The Quarter-life Breakthrough

with our guest: Smiley Poswolsky


Today my guest is Smiley Poswolsky, a millennial workplace expert, keynote speaker, and bestselling author of The Quarter-Life Breakthrough and The Breakthrough Speaker. Smiley is somebody that I met through friends. It turns out I’ve got three or four friends, who aren’t friends with each other, who all know Smiley. In our conversation today, we talk about the qualities of a good prank, the value of making the ask, not waiting for permission, the gatekeeper is often yourself. Smiley talks about writing the book you need, writing about whatever people are asking you. And then he gets into a few tips about public speaking. So, if sharing from a stage is something that you’re interested to do, Smiley’s a good guy to know. One of the things I love about this conversation is Smiley talks about his lifestyle. It made me think about the healthy writer’s lifestyle as opposed to maybe the unhealthy writer’s lifestyle. Where Smiley’s not fueled all the time by caffeine or alcohol or amphetamines or some of these things that might be conducive for productivity in the short term, but have a very bad outcome. I think Smiley is a great example of somebody who lives a very workable lifestyle that makes a big difference in the lives of many others while simultaneously earning money and having a good time doing it. 


00:02:25 – Burning man prank.
00:11:54 – Camp grounded.
00:18:33 – Who Adam writes to.
00:33:39 – Inner vs outer authority.
00:55:16 – The most surprising thing learned over the course of writing.
01:02:59 – Lightning round.
01:11:57 – Discussing the craft of writing.
01:27:35 – Adam’s process for finishing a book.

Bryan:              00:00:53 Today my guest is Smiley Poswolsky, a millennial workplace expert, keynote speaker, and bestselling author of The Quarter Life Breakthrough and The Breakthrough Speaker. Smiley is somebody that I met through friends. It turns out I’ve got three or four friends, who aren’t friends with each other, who all know Smiley. In our conversation today, we talk about the qualities of a good prank, the value of making the ask, not waiting for permission, the gatekeeper is often yourself. Smiley talks about writing the book you need, writing about whatever people are asking you. And then he gets into a few tips about public speaking. So if sharing from a stage is something that you’re interested to do, Smiley’s a good guy to know. One of the things I love about this conversation is Smiley talks about his lifestyle. It made me think about the healthy writer’s lifestyle as opposed to maybe the unhealthy writer’s lifestyle. Where Smiley’s not fueled all the time by caffeine or alcohol or amphetamines or some of these things that might be conducive for productivity in the short term, but have a very bad outcome. I think Smiley is a great example of somebody who lives a very workable lifestyle that makes a big difference in the lives of many others while simultaneously earning money and having a good time doing it. Smiley, welcome to The School For Good Living podcast.


Smiley:        00:02:14 Thanks so much for having me. It’s great to be here.


Bryan:              00:02:16 Just before we started recording, we were talking about how many friends we have in common. Yet this is the first time we’ve connected one to one, but it’s a, it’s really a pleasure.


Smiley:        00:02:24 Yeah, I’m excited.


Bryan:              00:02:25 So one thing I really want to be sure to ask you about is an experience that happened at Burning Man. Something with Shmoo in some prank that was pulled. Will you tell me a little bit about what happened there?


Smiley:        00:02:36 That is not what I thought you were to ask. That’s great. I’m wondering where that came from, but I wonder if, if Bubbles seeded that. This, yeah, so this is my…have you been to Burning Man Bryan?


Bryan:              00:02:53 I have not yet gone.


Smiley:        00:02:54 Okay. Okay. I highly recommend it for everyone out there. It’s a very much a life defining experience. Even if you only go once, I think it’s something worth doing just to kind of be in the presence of a 70,000 people that are basically just being themselves. Um, and kind of standing in their creative truth, whatever that is. A it’s a pretty powerful. Um, so, you know, even if it’s something that you hate but you experience once, I think it’s, I think it’s worth going to. But this is my third year, um, and I’ve always gone with, um, a close group of friends. Schmoo who you referenced being one of them. Um, and so the first year I went was 2014. I went with a Schmoo, with actually Schmoo’s a younger brother Levi, a Fidget as his nickname. He took me for the first time, him and his girlfriend and their whole crew of friends. and that was like my first Burn. And then the next time I went was last year 2017. Um, and we went actually because Fidget had passed away. Um, so leave, I, my, my buddy, one of my best friends who had brought me to Burning Man had died earlier that year, from a brain tumor, from a brain cancer. A young guy, a about 30 years old. I’m 32 actually, who started this thing called Camp Grounded, which is a summer camp for adults. Which is how I know I’m army, haven’t climbed in. And so we went to celebrate his life at Burning Man. There’s a temple which is this beautiful place where people go and cry and write letters and just kind of sit with and mourn and be in the presence of people that are no longer with us. Um, it’s a really beautiful, powerful place to be. Um, and so then this year I went, um kind of on my own. Our whole crew and go this year, except for Schmoo, who is Levi’s older brother. And we were camping with a bunch of, some people we knew, but a bunch of strangers in a big live music camp. and Schmoo with the help of his younger brother. Levi’s, there’s three brothers, Schmoo, Levi and Zev had made these flyers, 300 of them that they put in port-a-potties with my face on them. that said, um, if you’re having any trouble on the Playa, a call, and you need a lawyer, call Barry Lacroix, with my face on it. And it said, call five five, five dash five, five, five, five. You know, if your camp made stole your beer, if you’re having trouble taking a poop, if someone’s giving you shit, if all kinds of these weird little things, if you’re having any trouble on the Playa called Barry Lacroix, a attorney at law and he’ll, he’ll take care of it. And they had taken. Zev is a graphic designer. He actually did all the graphics for Camp Grounded. He’s a really brilliant creative and did all the logo and branding for camp. He had made these, he wasn’t even at Burning Man this year, but he had made these flyers. Um, taking pictures from my facebook and my social media profiles and put them on these and printed them out. And, and, and Schmoo with the help of I guess a couple of other people put them on port-a-potties. Obviously at Burning Man, everyone uses port-a-potties all around the Playa. so all, as soon as I got there had these people coming up to me and me being like, “Hey Lacroix, hey it’s the lawyer Berry Lacroix!” I was like, what is going on? And then I went to the bathroom about an hour or two after I got there, naturally. And I go in there and I’m like, why is there a picture of me in the toilet? Um, it was an amazing prank. And the good, the beauty of it, it’s pretty, I mean it’s a beautiful thing because Levi was at its very essence of prankster. That’s kind of why he started Camp, was just to kind of mess with people. It was a digital detox kind of screw with people about, you know, the reality and what was happening in the world. And we’ve had a human powered search instead of google and pet rocks and like your friends in person instead of liking them on Facebook. And the whole thing was kind of a prank to see the experiment of taking people out of their real world and into the Redwoods for a few days. So it was pretty fitting that, his, his brothers and my friends kind of a, he would have been very happy to see that prank. And it, you like pulling off a prank is really hard, like a good prank. There’s an art to it, you know, like I think people do often do bad pranks, which is just like they make their friend look bad or they make fun of somebody. But a good prank is actually funny. And so every time it was, it was bringing a good prank actually brings joy to people. So it was bringing joy to the people. So they go to, you know, going to the port-a-potties at Burning Man is not a pleasureful experience. Right? You know, people are tired, they’re dehydrated. Um, maybe they’re partying or they’re drunk or something and they go into the port-a-potty and they see this flyer in this guy’s face. And then they would bump into me. These are complete strangers. “Oh my God, is that Berry Lacroix? Are you the guy from the port-a-potties?” And I can’t tell you how happy some people were to stumble upon me. Like I had this guy saying that it was the, his best moment of Burning Man. Which I kind of felt bad for his wife who he was hanging out with. And I’m like, this is your best moment is running into the guy who’s flyer was at the port-a-potties. But anyways, you know, maybe he was having a spiritual experience or an out of body experience, you know, a lot of stuff happens at Burning Man. he was like, oh my God, and he offered to work for me. He was like, I’ll be your intern, I’ll be your paralegal. So anyway, it was a beautiful prank because it brought all these people joy and it was very funny to me because every time someone came up to me it made me smile and laugh and I’d pretend to be a lawyer. You know, I’m obviously not an attorney. I pretend to be a lawyer and be like, “Oh yeah, I’ll take your case. Maybe we can meet on Tuesday afternoon a, dial in my conference call or put your file in my briefcase.” And I actually was carrying them out a little briefcase for awhile. Um, anyways, it was, it was an amazing prank and Schmoo and um, Zev are great, are great homies. And Levi’s is looking down from somewhere, laughing somewhere, rolling around in a, and you know, cracking up about all this. So it was a, it was a really beautiful moment actually one of the highlights of, of, of not just Burning Man but of the year. So it was. And now I, now I have to get them back. I have, I have, I don’t know how it’s going to happen but I don’t know how to top that. But I think like every group of friend should have like, loving pranks that they keep trying to one up each other on. You know.


Bryan:              00:09:38 Yeah, no I love that perspective about a prank. A good prank is one that brings joy to people. And, and so when you’re thinking about how you get them back, it’s not some malicious thing. But how can you, yeah. Like you said, how can you top that.


Smiley:        00:09:49 It celebrates people. I mean, the other part of it that was amazing is that it was kind of messing with me. And I have a whole, a little bit of a, as other people out there that are, you know, um, personal brands or authors or speakers or kind of putting themselves out there. There’s so many beautiful things about that. But it’s also a little bit challenging a of being kind of a, you know, a public personality and I kind of struggle with it. And part of the prank was a little bit messing with that, you know. Because like, Zev and Seth, Schmoo, would make fun of me. Um, sometimes when we’d be at Burning Man, like, you know, running around like wearing onesies. Being silly and someone would be like, “oh my God, Smiley Poswolsky I read your book.” And they like, make fun of me. They be like, ha ha, like it’s just like a silly thing that someone is recognizing you for that in this moment. But then it was cool because the people were recognizing me to be Berry Lacroix, a fake lawyer, from the port-a-potties. which is kind of messing with my, um just like, my brain and my ego. Which is actually quite beautiful and made me realize that all of this is kind of bullshit anyway. So it was like a, it was like, you kind of just like, don’t, don’t take yourself too seriously. I would say like the conclusion there, do important things in the world, but remember that it’s all, if you can’t laugh at yourself and laugh at the people around you and bring joy to the people around you. What’s the point?


Bryan:              00:11:15 My, one of my takeaways from that is that advertising works, right?


Smiley:        00:11:19 Totally.


Bryan:              00:11:23 That’s a career change strategy you didn’t include in The Quarter Life Breakthrough, but maybe it deserves a 10th anniversary edition or something.


Smiley:        00:11:30 Yeah, it’s true. I, I was surprised at how perceptive people were and how much they were paying attention to what was in the port-a-potties. And it struck me as interesting that I don’t think I ever pay attention to what’s in port-a-potties. Um, but also that, um, flyers are old school and actually can work to get


Bryan:              00:11:52 Yeah man..


