Brendan Leonard: Quitting IBM to Become A Full-Time Adventure Writer

Starting in the world of professional journalism, Brendan Leonard eventually found himself with an amazing work-from-home job with IBM. While he enjoyed the work with Big Blue, it really wasn't who he was.

Using most of his life savings, he bought a van, moved out of his apartment and began to travel the American West, pursue outdoor adventures in his free time. However, to fulfill his dream, he had to give up the big salary, the benefits, and the security.

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Brendan Leonard

Brendan Leonard

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Shea Oliver: Hi I’m Shea Oliver. Welcome to the Priority Paradigm. I’m sharing stories of amazing people who have made radical changes in their lives for something more important. Today I am joined by Brendan Leonard who has a fascinating story to tell us. So without further ado, Brendan, tell us your story.

Brendan Leonard: Awesome, thanks Shea. I will try to make it amazing and fascinating. My story is one of kind of leaving full time work to pursue creative endeavors as a writer. I grew up in the Midwest. Went to college. Got a marketing degree. Decided I didn’t want to go into that and got a Masters Degree from the University of Montana when I was 25, this was in 2004, and at that time, what do you do with a journalism degree, you go work for a newspaper.

Brendan Leonard: So I tried really hard to find newspaper jobs, tough… but I did find, I worked for, I guess a little over 4 years, 3 ½- 4 years for small circulation suburban weekly papers, but didn’t find it amazingly fulfilling. It was a tough time to be in the newspaper industry.

Brendan Leonard: I left to work in a non-profit after that, and all the while I was convinced I was going to become some sort of adventure writer, you know, I write for some climbing magazine, climbing magazine, those types of things you pick up in the bookstore and the supermarket you know read about adventure in and leaving the newspaper industry kind of felt like I was giving up but, on, you know, journalism full time but conveniently I had taken a pay cut from a newspaper job which was actually kind of  difficult thing to do at that time so I had to supplement it with freelance income.

Brendan Leonard: So basically, I worked for, gosh I would say probably seven years before I started to make any inroads to, you know before magazine editors in the outdoor industry started to listen to me. You know, I would get a few bites here and there from, you know somebody at backpacker or the smaller publications at the time, and we, you know, I’ve just never got anything published until probably, 2011.. yea I guess 2011. Started to get a few articles here and there.

Brendan Leonard: By that time, I had started a full time, working from home, copywriting job with IBM, which was, you know, one of those jobs that I would describe as, you know my dad would think I was an idiot for ever leaving. A year and a half into it, I had started to start my own blog right about the same time when I got that job I was, I decided I didn’t want to just write for IBM, like that wasn’t my whole personality, I didn’t want to fully commit to that.

Brendan Leonard: I wanted to have some connection to the outdoors because that’s because that’s kind of what I spent all my weekends doing, was going hiking, climbing, trail running, skiing… so I started a blog called I just kind of thought up the name. I thought this is short. I can get a Twitter handle. I could, you know, sounds like a good brand, or a decent brand. No research much, really much thought going into it and I started to write one post every week on Thursdays. I said, I am going to do this until I get bored of it, or until something happens and within, I guess, probably about six… five- six months, people started to, you know, the articles started to make their way around the internet a little bit, and a few people started noticing at different websites and publications, and saying, “Hey, we would like for you start writing for us” and to drum up a bit of a side hustle writing for adventure publications. Not making tons of money or anything, but a few hundred dollars a month, and you know, at the time, I was working doing what was actually pretty fun work for big corporation that had tons of money. I had, you know, a really nice salary to sit at home, type things, do a few conference calls. I had great health insurance. I had dental insurance. That was the only time in my life that has ever happened. But I continued for the next year, year and a half, to try to keep growing my side business and keep writing and keep writing my blog and you know, get people to notice it and try to get more articles published in magazines and it started to grow and grow and finally, you know, a year and a half after I started  my blog, I had been published in climbing, backpacker, a few other magazines. I’m starting to make a little bit of a regular income from it. Climbing Magazine asked me if I wanted to be a contributing editor which really didn’t mean much, just put my name in the masthead, you know, of the magazine, you know, said that I would write for them instead of any other climbing magazine which if you are into climbing magazines there’s only basically three of them right now, so it wasn’t that big of a stretch to say, “yea I will only write for you guys, first crack at all my stories”.

