How To Tame The Shadow Side Of Solopreneurship - Darren Joe (Podcast)

[01:39] Paul: Today we're talking with Darren Joe, who is a friend and calling from Vietnam, where he has been living for a while. He is the newly published author of Failsafe Entrepreneur and has been a solopreneur for more than a decade. Comes from a former prestige hacker background like me, and we're going to dive into his path, what he's learned along the way as a solopreneur, what he's learned from writing, and a bunch of other stuff. So welcome to the podcast, Darren.

[02:13] Darren Joe: Thank you so much, Paul, for having me. And seriously, thank you for all the work you're doing with bringing your unique perspective to this space, which I really appreciate.

[02:25] Paul: Yeah, I love what you're doing. And we talked, you actually interviewed me a year ago, almost 2 years ago now, I think. But we dove into the solopreneur path, what we've learned, some of the challenges, some of the unexpected painful parts of being a solopreneur after leaving a full-time job world. Relationship with their parents and things like that. But I thought a good place to start was just your childhood. You were actually one of the top tennis players in your area of California where you grew up.

You were also a top gymnast. You were also a top academic performer. Talk to me about that. And like, when did you first start to identify as like this very successful person?

[03:18] Darren Joe: That's funny. So my, my mom would always joke that she knew I should be an athlete because I would literally take a handball outside my old home when I was 5 years old and literally just play handball against the wall by myself for hours on end. She's like, okay, I think this kid is really into sports. So They put me into gymnastics. I'm a Chinese American growing up and, you know, China was really good at gymnastics. So I guess they felt that would be a good fit.

And yeah, I just really started competing in gymnastics since I was 6 years old. And yeah, all 6 events on the male side and did really well. I was, I mean, I did enjoy it. Yeah, I really did enjoy the sport and performing. But I realized like that was kind of the pattern that was set in those early gymnastics years. You know, I'm not sure if your audience knows about gymnastics, but you're basically scored out of 10.0 on every event.

So you do a routine, you perform the best you can, and then you're scored, right? And that's how you get the gold medal. And I think that really continued into playing tennis because I unfortunately broke my wrist in gymnastics. I fractured my wrist pretty badly on the high bar. So I started picking up another sport, which was tennis, and that, that continued solo performance, right? Just going to, going to war, going to battle.

And I do love to compete and I do love sports. Um, so I guess I always had that in me.

[04:54] Paul: Do you remember when that turned from, okay, I, I love competing, I love getting better at things to, uh, perhaps thinking maybe there's pressure on me to be like this and that there's a larger game you're playing?

[05:10] Darren Joe: I think probably it flipped maybe around middle school and high school when I realized that, and my parents realized that tennis could be a ticket into a top university, right? It's not just for the sport. This could actually help get me into a good college. And then, you know, that's when I started to become aware of grades and how important those were to get into good schools. So it was really about getting into good college. I think that's when that switch flipped for me.

And so there was definitely additional pressure to perform well, you know, in the tennis circuit in Southern California, try to be the best player, you know, in my high school and in my region. And of course, get the best grades. I mean, just give myself the best chance to get into a great college, 'cause that was the dream. That was the big goal.

[05:55] Paul: Did it kill some of the joy for you?

[05:58] Darren Joe: It did a little bit in the sense that, I got so much status from being like the number one player in my high school, being, you know, Marmonti League, XYZ, blah, blah, blah, blah, valedictorian. But so that was nice to get that recognition, but I didn't allow myself to really explore things I was really interested in as a teenager, which is such a great time to do those things, right? Whether that's music or dancing or comedy or writing, all things that I've come back to as an adult. But I think during that, those very formative years, once we realized kind of the formula, right, that, that would give myself the best chance, I, I, I didn't do those things.

[06:38] Paul: There's a narrowing of the imagination, right? And I, I don't think I was pushed too hard. I was more, I more had the idea that, okay, I'm pretty good at school, I need to go to college, but it didn't really matter what college, like I was mo— mostly just wanted to go to UConn, uh, in Connecticut, uh, 'cause they had a good sports team and I wanted to go be part of that. But it, the general idea was that like, okay, you just go to college and you go work. And college, the whole point of going to college is to get a job. So like, it wasn't even that I didn't think to explore things.

It's like I didn't even know to know that people explore different things and are pushed in different areas. Um, And I wonder if this is just every— something everyone experiences in the way like our cultures are set up now and that everything is so instrumental. Um, is it a bit weird looking back on this and just thinking like, man, I wish somebody had like pushed me or asked me a couple questions?

[07:43] Darren Joe: Yeah, I, I just, it is weird looking back on it cuz I was such in this bubble where that's really all that mattered, like education, prestigious education, getting into that school, getting into that prestigious job. But I didn't really question it. And that's why it's taken me a long time to overcome these things. It does seem weird in hindsight, but I was just so wrapped up in that world. And I'm sure there's a number of like bubbles or communities like this where it's The parents, that's what, that's what validates the parents too, right? It's like, oh, my kid is valedictorian.

My kid is, is got into, you know, this top school.

[08:25] Paul: Yeah. I think that's something I've noticed is that from leaving my former path, which is a successful one, quote unquote successful. Yeah. Right. But the people around me no longer have a story, which is easily transmissible as a story to other people. Right?

So if you wanna say like, I'm a good parent, there's no longer very easy and like easy proof that other people are like, oh yeah, I get that. Yeah, they make good money. They're, they're at this institution, they're at this school. And I, I think that's what leads to a lot of pressure to people staying on these paths for a long time. What was your mindset in your early 20s? You went to a, a top school, you were very driven, you were working full-time, like what was your mindset and what were you thinking about like in college, right after college?

