Mark Manson
host: Mark Manson
jobs, professional pests, circus, career failures and successes, investment banking, dating
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Transcript:
Mark
We should bring the pest business back. Man we’re both retired. Come on. I’ve seen on the internet people have marketed you as a circus clown. Were you ever a clown?
Mark
How does a circus clown end up becoming a multi-millionaire? How does a bouncer get fired from a bar and then later get paid to go drink in that same bar? You know, when people do podcasts with all these ultra successful people, it’s always about their greatest successes. What did they do right? What were their best decisions? How did they overcome the obstacles? How did they figure out that genius chess move?
Mark
Nobody asks them about all the things that went wrong, all of the jobs and companies that failed, the times they got fired, and of course, all of the times they embarrassed themselves in the career paths that didn’t work. So I decided to sit down with my old friend Derek Sivers and do just that. See, it just so happens that Derek actually is the circus clown who ended up a multi-millionaire. He was the ringleader of a circus in his 20s before he went on to found CD baby, one of the most successful music startups of the last 30 years. Now, between the two of us, Derek and I have had some pretty weird and terrible jobs telemarketing, investment banking, Japanese rock band. Derek got paid to harass college students while wearing a black Lycra suit. I’m not making that up. You’ll hear all about it. And of course, I got paid to take guys to bars and help them pick up girls. These are all the hard earned life lessons of the career paths that didn’t work out for us, but inevitably made us who we are today. This is how all of our unexpected failures helped us learn and become successful. And of course, these are also some of the most entertaining and ridiculous stories from our lives. Enjoy!
Mark
My good friend, one of the wisest people I know, Derek Sivers. I don’t know if you have a place that you would like to start, but I’m curious, like, how did you get involved with the circus?
Derek Sivers
A very tiny tale and a very tiny lesson. I was 17 years old at Berklee College of Music, an aspiring musician, and I was in a band where the bass player in the band was more successful. He was like playing in like ten bands around town. So he had an agent and he said “Hey, my agent said there’s a gig. Somebody wants to pay $75 for a guitarist to play at a pig show. I don’t want it. You want the gig?” I said, “Fuck yeah. 75 bucks, my first paying gig. All right.” So it was like a $50 round trip bus ticket up to Burlington Vermont from Boston to get a $75 gig where I walk around for like four hours playing guitar at a pig show. No direction. Just “Show up there. Somebody will pick you up at the bus station. Just go play music and I’ll pay you 75 bucks.” So I got home. Got the 75 bucks, but then the agent called me and said, “Yeah, I got the report from the pig show in in Burlington. You did a really good job. So, listen, I’ve got this circus and the musician just quit...”
Mark
Sorry. What is a pig show like?
Derek Sivers
You know, the awards, the most beautiful pig, show your pigs, weigh the pig. Guess the weight of the pig. I don’t remember, I was just there playing music.
Mark
Okay. All right.
Derek Sivers
You know, I strapped on my acoustic guitar, and I just kind of walked around strumming guitar and singing some songs. I don’t know why.
Mark
Ignoring the pigs around you.
Derek Sivers
Yeah, I don’t really remember it that much. But I remember what happened after because it was because that one little $75 pig show gig that the agent called me and said, “Hey, I run this circus. We do about 3 to 4 shows a week. The previous musician just quit. You’ve kind of got the gig, but just come out and let me see what you can do.” So I got the gig and for the next ten years of my life, I did 2 to 4 shows a week as the ringleader MC of the circus from the age of 18 to 28. And I only stopped doing it when CD Baby took over my life. But yeah, for ten years of my life, every single weekend I was up touring the northeast, performing in front of audiences as a ringleader MC of a circus. It was because I said yes to the $75 Pig Show gig. So to me, the lesson learned was when you’re early in your career, you just say yes to everything because you never know what stupid little thing is going to lead to a bigger thing. It just opens doors everywhere to just say yes to everything.
Mark
Early in your career, you should say yes to almost everything. And then later in your career, once you’re like established, you should say no to almost everything. And I found that transition of knowing when the switch over to be very, very difficult. And it’s almost like retraining your brain over a long period of time. I’m curious, what was your favorite circus act?
Derek Sivers
Oh I wonder if the website is still up, but I think you can go to professionalpests.com. And if you see a picture of somebody in a black shadow fabric, that’s me in there. It was one of the bits during the show was like a little dance routine where this woman would come out of the bags and she would be inside like five layers of bags and keep shedding the bags to this piece of music. And so whenever we do a show, it would be like a one hour show, a 90 minute show, and then we’d take a one hour break and come back. So during the one hour break, I would take her black fabric lycra bag and get inside it and just go running around the audience bugging people. And I had so much fun doing that, just like annoying people inside this black shadow that later I found out that universities have a student and activities entertainment budget. And so I decided to market myself as the Professional Pests, where they would pay me $1500 bucks to come to the campus and run around and bother people for a few hours, because it was funny and I had so much fun doing it. I would put on an elbow pads and knee pads inside so I could do really crazy shit, like crawl around on the floor and jump up and scare people.
Mark
You got paid $1,500 to go fuck with college kids for a day.
Derek Sivers
Yeah, for three hours inside a black shadow bag.
Mark
Dude, how?
Derek Sivers
It was amazing.
Mark
That’s the best gig in the world, man.
Derek Sivers
Yeah, I forgot that as, like, a gig that I did. When I was thinking about my jobs, I was thinking about employers. Yeah, but now this is a thing I created myself. So I looked at the university college scene mostly because I wanted to be a successful musician. And this was a way that you could get your band a bunch of gigs, but you had to pay a certain amount of money just to get into this scene. It’s called NACA, National Association of Campus Activities, and you had to pay a fee just to be a member. So once you’re in as a member, you can submit unlimited acts. So I thought, “Well, I’m joining this for my band’s sake, but as long as I’m here, I guess I could take this thing I do with the circus and I can market that, call it professional pests.” But sure enough, that took off, right? Because there are tons of bands, tons of guys with guitars. But there was only one professional pest. It was a really unique act.
Mark
You were filling a niche.
Derek Sivers
Yeah, I conquered that niche. Guy is running around in a black shadow bag, annoying people for money. And it was so much fun. So a college would just do it unannounced. I was what was called a roaming artist. Where no need for a stage, no need to announce me. Just suddenly on campus that day was like a guy inside a costume. So you’d be kind of in the cafeteria queue, getting your food, and suddenly there’s like a guy stealing the milk off your tray or crawling between your legs or whatever. And it was just a blast. And then other people would enjoy watching people get scared by it, and some girls would get really freaked out and scared, and then some guys would get really aggressive. And it was just funny for people to watch from a distance, like everybody’s reaction to the shadow.
Mark
And this wasn’t announced. You would just show up and.