Brendan Leonard: So I started to make some inroads, you know. I had some of this cush job but I was even thinking about four months I thought, you know, what I think based on what I have coming in, money wise, I might be able to make a go of it and I had been also coincidentally for about a year, living in a car. I lived in my car for, gosh, almost a year and then I bought a van and then I moved into a van, you know nowadays… this was back in 2012… nowadays you see people in Sprinter vans that are all built out, have this nice cabinetry, and you know you can stand up inside and cook on a little stove and there’s like, maybe even a little sink in there… but mountain bikes and stuff.

Brendan Leonard: I had a 2005 Chevy Astro Van with 129,000 miles on it when I bought it. All sorts of problems. I emptied out my life savings, which at that time was like, $6,500 to buy the van so I could live out of it. I built a really simple platform in the back to put a bed on, and I drove around the west and wrote about adventure while working for IBM. If I needed to take a conference call, I would try to be in a place where I could have access to the internet. A lot of times I was in a Starbucks somewhere like Bishop California, trying to act like it wasn’t loud in there and you know, “yea, sorry guys I’m just in a little bit of a loud coffee shop.”

Brendan Leonard: So, I’m living in my van, I’m writing on the side, doing all sorts of fun adventures, you know. At this point I would say I’ve built up since 2004 about eight years of experience kind of spending lots of my spare time, you know over a month a year, at least, you know climbing, backpacking, sleeping in tents, going skiing, backcountry skiing and I finally get up the nerve, I’m in Salt Lake City, staying at a friends house on his couch… and I’m gonna quit my job for IBM, you know, so kind of get ready to send an email and say, “you guys, thanks so much for this but I’m like, I gotta put in my two weeks and you know get done” and they said, “ok, you know, if you’re sure, if that’s the decision you need to make, okay great.”

Brendan Leonard: I had this moment, going to ship my computer at this, you know, I would get… you know, they have so many resources. This is a company of 400,000 employees, you know, if my computer broke, I would literally email someone and say, “hey, my computer wont turn on, what’s the deal” and they would say, “okay, were overnighting you a brand new computer with all the software on it for you, you may need such-and-such codes to get into it, access to the VPN blah, blah, blah, it’ll be shipped right here, pick it up, put the other one in the box, ship it back to us. It’ll overnight to us.”

Brendan Leonard: Wow, okay, you know, so I’m shipping my computer back to them and handing it across the counter to this guy, not even like a FedEx store or anything, it was like a Mom and Pop shipping place in Salt Lake, going “Man, are you really doing this?” and I can hear my Dad’s voice in my head going, “Wow, full benefits, big salary, what are you doing” and I thought, you know, this is what I’ve got to do. I have got to cut the cord. This is the last secure thing that I have that holds me to a regular job and if I really want to focus on what I want to do in life which is to tell stories about adventure, I have to stop having one foot in a safe place and jump in with both feet. So, I shipped my computer and I go back to my friend, Chris’ house and I’m like, okay, its time to hustle now. I don’t have much money in the bank. I hope I can, you know, I didn’t have rent at that time, but I needed to put gas in my van, I needed to eat, pay for my cell phone, etc., etc. and I’m sitting there just kind of horrified at what I’ve just done, thinking this may have been the worst decision of my life, and Chris comes home and he actually worked for a climbing gear manufacturer at the time, and he was, you know, well versed with the people. This sort of idea that people would eventually quit their jobs, or you know, follow their dream and I’m sitting at this kitchen table and he came in the door and said, “What did you do today?” and I said “well, I quit my job” and he said, “Man, that is so awesome! Congratulations!” Just the exact opposite of what advice you would get from anyone who, you know, had your own personal security in mind and I kind of took a deep breath at that minute and said, “okay. All right. I think this might work.”

Brendan Leonard: You know, I was worried about money for a few months, and a few contracts came in, and it became pretty clear that I wasn’t going to get rich doing this. I wasn’t going to pay a mortgage, or put down a payment on a really nice house or drive a better car, but I could still live the lifestyle… and right… and my life since then has become, you know, a friend who is mentor told me, “you will be the toughest boss you ever had when you work for yourself” and you know, I probably daily think about how right he was… you know, how much you will work from your home to avoid working 40 hours a week for someone else at an office. And every time I take a job or I do my own thing, or I sign a contract to do something else, or whatever, I always have to remember the two points are to make art and to tell stories, and number two to have my own personal freedom that I don’t have to commute. That I don’t have to do things that I don’t want to do. If I want to travel, I will travel. I can blow the money. I am responsible just to my own bottom line, to dream. Whatever that is.