[09:21] Darren Joe: Yeah. So when I was 22, yeah, coming outta school, I just knew because I had spent one semester abroad in Hong Kong studying abroad there that I had to get back to Asia. So my mindset was, let's have some fun for one year, let's travel the world. So I did this program called Princeton in Asia in Singapore where I was teaching statistics. But honestly, after that, when I started thinking about, all right, now let's start building a career. I didn't know what I really liked to do, Paul.

Like, I, and, and, and this is the problem with like living out, you know, that script that, that's not really examined where you don't really know what you want, right? I had no idea what I wanted to do. So my strategy then was, okay, I'm just gonna find the best people to work for because I don't know what industry I want to be in. I don't even know what I'm good at, you know, in the business world. So I'm just going to find mentors. And that's how I kind of approached my early and mid-20s, just trying to work under the best people I could.

And, and by best, yeah, the mindset was still, okay, CEO of this company, uh, vice chairman of that company, right?

[10:32] Paul: So very legible status markers, but that's still pretty open-minded, like I don't even think I was that sophisticated about things. Mine was basically work for companies that other people are impressed by. I mean, you went to one of the best schools in the world in the sense that it gives you opportunities to like very prestigious job opportunities. Why didn't you go take the very obvious path to be impressive?

[11:00] Darren Joe: I think there was just something, you know, I've always had this kind of stubborn independent streak, and I think it was there. So as much as I was following that path, I also kind of rebelled against it. And maybe I also couldn't get through a first round of McKinsey interviews.

[11:18] Paul: Fair.

[11:19] Darren Joe: Yeah.

[11:20] Paul: So, so that's always been in you. You've always had this voice that's like, you're, you're playing a slightly different game, always trying to like carve out that freedom. Because I, I think that's something in my path too. Too, I was working for these impressive consulting firms, but I was like blowing it up every 2 years and like moving to a different firm before I got promoted. And I was able to disguise all this, like shifting around and trying to make it work for me because I was still employed.

[11:50] Darren Joe: Yeah.

[11:50] Paul: And then when I became self-employed, people were like, what are you doing? Why, why are you, uh, taking this crazy risky path? I think that's similar for you.

[12:02] Darren Joe: Yeah. The word disguise that you used is really interesting to me. I'm curious, did you feel like not— like when you say disguise, do you mean you were a completely different person in these jobs or you just felt like not at home or— because that, yeah. Well, let me ask you that first.

[12:21] Paul: Yeah, I think there's a very practical when you're switching jobs after My first job, I left after 10 months, and then my second job was 2 years and I went to grad school. That was a little smoother. But then like a job after that was I stayed for 14 months and you're leaving and people are questioning you and everyone buys into these scripts that you stay in a job for 2 years. So I had to come up with these stories, right? Oh, I'm leaving because I'm really excited about what you're doing. What?

And the truth was I was bored as hell. I was either working for assholes and I wanted to escape and I like wanted to keep learning. But you can't just say, I want to keep learning and I'm working for assholes. You need to come up with a more creative story. So I was disguising it in the sense that I always knew I was like lying or altering the truth to keep moving to these new roles. When the reality is like my real answer should have been like the best answer, but there it's taboo to say these things.

[13:19] Darren Joe: For me, it was less a disguise and more of a I just felt like I had to put on a different self. I mean, that might sound similar to disguise, but I couldn't be completely myself in these roles, in these corporate roles. I felt, you know, from the clothes to just the whole MO, I just, I'm like, man, I can't wait. And I write about this in my book. Like, I can't wait to get home and just like strip off all my work clothes, take off like these tight clothes and, stiff shoes and just be free. And I always felt that way from the beginning.

I always wondered, like, is this really it? Even though I was working under some very successful businessmen and big companies, just like, is this really what work is about? And I'll never forget that feeling, like, even that lasted.

[14:13] Paul: So what were you doing at that time when you were thinking that?

[14:16] Darren Joe: So the first job, the first like corporate job I had was I was basically an internal consultant for the world's largest energy shipper. They would ship oil and gas around the world. So they had these giant tankers. So I was in the shipping industry, working under the head of corporate development and yeah, writing strategy reports, also trying to do internal sort of consulting for them. And then the second job I had after that was working for the vice chairman of the world's largest scientific publishing company, Elsevier, which some of your listeners might know about. And yeah, that one, the second one was in New York City.

Yeah, those were the main two corporate experiences.

[15:01] Paul: When was the first moment when you started to think about a path outside of full-time employment?

[15:08] Darren Joe: The entire time. I mean, really, I mean, after like working, you know, in the shipping and my shipping job for 3 months, learning everything I could about the shipping industry, I would find myself like looking online for copywriting courses or, you know, like side hustle sort of businesses. Like at the time I was like, okay, maybe I can help people with college admissions essays.

[15:33] Paul: And what year was this?

[15:34] Darren Joe: 2003, 2004.

[15:36] Paul: So this is really early. Like, no, nobody was like self-employed or working solo at the time. Like, who were your influences? Where were you getting these ideas from?

[15:47] Darren Joe: Paul, I, I can't tell you. I just, um, it's just something. I, I think I'm just— I, I have to create stuff, and I, and I have kind of a control issue, and independent, like I want to be independent, so I just want to do my own thing.

[16:02] Paul: Yeah.

[16:02] Darren Joe: And so I've always had that.

[16:04] Paul: Yeah. Yeah.

[16:05] Darren Joe: No one like planted the seed. Maybe Tim Ferriss planted the seed for like complete location independence, but like before that book came out, it was just like, oh, I want to do my own thing.

[16:16] Paul: That's fascinating. And I think the way our world is built now, those opportunities have almost disappeared. Like you look 100 years ago, almost everyone was an entrepreneur. You had to do things locally, right? You had to make your own stuff, handle your own food, like solve your own problems locally. In many ways, we've taken away the ability to have those autonomous independent lives.

And I guarantee like tons of people are like you that are just like, I just want more control.