Smiley:        00:11:53 To spread an idea.


Bryan:              00:11:54 Yeah. So that is another thing, Camp Grounded. Something else I wanted to ask you about, um, I read in The Quarter Life Breakthrough about the fact that you were a counselor there. Will you tell me just a little bit about what were your big takeaways as you lead other people through these, this digital detox and this kind of connection to nature and what, whatever? I’ve actually never been to Camp Grounded yet either.


Smiley:             00:12:16 I’ve been a counselor. A camp started in 2013, it’s on a little bit of a hiatus now. Hopefully it will come back. Um, so I think altogether I was a counselor about 13 different camps over five years. and basically Camp Grounded is a digital detox. It’s a four day, essentially, retreat experience in the Redwoods. Um, we’ve done them in northern California, in upstate New York and Texas and North Carolina. Um, all in, all in nature, all in the woods, all digital detox. So we lock people’s phones away and laptops or Apple watches, if they have them, for four days. and really it’s just about reconnecting with yourself and reconnecting with others and play. It’s about kind of giving people that sense of what it’s like to be a child again. Where they can just not be on their schedule, not be on Instagram, not be worried about what’s going on on social media and just be in the moment, be present. There’s no real names. So we use nicknames. So for example, I use Smiley or there’s Cookie Surprise or Bubbles or Schmoo or Mobius. Um, a you know Sparkle Pony, whatever it is, um Ocelot. Um, and the whole point of it is just to kind of connect with a different identity that’s not your name and not your work. We don’t talk, we have a no “w” talk rule. So there’s no what you do? There’s no, “Oh, on Linkedin I saw that you’re an entrepreneur. Oh, you work at Dropbox, that’s so cool. Or you started three companies or your you know, whatever fellow.” There’s none of that. Um, so it’s really just about being like, “oh, you’re an awesome poet, or I really like your face paint or you were really cool when you were Hula hooping over there.” The point being connecting with people in a way that’s more unique, raw, authentic. Um, and I think a really breaks down barriers and lets people become very close very quickly and just channel a different side of themselves. so for me it was a really powerful experience. I think, what I saw most of all is that, um, when you allow people to express who they are, it’s when they, when you allow people to, when you give them kind of this space and the permission to be who they really are, a amazing things can happen. when you kind of take down some of the, um, rules, expectations, guidelines that I feel like society often gives us a, this freedom emerges and, and people are not only are happier, but they channel this kind of creative power. And I think a similar thing can happen at Burning Man, but this kind of creative power that’s not present normally in society. so they’ll start writing, they’ll start doing spoken word or improv or building something or having a conversation that they’ve never had or having an insight that they haven’t had in a year about maybe a job, a relationship, someone in their family or something that’s not working in their life. Because they have now the space and the permission to do so. Um, it sounds very simple and I think it is actually quite simple, removing distraction, removing some of the digital technology, but also removing that kind of, “I am Adam Poswolsky, I am an author. I, this is my how many followers I have and on Tuesdays I’m responsible for this, this, and this.” Just to be like, “okay, no, you’re Honey Bear. Like you have dinner in a few hours. Between now and then like you can do whatever you want and what do you want to do and who are you and what do you care about? What do you want to talk about? Do you want to go sit in a hammock? You want to read a book? Do you want to go play with that person? Do you want to go to this thing?” Um, and amazing thing happens when, when you kind of give people that space. You know, it was very profound thing. I think a lot of people, I have friends that kind of like, we’ll look at that have never been to Camp. That from the outside would say, oh, basically you’re just like going hiking or you just going into the woods. Like you have a digital detox when you go to the woods. And on some surface level that’s correct. But on the other hand, it’s this sense of going, a shared intention. Amazing thing happens when you have a shared intention with a group of other people and you all kind of agreed to say, okay, “we’re not looking at our phones. We’re not using our real names. We’re not talking about work, we’re not paying attention to time.” Um, it’s really powerful. Um, it’s, it’s, it’s an incredibly powerful experience. So, um, I saw, I saw people, um really kind of come out of their shell. I saw people decide to quit their job. I decide, I saw people that were decided they were gonna write a book or start some sort of entrepreneurial effort. I saw, witness people being like, I need to get out of the relationship I’m in that’s toxic or I need to, um, you know, change where I live or change something about me. Or I feel comfortable with who I am for the first time or I could feel comfortable being gay and I’ve never felt comfortable being gay before. Whatever it is, like I saw all of these things because people were finally kind of given permission to be who they really are, which is quite powerful. Um, so I’m very grateful to Levi to Fidget. I’m grateful to Camp Grounded, for creating that container. Over about, I think about 3000 people experience Camp in one form or another, in, in five, five or six years. and hopefully, hopefully it will continue. It’s on a little bit of a break right now, but hopefully you’ll get a chance. Bryan and, and other folks listening will get a chance to experience it when it comes back.


Bryan:              00:18:02 Yeah, I hear all the best cults begin that way. They take away all your electronic and all your identity and no. It does sound really fun.


Smiley:             00:18:11 There are cultish, there very much cultish aspects to it. As cult, a cultish aspects to anything that is a gathering of like minded souls are. Um, but I think it is a best kind of cult of. It’s just a very nurturing, encouraging, supportive group and community.


Bryan:              00:18:33 No, that’s awesome. So I want to ask you about your books, about The Quarter Life Breakthrough, The Breakthrough Coach. And I realized the answer to this might be different, so if so that’s fine, but maybe it’s the same. Who did you write these books for and what did you want the books to do for them?


Smiley:             00:18:54 Yeah, so different answers for, for both of the books The Quarter Life Breakthrough and The Breakthrough Speaker. The first book a really came out of my own quarter life crisis. So I started writing this. I wrote two versions of the book, actually. The first one I self published back in 2014 and I really wrote it for myself. What I was going in through the quarter life crisis, you know, they, they, they say write what you know, and I really wrote the book I wish I had. So I wrote the book for, you know, what I felt like I was going through and people around me were going through and that they’re sure there’s a ton of career resources out there. There’s even books about the quarter life crisis. I didn’t find any, I didn’t have that book when I was going through it that I was like, this is my guide, this is my north star, this is the thing that’s gonna get me through this. I just kind of felt lost. So, you know, when I was in my late twenties, I was working in Washington DC in federal government. Had a great job on paper, good benefits, good salary, good healthcare. was working for the US federal government and kind of felt stuck because on paper it was perfect. It sounded good to everyone. Um, everyone was impressed. People really been jealous, they wanted my job, but I hated it and I didn’t want to be there and I didn’t really know how to get out of that. And I knew I wanted to do more writing. I knew I wanted to live in San Francisco and California support social entrepreneurs. I just didn’t know how to do it. I didn’t know the roadmap, the path, and I’ve learned that there isn’t necessarily one path at all or a straight line at all. but I definitely didn’t feel like that there was any resource out there to help me. Um, and if anything, all of the books people named just seemed overwhelming and just seemed kind of like generic career job hunting figure life kind of stuff. but not something that was like exactly meeting me where I was. Like, “okay, let’s talk about this. This is ridiculous. Let’s talk about Fomo and Facebook and being fear of missing out and being jealous of what your friends are doing. And being like, oh my God, that person’s in Bali making all this money. That person’s in business school. That person’s opening a food truck. Maybe I should open up a food truck. I’m not a good driver. I’m a bad chef. Probably bad idea, like let’s talk about this honestly.” Um, you know, and kind of with the whole millennial and millennials in the workplace, what’s going on, this type of thing. So I, I really, if I’m being honest, I wrote it for, for prior, for my past self and for a lot of the people that were also going through it. I think one of the things that I do as a writer that is, just kind of how I like to write is I. A lot of people like, you know, the, I call it, like the Tim Ferriss model. They’ll like write about really successful people. Which is cool and probably from a marketing perspective, like make sense. Like let me get the most famous people in the world to give advice. It’s kind of like, or like the Warren Buffett.. “Who’s the, like, let’s find the richest people and most successful people, most famous people and put them in a book.” I’m like, let me write about my friends. Right? Which I get it, probably people don’t care about, Smiley this guy Smiley Poswolsky’s friends, but I’m like, they’re my friends. I talk about life with them. I know their stories. for me it’s more real. So that’s how my, my approach actually in both of my books has been, is I write about the people I know what they’re going through and where they’re at. Because I think that that’s actually more relatable, for me at least. Like I don’t like, yeah, Tools of Titans and Tim Ferriss and this. I just can’t, I, it’s 17 steps. It’s 38 steps from where I am. I want to know like two or three steps. Because it’s so far and it’s like, okay, that person makes 6.8 million a year. I’m trying to make like 60 grand or 100 grand or like 110 grand or like 160 grand. Right? Like give it to me so that it’s like where that person like, actually when they started and it’s almost more interesting that they just got a little bit further than like, oh my God, they’re a global sensation, blah, blah, blah, blah, blah. It’s like, no, let me tell you about my friend’s story. So for The Quarter Life Breakthrough, I really, if you look at the book, I really just start profiling people around me. And these are not just random people that are not inspiring or not interesting. These are awesome people that have started really cool companies that are building amazing mission driven for-profit businesses and nonprofits and have written great books, but they’re not famous. I hope one day they become famous and there maybe, that they’ve gotten a lot of traction. But I really just wanted to write about people that were in my life that were doing really cool shit because I actually find that a lot more interesting and relatable. Um, so the book was really, you know, I wrote it for myself, but I also wrote it for them and wrote it for a lot of the people I profiled. That had kind of had a major transition of going from something that they’ve really found um, not meaningful, not fulfilling. Maybe their life was a little bit depressing. Maybe they felt like a lot, a lot of anxiety or they felt stuck and, and they got to a better place. And how they did that.


Bryan:              00:24:14 Did that ever cause any problems writing about the people you knew? Like maybe you ended up getting facts wrong or you shared something that somebody’s wish you hadn’t. I mean, how did you, how’d you navigate that? How that will work out?


Smiley:             00:24:25 Um, I’m pretty good about fact checking and I always kind of, you know, I do like a different stages of like, hey, is it cool if I include you? Um, here’s some questions. Let me write something up and send it back to you to get, um, to kinda make sure that I have it right. And, and, and kind of do like a final, is this, is this correct? I don’t often always let people completely edit their things because…


Bryan:              00:24:51 There’s no end to that.


Smiley:             00:24:52 Or is this correct. Right, exactly. People always are going to want to make it different. But is this correct? Is that, am I factually, am I getting the facts right here? Um, is, is everything accurate? And then maybe my analysis is a little bit different and if you have a major issue, let me know. But otherwise, basically are you okay with me printing this? Uh…


Bryan:              00:25:12 That’s a lot of work.


