yeah, with that link, we have this awesome kind of synthesis. Oh, oh, we have awesome Mic is all—

[59:36] Paul: No, you're good now.

[59:38] Khe Hy: I'm good. So we have this awesome synthesis. Is it working? Yeah, you're good. Because I'm hearing an echo.

[59:49] Paul: You're fine. Now you're not working. You unplugged it. Well, K has given us a freebie. The link is right here. I think Kay's calling it.

Thank you. You can still hear us. Follow him on Twitter. I'll follow up with the link for people too. You can follow me on Twitter if you want to check out—

[01:00:20] Khe Hy: I'm back. Oh, she's back. I'm back.

[01:00:24] Paul: I couldn't— oh, the audio is even better now. Before, I think you were talking into your headphones.

[01:00:29] Khe Hy: Oh, Jesus Christ.

[01:00:31] Paul: Oh, this is beautiful.

[01:00:34] Khe Hy: Um, but yeah, thank you, thank you, Paul. Thank you to all of our friends here. I see so many— I mean, this is our tribe, right? I see them all in the chat.

[01:00:46] Paul: People, I'm just playing with all these, uh, streaming features. It's fun.

[01:00:53] Khe Hy: Cool.

[01:00:54] Paul: Well, uh, looking forward to seeing everyone around on the interwebs and, uh, in real life hopefully as well. Thanks again, Khe. Keep doing you on this journey, and I'll still be following along.

[01:01:06] Khe Hy: Sounds good. See you, everyone. Thank you, Paul.