[16:47] Darren Joe: I just want more control. And maybe like you, Paul, like the, maybe the best inkling of that was my desire to travel. My desire to really get out of Southern California where I grew up and get out of the US, see all of Southeast Asia, like China, Taiwan. I just wanted to see it all.

[17:06] Paul: Is part of that, um, growing up as a Chinese American in the US, like kind of just feeling like you don't have that connection to Asian culture, or I mean, growing up in California that it's pretty diverse and you can easily feel at home, but it's not Asia.

[17:27] Darren Joe: You know, I've never really thought about that, but now that you say that, I think there is an element because I grew up in a predominantly, you know, white neighborhood. I was always kind of the token Asian person wherever I went, even at Princeton to some extent. So I think there was a sort of like, oh, I look like everyone else out here. I mean, as dumb as that sounds, I think, yeah, I found a strange sort of comfort in that.

[17:54] Paul: The funny thing is I had no desire to travel and I think it was one of these like, don't know what I don't know. I even remember working in consulting. I had a trip to Europe and my friends were staying on a few days and I was just like, ah, I'm just gonna go back. I wanna be back home. They're like, it's a free trip overseas.

[18:11] Darren Joe: Right.

[18:11] Paul: You just have to pay for the hotels. Um, but I just didn't have that curiosity. And I think I just kept all these like urges to explore, be adventurous, like very submerged. And then over time they gradually just kept showing up and asking more questions. And here we are like 4 years later of location independent, like whatever the heck I'm doing with all my, um, businesses. But it's been an interesting journey.

And I think one of the most interesting things of it is that the lives we're living now are way more possible than ever. Like for people to just opt into this, even for a couple years, it's super easy, like relative to the early 2000s. When did you take the leap?

[19:00] Darren Joe: So I first took the leap trying to start my own business in actually 2007, and this isn't in the book at all, but I started a retail shop in Singapore with two partners and it was an import-export business and we sold these kind of charming little collectibles and we had a store. It was absolutely wild. They were actually called Ethnic Voodoo Dolls. Wow. Yeah, exactly.

[19:24] Paul: Not 2021 friendly.

[19:29] Darren Joe: Absolutely not 2021 friendly. And they were found in Taiwan. So I actually franchised this from this chain in Taiwan, brought it to Singapore. And we had a 1-year go at it. I was a total business newbie. I had no idea what I was doing, you know, entrepreneurship-wise.

That was a good experience, but then I needed to make some more money, so I jumped back into a job where— so I was basically an MBA admissions director for a top business school in Singapore. And then I took the real official jump in 2011, and I haven't had a job since. Yeah.

[20:00] Paul: Yeah. So you've been writing about this journey where you come up with the term fail.

[20:09] Darren Joe: Yes.

[20:09] Paul: So, so break down fail for me, what that means.

[20:13] Darren Joe: Yeah. So I call my book The Fail-Safe Solopreneur because I believe that my view is that we don't talk about the costs enough of this life. And I think there are true costs. As great as, you know, our freedom is, Paul, and that we get to travel, we also— and I know you've had to deal with these things. Have to deal with the costs of these work-life values that we so desperately crave. So the acronym FAIL stands for— okay, well, let me start with the work-life values that we crave.

I think it's ingenuity. So being creative. I think it's freedom. I think it's adventure and meaning. I mean, at least for me, I don't know about you, Paul, if you match there, but those are the 4 things I I really want. And, and that's one reason I'm on this path.

[21:02] Paul: Yeah, yeah, I'm probably 90% overlap with that.

[21:06] Darren Joe: Yeah. And so I think the shadow side of those values is FAIL. So F stands for failure, A stands for anxiety, I stands for instability, and L stands for loneliness. And I think that if we can expect and manage these shadow sides of this path that we're on, we can do our best work and make the most of our life. But unfortunately, no one's talking about this as much as I think it should be talked about. And so we might feel even more lonely or even more anxious about our journeys when really this is what we all have to go through.

This is just the flip side of what we're doing, of what we want the most. It comes with the territory. That's my point. So yeah.

[21:49] Paul: Yeah. I think what I've found is that these things are human, right? We all deal with anxiety, uncertainty, loneliness. It's just that when you move, for me, when I moved from full-time employment to self-employment, they're active in-your-face questions. Like when I was full-time, you can actually avoid these questions. Yes, you can hide from them because no one will ask you why you're doing what you're doing ever.

[22:22] Darren Joe: Exactly.

[22:25] Paul: Like, it's astounding to me looking back, like it didn't matter how much I disliked my job. Nobody would ask like, well, why are you doing this? Why don't you explore something else? But now that I'm like self-employed, people are like, why are you doing this? Aren't you worried about this? Aren't you worried about— it's like, yes, I worry about these things all the time.

I feel like an idiot every other month. I feel insecure. But the only way I've learned to manage these is basically just stare them in the face, tango with them, and actually look at them as a feature, right? So it's like, I love these, I love these small existential crises. So like, I'd rather be insecure a little bit every day. And it's like, okay, I can, I can dance and tango with this.

[23:11] Darren Joe: Yeah. I mean, so, you know, Tim Ferriss famously calls this the void. In his book, in the last chapter of his book. You call it like, you know, tango with these things. I call it the question because when you're on the path, like you're a, you know, successful management consultant, no one's gonna ask you, right? Like, why are you doing this?

Because you're on that proven set path, or at least known path, maybe not proven, but known. But then when you're like us and you have the freedom to choose your day, that question can, be overwhelming sometimes. Yeah. I mean, it sounds so privileged to say, but trust me, when you get there, you'll know. I mean, it's like, okay, what, what should I, what, what really matters to you? You really have to wrestle with those questions.

So it's my belief you need more battery power to deal with these things, you know? And, but as long as you're aware that it's coming, that's the key.

[24:06] Paul: Yeah. What are some of the strategies you've learned to develop to like deal with insecurity and uncertainty, right? Because that's one of the biggest ones.

[24:16] Darren Joe: Absolutely.