Smiley:             00:25:12 And never really had the. Oh yeah, it is. Yeah, definitely. Um, but, you know, I’ve never really had someone say, I really wish you hadn’t printed this. I think people really want to see. It’s really, um, it feels good to see yourself in print. People take a lot of pride in being in a book, you know, especially like, you know, this book was originally self published, but then it got published. To see your book, see your name and your story in a book that’s in bookstores is very, very powerful. Right? And then to know. And the coolest thing is that I’ve had some people that are featured in the book say that, “Oh, I read about you in Smiley’s book,” like, Oh, you’re that guy. You’re, you know. Um, my, there’s a story. I’m happy to share it. I’m about a guy named Burnot.


Bryan:              00:26:00 Oh yes. This, the guy you talk about in your TED Talk to, right?


Smiley:             00:26:03 I talk about it in my TED Talk, who I met on a bicycle. He’s had people being like, I read about you or I saw you, my TED Talk. I saw you in Smiley’s TED Talk. Um, you become like a character. And it’s actually quite cool mostly because then you’re actually, not me as me the author, but the person that I’m profiling is one inspiring other people. Um, that’s the cool thing about writing. It’s not, I mean, I compiled it, I made it happen. But the people that are actually the ones inspiring leaders or the people I feature, it’s their stories.


Bryan:              00:26:36 It’s powerful.


Smiley:             00:26:38 It’s their lives. That’s the beautiful thing about writing. Um, is that you really start to kind of have this ripple effect. And um, I’ve been really, I, I’ve, I, that’s one of the coolest thing for me is to kind of see which stories people identify with or resonate with and…


Bryan:              00:26:58 Yeah, and for anybody that hasn’t seen your TED Talk, even though it’s been viewed more than half a million times. There’s still a few people that might not have seen it. But would you be willing to share that story that you just mentioned and also what, what your takeaways from that were?


Smiley:             00:27:12 Yeah. So it’s a great story. It’s completely real story. Um, but um, basically a few years, this is now, I don’t know how many years ago, but several years ago. I was biking home in San Francisco just on my bicycle, because I don’t have a car. And all of a sudden this guy bikes up alongside me and says, my name is Bernot, I’m from Spain. And I was like, I have no idea who you are. Please leave me alone. You know, San Francisco, there’s all kinds of people roaming around. It’s, you know, good idea to probably not talk to every stranger you meet. Although that kind of contradicts what I was talking about with Camp Grounded, but still, you know, it’s, you probably are not going to be talking to a completely random people all the time. So he keeps biking alongside me as I bike away. He’s like, “no man, my name is Bernot, I’m from Spain. I’m looking for a job.” I was like, sorry man. I gotta go, you know, leave me alone. Keep spiking alongside me. My name is Bernot, I’m from Spain. I’m from Barcelona. I’m looking for a job here in San Francisco. I’m a Ux Ui designer. Um, there’s, there’s really bad unemployment in Spain right now. I got to find a job here in the bay area and I kind of was like, oh, Barcelona is a beautiful city. Actually my, my best friend used to live there. I visited once. A great city and he asked me, he says, “oh, well, what are you working on right now?” And I tell them, I’m working on this book, about, you know, millennials figuring out what to do with their lives, careers. And he says, “Oh, well, do you have a cover designer yet?” And I said, no. He says, “well go home, check out my website, maybe we can work together.” I go home, I check out this guy’s website. And I was like, man, this guy is a really good designer. Like he had been done all this really interesting Ux Ui work. He had done some CGI stuff. His website, his portfolio is really great. So I posted on Facebook right after I got home. Bernot when I was biking home. Um, tonight in San Francisco. He hails from Spain. He’s looking for a job here in the bay area. He does, he’s a designer a, if you know of anything, let him know. And about five minutes later by my buddy Yee comments on the thread and he said, oh, Bernot should meet with my friend Mark. they’re doing this mobile startup in Palo Alto. There’s like five of them. They don’t really know what they’re doing. They need a lead designer. Maybe they can work together. Bernot meets with their team. He gets hired to be the lead designer for this tiny mobile startup in Palo Alto. He, um, he gets a work visa to stay in the United States, which is a very big deal. Brutal unemployment in Spain. He ends up designing the cover for my first book. Um, for the self published edition and and, and he thanks me. But then a couple years go by really maybe a year and a half or so, maybe two years and I don’t really hear from him. All of a sudden after that, two years later, I get a text message from Burnot that says, “Smiley, I’m taking you out to dinner anywhere you want to go.” And I was like, sweet, I’d love to get taken out to dinner. That’s awesome. I was writing my, writing at the time. I was completely broke and it turns out we’re at dinner and I’m like, hey, why are you taking me out to dinner? What’s, what’s going on? It turns out that the mobile startup he had been working for had just been acquired by Yahoo for $80,000,000.


Bryan:              00:30:39 Wow.


Smiley:             00:30:39 And he was like, the fifth employee at the company. Had equity, lead designer, he can definitely afford to take me out to dinner. And you know, he says, you know, he’s like, “hey man, like thank you, like this wouldn’t have happened if not for you.” And I said to Bernot, I was like, thank you man. Like, like this guy, you know, like, thank you. Like this guy talked to a random stranger. Like in a city he didn’t live in. In a country he wasn’t from, on a bicycle. Like who does that? Right.


Bryan:              00:31:10 That’s bold.


Smiley:             00:31:11 So that’s the lesson there is make the ask. You know, and I have, and I talk about that every time I, every time I give a presentation. But I think that that’s what it’s about. I think that you have to be bold, you have to put yourself out there. Um, maybe not the best idea to harass random people on the street all the time. But you have to have that perspective. If you want something in this world, you have to go out and make it happen. And you have to be willing to put yourself out there and make those big, bold, ridiculous asks, um, because otherwise people can’t help you, you know? And it’s not like every person you’re going to ask is going to be like, “Oh yes, I’ll hire you right now.” Or “Oh, you want a book deal? I’ll give you a book deal.” Like that’s not how it works. And a one out of every one of those is going to come through, right? Or someone’s going to get you one step closer to the going to say, oh, I, I can’t do that, but my friend can. Right? Or we’re not, we’re not hiring right now, but check back with, check back in with me in six months or you’re not ready to get a book deal with us right now, but why don’t you self publish and we’ll take a baby or how about you write this article for me? Or whatever it is. It’s these baby steps. But it starts with that perspective of making the ask. And I think we’re too scared often to put ourselves out there, um, that we don’t even start or we don’t even, we have all these things we’re working on and no one ever sees them because they kind of just stay in our, you know, they stay in our google docs so they stay in our desktop. And I’m sure there’s someone out there listening that’s like, “Oh man, like I’ve been working on this manuscript for six years and no one’s seen it.” It’s like, that’s a problem. You know, like someone needs to see that thing. Does that mean? It’s perfect. Does that mean it’s ready for Penguin Random House? No, but it means someone needs to see it and you need to get some traction on it. Even if it means you need to write half of it over, like you have to take some. You have to. I, I know it all. People always say this, but it’s, um, I, I think the, one of the biggest lessons I’ve learned with writing is that there. It’s not like there’s not magic here of, um, you know, someone, um, like being like, you are ready to write a book, you know, like, have you like, like, like you’re gonna wake up someday with this, this inbox, this note in an inbox. It’s like, oh, we’ve been following you. We think you’re great. Now’s the time. It’s like no one is ever, ever going to do that. Um, you have to.


Bryan:              00:33:39 And you talk about that right in your book, talking about the difference between inner versus outer authority.


Smiley:             00:33:44 Totally. Um, that’s huge. I mean, I think it’s, you know, we’ve been trained and conditioned for this external authority of; and I think this is increasingly relevant in this day and age, of, you know, okay, get the degree, get the master’s degree, get this certification, get published to your, get the gatekeeper to sign off on it. This is like the world we live in where we’re just like getting amassing gold stars are amassing awards for whatever purpose. Um, I’m not sure, like basically making, padding their resume or making ourselves feel good or some sort of ego boosting thing. Um, the actual jump to do something really important in the world comes from within. It’s just saying I’m ready for this, I’m doing it. That’s it. Right? And if it’s good and it matters, people will care. Um, that’s, that’s the biggest thing. I, I think that that’s the, the, the biggest leap is not getting, you know, the attention of TED or a publisher or especially with the tools that are available today. it’s much more about putting yourself out there, about creating something worth creating about creating something that matters and sharing it with the world. Again, that doesn’t mean that if you haven’t practiced and if you haven’t worked hard and if you don’t have anything really to say that people are going to care. Um, right? But I am saying that it comes. I think all too often I talk to people and it seems like they’re waiting for a permission slip. They’re waiting for someone to say, “Oh yeah, you’re awesome. Can I tell you how, how awesome you are. Like everything you’ve ever written is amazing. It’s amazing. We’re just going to give you $6,000,000 for everything you’ve already done. Actually, you don’t even have to do anything. Just sit there and we’ll just going to pay you.” It’s like, no. It’s like.


Bryan:              00:35:35 It doesn’t happen.


Smiley:             00:35:36 It doesn’t happen. And, and, and, and I say this, I’m, I, I’m so grateful for, you know, that I’ve been able to publish. But if you really look at my journey, I don’t know how much, we didn’t talk about the second book and I will. But I actually so I, I self published the first version of The Quarter Life Breakthrough. I pub… I got the opportunity to publish a book deal to publish the new version of it in 2016 with a TarcherPerigee Penguin Random House, which is awesome. It’s in the bookstores. A, not every bookstore, but most bookstores. I was just traveling in Asia and the Philippines and I saw my, my book in a bookstore in Manila, which was like the coolest thing in the world. This guy that told me, he bought me that it’s really cool. And then most recently, my book that just came out about two months ago, I self published because the publisher wasn’t interested in it and my agent and I didn’t get any real real bites on it. And I went, meaning I went right back to where I started. And it was a humble reminder of like, who cares? Like, I’ve done this before, this is a great product. I’m getting great, great, great reception for it. Maybe will get picked up down the line and maybe not. The point is if you have something to put put out there, um, in, in this, in the world we live in today, in this day and age, um, stop waiting for permission. Make it happen. Um, ship and, and show your work, ship your work. Um, and if it and if it’s good, if it needs to be out there, you’ll build an audience around it and people will care. Um, there’s so many tools available now, whether it’s Crowdfunding and Indiegogo and Kickstarter and um, self publishing. Um, and I think we’re only going to have more of those. The gatekeepers, the gatekeeper is yourself, right? And the gatekeeper is, is creating. It is getting over the fear of creating great work, and putting it out there. Um, I, I still think that there will always be a place for these kinds of, of the, the famous people to have their agents to have their book deals. To have the people that are their managers and whatever, but most of us that are just kind of creating important stuff, we’re going to make it happen and make a living by just by finding, by finding our audience and making it happen ourselves. and with the tools, the technological tools that are available.


Bryan:              00:38:02 Yeah. There’s, there’s fewer excuses every day, right. Between all the technology and all the other examples we have. And I love that perspective of, you know, the gatekeeper is yourself. Yeah. Getting over it and getting into action. Where did, where did it take you to dinner?