Derek Sivers
Yeah, the college would just pay me $1500 bucks to come out to Connecticut or upstate New York or whatever. And I’d show up and do this for a few hours.
Mark
Oh, God man. I’m in the wrong business, Derek--
Derek Sivers
I miss it
Derek Sivers
That’s my fault. I mean, I did sometimes put on face paint with the circus, but really, I was the ringleader MC. If people call me clown it’s my fault, because I included that in my bio at some point for the fun of it.
Mark
Oh, gotcha.
Derek Sivers
Former circus clown.
Mark
We’re gonna market the shit out of this episode. Derek the circus clown Sivers. The professional pest.
Derek Sivers
Okay, I’m dying to hear your stockbroker experience.
Mark
Oh, God. First of all, disclaimer to everybody listening to this. It’s really funny., Derek. I often get emails from people asking for career advice, and I always tell them, I’m like, “You’re asking the guy who has never held down a real job for, like more than a couple of months.” So, take this all with a grain of salt. But this is how naive I was in college. I got really into poker in college, and I bought all the books and I studied everything. This was back when you could play online in the States, and it was this was like 2006, 2007 for a college kid. I won quite a bit of money, probably between 5 and $10,000. And all of the other guys that I that took poker seriously, like the my poker buddies, basically they were all going in the finance obviously, and in my head I’m like, well, I’m good with math, I like numbers, poker is fun. Like all my friends are going into finance. I should go into finance too. They make a lot of money. Why not? So I actually got a job at an investment bank, as like a low level grunt. And I’ll never forget first day of training. And I remember looking at my watch when it was like 10:15 and thinking to myself, “How long do I have to stay here before it doesn’t look bad if I quit?” And I was like, “Dude, you’re like only two hours in on your first day and you’re already thinking about quitting. This is a really bad sign.”
Mark
It was very much a lesson in corporate culture. I was a naive 23, 24 year old. I didn’t understand why things were the way they were. So to give you an example, I was basically a data monkey. So our job was literally just fill in spreadsheets, collect data, organize things in the charts, fill out forms, shit like that. And I remember after a couple weeks, I started thinking to myself, I’m like “Man, so much of this stuff is publicly available. Like, why don’t we just automate this?” And I knew a little bit of like basic programming. I was like, “I bet I could program like a macro like scrape some public databases and just automatically fill all this stuff in.” And so I got super excited about it. And I remember I went to my boss and I sat down then like, “Hey, I got this idea, see this thing that I, me and like the other 20 people on my team are doing. All day, every day. I bet we could automate like 80% of this with a simple program.” And I started to explain it to him, and his eyes just glazed over and he like, interrupted me. And he was like, “Go back to your desk and get to work.” He looked at me like I was lazy, you know, like I was trying to talk my way out of something.
Mark
And I remember just being absolutely stunned that not only was my brilliant idea of automation shot down, but that he seemed almost offended that I would suggest such a thing. Now that I’m older and I have a little bit more perspective, and I understand why very, very large companies operate the way the way they do. I get it now. It’s like you got this guy, he’s in this big corporate job, starts talking about like some computer program. He can make. And his only thought is like “Man, this is gonna put half the people on this floor out of a job. Like, get the fuck out of here.” You know, like, I need my paycheck. I want my bonus this year.Don’t automate anything. Like, get out of here. Anyway, that was very strange to me. Like, I didn’t understand that at the time. Why would you not make something more efficient? The reason I quit, I remember there was one day we were all sitting aroun,d me and it was a bunch of other 20 something year olds. So we were just data analysts, data monkeys. The path was, if you put in a few years of that, say, 3 to 4 good years, the bank would pay for you to go get your MBA. And then once you get your MBA, you get to come back and you get like one of the higher up jobs and you start making, like really, really good money.
Mark
That was the trajectory that everybody was on. And so my coworkers, the team one day, everybody was sitting around like one of their favorite conversations was to talk about all the shit they were going to buy once they came back from their MBA and were making like a quarter of $1 million a year, or $400K a year or whatever it was. And, you know, this guy was going to buy a boat and, you know, this guy was going to buy a BMW. And then, you know, this guy was going to buy a lake house. All this shit. It was like, that was the whole conversation, like, “Oh, man, what kind of boat? Oh, that’s sick bro. Like, I’m gonna get this car.” You know, like just on and on. And I remember one day one of them turned to me and said, |What are you going to do, Mark?” And I was like, “I don’t know. I think I’d like, take a sabbatical and travel around the world for a year.” And if it was a movie, it’d be like a record scratch, you know? Like everybody just stopped and looked at me like I just farted in an elevator. And I was like, man, I am so in the wrong place right now. Like, this is just awful.
Derek Sivers
So the takeaway from that is that it was the wrong fit. But also, I feel like you got a lesson in, I call it the metaphorical time zone because I live in New Zealand. If somebody in California says, “What day is it?” It’s like, well, it’s Tuesday for you, but it’s Wednesday for me. If I were to say it’s 8:00, I wouldn’t be wrong. But it’s not the only answer. Just because it’s true for me doesn’t mean it’s true for everyone. And so when you go to your boss saying, we can automate this, it’s like, well, that’s true, but it’s the right answer for you. It’s the wrong answer for him, for his needs. His motives are different than yours.
Mark
One of my really good friends worked at a very large corporation, and I remember telling him this story soon after I quit and he wasn’t surprised. He was like, “Oh, of course.” And I was like, “Really? Why?” When you’re running a company with 50,000 employees, with $100 billion market cap or whatever it was, you got to be really careful. Creativity is destructive, right? Like automating one aspect of data collection, not only is it disruptive internally, potentially puts a lot of low level people out of jobs. It potentially affects, like what the higher ups need to know and understand. It affects the company’s relationship with the data providers. It affects the company’s IT department. You know, large organizations move very, very slowly for a reason. And it’s because it’s the status quo. It needs to be protected and not out of any sort of like ideological. You have to be careful, like stuff breaks easily. And when you’ve got that many people on that much money on the line, what you have works. So like really only change it if you’re really, really sure that the new thing is gonna work. And if some smart ass 24 year old comes in and starts telling you he can program this thing. You know, maybe don’t believe him at first blush. And maybe tell him to shut the fuck up, go back to his desk, put in six months, and then come back and talk to him about it. Right? Like I didn’t even know how to do my job yet, and I was already trying to think of ways I could program a computer to do it for me. So an older man now, I get it. But at the time I was just like, absolutely shocked. But again, it comes back to-- it’s a culture thing.