Brendan Leonard: So it's been an interesting ride and there was a year and a half, or two years there where I made every decision I made, I made the opposite of the secure decision. I said, what would a person who grew up with your upbringing do in this situation. They would, you know, they would keep the steady job. They would not move out of their apartment. Move everything into a van and live out of it. Not buy a crappy vehicle with their life savings. Number one, they would have way more money in the bank at age, I was 32 then. They would have a 401K. They would not pay their own health insurance. So, I did that for about two years and what resulted is this life now. It’s become… its been a very fun thing, you know. I think about how many vacations I would be able to take if I were working a regular job and you know for a number of reasons, when you are in an office its really tough to get away. Its proven that Americans don’t feel that they can take their allotted vacations they get every year for many reasons.

Brendan Leonard: One, is just like pressure that they perceive from their co-workers or their boss, even though it doesn’t exist, they still perceive it, and I get to do things that, because I am an adventure writer and filmmaker, I get to spend a lot of time in places like the Grand Canyon, going to Switzerland next week to be in the Alps, you know mountain ranges all over the U.S. and you know, I get to do these things which would be a vacation if I could quote-unquote, clock out. I can’t clock out. I’m always, sort of “on”, always thinking about things to write, about to draw, sketches of make films about but if I had worked a real job, I may not have been in those places in the first place. So, its sort of a semi-paid, semi vacation lifestyle a lot. You're never quite on vacation, but you get to go to a lot of places that are really cool and I never would have been able to be in those places for as long, had I stayed in that career. So, I guess, that’s probably part of my story that is most relevant to you and to the audience that you are speaking to, I guess.

Shea Oliver: Cool. So, that is actually really cool. So, you actually did the van down by the river from the Saturday Night Live sketch? You actually did that for a while?

Brendan Leonard: You know, it's funny I have my friends from high school. We re-enacted just like for the variety show in a small town in Iowa… we weren’t in theater or anything. We did the Matt Foley skit on stage. And, I was not Matt Foley. My friend was, I only had one line in the skit and I actually have a copy of this, I put it up on Vimeo for those guys and this is verbatim from the Saturday Night skit where Matt Foley asks one of the kids “What do you want to be when you grow up” and I say “I want to be a writer.” Matt Foley tells me, you know, “If you want to be a writer, I can’t see too well… is that Bill Shakespeare over there?” and then he says to me, “You're gonna end up living in a van down by the river.” And, I guess by 2013 I had achieved both of those things…. Being an adventure writer and living in a van.

Shea Oliver: That is awesome! So, as you look at it all right now, was it all worth it?

Brendan Leonard: I mean… there was really no cost to me… I mean, all there was was this initial decision to jump, really… I mean, when you think about it. I wasn’t risking a lot…. And a lot of that… I was just talking to my dad about this last week. You know, things really hit the fan, I could go live with my parent for a few weeks or whatever. They live in Iowa. They live in a small town in Iowa which is not really conducive to the way I make a living…adventure storytelling… I kind of more or less need to be in a place with mountains or access to things like that, but yeah, I mean, really I’m not risking that much and I was already homeless and sleeping in a van and by the time I was 32 I had a lot of friends who had a guest bedroom, if not a couch. Which is not so much something that you talk about, like oh year, I ditched that lifestyle.. but thank God I have all these friends who didn’t ditch that lifestyle who have guest bedrooms I can sleep on when I come to town.

Brendan Leonard: You know, plenty of folks who I guess, when I write, my blog is very much concerned with the every man’s and every woman’s experience in the outdoors. Not so much the high achieving people you see in films and read about in climbing magazine. You know, people.. most of us are just having a good time out there. Pushing ourselves, but not making headlines at all and most of my friends whose couches I’ve slept on are in that category, and you know, I show up and we go hang out.. we go do something fun and that’s how we bond. It's been interesting trying to reconcile all those things. I moved out of the van in 2015 and moved back into an apartment and you know, I take a lot of the skills I learned living in a van. My computer is sitting on the first desk I have ever owned as a creative, as a freelancer. So that was 6 ½ years of working in a kitchen or on kitchen tables or coffee shops and airports and laundromats and stuff like that. And now, I finally have a place where all my stuff is. It's kind of shocking, but kind of great. Like I just bought this like literally two weeks ago.

Shea Oliver: Ok, so let's go back to that run-up to making that decision to say, “mmmm, bye bye IBM.” Did you talk to many friends and family and what was their reaction to your.. if you did… your I’m Outta Here and going to do my thing and not work for the big corporation?