Smiley:             00:38:18 Foreign Cinema. It’s a very, a delicious restaurant in San Francisco.


Bryan:              00:38:23 But he waited to tell you at dinner about why he was taking you. It might’ve been a different choice if he told you before, I imagine.


Smiley:             00:38:29 Yeah, totally. Oh yeah. Well, Foreign Cinema’s nice, but I probably would have been like, all right, well let’s, let’s go to the a eight, five star, you know, 18 course meal or something. Or a $80 million dollars. I thought it was great. You know, there was like, you know, he, he, I think the coolest thing about that is that, you know, he was very thankful when he got the, original job. It allowed to stay here in the US and um, he’s actually still here. He’s now, um, I believe married, but um, so it’s just really funny kind of how one connection or this kind of synchronicity can work sometimes. I, you look back and I mean, I think we’ve all had those types of people. If you look back like why, how did this come to be? And you and you trace it back and it was one, one person writing an email, a connection, right? Or like, how’d you get that job? Or how’d you end up in India? Or how’d you end up volunteering? Or how’d you end up getting that book deal? Or how you end up having the opportunity to speak there or whatever it is. And of course it’s all the things you’ve done in your life and all of the work you’ve done. But sometimes you look back and like, oh my God, like that person that I met at a Starbucks wrote an email because they said hi to me or something, or because they liked what shirt I was wearing. I don’t know, something random. These little random things just goes to show kind of like pay attention and keep your eyes open and, you know, talk to strangers. I think that’s the other big thing I um, took, took away from the Burnot story is, I literally was biking by. That’s it, you know.


Bryan:              00:40:16 it’s pretty random.


Smiley:             00:40:17 I was biking by, I don’t know how. And he told me he was kind of trying to talk to us like literally anyone he made eye contact with, that was job hunting because that’s just how he is. But there was nothing really special about our interact. Like how we met in that. I literally biked by on Valencia street, I’m going to get tacos and maybe I was wearing like a cool backpack or something I don’t remember. But like um,


Bryan:              00:40:43 Maybe he’s selling your aura Smiley.


Smiley:             00:40:44 He’s, he’s a very, he’s a very, a perceptive, a perceptive human being. So…


Bryan:              00:40:50 That’s awesome. So let’s talk about your second book, The Breakthrough Speaker. You said that you self publish this one, um, and you said the answer was different to the question. Who did you write it for and what did you want it to do for them? Who did you write this one for?


Smiley:             00:41:03 This one I wrote this, so this is a very, it’s a practical book for people that are starting or emerging in their speaking career. So it’s really for, um, people, um, that are trying to make a living from public speaking or at least to increase their income and revenue from speaking. Um, so, you know, one of the things I noticed when I was, um, through, through my publishing career was that, um, I loved writing. Um, I was good at it. It was fun. Um, but it was very difficult to make actual, enough money to live on. Um, just between, you know, you’re, you’re kind of relying on these book deals or, or, or selling books is very challenging. Um, and it was, it was, it was hard to just make money from writing and that writing was actually really a calling card for other work.


Smiley:          00:42:00 I think, um, this isn’t talked about as much. you know, I think a lot of people will just say, oh, go write a book or write a book, write a book, but they’re not actually talking about the why. Or how the book fits into your business and kind of how you, whatever it is that you specifically do, you know, they’re just kind of following. Oh, again, what I call it, the Tim Ferriss model of just, I got to sell many books as possible. I got to sell millions of books, New York Times Bestseller, get me out, you know, like all of this, whatever other metrics that everyone that they read online is following without being, like, how is this book going to help me, Bryan and what Bryan’s goals are, right. Where does, what does this book for, going to do for, for me, because I’m different, right? The co… like maybe a coach is different than someone who’s trying to get hired as a designer. That’s trying, that’s different than someone who’s a public speaker. That’s different from someone who’s looking for a job that’s different from someone who’s a wants to eventually write for the New York Times versus someone that’s a professor. So thinking about how the book fits into who you are and what your goals are. So I started to realize with, with the book that writing was difficult to make money from. But actually where people were really getting interested in Quarter Life Breakthrough and millennials in the workplace and future of work and my kind of philosophies on the changing nature of jobs and careers and young people really wanting meaning and purpose in their lives and this non linear path, which is what a lot of the book is about, was actually through my talks and through speaking. So I found that people were really digesting the material through talks and through speaking. So I started to do a lot of public speaking and I realized actually that was actually by far a much more effective way for me. Again, this isn’t prescriptive to everyone, but for me to make a living. Much more so than just writing. Um, so I started kind of this, this speaking career, and again, similar to this first book, there weren’t that many resources on it. There are a lot of books about public speaking and the art of narrative and, and communications and how to craft a compelling story. A lot of books about storytelling, if that makes sense. Um, or the art of getting in front of the room and where to put your hands and how to develop a narrative. And should you have photos or what word should be on the slides or what, you know, this, all this stuff. There’s a lot of psychology around that, but there wasn’t a lot of books about how do you actually make cash from public speaking. Um, in fact very few. and, and if there were a few they were pretty sleazy kind of online marketing tip of the books. Um, so I thought that there was a need there again. Um, they say write what you know. And I think that that’s quite, um, you know, useful. I also think it’s right, something valuable, right? So I started to meet all these speakers and we were talking about, you know, what to charge and how to negotiate and how to get in kind of the corporate speaking circuit and all these things. And I was having these same conversations. I kept getting hit up, right? Like I, I would people be like, hey, you know, the, the, the, um, um, can I pick your brain conversation, right? So every pick your brain thing for me was, how do you make money speaking, how do you make money speaking, how do I, how do I do it? And I started to be like, I’m so tired of these phone calls I put, I started making like an FAQ’s of all the things people were asking me and all the things I thought about. And people kept being like, that’s brilliant. Oh my God. And I was like, that’s the exact same thing I said on the last five phone calls. Maybe there’s something here. So the first lesson I learned with the first book was write what, about your own struggle? Right? About what? Write the book you need. And then the second for the second book it was right the book. Whatever you’re getting hit up about, that’s the book you should write. Whatever the questions people are asking you all the time, like whatever people come to you as like the main thing people come to you as that’s the, that’s, that’s your book. Does that make sense? So it’s like, and…


Bryan:              00:46:03 It’s like the universe is kind of laying a path out for you, if you’re paying attention.


Smiley:             00:46:06 If you’re paying attention, if you’re the person that everyone’s coming to being like, should I break up with my girlfriend? Should I break up with my partner? Should I break up with my boyfriend? Like that, you’re probably the relationships person. Like clearly you either have a good relationship, had a good relationship or just…


Bryan:              00:46:21 People think you do.


Smiley:             00:46:22 People think you do or you’re a loving person or you make people happy or something. That’s probably, there’s a book there. If people are always asking you like coaching questions on what should I do with my life? Am I happy? How do I get happier? Blah, blah blah. That’s probably your book. Like what are the things. I’m not just talking about like one or two people asking you, but if you start to have the same conversation like, man, I’ve had this conversation like 10 times in the last month or 50 times in the last year of this. Literally the same people asking you to let the people asking you the same types of questions. Something about you is emitting knowledge or expertise. It’s in you. Um, so for me it was around public speaking and it was weird because I was like, um, it just seemed like a kind of an interesting book to write. But when I sat down to start writing, that’s what came out of all these FAQs and I had kept kind of a document that was kind of speaking FAQ’s. Um, which really turned into the second book. It’s really structured around kind of, um, these, like very many digestible, easy to read little mini chapters, each one with kind of a key lesson I learned on my journey around speaking. Um, and so it’s for all the people that were asking me those questions. And the best thing about it is, um, you know, there’s, maybe there’s a bias against self publishing, but I gotta tell you I’ve had so many people tell me about the second book. Like, this is exactly what I needed. This is so helpful. Like this is a, it’s such a practical book. So it’s giving really, really tangible advice, um, of actual things you can do an actual strategies and actual kind of step by step, kind of like a, a playbook. A writing, something that people can immediately use and is, and they’re able to kind of implement right away. And that’s going to help them with their business, share their story and make money. If you’re helping people, if you’re writing about something that’s going to help people get more work and make more money, um, that’s going to be very, very powerful.


Bryan:              00:48:30 That’s valuable.


Smiley:             00:48:31 Again, I actually think that that’s the right word there. you know, that is value. Um, a lot of people, um, will approach, and I talk about this actually very much in the speaking book, and you’re, you know, you’re, you’re in the space of, of helping people and, and, and podcasting and helping people think more critically about their lives and life advice. The word that always is thrown around is passion. I actually think that the word passion is, is toxic. And it’s actually not. It’s, it’s, it’s obviously you can’t do anything meaningful in the world without passion, right? like I’m not going to go do something I’m not passionate about. That’s obvious, right? You have to have passion for anything you do in this world that’s meaningful. But the more important world is value, the more important thing is to not just think about yourself. It’s the thing about where yourself and your gifts and your strengths and what your experiences interact with, what people actually need. Too many people are out there writing about what they’re passionate about, right? Frankly, I don’t care that you’re passionate about yoga. Right? That’s cool. But what’s more interesting is how people really are asking for those tools. Right? Or, or that they need more balanced in their lives or that they’re overworked or overwhelmed. That’s where you’re going to write a book that’s interesting. Right? So it’s not just about you, it’s about others. And I think this is incredibly important when it comes to actual business and making money. with speaking, I meet so many speakers that are like, they launched into their thing about, oh my God, here’s my life story. Here’s what I learned. I, I quit my job, I moved to whatever, Thailand. Um, I’m amazing. Here’s what I care about. And not once, not once in like a 10 minute or 20 minute diatribe had they mentioned the audience.


Bryan:              00:50:21 Yeah…


Smiley:             00:50:21 You know, that’s huge. And I, and I think for, if you’re talking about, sure, if you’re talking about just like what are you gonna you, you can just like sit on the corner on a street corner and talk forever. Great. If you’re actually trying to make money as in someone else’s paying you, other people have to care about your topic. and I think we need to talk, that needs to come out more, especially in the kind of entrepreneurship world. It’s not just about you, it’s about other people and what’s really in demand and where there’s a huge need and where you can add value.


Bryan:              00:50:57 Yeah. And that’s one of the ways that I think, and I haven’t read The Breakthrough Speaker yet, but I’ve read The Quarter Life Breakthrough and I think that what you’re saying about these books are they are valuable and they are full of practical advice that people can apply immediately. It’s not just theory. I mean the stories are great because they’re examples of where people have done this and it, you know, it shows what it can look like in somebody’s life. And even in the back of The Quarter Life Breakthrough, how you have a roadmap that people can create themselves, but you provide the structure. And if people answer the questions honestly, you know, then they’re left with something that’s truly valuable. It can change the entire course and quality of their life. That’s amazing.


Smiley:             00:51:41 Increasingly, I, I see that, um, people are really asking for. I’m looking for is, is this is a practical, tangible, valuable tools that they can implement.