Mark
I think certain people’s personalities are well suited for certain environments. My personality was absolutely not suited for that environment. And it taught me, I guess just because you’re good at something, like I’m good at math, I enjoy numbers. Just because you’re good at something doesn’t mean you should do it. And especially with an occupation or a job, you know, there are a lot of considerations around social relationships, culture, identity. You could be great at the job, but if you’re in a terrible environment, then it’s not going to be satisfying, right? Funny thing, I just thought about this, one of those guys on my team came to one of my events years ago. It’s funny, he didn’t tell me this personally. He like, got up at the Q&A time and told the audience. He said that when I quit, everybody was shocked because I told my boss. I was like “I’m gonna quit.” And he was like, “What are you going to do?” And I was like, “I’m going to go make a website.” And my boss was like, “All right, good luck.” And it’s it’s a very competitive environment, a lot of people who were there fought very, very hard to be there. And this guy at my event said that when I left, people made fun of me for a long time, like, “Oh, are you gonna you’re gonna go create a website. Is that what you’re gonna do? Good luck.” But he told me later, he was like, “Yeah dude, that place sucked. Almost everybody left after a couple of years. Like, it was just absolutely soul destroying.”
Derek Sivers
You know, I went to my class reunion when I was 28. I was a full time musician at that time. I was a professional musician, touring the world, making my full time living doing gigs. And I just happened to be in Chicago when I got some kind of announcement that our ten year class reunion. So ordinarily I wouldn’t have gone to that kind of thing. I’m like, “Yeah, sure, I’m in Chicago. Why not?” I showed up and my long hair and my weird purple shirt and everybody else was 28, but holy fuck, they looked 40. They were all like, in suits with double chins and just baggy eyes and just like pushing papers from left to right and across a desk from Motorola, like, everybody’s job was like, “I’m a manager at Motorola. I manage the regional Midwest telecom division.” What are you people doing? I was like you had dreams. You wanted to be things. What the fuck? And they looked at me with the same kind of thing. Like, I was always like the freak with the heavy metal patches on my jacket and the long hair that they were trying to get into a good college, and I looked like I wasn’t going to amount to anything. And at the class reunion, they said, a few different people, either in the moment or a few emailed me later saying that they were kind of like jealous that I stuck with my dreams and they gave up their dreams just to take some dumb job. And it reminded me of something that’s worth mentioning in this episode is that I never work for money. Even as a teenager, nothing I’ve ever done has been for the money. Any job I took, it was only if I would have also done that job for free, because everything had to be a learning experience. It was like it was all leading to something more. I’ve never worked for money in my whole life.
Mark
I’m curious, like, what was the first job that taught you something?
Derek Sivers
So yes, telemarketing was my first job because I was 16 years old and I had really long hair, so I was not presentable. So I went for a job at Time Magazine. I grew up in Chicago. My job was on a huge floor with like 100 people on the phones, calling people that already had a subscription to Time Magazine or Sports Illustrated or Life for People Magazine, and to renew their subscription over the phone. So I worked there for a few weeks where I would call people and say, “Hi, my name’s Derek Sivers, calling from Time Magazine. I’m calling to see if maybe you might want to renew your subscription today.” And they’d say, “No, leave me alone.” “Okay. Thank you.” And I did this for a couple of weeks, and my manager was told that she had to fire me because I was terrible. And she said, “Look, you remind me of my little brother. I asked my boss to let me give you another chance. So let’s do this. Come here to my manager’s desk, listen to what George Amos is doing.” So I put on her headset. And I got to listen in to another salesman that was the top performing guy on the floor. So what George Amos would do is he would call people up.
Derek Sivers
He’d say, “Hey, I’m calling from Time Magazine in Chicago, is this Mr Williams? ‘Yes, it is.’ Mr williams. You still living at 321 Main Street? ‘Yes. Yeah.’ All right, Mr. Williams, I’m just calling to renew your subscription today. We’ve got you in for a much better rate than you had last year. We’re going to renew you for three years this time. We see that you’ve been with us a long time. We appreciate it. So we’re going for the three year renewal. It’s going to save you a lot of money. Instead of you paying $50 a year, you’re just going to be paying $21 a year. Lock you in at that rate for three years. All right, Mr. Williams. All right. Thanks for the call. Bye bye.” Just like that, George Amos was getting these three year renewals every few minutes, whereas I was struggling to get one renewal a day. So I listened to this and went, wow. All right. For one lesson in confidence, just assuming the sale, not asking for the sale. Just like, yeah, we’re going to do this today. We’re here to get this done. That’s just assumed. But to me, the bigger lesson was I don’t have to be myself. Like, this is me being myself. Like, “Hi, I’m Derek, just want to know if maybe you want to renew your subscription.” That felt like the real me. So what I had to do was get on the phone and imitate George Amos. I had to not be myself.
Derek Sivers
So I did it. I got on the phone, I said, “Hi, my name is Derek. Is this Mr Hipkins? All right, Mr Hipkins, are you still on 23 Elm Lane? ‘Yes, sir.’ All right, Mr Hipkins, I’m just calling to renew your subscription today. I see that you’ve been with us a while. I appreciate your business. So we’re going to give you a much better rate than you had before. Instead of the $52 a year you’ve been paying, we’re just going to renew you for $21 a year. That’s our three year subscription rate. You won’t have to do anything for the next three years. You’re all locked in. All right. Okay, great. Thank you.” That’s it. And I was like, bang, bang, bang. I was making these three renewals and within a week I was the top selling guy on the floor. A team of like 120 adults and 16 year old Derek was the top seller on the floor because I was imitating George Amos, I still felt like my internal self was not the guy that was saying this stuff on the phone. That was George Amos. That’s his real self, you know? That’s who he really is. Me, that’s not really me, but I’m acting like George Amos to sell more subscriptions. Later when I was the ringleader mc of the circus, I had to do the same thing because, again, they asked me to be the ringleader.
Derek Sivers
And I was really bad at first, and they were almost going to have to fire me. And they said, just be more sensational. Because at first I would just get up on stage and go like, “Hey, everybody. Well, yep, we’re the circus. So, I guess take a seat and we’ll come out pretty soon and entertain you.” You know, I was just being casual. I was being more me. And they said, “No, don’t be yourself, be a ringleader.” So I went out there like passive aggressively. One time I was lik all right, fine. I went out there and I was like, “Ladies and gentlemen, what you’re about to see is one of the most amazing shows you’ve ever seen. We are the Mime Circus. We are going to have entertainment. We’re going to have this, that you’re going to take your seats and get ready for the show.” And I went backstage, almost like aggressively like, “There I did what you said.” And they were all applauding. They’re like, “Finally, thank you. That’s what the audience needs.” and I was like, “Oh, really?” And so that was it for the next ten years. I would put on the ringleader persona because that’s what the show needed. I was like, well, all right, that’s not being me.