[24:16] Paul: You just don't know if your business is going to fall apart next month or if you'll have money.

[24:21] Darren Joe: Yeah, I'm so glad. I love how you just plainly say this stuff, Paul. That's why I really, you know, vibe. So I think the tool that has helped me the most and my friends that have read the book is this idea of the perfect day.

[24:37] Paul: Yeah.

[24:38] Darren Joe: I think it's a really simple and effective way to manage that question or the uncertainty. Actually, when I originally started writing the book, it was called The Perfect Day because in 2017, my business, you know, I'd made the most money with my business ever, yet I was totally lonely and lost. And so, I realized that, you know, I had to figure out like, what did I really want, right? What is success for me? I thought I had achieved it with, you know, a good income that year with total time and location mobility, but I wasn't, it didn't do it. So basically I started writing this book for myself and it was like, all right, what's my perfect day?

Okay. Like imagine that, that takes 10 minutes and I've asked 50 people about this. Everyone knows their perfect day within a second. It's not something like, oh, what's your future in 10 years, Paul? And you're like, uh, right. But if I ask you what's your perfect day, you're gonna know pretty much.

Um, at least that's what I found.

[25:48] Paul: Yeah. Well, I might be a little more advanced, so like I've figured out my perfect day, but I've also figured out that's not the I don't think that's the right level for me of thinking about things. It's actually like, what's the perfect month? And then what's the perfect like 3-month chunk?

[26:07] Darren Joe: Yes.

[26:08] Paul: Cause like if I, if I can get the balance right in like 1 month, like that, I love that, right? Yeah. So it might involve like a couple days of like going really hard on stuff, but then it's balanced by other stuff. And then also at a year. It's also the same thing where it's like, okay, these 3 months I worked really hard on this project. Like I learned Chinese earlier this year and like that was my learn Chinese quarter.

This is my like work on the book quarter. This next quarter is like, et cetera. Um, and then when I like balance all these things, it's like, damn, this is the life I want to keep living.

[26:47] Darren Joe: Yeah. No, that, that's.

[26:51] Paul: Not to like dump on the perfect day, but like, I think the perfect day is where I started, right? Because self-employment is basically staring that question in the face every day. You need to wake up and be like, what the hell do I do today? Because I can do anything.

[27:07] Darren Joe: Yes, yes, exactly. So I love like your chunks of time. I think that's great. Like for me, why I like the perfect day is because there, you know, sometimes when you're grinding through something or, you know, you're not landing customers or customers cancel on you or just things don't go as well as you planned. Like it's, I'm all about, okay, let's try to turn that course around as soon as possible. So that's like the shortest chunk of time, right?

So that's why after imagining your perfect day, I think a key part of this whole exercise is ranking your day. From negative 2 being a shitty, awful day to 2 being, you know, a fantastic day. 0 would be neutral, right? And over time, because you're dealing with this uncertainty, Paul, like, you start to realize, all right, I rank my days 1s because, you know, I saw my good friends, because I exercised an hour that day, and because I got like one thing that move the needle of my business forward or whatever. And that's gonna be different for whatever, whoever you are. But I think that sort of knowledge is so important in creating, I don't like the word template, but it helps like narrow the uncertainty of the day.

And of course you're gonna evolve as, right? And this will change. But I think this sort of daily score and writing down what I did that day and why I scored that day, that has been so helpful for me to like, you know, stay stable on this journey.

[28:43] Paul: Well, I think the biggest values are quitting the things that drain your energy.

[28:49] Darren Joe: Yes.

[28:50] Paul: What are the biggest things you've eliminated from doing this kind of reflection? And I, I think a lot of the value is just literally doing the reflection.

[28:59] Darren Joe: Yes. Yes. So I think that I, so probably the biggest thing is working nonstop. I mean, it sounds so dumb, but when you have so much time and if you don't fill that time with other interesting hobbies or then your whole identity is working. And so I think a big part of figuring out my perfect day was like setting limits. For example, no work after this time.

Or it's okay to take X days off a week and then, you know, recharge. Like that has been, so I guess subtracting work has been a big part of my perfect day.

[29:42] Paul: I actually, so I've like never struggled too much with this. I actually look at it from the other perspective, which is like, how do I design things such that I'm super excited about work, cuz like my whole goal is to like find the work I want to keep doing, which is a much harder challenge than like find work that will make money. Like if I, if I'm just making money, there's ways to do it, but my motivation will be destroyed super fast. So on an average day, I'm like totally fine not working, but I am happiest over long stretches of time when I'm working on things I'm excited about. So I'm always thinking about, okay, can I create a 1-month challenge for myself? Can I create public, public commitments such that I'll be excited to follow through?

Can I help people such that people are cheering me on and things like that?

[30:43] Darren Joe: Yeah, I love that. And maybe one more thing that I found I just wanna mention was like keeping my mornings open for that creative deep work. That was probably, that's probably been the biggest, you know, one of the, you know, impacts my score the most.

[30:58] Paul: Like what? Writing?

[31:00] Darren Joe: Writing, hosting, just blank page type stuff.

[31:05] Paul: Yeah.

[31:05] Darren Joe: Type.

[31:05] Paul: So do, do you do any, do you have anything ever scheduled in the mornings?

[31:11] Darren Joe: It's, it's basically, uh, 3, I schedule like 2 time blocks of sprints for, of creative work. That's usually 50 minutes, 2 or 3 sprints of 50 minutes each. Yeah. And that like, oh man, you still schedule stuff though. It's a loose schedule. It's not like, you know, penciled in every hour, but it's like, okay, I'm gonna spend, you know, 2, 3 hours every morning doing my most creative work and not being bothered by anybody or anything.

And then the, yeah, yeah, yeah.

[31:47] Paul: And then do you work 5 days a week, 6 days a week, 3 days a week?

[31:51] Darren Joe: 5 and a half.

[31:53] Paul: 5 and a half.