Bryan:              00:51:53 Yeah. And, and even that graphic that you show that the intersection, right? If we’re asking people to think really deliberately about what is the intersection of your gifts, the community that you serve or you want to serve, the quality of life you want to have an end, the impact you want to make. And like you’re saying, not just thinking, what’s my passion, which when I first met you, kind of dispassionate, passionate. The minute I was like, don’t tell Tony Robbins. That’s. But then the second thing he says, and business mastery is always first of all, fall in love with your customer, not your product or service. And understand, you know, what business you’re really in, what, what the value add more value. It was like his mantra and it’s exactly what you’re saying and you’re living it. It’s not, again, it’s not just theory, but you’ve, you’re, you’re living it every day.


Smiley:             00:52:37 Yeah. This is, I think this is a really good lesson for writers, for speakers, for business in general. But, the more you’re adding value, and, and I think because if you’re adding value, that means you’re…Tony Robbins quote is quite relevant, is the more you actually are listening to people, who are either paying you or want to be paying you. Right? there’s a quote from my friend who’s a speaker in the, in this book, Antonio Nebs. He says, “public speaking isn’t, isn’t about you, it’s isn’t, isn’t for you, it’s for the audience.” And I think a lot of, a lot of the, you know, people that have want, I call them, you know. In the intro I have a chapter on wannabe speakers, kind of like what does a wannabe speaker look like and the wannabe speakers are out for them, right? They’re out for like, “I’m so cool, I’m speaker, I’m on Instagram, check me out. I’m the shit.” You know, like, let me see how many followers I have. Let me, it’s about the brand. It’s about them. They haven’t realized, hello, it’s about the people that you’re in the audience, no one cares about you. I mean, they do care about you, but it’s really about how you’re connecting. What are you inspiring? What material? What lessons? What takeaways? What, what, how can people implement your material? What is it related to that’s going on in their lives? What are the key issues that people are dealing with? And how are you helping them navigate those challenges? Um, it’s, if you’re talking about companies and organizations, how are you improving an organization’s performance, profit? Um, productivity, um, you know, workplace, a, management, all of these types of things. It’s not about you. Like, yeah, you’re a good looking. Okay, cool. Like nobody cares. You know, like nobody cares. Like, I mean, I think that that’s a huge. And the social media piece of this and the personal branding pieces kind of misguided folks, because it’s so easy. I think people just assume, oh, they want to be a speaker because anyone that’s influential is a speaker. Um, not the right assumption to make it. It’s the people that I know that are actually making cash, good money from this. They figured out a niche. They figured out a highly value, a huge value add that they’re providing to audiences. That’s it. That’s the biggest piece there, right? They’re not just awesome. They’re not just cool. They don’t just like have an inspiring, motivating talk. Like everyone has a motivating talk like look at, you know, how many millions of TED Talks are there. It’s more about, are you actually adding value to the people that are sitting in the chairs in the room? Um, and how are you adding that value? That’s the key piece.


Bryan:              00:55:16 Yeah. What, what’s the most surprising thing you learned in the course of writing or researching this book on speaking?


Smiley:             00:55:23 That’s a good question. Um, so I think that the, you know, the other piece there is, there’s, there’s no, there’s no one way to do this. People come to speaking from a lot of different angles. Um, they, you know, some people are natural speakers and storytellers, facilitators. Some people start with the book or they kind of do like a, I call it an anchor. They really developed their, a body of work or something that’s really remarkable or they kind of a, maybe they start a community or they launch a product or they build a company or they, um, start a social movement and then they get a lot of notoriety and then they start speaking. There’s not really a one way, to do this, but all the people that kind of, um, are featured in this book and that are making, are starting to make a living or making a really good living from speaking do share, you know, they, they share something in common. and, and I think that, that, that’s, that they, they deeply, deeply are committed, um, to, to putting themselves out there, and to trying lots of different things. So I really wanted to structure this book around. There’s not just one way to do this is not one kind of answer, but that these are kind of a menu of options and many of these things, when combined do, will work. Um, but like there’s not one way to do it that, that was the key I wanted to show. Okay, I think I cite, I don’t know, 50, 60 different type different speakers in the book. People that I’ve crossed paths with. Not one of them has the same path, but they all were deeply committed to something, tried a bunch of different things, put themselves out there and we’re, um, really, really committed to this work. And they didn’t just kind of snap their finger and make it happen. Um, they actually, um, where they were. And the other thing you said, I think they were in it for the long game. I’m the, they know that it wasn’t going to happen overnight. I think that, that, that’s a big piece here with anything millennial related or a business related, but especially for an audience of 20 or 30 somethings to remember. And I think the same thing applies frankly, with The Quarter Life Breakthrough. And when I talk about career, career success or meaning in your work, um, I think that people want the easy fix, right?


Bryan:              00:58:02 Yeah, for sure.


Smiley:             00:58:03 Um, I, I think that most people, my journey is probably a little even rare in that it’s been about five or six years I’ve been doing this work and you know, I make a living as a public speaker and I’m, I’m able to do that. That’s actually probably shorter than most people, right? I, I would, I mean there’s probably people that can do it in a year or two. That’s awesome. But I would say that most people, most, it would take five to ten or more years to really make this happen or, or even maybe longer. Um, and I think that that’s a reality that people don’t want to admit because they see everything else happening so quickly. We’re so used to swiping social media and that this kind of, oh, anything can happen so quickly. Tools are available and that’s true and when it comes to something like public speaking and publishing, these things take time. Um, and no one ever wants to talk about that. But I, again, I think the passion word is overplayed and toxic and a better word would be patients. So we’ve talked about value. So a better word than passion is value. Another better word be patients. Um, and um, patients is not sexy. There’s not really like good Instagram quote pics for patients, right? And no one, it’s not a great popular facebook post to be like, it’s gonna take me a long time to do this, but it’s much…


Bryan:              00:59:25 But I’m patient.


Smiley:             00:59:26 Right. It’s more positive like I did it, I’m doing it, I’m making it happen. Like, look what I did already. Like, that’s, that’s popular. But the patient’s piece, um, is, is, is huge. That doesn’t mean you’re not working hard, you know, it doesn’t mean you’re not hustling. Hustle is sexy. But I call it, I think patient hustle. I was gonna, one, one idea I had for a book or at least an article is called like the patient hustler or something, which is like, you’re working really hard. You’re always, you know, and this look, if you do all the things in this Breakthrough Speaker book like that is hustling for sure. There’s 67 things in this book. that’s gonna take you some. It’s a lot of hustle. You’re writing articles, you’re doing blog posts, maybe you start a podcast, maybe you do a TEDX Talk. Maybe you do a little talk at your friend’s coworking space. Maybe just record yourself doing a video. Maybe you’re posting Instagram videos. Maybe, your um, you know, going to conferences and just observing other speakers. There’s all of these things, that’s hustle, but also mixed with the overlay of I don’t expect this to happen overnight. I know that all the things I do are a piece of the bigger puzzle. Um, and I, and I’m in this for the journey, and not to get like one gig or one paycheck or you know, some sort of, again, stamp of approval. But this is, I’m, I’m doing this as, as a, you know, because I truly believe in what I’m talking about and I know that it’s part of a longer journey towards something meaningful. Um, and if you have that approach, that’s, that’s when, that’s when you actually will be successful.


Bryan:              01:01:07 Yeah, I know you’re right. And, and I don’t mean to make everything about Tony Robbins, but I saw this…


Smiley:             01:01:14 I haven’t been to, to any of. I mean, I, I watched, um, what’s the one, the Netflix.


Bryan:              01:01:19 I’m Not Your Guru.


Smiley:             01:01:21 Yeah. And I’ve always, I’ve been curious to go to the big, the big one, is Date with Destiny. Is that, no.


Bryan:              01:01:26 That’s right. That’s right. And I, the only reason I went, you know, I’ve been studying personal development and leadership and coaching pretty intensely for about the last seven years. And I had never been to a Tony Robbins event until just a couple of years ago. And the only reason I went is because I heard Peter Diamandis on Tim Ferriss’ podcast talking about the most transformational seminars he’d ever been to and he said Date with Destiny was one of them. And when I heard Peter say that and I had been to the other one, he mentioned, he said The Landmark Forum and Date with Destiny. And I was like, “Oh, if Peter saying that’s in, you know, at that caliber all go.” So I signed up and went just a couple years ago and never been to one before. It blew my mind, the production value, the just the quality of the material for me that the community, like I told you. I ran into Ryan, you know, down there. And it was, it was just incredible. And I came home and I thought I’m going to read Tony’s, Awaken the Giant Within. You know, he wrote that book back in the early nineties and I get the book and I read it and I have a second hand store that I shop for used books here in Salt Lake. I love buying these books for a dollar or two dollars. Well this was one of them I bought. So I read it and here 25 years later I call the 1-800 number printed on the back of the book just to see if it still works and it worked. You know, Tony Robbins, 25 years ago has this and it’s still got that. Got An office in San Diego and it was like talk about patients and playing the long game for sure. That’s the guy who’s doing that.


Smiley:             01:02:51 Yeah, totally. Oh Man. Yeah. He’s built a incredible business.


Bryan:              01:02:54 Yeah. So okay. That’s probably my last Tony Robbins reference.


Smiley:             01:02:58 We’ll see.


Bryan:              01:02:59 But yeah. And I know we’re coming down the stretch here on this interview. I want to, I want to turn our conversation now to the lightning round. If you’re up for that, it just a few brief questions if you can answer as long as you want, but they’re designed to be answered briefly, so. Okay. Question number one. Please complete the following sentence with something other than a box of chocolates. Life is like a blank?


Smiley:             01:03:27 dance party.


Bryan:              01:03:32 I knew you were going to say that. No. Number two,


Smiley:             01:03:38 Wait, it needs to be like, dance party then like you never know. It’s like dance party; you can either, you can either sit back and watch or get in the middle.


Bryan:              01:03:47 I love it.


Smiley:             01:03:48 I’m doing like the, like, like box of chocolates. You never know what you’re going to get kind of thing. Like the thing with the, with the explanation.


Bryan:              01:03:56 I love it. Number two, what, what’s something you wish you were better at?


Smiley:             01:04:02 Um, accounting.


Bryan:              01:04:06 Number three, if you were required every day for the rest of your life to wear a t-shirt with a slogan on it or a phrase or a saying or a quote or a quip. What would the shirt say?


Smiley:             01:04:16 That’s a great question. look up.


Bryan:              01:04:23 Love it. Number four, what book other than your own have you gifted or recommended most often?


Smiley:             01:04:29 Man’s Search for Meaning by Viktor Frankl.


Bryan:              01:04:31 That was my last guests. That is actually the most common mentioned book. Yeah. What about, let’s, let’s reverse that question. Which one, what book is recommended or gifted to you most often?