Mark
But this raises a really interesting question of like, what is an identity in the first place and what is authenticity, right. Because you know, what you did is classically known as like modeling behavior. It’s a basically it’s one of the fundamental ways that humans learn. But from one perspective, the authentic Derek was insecure, quiet, nervous. A little bit too casual and he had to take on or assume a lot of traits and behaviors that weren’t authentically him. But if you really start thinking about it, what we generally consider authentically us is just learned behaviors from before that we modeled off somebody else at a different time in our lives. So in a way like authenticity or identity in general, it’s a very fluid thing. And this is actually something we recently did a video about Korean culture. And when I was doing research on that video, I was reading a lot about Confucianism. And one of the things that I discovered is that a lot of East Asian cultures, like in Japan, Korea, China, they don’t have this notion of a fixed identity like Westerners. We like to think that like Mark is Mark, whether he’s on a podcast or he’s hanging out with his mom or he’s at the grocery store, he’s always Mark. Whereas in some of these East Asian cultures, it’s accepted and assumed that you behave differently in different contexts. There’s a podcast, Mark. There is a business Mark. There is a family Mark. There is a public facing Mark. There is a private Mark. Not only is it not seen as inauthentic to be different in all those contexts, but it’s actually seen as immature. If you are not different in those contexts, you should treat your boss differently than you treat your mother. You should treat your best friend differently than you treat your wife. You should behave differently at home than you do at work, and there’s shame in not doing those things differently. So I thought that was really fascinating, that this kind of obsession of authenticity in Western culture, especially recently, it might just be a moving target.
Derek Sivers
I like that.
Mark
When I was a senior in college, I got a job as a doorman at my favorite bar, and at the time, you know, when you’re 22 and your entire life revolves around girls and parties, this was like the coolest fucking job in my mind that I could have. And I remember it was really interesting because. It taught me how arbitrary authority is. You had this bar. I used to go to it all the time, probably 2 or 3 times a week. It used to be a line down the block. Sometimes you’d try to cut your way in, talk your way in, find somebody you knew in line to get in. And then one day I saw that they were hiring, and I just went in and applied, and I immediately got hired. And the next night I’m the guy at the door deciding who comes in and who doesn’t. And I remember just thinking, I’m like, “Wow, in less than 24 hours, the dictation of who has the authority to decide who gets to go into what space is like, completely flipped and it’s made up.” There’s no like, I don’t know, higher power, like dictating. You must wait in line. So it gave me an appreciation of how, I guess fragile order is in general, like it doesn’t take much to just kind of rewrite some rules or put yourself in a different spot.
Mark
This was probably the first time in my life that I learned that you don’t necessarily always want to get a job in an area that you love. So I always assume that working in nightlife would be extremely exciting and fun, but it turns out, it’s unbelievably boring and dull. It’s very repetitive, and it’s actually obnoxious because you, you’re basically being paid to babysit all the drunk people who are having fun, which is the most unfun thing you can possibly imagine. I got fired after three weeks because I was talking to too many girls. I kept getting yelled at by the manager because I was not paying attention or doing my job. Like, the whole reason I took the job is because I want to get paid to be at the party. And it turned out that I wasn’t getting paid to be at the party. I was being paid to regulate and administer the party, which was not exciting to me. So it’s actually the the fastest I’ve ever gotten fired from a job was three weeks.
Derek Sivers
Didn’t doing that job though give you this insight now like bars are everywhere on earth and now every bar you see you’ve got a little bit of insight into what it’s like to be on the inside. You’ve got some empathy with the people that work there.
Mark
Totally empathy and a lot of respect, especially like the people in the back, the bartenders, but also like the busboys, people like replacing all the liquor bottles, cleaning the floor like there’s so many thankless jobs in that industry. It’s also one thing that’s not talked about a lot with that industry is that it completely overhauls your social life because you work such strange hours. Your peak work week is, Thursday to Sunday like 5 p.m. to 3 a.m. so you have no social life on the weekends, you’re working. So your free time is Monday, Tuesday, Wednesday, which basically limits you to only being friends and hanging out with other people who work in bars and restaurants. So when you are part of that world, you realize that it’s like this weird parallel universe that most of us aren’t exposed to, and everybody in that industry knows each other as well. So it’s like because every bar, you know, every bartender was a bartender at some other place, and this door guy was used to work at this bar across town. And so everybody knows somebody somewhere. So it’s like, if you really get embedded in that world, which I did not. It’s like a whole subculture. It’s really interesting.
Derek Sivers
You know, when people ask you for career advice, I feel like I’d almost prescribe this to people. It’s like, go work at a bar for three weeks and get fired. Go work in a kitchen at a restaurant for a few weeks. But this idea of like, just even a few weeks of experience with something can help give you an insight into this thing. And for the rest of your life, you’ll be able to understand this little subset of humanity a little better.
Mark
All of the employment that I’ve had, I’ve never lasted more than a couple of months. Two of them I got fired and then two of them I quit. Like getting fired never bothered me. Like, I don’t know, maybe that’s just me being naive, but like, I remember the manager threatening to fire me, and I was just kind of like, “Well, yeah, I mean, if I get fired, that’s fine. I’ll just go find something else.” I don’t know, there was no deterrence. I had no sense of man, I better shape up and do a better job. I remember when I was young, I lived on a friend’s couch for about six months. I built my first websites on that couch, and I remember thinking to myself very clearly, like, this is the point in my life where I’m going to have the fewest attachments. I’m going to have the fewest things to lose. And if I can be comfortable with nothing, then like nothing, nothing can ever control me if I’m never afraid of being broke. Then nobody can control me with that. Nobody, no paycheck is ever going to feel more important than to your point like doing something that feels more important. That resonates on a very deep level for me. I think I’ve always been the same or usually been the same. I also just think that, like, I don’t really mind hardship. Like it doesn’t seem to bother me as much as it bothers a lot of people. And it’s not to say that it doesn’t suck, it does suck. But like, I’d rather be doing what I like with my time and be broke than the opposite.
Derek Sivers
Okay, I’m going to sound like a new age asshole for a second, but the saying hardship sucks to me it depends on where you’re focusing. I’ve never felt that hardship sucked because my eyes were always up here on the horizon. I was always looking there towards where I was going, and if I tripped over a rock for a second or stubbed my toe, who cares? All right, whatever, I’m going there. Whereas I think that if people get to present focused or to kind of narrow focused, they metaphorically might just be looking down at the muddy trail they’re on and they’re like, “Oh man, there’s rocks.” Yeah, it’s muddy, but it’s like, I don’t care. I’m looking up here. I don’t look down, look up where you’re going. And sorry, I know that sounds like such a cliché, but there was a time when I was running a CD Baby, I was speaking at a conference and the moderator asked for questions from the audience. Somebody from the back said, “What’s the hardest, most difficult thing you’ve ever had to do running this company or been the hardest time?” And I sat there and I thought for a second, I’m like, “Nothing. Nothing’s been hard. There hasn’t been anything hard about running the company.” And the guy came up to me later after the panel was done and he said, “I think you’ve just got a positive mental attitude. I’ll bet you’ve actually had difficult things happen in the last ten years. You just don’t even think about them. You’re just not focused on them because you’re focused on something else.” Well, I guess I don’t know. To me, it really does sincerely feel like, no, I haven’t had any difficulties. Nothing’s been hard. There have been no setbacks. Everything’s been great. But maybe, like, maybe if I went back into my diary, I’d go like, Oh, yeah, five years ago. That was tough.” But I’m just not thinking about it. I just keep my eyes up here on the horizon.