[31:54] Darren Joe: Yeah, Saturday. I enjoy it. I enjoy it.

[31:56] Paul: And when you started out, um, being self-employed, how did you think about work? Cause I think that's something that's interesting for me is like, I used to look at work as like something to minimize. And then because of that, in 10 years of full-time work, like I never wanted to work weekends or nights. Um, but now like self-employed, I, I really don't care if I'm working on stuff, but it took me a while to like stop seeing work as like something evil to minimize and like work being something, oh, I might actually enjoy to like write on a Saturday and it's not a bad thing.

[32:30] Darren Joe: Hmm.

[32:32] Paul: Did you go through anything like that or?

[32:36] Darren Joe: No, I think I was just concerned with surviving at first and just making enough money to sustain myself. Yeah. So I, the first few years was just me pounding my my head against the wall, like trying to make someone to click a PayPal button, you know, like just, and being a bit stressed about it honestly, because all I saw online at the time was like, oh, it's so easy. You just like do this and that and then you're going to be making, you know, a couple thousand dollars a month and that'll turn into $10,000 a month. And of course, well, maybe not of course, but for me it took me a long time to, you know, make my first sale and like, you know, so it was a bit stressful. But I didn't mind the work because I knew I was trying to get to a certain point.

[33:22] Paul: Yeah. Do you think if you had to go back, would you give yourself advice to do anything different? Or would you just be like, take the same path?

[33:31] Darren Joe: Oh no, no, Paul. I would, I would absolutely give myself advice. I would say, Darren, you can't study or read your way into a new identity. And I think that's something that has impressed me so much about you, Paul, is it seems like you've really dived into circles and communities that can kind of hold that space for you and where you can meet people doing the same. And I think that's why your rate of success has probably been a lot quicker than mine because I just thought, oh, I'm going to treat this like a paper. Like I'm just going to study this and I can do it.

No, no, no, no, no, no. I should have jumped into communities of people earlier that were living these location-independent lives, just see how they're going about their life, how they're dealing with all these challenges, how they're making their first sales. And it was only after I did that, maybe 18 months into my journey, that I really started to— it started to click and things started to work. Because in that time of transition, like, you don't know what cause and effect is. You're not an expert at that, right? You have to jump in that complex space and like, probe.

And that's new relationships, that's new activities, that's new ways of being. So, uh, I really believe in like play experimentation and like joining communities as we've talked about before. That's so important.

[34:52] Paul: Yeah. I don't know why I had this hunch. I had this hunch that making friends was going to be more important than anything. And that's it. I think part of this is I've always been wired that way. I just like hanging out with people.

So part of it was selfish, but it was really the thing that I prioritized starting 6 months into my journey. And to be fair, I think I got lucky and the timing. I benefited from people like you who started this journey a decade ago and like built these communities and started writing about these things and sharing lessons. I mean, you, you were pretty early and it was arguably a lot harder in 2011 to figure this stuff out. Yeah, I, I, I felt very on my own and you probably knew, like once you started meeting people, you probably knew like the 50 to 100 people experimenting with this, right? Like I, I was laughing that you were like having convos with like Derek Sivers, who is now like seen as like a very like influential person.

Um, but he's just like, like you trying to figure it out.

[36:06] Darren Joe: Yeah. And I have to give a shout out to the guys at Tropical MBA Podcast. Yeah.

[36:11] Paul: They were early on this for sure.

[36:13] Darren Joe: They were early on it. And, you know, they have like their community and it was wonderful because I could be in Saigon, I could be in Bangkok, I could be, you know, somewhere in Malaysia and then find one or two other people who are also trying to do it. And this was in 2012. And I can't, like that sense of communion when you meet someone else who's also doing this crazy thing at the time, like instant bond. So they stumbled onto that vein really fast and they created something really wonderful there.

[36:43] Paul: Yeah.

[36:43] Darren Joe: So that helps me a lot.

[36:46] Paul: Well, part of the bond is you don't have to actually explain your life.

[36:51] Darren Joe: Oh, you so, so true. It's just like.

[36:55] Paul: Yes, you can be vulnerable together. It's like, yeah, I have no idea what I'm doing and I'm really scared. Oh, me too.

[37:01] Darren Joe: So like when I was in Singapore and I wanted to start my business, all my friends were working, you know, cushy corporate jobs and like, you know, Sunday avocado toast brunches that are like $40 in Singapore. And I'm like, oh my gosh, I'm going to, I'm going to run out of money. Like, how am I going to do this? Yeah. When I moved to Saigon and I met, you know, 10, 20 of these types of people that were also trying to do the same thing as me, those Sundays turned into, okay, wow, like we found this coconut vendor so we can get 20 coconuts and 20 banh mis for $20. Let's like get together and talk about, you know, marketing, like funnels.

And it was such a, but it was awesome. It was great. Yeah, it was amazing. And like, no bullshit, just like, yeah, what, what are you working on? Like, what are you using? It was really fun.

[37:51] Paul: I think the, one of the hardest things you wrote about this in your book, everyone I know deals with this. There are some exceptions and they're very lucky, but parents do not like this lifestyle. Like you're 10 years in and it sounds like your parents are still pretty uncomfortable with it. They are.

[38:14] Darren Joe: In fact, I opened the book with my mom saying, you know, Darren, if we were like other Chinese families, we would've disowned you. And I'm a 40-year-old grown man, right? And like, there's still no—

[38:26] Paul: That's painful. That's painful for me to hear, but it's also like, I can understand it a little bit better being married to someone from Taiwan. It's like, okay, that probably isn't as painful as if like my parents said it, but it's still like, man, that is vicious. Yeah. Yeah.

[38:45] Darren Joe: And You know, I've learned to, you know, it's been hard. Don't get me wrong, Paul, it's been very hard. You're so right. And it's taken me years to overcome this script of, okay, I'm only a success if I please my parents. I'm embarrassed to admit that as old as I am, but you know, we have to be aware of these things and kind of embrace them in a way, right? Because that script was also my superpower.