Smiley:             01:04:47 that’s a great question. I think The Untethered Soul has been gifted to me once or twice, Michael Singer, great book. Um, Artist’s Way Work of Art. Um, Steal Like an Artist. A Bird by Bird. Invisible Man. Great Book.


Bryan:              01:05:13 Ellison book?


Smiley:             01:05:13 Yeah. Ralph Ellison and I just read an interesting. A couple people and I just read it because they had recommended a great book called Winners Take Off. Have you read this book? It’s new.


Bryan:              01:05:26 I don’t know this book.


Smiley:             01:05:27 It’s a different category than the other books which are, I would say are in the canon of any books, any creative should read. This is a book about the subtitle is, The Elite Charade of Changing the World. And it’s really about kind of getting at the crux of what it is that people are doing with their lives and is… When people say they’re changing the world, are they actually? so it’s definitely a powerful book for people that really want to be a little bit more thoughtful about how they’re spending their time. Um…


Bryan:              01:06:00 Interesting


Smiley:             01:06:00 Winners take all.


Bryan:              01:06:01 Cool. Thanks. Thanks for that. So you travel a ton. What’s a travel hack? Something you do or maybe something you take with you when you travel to make your travel less painful or more enjoyable?


Smiley:             01:06:14 Um, well two things; I run every, the first morning I’m in a new place I take a jog because I just feel like it centers me and I get to explore the place and all you need to bring for that as running shoes. And then I always go look up like the, not like the best fanciest restaurant but like, like the best delicious restaurant wherever I’m going because I.


Bryan:              01:06:39 How do you find it? I mean obviously online maybe concierge. But what do you do.


Smiley:             01:06:40 I asked, I asked people I use the internet and then I ask anyone I know that like I’ll post on facebook or um, or I’ll ask people that live in the city or have lived in the city. But mostly I do online searches and then see because that makes it fun. Because otherwise I think that travel can, can get quite laborious and exhausting. So food makes it, makes it more fun for me.


Bryan:              01:07:02 Yeah. You have any apps that work well for you that like you do TripAdvisor, Yelp, something else that works. It’s kind of like your go to.


Smiley:             01:07:10 Every now and then a TripAdvisor, not really. I have used TripAdvisor in the past. Um, I, not really. No. Just do kind of search google searches .


Bryan:              01:07:23 Right on. All right. Number six. What’s one thing you’ve started or stopped doing in order to live or age well?


Smiley:             01:07:31 Great question. I’m looking at email first thing in the morning.


Bryan:              01:07:36 You started doing that?


Smiley:             01:07:40 No stopped.


Bryan:              01:07:40 Good for you and what differences has that made in your life?


Smiley:             01:07:43 Just more creative bandwidth and less stress. More ownership over my day.


Bryan:              01:07:50 Yeah. Do you make your bed everyday?


Smiley:             01:07:53 I do. That’s a good one.


Bryan:              01:07:54 Very Navy Seal of you.


Smiley:             01:07:57 Yeah, exactly.


Bryan:              01:07:58 That’s great. I started doing that because my wife did that. I just, it never made sense to me, but now I do it and I feel I really do feel better every day. Alright. Number seven. What’s one thing you wish every American knew?


Smiley:             01:08:15 Um, that, people who are different or, um, are actually amazing.


Bryan:              01:08:21 Hmm. Do you know Jonah Wittkamper with Nexus?


Smiley:             01:08:26 No.


Bryan:              01:08:27 I think you’d really like this guy. Based on that answer. He’s pretty amazing. I want to. I want to introduce you actually if you’re open to that.


Smiley:             01:08:34 Oh totally.


Bryan:              01:08:35 He’s pretty extraordinary human being.


Smiley:             01:08:36 I’ve heard great things about Nexus. I’ve never been, but I know a few people involved.


Bryan:              01:08:41 He’s one of the co-founders and he’s one of my favorite human beings. I know I shouldn’t have favorites, but he’s also. That’s my favorite community it’s incredible. So yeah, awesome. All right, number eight. What advice did your parents give you that has impacted you or has stayed with you?


Smiley:             01:08:59 Um, love the people around you. A family, importance of family.


Bryan:              01:09:08 What’s the best way if people want to learn more from you or connect with you, what should they do?


Smiley:             01:09:15 Um, yeah, you can. So a couple things you can um, everything about me is on my website. Sign up for my email list there and get my books. Um, Instagram and Twitter @What’s Up Smiley. W H A T S M I L E Y.


Bryan:              01:09:36 What’s the most common way your name is misspelled?


Smiley:             01:09:38 Oh, people mess up Poswolsky all the time. I don’t even at this point get upset.


Bryan:              01:09:43 They put a Z in there and stuff.


Smiley:             01:09:45 Poswalsky or they put an I at the end because they’re very used to that spelling. Not the why they mess up. Yeah, it doesn’t. I’m not. I’m used to it. It doesn’t bother me.


Bryan:              01:09:55 People can. People find you online and of course they can find your books on Amazon or in bookstores around the world, including in Manila.


Smiley:             01:10:03 Yeah, that’s probably easier. Amazon paperback, Kindle. Um, but support your local independent bookstore obviously. Um, Breakthrough Speakers. Probably not in your local bookstore, but it’s definitely on Amazon. But Quarter Life Breakthrough, it’s probably everywhere. So, um, yeah. Hopefully get working on my new book. Couple of new books, ideas soon. That’s always. Um, I do a lot of writing over the holidays because I find that it’s quiet and less distractions. So for any of you being like, “Oh man, I haven’t written a book.” Like 2018.


Bryan:              01:10:40 Here you go.


Smiley:             01:10:41 December, December, January. I actually wrote most of the Breakthrough Speaker last, last holiday season. I, I, I went back to it and did a deeper dive, but I wrote the bulk of the manuscript, over a period of six weeks basically. So.


Bryan:              01:10:58 Awesome.


Smiley:             01:10:59 So you have time to write.


Bryan:              01:11:01 Yeah, that’s right. In fact, in we’re in November now. The NaNoWriMo. Yep. I hope people. I have a friend that keeps saying he’s going to do that every year. I said I new I’m not a novelist, so it’s not, not for me, but anybody who wants to bang that out. Um, well let me share this with you before we just spend a few minutes talking about writing. Um, I want, I want to be sure to get this in here. So I’ll say it now, that as a way of expressing my gratitude to you for making time to talk with me and share your experience and your knowledge with me and with everyone who’s listening. I’ve gone online and I’ve made a $100 micro loans through on your behalf to an entrepreneur named Maria who lives in Bolivia and she’ll use this loan to buy groceries that she can sell in her neighborhood store to improve quality of life for herself, her family and the people in her community. So that was one, one small way. I just wanted to say thank you.


Smiley:             01:11:54 Oh, that’s very sweet of you. That’s awesome. I love Kiva.


Bryan:              01:11:57 Yeah, that’s amazing organization. Well, cool. Okay. So with just the last few minutes we have left, I want to turn our conversation now to the, the craft of writing. Um, I’m, I’m really interested to know what does an average day for you look like? As you’ve mentioned already in this conversation, you spend a lot of time speaking and people ask you questions quite a lot. It sounds like you spend time responding to people one on one and you are a writer. How do you divide your time as a writer and what does it, what does a typical day, if there is such a thing look like for you?


Smiley:             01:12:36 That’s a great question. It really depends. If I’m in deep, deep writing mode, so like some writers will write every single day. I’m not going to lie and pretend them, that’s me. It’s not, a, if I’m in kind of the part of my year where I usually write a lot in winter and spring because I’m less on the road. Um, with speaking, it’s difficult for me with travel and with speaking to be on a, on a daily writing schedule.


Bryan:              01:13:03 What’s your optimal speaking engagements per month? Do you kind of look at it that way or per year or something like that?


Smiley:             01:13:11 It’s more, it’s more I try to do, about a, 50 to 75 a year. Um, which to me feels good but also not, but also not in the level of where I’m never home and always on the road. Um, I know some speakers that are on the road for over 100, 150 days a year. It’s kind of seems miserable to me, but, um, you do make more money, but um,


Bryan:              01:13:35 There’s a trade off.


Smiley:             01:13:35 A little bit of a trade off. Yeah. So for me, when I’m, when I’m on the, in the writing kind of mode, I’ll wake up, I’ll go for my run ,a comeback, a meditate, breakfast, be at the desk, a do about three ish hours of writing, three to four hours. Like I actually think that that’s a good, you know, daily goal. I have a friend who’s kind of a professional writer, writes a lot for the New York Times.He says if he can get in three to four hours even, you know, even three, a that’s like a day and then he’ll go for a walk and kind of maybe come back to some stuff and edit. But in terms of actual pure writing, that’s what he’s going for. Um, so that would take me to about let’s say 1:00 or 2:00 PM, go for a walk, have lunch, and then kind of do emails and calls. I try to bulk do all my calls in the late afternoon, when I’m, I’m more creative in the morning, so I try to do any kind of creative writing or creative work, um, as early in the day as possible. Because around 3:00, 4:00 or 5:00 PM, I start to slow down. And I can go back and edit stuff then or kind of do emails or online research and stuff like that. And I generally do a lot of reading and a part of my work with speaking is I really have to kind of, I read a lot of like, you know, research and reports and books and I actually think of that is work. it is work as part of kind of staying on top of your industry and your topic and expertise and building it into your keynote and what you talk about and also knowing all the stuff that people are talking about is part of what you need to do. Yeah. And then hopefully go see some friends for, or go to yoga or something like that in the evening.


Bryan:              01:15:25 You know, one of the things that I love in your, in The Quarter Life Breakthrough was that you did include the self love exercises. The things that kind of help us rejuvenate and stay sane. Where I know a lot of books will just talk about; do this, push yourself harder, more willpower, you know, stuff like this. But um, I could tell that book was truly written from experience when you made the time to include something like that that can help us to preserve our enthusiasm for our work and just our stamina. Because I watched my dad push himself super hard to build a very successful group of companies. And he didn’t build in that kind of time to rejuvenate and restore himself. So what do you do that helps you? I mean, you’ve talked about some of your morning ritual and how you organize your time and your work. What are some of the things you do to help you stay, so that you don’t burn out? You know, that you’re able to sustain this pace?