Mark
Well, it’s also if you enjoy whatever you’re struggling against, then it doesn’t feel like suffering. It actually feels the opposite. It feels invigorating. I look at my own experience and like writing is a great example. Some people writing is torturous and I mean for me at times too, it can be difficult, but like it’s a difficult that I like, I enjoy it. Like it’s very satisfying and I’ve run into this recently in terms of fitness. So I started training for a marathon a couple months ago, and I discovered I worked up to about 13 to 15 miles. And I discovered something, which is that anything under eight miles I really enjoy. And it’s like, even if I push myself and I’m exhausted and I’m like trying to go for a best time or something. If it’s like a 10K or something, I really enjoy it. As soon as you get up, up over 8 or 10 miles. It fucking sucks. It’s a suck that I don’t enjoy. I don’t like the struggle of plotting at a very slow pace for 2.5 hours. So I said, fuck it. So I gave up that goal and I set other goals. And it’s funny because like a lot of people in my life are like, “No, you can’t do that. You’ve been training for two months. Like you can’t stop now.” Then there are other people who are like, What is your audience gonna think?” And I’m like, my audience is going to get a lesson and don’t stick with a goal that makes you fucking miserable. Like it’s not worth it. If you find the struggle you enjoy, you don’t suffer through it.
Derek Sivers
Wait, have we talked about landmark before?
Mark
No.
Derek Sivers
I’ll just say this quickly. Landmark forum are two of my dear friends, are really into it and said I would love it. One of them basically made me go. She basically signed me up against my will and said, “There, I just signed you up, just show up Saturday, go!” And it was dreadful and awful, but it had a wonderful punch line that--
Mark
I’m trying not to laugh. I’m going to get a cease and desist letter.
Derek Sivers
No, it had a wonderful punch line. That basically nothing has any inherent meaning. Life is underscore that word is blank because life has no inherent meaning. Nothing has any inherent meaning. This microphone does not have meaning. This podcast does not have meaning. It’s just a podcast. If you say it means something, that’s you putting meaning into it. And they kept emphasizing this point over and over and over again. To me, it it was just like, “Oh, I love this. So yes, I hate this weekend, but I love the punch line.” I liked it so much that I signed up for the Advanced Landmark Forum a month later. So I went to the advanced one and kind of like you, after the eighth mile, I was like, “Oh, I don’t like this. This is all about like group dynamics and I’m just not enjoying this. And I think for what I want in my life right now, it’s not this. There’s other things I want to be doing with my time right now.” So two hours into it, they said, “Okay, we’re going to put you into groups of six.” So, you know, literally just 30 seconds after they put us into a group, I turned to the other five. I said, “Guys, I’m leaving.” And they said, No, you’re breaking your integrity. No, this means it’s something, something you have.” And they kept telling me all these things that it means, this is what it means, that I’m leaving. I said “No, like it doesn’t mean anything. It means I’m leaving. That’s it. It has no other meaning. I’m leaving now. Goodbye.” And they’re like, “No, you can’t. Because integrity, because--” I was like, “Goodbye.”
Mark
Your goal should serve you, not the other way around. Just because you set a goal doesn’t mean you have to be a slave to it. And I think there’s a little bit of a romanticism of like, “You gotta grit through it. You gotta suffer, bro. You gotta like, fucking nearly die to get there.” And it’s like, do I really like, I’m okay.
Derek Sivers
Yeah. It’s like, well, I’m doing this for my health. Yeah. And there are other things I can do for my health. This one makes me want to die, so that’s not good for my health.
Mark
Not to mention, running a marathon is actually not that healthy.
Mark
I like what you said about when you were talking about finding a better reason than money. It reminded me of like when I was starting my online business and blogging. I made no money for like a year, two years, and there was a period of time that I was living with my girlfriend at the time, and she was financially supporting me, and I remember talking to her.
Mark
And telling her, I said, “You know, even though I’m broke now, I feel like I’m learning skills that are going to serve me for the rest of my life.” Say like take marketing or copywriting. I was terrible at it the first year or two, and I didn’t sell anything, but I had to go through that to get to the point where I could sell anything. And that’s a skill that served me ever since. It’s almost like it’s an investment, like it’s like putting money into a retirement account or something. Like, there are a lot of things in life that you can do that actually end up being a more positive ROI than just a paycheck in the long run. And I think that that relates to your keeping your eyes on the horizon thing. Like if you’re always just looking at where the next paycheck is coming from, you’re not thinking about, well, maybe I take less money to learn this skill that will help me develop my career. And then five, ten years from now, I’ll actually be in a much better place. And not to mention the psychological benefit of having that long term vision and goal for yourself, which keeps you motivated, keeps you happy, keeps things feeling not difficult. Even if there is some struggle along the way.
Derek Sivers
Yeah. And again, it sounds like such a cliché, but it puts everything into perspective. You know, whatever you stumble over today is no big deal if you keep your eye on that. I wonder about your former colleagues, if they were happy when they got the BMW, “There. Did it!”
Mark
I’m guessing not. I’m guessing they needed a Porsche or a Ferrari or something. I don’t know, I’ve met enough people to know where that ladder goes. I remember when we met, you gave a talk. We met at a conference many, many years ago. And you gave a talk at that conference. And I remember the thing that stands out to me that you said at that conference. And this is notable because at the time I was not wealthy. And you were. So you said, “Luxury is a trap because it’s enjoyable for a short period of time, and then your brain adjusts and then anything less than that feels like suffering.” And so, I remember you had this whole thing about intentionally choosing high friction things, you know, fly economy, stay in a shitty hostel, walk to a place that feels a little bit uncomfortable to walk to, because it just keeps you grounded and keeps resetting your baseline expectation of what life should be giving you.
Derek Sivers
I still avoid comfort. I still do that. I was thinking about my kid’s education because the New Zealand school system is not very good, and so I feel like it’s kind of--
Mark
Now I’m gonna hear from Landmark people, New Zealand parents. This episode, we’re gonna get a lot.