That's what, you know, helped me perform so well and allowed me to build relationships too. Everything that that script, you know, made me. But it also held me back in so many ways. And that's why I believe, you know, you have to find a new family to support you. And, you know, I still have a great relationship with my parents. I think they're wonderful parents still.

You know, it's just they have a completely different view for what my life should be and what what a good life is, and that's fine. But I had to come to that point where I'm okay with that and they're slightly more okay with what I'm doing.

[39:52] Paul: Is there anything that helped shift their mindset? It sounds like you kind of went outta your way, and I resonate with this too, of like trying to like reframe what you're doing into their language such that they might understand. I did this as well and I think it was, I always felt a bit like desperate doing it. Like I'm trying to like show income statements and like show like, hey, I'm making money and like I'm, I'm an entrepreneur, even though like in other communities I don't refer to myself as an entrepreneur and I don't talk about money.

[40:26] Darren Joe: Right.

[40:27] Paul: Because it's not the thing that matters to me. So how do you, like, what was that like for you? It sounded like you did something similar reading from the book?

[40:37] Darren Joe: Yeah. You know, just at first it was like an argument and then the argument turned into, okay, let me just try to show proof, right? Let me try to like, okay.

[40:47] Paul: Yeah. Like you said, what was the argument like? Walk me through that. Cause I, I think this will help a lot of people. So many people reach out about this and I think it's valuable to share.

[40:59] Darren Joe: Sure. Well, the argument didn't work, but I'll share the argument. The argument was. There's a lot of opportunity, you know, out in Asia and my business really fits, you know, I basically made like a market growth argument and that—

[41:15] Paul: No, I mean like what was the, like what's the disconnect with your parents? Like where, oh, okay. So they were just like, what are you doing? Like why, why do you have to go live this life? Why do you have to be an entrepreneur? Like what was the disconnect?

What were they unhappy with?

[41:33] Darren Joe: The lack of stability.

[41:35] Paul: So they didn't, they didn't even care if you made more money. It was just socially unacceptable what you were trying to do.

[41:42] Darren Joe: Well, to them, the stability was the most important. They knew I was, you know, trying to make ends meet at the beginning, right? They're like, Darren, you have a great education, work background. What are you doing? Like your ancestors escaped China and Asia to come to the US to work, and now you're going back there. Like come home, get a stable job, start a family, the traditional kind of script, uh, which I don't blame them for having, honestly.

[42:08] Paul: Right.

[42:09] Darren Joe: Yeah.

[42:10] Paul: Yeah. And I can understand that, um, being in Asia now, I think, I mean, the US, I think a lot of people in the US don't appreciate how much economic opportunity they have just from being born there. Right.

[42:24] Darren Joe: Absolutely.

[42:24] Paul: It's like, holy crap, what an incredible labor market. You can work an average job at a corporate job and become pretty well off financially, but that shouldn't be mistaken as the point of life.

[42:39] Darren Joe: I mean, don't get me wrong, I think all that stuff is important. I'm sure you would agree too, but it, you know, does it have to be the most important thing? Like, life is too short.

[42:53] Paul: Yeah. Yeah. So parents weren't, didn't love that you were trying to make an argument that there's all this opportunity. How did that relationship evolve over time and like what were some of the things that might have improved it, if anything? Oh man.

[43:07] Darren Joe: Well, that's a really deep question.

[43:11] Paul: It is still, I just know the pain of it. I know, I know it's real.

[43:15] Darren Joe: Yeah. Oh man. It's, it's, you know, at first I tried to, again, win through arguments. The arguments didn't work. I come home. That makes a lot more sense, Darren.

Then I tried to win it through proving myself, you know, through success with the business and so forth, just showing I could do this. But still, that didn't work either. And honestly, Paul, we haven't reached an agreement on it. I think I've just come to a better understanding that I'm more comfortable with them not approving of this path.

[43:51] Paul: Yeah.

[43:52] Darren Joe: And I, I don't want to do something, Paul, because out of guilt. I want to do it because this is, you know, what the life I want to live, and I want to be with my parents and like gratify them as much as I can, but because I want to do it, not out of this like cloud of guilt that's, that's hanging over me. Um, yeah. And honest. So before I published the book, I had like one week before I had this conversation with mom and dad, cuz they didn't know I had written about them.

[44:25] Paul: Yeah.

[44:25] Darren Joe: You know, the first chapter is about this relationship and I was ironically very scared, of course. Uh, worried about their reaction, but they, Paul, it was liberating. Because I had this conversation with my dad. I said, Dad, I included that line in the book that, you know, if you didn't get into Princeton, all the investment into your tennis career, tournaments every weekend, tennis lessons, wouldn't have been worth it.

[44:50] Paul: Yeah.

[44:50] Darren Joe: I included that in the book. And he said, yeah, that's true. That's fine.

[44:57] Paul: Oh God. It's like, yeah, you're not gonna—

[45:00] Darren Joe: He was totally cool with it.

[45:01] Paul: He's not gonna— yeah, you're not gonna change that story for him.

[45:05] Darren Joe: Yeah, exactly. So my point is, a lot of this stuff is in your own head too. And in the end, they were so supportive of me. They could see how joyful I was to write a book, a life dream. And, and so that really brought this whole journey full circle, Paul, because then I realized, like, you know, push comes to shove, they just want me to I'm going to do my best and be happy, but even though we might disagree about the path. So in other words, being open with it, trying to talk it through, being vulnerable, I think maybe those things will help.

[45:41] Paul: Yeah, I think, I mean, a lot of people I talk to, I challenge them with a question. This is one of the things that's hard to figure out if you're going to take a leap like this is like, are you comfortable If there's like a long-term dissatisfaction from your parents because of you making this choice, and that is such a wise question.