Smiley:             01:16:19 Yeah. My biggest thing is running. I mean I run pretty much every day. That’s kind of like my, it’s my bliss. It’s my thing that keeps you most balanced. it helps me eat well. It helps me meditate. It helps me just relax, get my stress out, my energy out. So I run first thing in the morning before I have any distractions, before I’ve eaten anything. Um, so that’s really big for me. Um, afternoon walks are really big. Whenever I’m stuck, I just take a walk, actually think that that’s, there’s research that shows that actually you’re better off. You, you focus better and you do better work by taking breaks. So again, I don’t think that that is slacking or procrastinating. It’s actually doing better work. Um, so I live right by Golden Gate Park in San Francisco, so I take walks almost every day. I’m reading is also a one way I relax. A phone calls to friends. I’m a big um, phone or in person, um, person. I find that those are actually really rejuvenating lunches or dinners that I talk to people. Actually give me material and rejuvenate me. Um, and just being outside a lot. A lot of exercise, um, and, and yoga or running. Um biking, I bike everywhere. Dancing. Just kind of being physically active for me is, it’s really helpful. Also journaling. Um, I tried it, I try to journal a every day. Um, I was doing it in the mornings, which is kind of how it’s done now. I’m actually doing it before bed because it substitutes me from watching Netflix or being on my screen. Which is actually also good from not looking at the blue light right before bed. Um, so I’m doing just kind of like a couple things that happened, something I’m grateful for and just generally anything I need to get out and then kind of actually helps me fall asleep because I’m, it’s like a little bit of a purge on the day. Um, which is nice.


Bryan:              01:18:23 That sounds really healthy. Because I’m thinking about that book, Daily Rituals: How Artists Work. Right. Did you read that?


Smiley:             01:18:31 Yup, I did.


Bryan:              01:18:32 I’m thinking I’ve, I’ve, yeah. Yeah, you know it. And I think about it, know of it. Yeah. I actually want to reread it and have a checklist to see because a lot of those artists and those writers definitely took walks, you know, and there was meditation, that kind of stuff. But there’s almost like, as I’m hearing you relate your day and how you’ve organized your life around, you know, what you do is that there’s probably like a healthy writer’s lifestyle and there’s an unhealthy writer’s lifestyle. And it seems like you’ve got nailed the healthy writer’s lifestyle because what I’m not hearing in there is that drinking, the carousing, amphetamines.


Smiley:             01:19:04 I really, I really barely, I mean I’ll drink on occasion like a wedding or like a friend’s birthday or we’re going somewhere and there’s a cool open bar. Or I don’t know, like this is the most amazing dinner party. Red Wine is really going to be part of the experience. But I rarely, rarely drink alcohol. It doesn’t sit well with my body. Um, and hasn’t for the last few years. I did, this is not to say I never did drink. I definitely spent drank a lot in college and in my early twenties. I literally just physically can’t anymore. It makes me feel like shit. And um, I like, like I get hungover after like two to three drinks, two drinks basically, which is really not useful for writing. It’s not useful for anything but especially for being, for being, doing something meaningful or creative. but actually like, I know that a lot of people have this whole like, oh yeah, like I’m most creative when I’ve had three whiskeys. That’s all bullshit. Like, I mean the Hemingway legends and all that. I think, you know, and the who…I think that that’s crap. I mean show me, I just like, there are a couple of maybe writers or musicians or artists that are tapping into that, you know, you’ve created, create better when you’re messed up. But I think that that is such a excuse. And um, especially, you know, it’s like if, if you are already that person, you’d already be that person. If that, does that make sense? Like if you’re already the person that’s like a genius that needs six drinks to get creative and is as addicted to drugs and writes the best poems in the world. I’m sorry, you’d already be doing it so you’re not so like don’t do that. Like stop drinking. So like get, like eat healthy exercise and make something that matters in the world. Like don’t, don’t hurt your body like it’s impossible to be doing important work with. I’m not saying don’t ever drink, like having a beer, having a glass of wine with your friends is awesome and it’s great. But like if you don’t use those as crutches, like make something important.


Bryan:              01:21:12 I think. I think there’s a lot of wisdom in what you’re saying. What. So we talked about the things you stay away from and the things that you do. What’s your writing kryptonite?


Smiley:             01:21:23 Like what kind of keeps me?


Bryan:              01:21:25 Yeah, like what, how do you. I mean we all have an inner critic. We all, to some degree self sabotage, right? We all have good intentions. So we make a decision in the morning that we don’t honor it later to the day. What are, what is the thing or some of the things that kind of trip you up?


Smiley:          01:21:40 Facebook… yeah. I think it’s like it’s social media. If I’m being honest. Like I’ve toyed. So I’ve spent, I’ve, you know, with digital detox and my experience with Camp and the last few years I’ve gone on various social media sabbaticals. Sometimes it’s just like a week here, weekend and sometimes I’ve done like a six week or two month thing. Um, but I’ll tell you, I wrote my first book, both versions of the first book on social media, media, sabbaticals. At least I think they were a month to two long, two month breaks. Um, and I’ve toyed with the idea simply because when I start going on Facebook, it’s a rabbit hole. Like a one or two things happened. I ended up spending my writing energy beyond comments or threads or, or I see that other people have already written something I wanted to write. Which is um, so I toyed with 2019 completely taking the year off of social media. Which would be challenging given my line of work.


Bryan:              01:22:37 Profession.


Smiley:             01:22:37 I mean, yeah, yeah, yeah. But I also think I’m wondering if I’m at a place in my career where I could make it happen just because I built up enough of a platform with the speaking and I have referrals. Like not many people book you because they see you on Instagram or Facebook. Um, now I definitely have gotten the opportunities because people have reached out to me through those platforms. And I think that is because they see a, like a, like the, the, the through line of you doing the work. If that makes sense.


Bryan:              01:23:09 Sure


Smiley:             01:23:09 Like they see, okay, I’ve seen what you’ve built out for the last year or two because of one post. But because like, oh you’re, you’re the speaker about this, I’m going to connect you to someone. So you never want to cut off something that’s bringing you income. But I’m just wondering like what it would look like. I just, how much time I would spend if I didn’t, if I didn’t spend any part of 2019 on, on Facebook or Instagram. I can’t even imagine. I like, I think I could write three books.


Bryan:              01:23:38 There’s only one way to find out Smiley.


Smiley:             01:23:40 I know, but I think what I’m going to do is take January. I’ve, I’ve really been thinking about this and the only way to do it is to see if I can. I think I’m going to do January off and I would probably like keep like Linkedin because it’s, it’s just, it is actually like for me professionally useful. and I have gotten actual tangible opportunities on there. And maybe I would keep Messenger so that I wouldn’t cut off like people contacting me.


Bryan:              01:24:07 That makes sense.


Smiley:             01:24:07 But I just said that that for me is the, the, the, there’s a clear, there’s a clear relationship between time spent on Facebook and time I don’t write. So that like when I don’t spend a lot on time on Facebook, I’m writing more. Because I’m like, oh, I need to say something because I’m not saying on Facebook. Or I’m not wasting time on facebook or you know. So our or so that, that, that’s mine. I’m for sure.


Bryan:              01:24:33 What about this; caffeine or no caffeine?


Smiley:             01:24:36 Oh, that’s a tough one. I love caffeine. I have a difficult relationship with it because I have, I get heartburn sometimes. So I used to drink three cups of coffee a day probably four if I’m being honest. Um, and I had to get off because it was just starting, similar thing with alcohol. Just hurting my body. So now I’m a green tea person. So I drink a two to three cups of green tea in, in the morning, early afternoon. A cutoff around, nothing later than 3:00 or 4:00 PM because otherwise it starts to mess with my sleep. Um, and then, I’m just being honest here. I do a, like a Latte or coffee if I’m traveling. if I’m traveling or if I have like a big gig, um, and as kind of like a reward. So and then sometimes on Saturdays. So I just, yeah, I’m not gonna pretend that I’m some sort of saint here like I have. I love coffee and I love the taste of it. I miss it very much. I just can’t drink it every day. So I kind of use it now as a special occasion type of situation.


Bryan:              01:25:46 What’s your favorite kombucha?


Smiley:             01:25:49 Revive, Spring Fling Kombucha. it’s, they changed their labeling. I think it’s not long. It’s like cucumber, lemon mint. Revive is a kombucha company out of Petaluma, California. So it’s local to the bay area. Fantastic. It’s amazing. And then my second would probably be like, ah, GT’s Kombucha, the Tumeric, um, It’s like, I think tumeric ginger or something like that.


Bryan:              01:26:16 Right on. It’s a new check that out. I haven’t tried that one. So. Okay. That’s what writing rituals do you have? Do you have like a certain pair of slippers you have to wear? Do you have anything like that that helps you just get in state?


Smiley:             01:26:31 Yeah, that’s a great question. Um, I have sweat pants I usually wear that are, you know, that are my writing sweatpant. But also, um, I have a playlist, couple playlists that are like writing playlist with various, you know, chill out music, Tyco and stuff like that and some Radiohead and um, yeah. So that’s, that’s more like the music I listened to and I’m always at my desk with in particular a part of the room and yeah. So…


Bryan:              01:27:05 So you, you write it, you do a lot of your writing at home when you’re.


Smiley:             01:27:08 I, I do a lot of writing at home. Yeah. I just feel not like…


Bryan:              01:27:11 You’re not the coffee shop guy?


Smiley:             01:27:13 No, I can’t. To many distractions. I can do other work at coffee shops or a co-working spaces. But for writing it’s like I need. I like to just have my tea, my snacks, food. Be able to take a walk and leave my stuff and not have like. I want to be able to control the music that’s playing. I don’t want people having a loud conversation and blah blah blah.


Bryan:              01:27:35 Yeah. So. Okay. So the last couple of questions and I really want to turn these two things that, um. Because I think these kinds of questions can be interesting for people to hear and maybe encourage them to adopt something that works for someone else or at least try it out or think of something maybe you hadn’t thought of before. But for just a couple questions and then we’ll wrap up. I want to ask about your process and about the advice you might give to others. Your example might be enough of advice, but how, when writing a book you approach it, you know, from the outlining to the organization to the execution. I know that’s a big project, a big question, but like what tools you use, do you use Word, do you use Google Drive, you know, Scrivener, Evernote, some Trello. Like how do you, how do you from the beginning to the end, what’s your process for getting a book done?


Smiley:             01:28:27 Great question. Um, not an easy answer. And also I would say that I don’t have an. I’m probably like my, yeah, my process is less dialed in and then others, if I’m being honest. I’m a Mole Skin person so I keep track of things in, in, in my. I have like a separate Mole Skin for every new book project. Right? So I had my journal and I have like my work notes Mole Skin, but then I also have like a new Mole Skin. Um, my friend Jenny, who is an artist started giving me these really big ones that she uses for watercolor paintings. So that you can kind of sketch out stuff like the really big, like the biggest Mole Skin they make. I think it’s like, it’s bigger than 8 1/2 by 11. It’s like 12 by 17 or something. A beautiful so you can start doing putting Post Its in there and, and um, stuff like that. So I keep notes in there. I use Notes, the Notes app and um, and Word. And I just, and I, and I go from there. I use a lot of Post Its so I’ll like map out all of the chapters and kind of a things I’m thinking of writing on Post Its, put them on a wall and then map them out based on kind of a table of contents structure as they start to come to fruition. Um, so I’m old school. I’ve always thought that Scrivener’s sounds so cool. I just, every time I go to use it on like a and I just don’t use it. So I think the biggest thing, my lesson there, people always ask about this is a, there are a lot of tools out there and check out which ones work for you and whatever one you’re actually using, just go with that. Like they’re, you know what I mean? The best tool is the one you actually use. So if Evernote something that works for you, awesome. If, if it’s Trello, awesome. For me it’s my Mole Skin, um, and, and Microsoft Word and that, that’s what works. Like at some point the book gets written and I’m like, I didn’t even realize it was getting written. It’s written now and I didn’t use any fancy tools. So I guess there you go. Um, I, I do think that the, I think it’s every, every, every person’s brain works differently to organize material. So I do, I love the idea of the Scrivener and Evernote or something where you can kind of put like put quotes in this folder, put chapter ideas in this folder, put stories in this folder. But it’s just like, it doesn’t, it doesn’t work for me. For me it’s just I have Post Its and then I start writing about that, post that, and then it becomes pages on the word doc and that’s that. So, um, the biggest obstacle I think. So I love the tools. I also worry sometimes that people get bogged down in the tool and then get scared of the actual writing. Because it’s easier to be in research mode or whatever mode. And really the whole mode of the book is you’re writing a book, so like you may actually write the chapter while you’re doing your research about the chapter. Does that make sense?