Derek Sivers
I was thinking about, like, okay, if it’s all up to me, what are the life skills? The know how that I want my kid to have. So I came up with some myself. Then I just decided to search the web for other ideas. And there was this one that was like, you know, I think it was maybe on the Art of Manliness or something that was like, “Got to know how to make a good steak. You know, you got to know how to, like, make a good gin and tonic.” Or something like that. And I was like, “No, these are those are all just fucking pleasure things. That’s not survival.” That’s like, who are you trying to impress your buddies at the bank, right? You know, “Mark makes a good steak. Maybe we should give him a promotion.” What the fuck is that? You know, that’s some fucking hedonistic pleasure shit. No, I’m talking about survival. Yeah, like I want my kid to be able to survive in any situation. Like survive in a crowd, survive in a disaster, survive in a new country where he doesn’t know anybody. Like you know, making a good gin and tonic is way-- because those are pleasure things. And again, I just realized, like, yeah, I do not value pleasure at all.
Mark
What’s the most pleasurable thing you do like.
Derek Sivers
Well, I think of it all as removing obstacles. So my definition of home--. The subject came up recently with friends we were talking about like, what’s home to you? To me, home is the place with no obstacles because ultimately I’m a live-to-work guy. Yeah, like I exist to work. I love my work. I don’t think of it as work obviously for money. I think of it as, like my life’s work. This is like the reason I’m on earth or I’ve decided to make it my reason I’m on earth. It’s like my kind of primal, “I am here, I exist statement.” This is what I’m doing. And so of course I’m fucking driven completely. I don’t sit around and hang out and do nothing. I try to use every single hour I can to work. So to me, home is the place that has no obstacles to my flourishing, which means my work. Like it’s not too cold or too hot. It’s not too noisy. That’s what feels like home. It’s the place with no obstacles. So if I’m seeking pleasure, it’s really more of just like seeking to remove obstacles.
Mark
Interesting.
Derek Sivers
I think you’re more balanced than me when we’ve talked about this. I’m actually really glad that you’re more successful than me. I feel very, like, monomaniacal, driven. And I think it’s really kind of reassuring that I think you’ve had a more balanced approach to life and yet completely thrived.
Mark
That may be the first time anybody has called me balanced.
Derek Sivers
Really?
Mark
Yeah. Yeah, yeah. .
Derek Sivers
You play games, you have a healthy relationship.
Mark
That’s true. I mean, I would say balance is a relatively new thing in my life. But I’m similar. Like when I kind of get obsessed with something, I have trouble not going all in on things. And similar to you, I’ve actually had to-- my problem is often been I have to consciously stop myself from working to allow space for other things in my life. So you had an interesting career as a musician, from a circus to playing in a band in Japan professionally. What was that transition like and what are the lessons there?
Derek Sivers
Okay.
Mark
Circus clown and Japanese rock star Derek Sivers.
Derek Sivers
Yes, exactly. The tale is, I was 22 years old. I was living in New York City. I was renting an apartment with three roommates. We were paying $333 a month each. One of my two roommates was an assistant engineer at a recording studio in New York City. And the Japanese pop star Ryuichi Sakamoto was there recording. My roommate was just the assistant, like, wrapping cables and stuff. But he came home one day and he said, Hey, Ryuichi said he’s going out on a new tour. He’s got the drummer from Peter Gabriel, the bassist from Miles Davis, and he doesn’t have a guitarist yet. Do you want the gig?” I went, “Fuck yeah, I want the gig so bad. Oh my God.” And so he got me a recording of like the tracks that they were working on. He took it home for the night, like he got home from the studio at 11:00 at night. I took the little recording and I stayed up all night long, literally till sunrise, writing guitar parts for Ryuichi’s new album that had no guitar on it. And I brought it into my little home recording studio, wrote guitar parts for it, recorded it, mixed it back onto the tape, gave it back to my roommate at seven in the morning as he’s like on his way to work.
Derek Sivers
I was like, “Here, give this to Ryuichi, tell him I want the gig.” So he was able to give Ryuichi his entire album now with my guitar on it. Then two more days I spent transcribing every cello part on his previous album, like in the, you know, bass clef on staff music, whatever, you know, with the quarter notes and eighth notes and 16th notes. Transcribed it myself, handed my roommate that I said, “Tell him I really want the gig.” And then finally I got the call a couple of days later saying, “Yeah, you come on in, you’ve got the gig.” So at the age of 22, I got to tour Japan. I was so fucking cloud nine. I was so happy, great gig. I think the lesson learned is when a gig comes up that you want, don’t be casual. Like, go fucking over the top all the way maniacal until you get the gig. Cause sometimes that’s what you have to do to prove that you want it.
Mark
It’d be so easy for somebody to look at that story and be like, “Oh, he’s so lucky.” But I mean, yes, there is some luck that your roommate happened to be the engineer when luck gave you an inch and you took a mile, essentially, like you literally put everything you could have done into the next 24 hours to make it happen. When life does hand you those opportunities, which we all get them, they’re very rare. But they do happen. Like that’s what I always tell myself is I’m always like, I won’t regret staying up another couple hours. I would regret not staying up a couple hours. Right. So stay up a couple hours.
Derek Sivers
The luck thing. There’s another minor lesson from this, which is to be in the place where things are happening that yes, it was lucky that my roommate was the assistant engineer, but that luck happened because I moved to New York City, even though I could only afford $333 a month rent. I lived in Queens in a shitty apartment with three roommates, because that’s what it took for me to be in New York City, in the middle of things where things are happening. I think it’s still true, even in the phone it in/work from home internet age. I still think there’s so many more opportunities that just happen if you’re in the place where things are happening, for sure.
Mark
I think Scott Galloway talks about this a lot. You know, one of his primary pieces of advice for talented young people is just go to a mega city, regardless of what career you want to get into. When you’re young, you have few attachments. Get to a big city because it’s just the concentration of talent, the concentration of industry, of companies, of opportunities. It’s all there. You never know who you’re going to run into. It’s funny because I grew up in a place that is now a great place to go for opportunity, but when I was a kid, Austin was not a happening spot. And from the age of 15 or so, I just knew I got to get to the East Coast.
Derek Sivers
Okay, I’m gonna wing it and to talk about something I’ve never talked about before. But when I’m in New York City, i feel that I’m surrounded by greatness and it makes me want to be a better person. I feel like it in a real way makes me work harder. It makes me lift my expectations of myself. I set higher expectations for myself because I’m in New York fucking City. Not only that, I’m in Manhattan, in Union Square. Some of the best writers ever have walked these streets right next to me, or are walking these streets right next to me right now, or are just a block away writing a great book. And I’m right here. Like, it elevates my expectations and I even get that from places I live. When I lived in Singapore, I was actually really inspired by the story of Lee Kuan Yew and what he did to lift Singapore out of the the muck and into greatness from 1968 to 1988. That was really inspiring to me. It made me want to be a better person. And again, I felt like it set higher expectations for myself. And I’ve thought about that now that I’m living in very comfortable New Zealand, but it’s just comfortable. It’s a lot of nature and I’m missing that sense of being around greatness. And I’ve noticed that I have to really generate it myself. I have to like, get it through the internet, you know? But I miss that energy of my time living in Los Angeles, my time living in New York, my time living in even London. I lived in London for just a year, but just walking, you know, W1, west London, just like, “Oh, man, such greatness has happened here. Like, I want to make something this great.” You know, like, it inspired me in a real way.