[46:04] Darren Joe: I'm so glad you asked it.

[46:05] Paul: Yeah. The more, the more blunt version of it is, will your parents love you less? And that, that usually is a little more, um, direct, but, but it's real because, um, parents have very specific narratives around how they see their kids and how they see their own like identities as parents. Like, I am a good parent if my kids do X, right? That, that is like very American too. There's different versions of it globally.

And what I've found over and over again is the people that end up taking these leaps, like, need to take them, right? They're— nothing's going to stop them. Like, the people that are like, I'm afraid of like losing money, like the people that tell you their fears for years and never take an action, like it's actually not as necessary for them to go do this. Where like, for me it was like I had to blow up my life. Like I was at the last moment. My leap was 5 years beyond when I had already started opening up to this new path.

[47:09] Darren Joe: Yeah, I love that. I mean, I think you're so right. And, and to, to at least be aware of those things that you feel like you just have to do. And, and, and explore them in, in, in small or big ways. I mean, yeah, sometimes it makes me wonder, like, do we even really— like, how much— uh, that's a whole nother discussion.

[47:33] Paul: But do it.

[47:34] Darren Joe: No, how much of this do we really control, right?

[47:37] Paul: Like, yeah, it is a crazy question. Yeah, it—

[47:41] Darren Joe: because these urges that, that come, like, we just have to— I just had to write the book. Like, are there a lot of rewards for writing a book? Not really. I mean, am I, I mean, personally, yes, but maybe externally, no, but I had to do it.

[47:55] Paul: Yeah.

[47:56] Darren Joe: I just had to, I had to start dancing salsa. You know, I had to do, move to Colombia, move to Vietnam. I just had to do these things.

[48:07] Paul: I think there's an awareness too though, because you can suppress those. And I think I was actually pretty good at suppressing those voices or not even being aware that they were there. Especially like when I was younger in college, after college, um, I was just, I set my life up such that those kind of interests or pulls or curiosities couldn't even emerge. Hmm. Um, so I think in some choice, some sense it's like you have to do these things, but at first, like you actually need to open yourself up. I think yes, two possibilities, right?

Like you need to have this existential opening.

[48:50] Darren Joe: And if, if I can just add one thing, one thing that has helped me is being with your, like those feelings that you really want to bury or that you're ashamed about, because I think it's when you allow yourself to feel those things that you become more aware of these, you know, undercurrents. As, um, so that, you know, that has really helped me instead of always trying to present like this certain person that you think you should be to yourself and to others, like be with all the messy parts too.

[49:24] Paul: Yeah. I think integrating the, the shadow side of you is really important for this self-employment journey. Do you think, did you struggle with integrating this competitive achievement-driven side of you?

[49:38] Darren Joe: Yes.

[49:39] Paul: Like, did you, did you try to like hide that or suppress that at first and be like, I just only wanna be this ideal version of myself?

[49:49] Darren Joe: Oh, yes. Yes. I mean, what do you mean by like, like competitive person?

[49:55] Paul: Well, I see it a lot, right? I think a lot of solopreneurs, they have this idea like, I wanna be nice. I wanna be like, I will. I wanna have more positive engagements with people. I don't wanna deal with like the ruthless corporate world, but often they're like suppressing these darker emotions, which might be like greed, competitiveness, um, all these things, right? And I think the key is not to like pretend they don't exist.

It's to like figure out, okay, am I envious of other people? If so, can I find people to be envious? Of that trying to be like them will make me a better person. Am I competitive? If so, how do I compete on things that I, I will enjoy? Like for me, I love being competitive about becoming a better writer.

I hate being competitive against other people for promotions at companies cuz I will destroy myself, right? Like I like being greedy on things where like making more money won't ruin anyone's life. Yeah, I don't like being greedy when I'm like desperately trying to grovel to my boss for a raise. Right. Absolutely. So, so it's figuring out how to harness all these things.

And I think like, uh, me and my wife talk a lot, like she has this competitive streak too, but she's always telling me like, I shouldn't like feel competitive against these other people. And I'm, it's like, there's other people doing similar things to you. You don't need to like destroy them, but you can like use them as inspiration to be better at something. You actually wanna improve at.

[51:34] Darren Joe: That it took me 10 years to figure out what you just said, but I completely agree that it's about embracing those dark sides. And I had to, yeah, like that. I'm very status oriented. I'm a very status oriented person, which, which is a, I would consider that a dark side, but how can I like employ that in a healthy way? How can I give that a healthy outlet? Like in the way you've done with your writing.

I believe in that so, so much and I'm still working on it, to be honest.

[52:04] Paul: And what's your answer now? Like how are you trying to lean into that?

[52:08] Darren Joe: So for example, instead of seeking my parents' approval for business success, right? I'm doing it just to be a better entrepreneur. Like I'm not going to compete. Maybe it's a cop-out, maybe your listeners will think this is a cop-out, but I don't wanna compete with having because I think that's like having is a, oof, that's a tough game to win. Like whether that's like having what, having money, having customers. Yeah.

Yeah. Like, okay, I'm not a success unless I make a million dollars or 10 million or a hundred mil, right? Like I want to take the status sort of dark, like status motivations I have and be like, have a high status in people in the game. My parents are career government workers that lived their lives in Los Angeles. Yeah, like, I want to, you know, earn my status from people that are creating like cool businesses that are really helping people, and no matter what income, right? Like, that's kind of how I'm, I'm framing it.

[53:14] Paul: Yeah, I think I call this creating your own prestige economy. So figuring out what groups are giving out prestige such that it fits with like who you wanna be, right? So like I put people who give generously and teach up on a pedestal. So like in my mind, you do have a lot of status, Darren, right? Whereas the like midlife person at Wells Fargo who's like, okay, with his company stealing and then just spends all time like denouncing people who like create online, like not as high status for me, even though they might have a higher income. But for other people that's flipped, right?