Bryan:              01:31:17 Totally.


Smiley:             01:31:18 If, if you have words coming out of you, get a pen and write them all down. That’s my biggest thing. If you’re like, oh, I think I might have something. Oh, I, it’s like you wrote it like what did you just, who cares, Google Docs, Word, put it in an gmail document and put it in an email in a medium post. The point is words on a page is a book. That’s it, that’s all the words on a page. So, um, for me it’s like, it’s like you trick yourself into being like, alright, I guess I’m sitting down. I guess I’m writing now. I guess this is a book.


Bryan:              01:31:51 I love that word, words on a page as a book. Like I might get that tattooed on my arm maybe to remind myself Because one of the, like I said earlier, one of the things we all have, we all wrestle with is this inner critic. What’s your advice for managing one’s own psychology and believing that this is worth saying that I’m good enough to do it, that I’m going to get there someday. Like all of that. How do you navigate that and overcome it ultimately?


Smiley:             01:32:17 Yeah, this is a tough one. I mean, we all have it. Um, I used to do something at Camp, like a, can I swear on the. I think I’ve already. Okay. Yeah, it’s a, it’s a, it’s a, it’s this. Actually I got this exercise from a great, one of my favorite books about writing is called Walking on Water by Dark Jensen. Um, I don’t know if you’ve heard of it. He’s an environmentalist. He writes a book, he used to do a lot of teaching writing in prisons, and he writes about, um, this exercise he used to do. It’s basically a fuck fuck your inner critic kind of exercise. Where you’re stretching your hands, and so you know, you’re stretching your thumb and your pinky and your index finger, your ring finger until you only have one, one finger on each hand and that’s your middle finger and you putting your middle finger up to your middle to your inner critic. And it’s just like the very powerful, just like physical exercise. Very, very not to mention your friend again, Tony Robbins. It’s a very, just like standing in your “Ah”, you know. Usually like that actually helps, you know. Because it’s just like, you know..


Bryan:              01:33:29 You feel it.


Smiley:             01:33:30 And you feel it and then it’s out. You know, it’s like you’re screaming, you just get it out. that, that’s like a physical thing that works. Um, that’s helpful to me. I also sometimes just like, look at things I’ve already written. So I’ll look at an article or a blog post. I’m like, okay, cool. I got this meaning like I’ve done this before. I can do it again. Um, as just like a confidence booster of like, cool. Been here before and I know, that’s, we’re gonna get through this. We’re good. Um, so, and now it’s easier for me to say that like I think like the second book. The cool thing about the second book is that, um, and now I feel this going forward is like you’re less precious about it and I like and I’ll get on the phone now the pick your brain conversations with people being like, all right, where do I start with the writing? And it’s just like, no, like, and I hate to say it like this because it sounds harsh, but it’s like nobody really cares. Like your book’s not gonna sell that well. I say these things that are just like really kind of a. If someone had told me that, I’d be like, oh, you’re kind of an asshole. But it’s true. Like your book likely will not be a bestseller. Sorry. Like it will likely not win the National Book Award. It will likely not win the Pulitzer. It will likely not be the best self help book ever written. Like let’s just be honest here. Like you know, no offense, maybe I really hope it is. I really hope it sells as many copies as Mark Manson, as a, you are a badass as Tim Ferriss. I hope you become the next whoever you want to be. You might not. Cool. Are you okay with that? Go write a damn book. Right, like, meaning like nobody, like. I know that, that sounds so harsh, but like one of the things I learned that was actually the most powerful thing I learned with this was this book is like, my books are great. They have inspired people, they’ve changed some lives and you wake up another day and you’re like, oh, I guess I got to do something else. Like it doesn’t really change that much. Like you make a little bit of money overall. Probably if I look at my writing career, I’ve. If you look at time spent versus financial reward, it’s not profitable. If you look at the overall, like I would have made more money that whole time, you know, slinging coffee. But the point is like, it’s incredibly meaningful. You create these things in the world that are out there. It’s such a worthwhile thing to do. Um, but like once you’ve done it and then you step back and like, okay, this exists, you become less precious about it. You, I know all of these authors that are like, my book, my book, my book, and you’re just like, dude, like you’re going to write it. Some people are going to like it. Some people are not going to like it. Most people aren’t going to care. And then you’re going to have to write another one. So like, get to it because the preciousness or raw. Like I, I just, I know that, that sounds harsh and I don’t want anyone to think that if your book doesn’t matter, it very much does. Your story matters more than anything. The point is there’s a beginning and an end and like if you don’t find the end like it’s, it, I just too many people are stuck in this limbo of like, um, you know, trying to make things perfect and it’s not going to be perfect. So I think that that’s actually probably liberating philosophy of when you kind of digest it, of just like, oh yeah, cool. Like I’m writing a book. It’s going to be alright. Exactly. Like it’s going to be pretty good. That’s pretty good. Is very useful to aim for, right? Perfection. The best book ever written, the most legendary book in this subject. Like these types of things create paralysis. And they, they get people to think that there’s something that they’re not. And I think that that is dangerous.


Bryan:              01:37:19 Good way to keep yourself stuck.


Smiley:             01:37:20 It’s a good way to keep yourself stuck. It’s a good way to keep yourself never finished because frankly, like you’re never going to be finished. It’s never going to be perfect. You’re never going to be fully done. You could always include another example. You could always make it a little bit better. I’m not saying like write crap, but I am saying like, you know what, like put something out there in the world that matters, spend some time on it and then move on. Because then you also creatively become liberated to do something new. That was the coolest thing about the second book is like, I was like, I had a lot of, I was stuck before it, um, the first time. Because I was like, okay, I’m never going to write something that is as meaningful or important to me as Quarter Life Breakthrough. That was about a huge period of my life. Very meaningful subject. Very deep. Took me a lot of time, a lot of research, and then I’m like, okay, cool. I wrote a book about public speaking. it took me a lot less time. Now I can write a book about something else. So it’s like…


Bryan:              01:38:15 Beautiful.


Smiley:             01:38:16 It’s kind of, it’s, it, it, it. Um, I think again, it’s, it’s the same thing as the permission slip. It’s the biggest critic. The biggest obstacle is yourself. So many authors, we’re in our heads on where does this fit into my career? What are People gonna think of me? Is this my best work and blah, blah, blah, blah, blah, blah, blah, blah, blah. Move on, you know, create something awesome. Then make something even more awesome or make something a little less awesome that allows you to make something more awesome after that. Like, the point is, yeah, you got it. You got to make a train going, um, or it’s just, you’re in a cycle of a really, really toxic cycle there.


Bryan:              01:38:58 I think that’s a really valuable perspective. Okay. So last question here is, um, what are the qualities of a great sentence and how can we write more of them?


Smiley:             01:39:09 Huh? Good question. Um, clear. Yeah. Write something that makes people understand what you’re saying. Um, um, write. I’ll, I’ll say, write something that, yeah, makes, makes people stop and stop, stop and think about, their behavior or their actions or what’s going on in the world I think is powerful.


Bryan:              01:39:37 Okay. I’m going to do that. And I hope people listening do that and I hope, um, Smiley I love at the end there just, um, you got a little animated about getting over ourselves. Right. And just,


Smiley:             01:39:50 I know because I’ve had these conversations recently, I get really fired up about that.


Bryan:              01:39:55 No, it’s, it’s awesome. And I think it’s exactly why people who will listen to this, we’ll listen to it. So that’s great. Um, I mean, I am curious, just one personal question. When you did your research on your speaking book, did you come across the book Confessions of a Public Speaker by Scott? Yes, I think it Scott Burkin.


Smiley:             01:40:10 Scott Birkin. Yep.


Bryan:              01:40:11 I love that book.


Smiley:             01:40:13 I have a, I, I, it’s in the resources section and it’s a, I mentioned that everyone should read it actually in the text.


Bryan:              01:40:20 Awesome. I’m definitely gonna check out your book.


Smiley:             01:40:25 That’s, that was probably one of the best comparable titles. Um, that I read, that I read in preparation for the book. I mean TED Talks by Chris Anderson is kind of like the Bible and, and also she is, is required reading and should be a more focused on the art of narrative and storytelling. But Scott’s book is fantastic because he’s really about like the life of a speaker and you know, he’s got a lot of experience and.


Bryan:              01:40:50 That’s the real deal. I could, I can tell you the real deal and I always think whenever I get up in front of a group now I think of that thing he says about any time in the history of humanity that we’ve been faced by many eyes looking at us, it’s usually not ended well. Whether it was a pack of wolves or a tribunal or something. Evolutionarily. Well, Smiley. This. I’ve really enjoyed this. I hope you have. It’s been super valuable for me personally. I, I intend to share this with as many people as I can and I hope. So, anyway. I just want to, I want to let you know that I’m really, really grateful that you’ve made so much time to talk with me today.


Smiley:             01:41:27 Thank you so much for having me. I’m A. Yeah, that’s great. That’s great. Great to participate.


Bryan:              01:41:33 Yeah, dude. I will, I will. I’ll plan not to contact you in January on social media, but I do look forward to the time I get to hear you speak in person. We get to connect somewhere in person. Do you have one of those flyers from Burning Man still, by the way?


Smiley:             01:41:46 Oh yeah. I kept one on my fridge.


Bryan:              01:41:48 That’s awesome. That’s really fun. About the…


Smiley:             01:41:52 I’ll send you the jpegs I have. They sent, I have…


Bryan:              01:41:56 That’s great. I’d love to. If you’re. If it’s okay with you, I’d love to just be able to share that with people through this broadcast to. That’d be really fun. So. Okay man. Well I will somewhere down the road. I don’t know where or when, but I’m sure our paths will cross again and I will look forward to that day.


Smiley:             01:42:12 Sounds good, Bryan. Thanks again for having me on.


Bryan:              01:42:14 All right, thank you. Talk to you later.