Mark
It’s funny, all my friends from New Zealand and Australia say that’s why they left when they were young, because they aspired to do something great. And New Zealand and Australia are amazing places, but they’re comfortable and they’re countries that are very optimized for a very comfortable life. And it’s if you’re really trying to do something extraordinary or push yourself extremely hard, it’s not conducive. It’s funny, Paul Graham has this thing, he says that every city is quietly whispering something to you when you’re there.
Derek Sivers
Actually, no. Sorry, I’ve got the little essay memorized. It’s one of my favorites of his. It’s, “New York is you should make more money. Boston is you should be smarter. Los Angeles is you should know more people. Bay area is you should have more impact.”
Mark
Funny, because that’s what drew me to New York. And it’s also why I left because it felt like no matter how successful I got, that feeling never went away, that I wasn’t doing enough, that I wasn’t earning enough, that I wasn’t successful enough. And I saw it too, in my successful friends in New York. I would hang out with guys who had ten times the money I did, and they still felt that way. They still felt like they weren’t doing enough, that they weren’t earning enough. And I was like, “Man, this is fucked. Like, if that guy feels this way, this is not a healthy place to be.” I have a very contrarian take on New York in that, New York is best experience broke because all of the great things about New York are free or not free, but they can be experienced relatively inexpensively. Like the great thing about New York is the proximity, the density. And you can experience that when you’re broke. As long as you’re in the city and have enough money to buy a sandwich or a coffee. You can experience it to some degree or another when you really try to actually like build a nice life the city doesn’t let you.
Derek Sivers
Interesting.
Mark
To use your term, you cannot remove all the obstacles. The city will not let you. And part of that is what makes it so great, because it keeps people like striving and fighting. But yeah, when you’re broke in New York, you feel like you’re getting the best bargain in the world. When you’re rich in New York, you feel like you’re getting screwed every which way constantly.
Derek Sivers
I could see that.
Mark
I’m curious. What did you learn from Ryuichi Sakamoto?
Derek Sivers
Yeah. The one thing was, I don’t have imposter syndrome. I was 22 years old. The other guys in the band were all, like, closer to 40. They were super accomplished. I mean, holy fuck. Victor Bailey on bass. He was like, cover of Bass Player magazine three times. This dude played with Weather Report and Miles Davis and oh my God, Manu Katché, my favorite drummer in the world. The guy that played on that song Sledgehammer by Peter Gabriel, it’s got such a style. And there’s me and I’m 22 and I felt just like, all right, fuck it, you hired me, I’m here, you’re stuck with me. And it’s like, I’ve got a valid reason to be here. I’m not the best guitarist, but I can do my little James Brown funk thing very well. And that’s what was needed for this gig. So I have every right to be here. And yeah, I was a bit of the punching bag of the rest of the guys. I was 22 years old and like, you know, I’m an enthusiastic dude. I’m the opposite of jaded. And of course, you imagine me at 22 in Japan for the first time, it’s even amplified. I’m like, “Wow, this is amazing.” And all these jaded 39 year olds that have seen it all, been there, done that. They’re like, “Yeah.” For them, the Ryuichi gig was just another gig. They’re just like, “Dude, calm down.” And they made fun of me a lot. But the main lesson I think was the giving it all for getting the gig, but then even doing it, this feeling of like, “All right, I have just as much right to be here as anyone.” But, um--
Mark
Do you think you had to earn that feeling, like through practice and developing your craft, there are some people who practice incessantly and are excellent at their craft, but they still feel imposter syndrome.
Derek Sivers
I had the right to be there because I knew I could do it, and I knew from the audience’s point of view or and even Ryuichi’s point of view. I was playing the parts he wanted me to play. By the way, I didn’t connect those two. He basically hired me to just play what I had played that sleepless night on the demo I made. He said, “Just do what you did.” I said, “Okay.” And so it’s like, all right. He’s basically saying, I like the way you play, be you. I’ll pay you. Come on stage.
Derek Sivers
Okay, I have to tell you the Alan Tepper story before I forget. So I’m working inside Warner Chappell Music Publishing in New York City, Midtown Manhattan. But the year was 1992, which in hindsight, I found out was like a pretty deep recession. I didn’t know it at the time because I just had my job that I would just show up at. It was a minimum wage, but it was a tiny office. Maybe only 20 people worked there, 15 to 20, but there was one room that wasn’t being used. One tiny, little windowless room hypothesized the little room I’m in recording right now. And one day a stranger showed up there and was working in that room and said, “Oh, hey, I’m Alan, I’m going to be working here now.” I said, “Oh, okay. Hi, Alan.” I said, “I didn’t know you were hired.” He said, “No, I’m not actually hired. I’m just going to be working here.” I went, “Okay.” Alan Tepper, it was a recession. He had been laid off from inside an advertising gig, and he looked at the world of music publishing. Music publishing owns the copyrights. So if you hear a Stevie Wonder song in a commercial, Stevie Wonder gets some money, but his publisher gets half the money. You know, the money is split 50/50 with the publisher and the artist. So Alan Tepper came in and he looked at Warner Chappell Music Publishing, which was the largest music publisher at the time, and he said, “You’re not doing enough to get your music into commercials. I think I can get your music into commercials better. Just give me a desk. You don’t have to pay me. Give me a desk. Let me show you what I can do.”
Derek Sivers
Because Warner Chappell was not hiring at the time. This is the key lesson here. They were not hiring, but he looked at their business and said, “I think I can make your business a lot more money. You don’t have to do anything, but just give me a desk and a phone and let me say that I’m working for you.” And they said, “All right, show us what you can do.” And within one year, Alan Tepper made more money for that company than everybody else in the rest of the office combined. He ended up becoming like the highest paid guy and the biggest success story of Warner Chappell Music Publishing for years afterwards. But he made a job for himself. They were not hiring. So when I hear people say, like, “I can’t get a job.” I think, well you got to have some gumption. You got to have some insight. You got to just look at a company that you like, have some, um--. What’s that word? Impetus to make something happen. Look at it and you can make yourself a job. It doesn’t matter if they’re hiring or not. If you go to them and show them that you can make them more money, you can make things happen. And to me, Alan Tepper was the perfect example of that. Find a way to add value. Make yourself a role.