[54:02] Darren Joe: Yes.

[54:03] Paul: So the choice is like, okay, what are the, what are the prestige games I want to play such that if I get the prestige, it's like actually a game I want to be playing.

[54:13] Darren Joe: That's, oh man, I think that's so wise. And like learning to figure out whose opinions you value is a lifetime skill, you know, being discerning about that. And, and, and yeah, like so helpful.

[54:28] Paul: It's hard though, right? Cause like, I mean, I don't care what strangers think and I can deal with that a lot better now, but like I'm still super vulnerable to like what my family and friends think. Like one neutral comment, neutral or negative comment can crush me for days.

[54:46] Darren Joe: Mm-hmm.

[54:48] Paul: Um, yeah.

[54:49] Darren Joe: And I've been there.

[54:51] Paul: Yeah. I, I think a hard thing I've really struggled with is, um, I've gotten zero to no, I've gotten little to no active encouragement. Right. So it's, it's easy to mistake. Lack of encouragement for disapproval. But sometimes when you're feeling more insecure, you actually need that active support.

And over the past couple of years, I've really leaned into some relationships to get that and just be aware that like, I need the support and active encouragement. Whereas like being on a default path, I don't think I needed it as much. Cuz like I wasn't feeling super insecure all the time, but now I am. And it's nobody else's responsibility to give that to me. And, but it doesn't mean it's easy.

[55:49] Darren Joe: Amen. I mean, I, I, I bet where you're smarter than me, Paul, is that you've, you've sought this out actively from the start.

[55:57] Paul: And I think not from the start, last year or two. Like I, I have a mentor, um, who's older. He's like a boomer and he's lived his life. He's really inspiring to me. And I, I told him recently, I'm like, I, I think I need to like, uh, just spend more time with you. Like I need the encouragement.

And like my aunt has been incredible. Like I have a friend Jordan, he's probably listening to this. He's always like boosting me up, like. I just love it and I'm like so appreciative of it. And it's like just valuing those people. Yes.

And just making sure they know such that they'll like keep giving me those like virtual hugs and hopefully real hugs once we all get back in person.

[56:44] Darren Joe: Totally. And, and I think that like we really need to be systematic about this and it's a practice that I talk about in the book, but that has really helped me, which is like actively seeking out this new inner family, actively seeking out this new super family. I'm using Dunbar's terms, right? But, but like that, because you're not going to get it from society because what we're doing right now, right now at least, is not, you know, is quite unique.

[57:11] Paul: It did become a little cooler in 2020.

[57:14] Darren Joe: Did it?

[57:15] Paul: Well, I think so many people experimented with nomadism.

[57:19] Darren Joe: Yes.

[57:20] Paul: I don't know about cooler, but it's less weird.

[57:22] Darren Joe: It's less weird. Like working behind the screen all day. Yeah. Um, but I, you know, like if your traditional, if your, you know, genetic family can't hold you up or your old circle of friends can't hold that space for you, you need to find, like you said, those 3, 4 people that are encouraging or that do see you becoming that thing. Or, yeah, that is so, I mean, that, that's, that's it really.

[57:53] Paul: Yeah. And I, I'm lucky too. I've, I found my wife and we're both on this weird journey together. Um, the, the added challenge of that is like, we're so deep in our bubbles sometimes that we like forget we have to like reset. It's like, oh wait, our life is really weird. We need to make sure we remember.

That when we're like engaging with others.

[58:15] Darren Joe: You know, sometimes, and just to remember to keep this all in perspective that like, we're, I don't know if you'll agree with me here, Paul, but something that helps me is just, you know, taking a very kind of Taoist view of this whole thing. And like, we're not, I mean, we're nothing really, right? Like I say, be a nobody. It's, you know, we're nobody. Like we build up a lot of this stuff and. It's no one really cares.

And in the grand scheme of things, it doesn't really matter that much. So I don't know, I find tremendous peace in that. Like when, you know, a customer cancels on me or like, you know, I have a shitty financial year or month or something, I'm just like, you know, it's, it's not, I mean, it hurts like hell, but it's not such a big deal. Like just what can you learn from this and move on? Very simple, like very Taoist. Like just go with the flow sort of thing.

Like don't, don't let your ego get in the way and force things that shouldn't be there.

[59:11] Paul: That's been one of the biggest benefits of this, playing with my path, playing with my story, playing with my identity is just detaching from it. And it's not as important as it was before. And I try to go through this exercise of all my digital properties, cuz most of the stuff I work on is digital. Just disappearing. And it's like, all right, what would I do tomorrow? I'd start writing again cuz I like it.

And it's like, I'd figure out what I'd do from there. And what does post-book life look for you? Do you see this as like an, do you see this as like an inflection point for you?

[59:56] Darren Joe: I do, Paul. I, I, I feel like The book represents a chapter of my life these past 10 years, and I'm kind of looking forward to the next thing and being a bit more, I'd say less independent and more interdependent. Like I'm looking to collaborating more with people. I'm looking to, you know, try to start new stuff. It's amazing, Paul, because after I finished it, like I'll never forget that feeling when you see your book come up on Amazon and it's actually there after 4 years of thinking and struggling with it. It's a magical, magical feeling.

Like no one can take it from you. You accomplished a life dream. You did it. And then you realize like, that's what the whole point of it was. It didn't matter. Of course I want people to buy it and all that, but like no one can take away that I wrote this thing, you know?

That's such an, oh God. Yeah, it's an amazing feeling, but it also, like within the week of publishing, I was like, all right, that's like, that was the old Darren. That was like 10, you know, 10 years of Darren in the past. And like, I'm already a new person, you know? So it's a really weird feeling because I don't really quite know how to explain it. But yeah, I'm ready to do new stuff for sure.

[01:01:21] Paul: Yeah. What, what are you working on these days? Where can people learn more and find out about what you're up to? Oh yeah.