Mark
I get a lot of cold emails, people pitching me on stuff, and there’s maybe 1 or 2 a year that I’ll actually bite. I’ll respond to. I mean, obviously there’s a lot of terrible ones, but the ones that kill me is they’ll have the great subject line, a great hook. They’ll offer something really intriguing. And in there, the close of the email is if you want to find out more, reply and we’ll get on a call. And I’m like, “No, just send me the fucking work. Like, dude, if you can live up to everything you just promised, just send me the work.” And I feel like a lot of people, they get really insecure about like, “Oh, well, I can’t work for free or I can’t give away my work for free.” It’s the best way to sell your services. It’s the best way to convince somebody that you’re valuable. If somebody gives me a day’s worth of free work and it’s valuable, my immediate thought is, “Fuck, I should hire this guy like he did this for free. Imagine what he’ll do if I pay him. Holy fuck.” People’s brain doesn’t go there for some reason. I don’t totally understand why, but it drives me crazy. It absolutely drives me crazy. No, I’m not gonna hop on a call with you. Just send me your fucking ideas. And if they’re good, then I’ll pay you. And if they’re bad, I’m not going to use them anyway. Oh, man. Well, speaking of, we’re talking about relationships earlier, I worked as a professional men’s dating coach for a number of years, so that was my first--.
Derek Sivers
I’m so glad you’re going to talk about this. You’re going to talk about it?
Mark
Yeah, I learned a lot, man. I learned a lot. So for people who don’t know, my first online business that got traction was men’s dating advice. And it’s a long story. I happened into it kind of unwittingly. Next thing I knew, there were a bunch of men in Boston who were like, “Hey, if I pay you $500 bucks, will you take me out and help me talk to girls?” And I was like, “Sure, what better way to to earn a living?” First of all, there are a lot of better ways to earn a living. Like anything. Again, it’s the lesson from the bar all over again. It’s as soon as you monetize an activity, it changes your relationship to it. And in some cases, the monetized version of that activity is way less fun or way less satisfying than the hobby version is. And I think that’s true about a lot of things. And I think it’s just important for people to be aware of. I actually struggled very much early on in that career, because it felt like a lot of my social relationships became objectified. You know, it’s like if I went on a date with a woman and it didn’t go well, suddenly that’s like a professional liability because it’s like, you know what if I’m out and some potential client sees me with a girl and she’s, like, shooting me down. It became really weird. It was like, definitely a mind fuck. But the biggest things I learned doing that job was, I was shocked how most of the men like when you really got down to it.
Mark
I did it for about five years. I worked with probably around 100 men. When you really came down to it, I think most of the men, it wasn’t about, I don’t know what to say or I’m nervous around girls or help me buy a shirt that doesn’t look like I’m a homeless person. Like, it really just came down to a lot of men had very unrealistic expectations about gender, dating and sex. Like their map of reality was very warped, either based on a fucked up family background or exposure to like some adverse events when they were young. You know, a girl who broke their heart, you know, they just had very strange understandings of women and dating and sex. And it was like a lot of it was just kind of like correcting that map, just being like, “Well, no, no, no, you don’t have to say or do all that. No, you don’t have to pay for dinner. Dude just be normal. Like chill out.” I was very shocked at how many, i’d say probably 90% of my clients had no present father figure in their life. A lot of it seemed like there was kind of this desperate need for a male role model. And whether consciously, probably unconsciously, but like part of my job was to kind of like be the stand in as that role model, to basically just tell these guys like, “You’re okay, you’re a good dude. Yeah, you deserve an attractive woman. There’s nothing wrong with you” It surprised me at how many of the clients it really boiled down to that the worst part of the job was the clients who they saw relationships very transactionally, which was why their relationships with women sucked, because viewing women transactionally is not a huge turn on the women.
Mark
It’s not a shocker there. But again, kind of coming back to this like inaccurate maps of relationships and dating and intimacy. I found that a lot of men just like, could not, they literally did not understand non-transactional relationships. They just like, they couldn’t process it. And if I tried to explain it, they just saw it as like another tactic to like, “Oh, I see what you’re saying. So okay, so I make it seem like I like her unconditionally because then that’s going to turn her on. And then I could get laid.” And I’m like, “No, no, no, no. It’s actually the opposite of what I’m talking about.” So that was always frustrating. Ultimately, I found it to be a very draining job. I honestly, I came away from it with the conclusion that most of these men actually need a therapist much more than they need a dating coach. Lines don’t really matter. Tactics don’t really matter. Like those are placebos that kind of just get guys over their anxieties and fears. It was very interesting. It was really just an insane amount of education into like human nature and psychology and relationship dynamics, understanding how men and women see each other and react to each other. I honestly think a huge percentage of my-- whatever insight I have that people enjoy is a lot of it came out of that period from just intense amounts of extreme social interactions.
Derek Sivers
Because you weren’t doing this just for the money. It was not five weeks, it was five years. So did you feel even at the time like, “Okay, well, I’m not just doing this for the money. This is helping me.”
Mark
I definitely learned, you know, that cliché about the teacher learns more than the student. I definitely found that to be true. I would usually learn way more from the guys I worked with than any women we met or talked to. You were dealing up front and personal with a lot of men’s insecurities and vulnerabilities, and seeing the patterns among those, especially two at a time where, like, those sorts of things weren’t really talked about publicly. There was like, I mean, there still is stigma. But back then especially, I mean, a lot of stigma around guys admitting they were insecure or anxious or depressed. So, yeah, it was extremely educational. It was not satisfying. It really wasn’t. I mean, there were some clients that it was like every once in a while you get like a really good guy and he’d kind of have a breakthrough and meet a nice girl.
Derek Sivers
But yet you. Currently are putting yourself into counseling type situations. You’re still choosing to help people. So you still get something out of it. Or what is that drive in you that still wants to help individuals?
Mark
Well, it is really fun to help somebody. I think the difference now is that I get to choose who I help. Whereas back then I kind of just took anybody who wanted to hire me. Towards the end, there were a number of clients who, you know, we would go out to a club or something. Start talking and then within an hour it’s just clear. It’s like, okay, this guy is an emotional wreck. And I would just kind of pull him aside. We’d go to a restaurant or something, and we would just spend basically the entire session basically kind of being a therapist, because I’m like, that’s what a lot of these guys need. Like, they just don’t have anybody to express this shit to. Like all their guy friends judge them for it, you know, call him a fag, make fun of him. Dad’s not around. There’s no brother. Like, they literally have nobody to talk to this stuff about. So I realized that after a while that they just need a fellow dude who will, like, listen to all their insecurities and be like, “No, man, it’s all right. You’re all right. It’s going to be fine.” That felt more impactful than the, you know, “Oh my God, I got her number. She’s so hot.”
Derek Sivers
Do you think that’s what put you on the path, then of writing articles from what you learned?
Mark
Totally. Yeah, what I learned is that there’s not really such thing as a dating advice. It’s really just a dating problem is just an emotional problem that is being experienced while dating. That’s all for this episode.