Brendan Leonard: Gosh, I don’t recall talking to a lot of friends but I did have… you know, where I grew up and with most of the people I interacted with, I guess this is probably true of the majority of American society, you don’t have a lot of models for living a life where you don’t go into an office. You are kind of aware that there are entrepreneurs and artists out there… and I had always joked that if I had said to my high school guidance counselor “I want to be an adventure writer. How do I do that?” I think he would have said “I don’t think that is actually a job.” It's more like, when you are 18 and you are sitting in that room with your guidance counselor or whoever, and saying, you know “What’s next?” and they are kind of asking you what do you want to do with the rest of your life and you know, if you want to be a doctor, you gotta get started on that stuff when you are 18 and to ask an 18 year old kid “what do you want to do with the rest of your life?” it's like… boy, that’s pretty heavy… so I didn’t have that.

Brendan Leonard: But I encountered those people through writing about the outdoors and sort of making a name for myself or exploring those sort of freelance opportunities. You know, I had a few role models where I would see that this person didn’t go to film school and yet they are a filmmaker and they didn’t have a day job… how did they make this happen, and you know, it just people are not.. like there’s not like, special people who get.. you know.. nobody applies to a job being a freelance writer and someone says, “ok, good, here you go. Here’s $50 grand a year, do what you will with it.”

Brendan Leonard: I had a friend Fitz Cahall who started a podcast called the Dirtbag Diaries and the origin of that podcast is that he is a journalist and he thought that he was going to go into political writing but he started writing about the outdoors, and wasn’t really having great luck, wasn’t getting his favorite stories published and the stories that he wanted to work on, so just sat down and started reading stories into a recorder in his closet in 2007 or 2008, and it started to take off and pretty soon Patagonia started to sponsor it and then you know, Fitz was able to call it a full-time gig maybe 3 years into it. So, I watched him and thought you know, that guy is just not, he’s just doing it, you know and that gave me probably most of the courage needed to just get started. But like I also said, there wasn’t that much risk… it was like, I didn’t have kids at home, like “oh, Dad doesn’t get a paycheck. Sorry guys.” I was doing my dream. It’s a lot different when you have a lot of commitments like that. I was young.. youngish, single guy and all I had in debt was student loans.

Shea Oliver: So did you, or do you now, but especially during that time, do people ask you “well, you’re doing this adventure thing, you’re making a living, but what are you going to really do to secure your future?”

Brendan Leonard: No, nobody’s asked me that. I do.. I do have a tiny bit of money in a retirement account. I finally… I’m like starting to do that but yea, but is anybody’s future really secure? It just seems like… we have all heard stories of the person who works their whole life and retires at 65 and six months into retirement has a heart attack on the golf course, you know, and like weird confluence where there isn’t like that sort of 401K, secure job doesn’t exist any more. You can't work at the Ford plant your whole life and then retire with a pension. Sometimes teachers can. But I everybody’s trying to figure that out right now and certainly don’t have that figured out but I don’t have a ton of stress about retiring. I feel like I certainly have a skill that I hopefully can do until very late in life with writing and if it's all-consuming as it is right now, I will be doing it until then. I don’t ever foresee a future where I’m like, good that’s done… like, now I can just golf or whatever.

Brendan Leonard: You know, I have a couple of friends who are retirement age and you know, one of my uncles, he was a dentist and he loves what he does and I asked him about retirement a couple of years ago and he said, “you know, I’ve thought about it a little bit, but I’m really at the point where I feel I am doing my best work I’ve ever done. My skills, my knowledge at this point.” And, he’s actually enjoying the work. I mean, you know… it was sort of this revelation to me as my dad had just retired and I thought, you know oh yea, he is so glad to be done. My dad didn’t love his job every day and my uncle maybe does, so hopefully I’m at a space where I can keep doing it in some way until then, I don’t know. Nobody’s got a secure future for real, but were trying.

Shea Oliver: So, as you were working at IBM, did you find yourself getting more and more reluctant, you more and more unhappy with having to put in the hours for them as you head said, “I need to go that way”?

Brendan Leonard: You know, the work was actually really, really cool for most of my stint there, especially the first few months there I was actually getting to write about the history of the company, which is kind of the history of computers.

Shea Oliver: That’s cool.

Brendan Leonard: It was really interesting to me even though I had never thought, “Oh, this is something I would love to research” but it was super cool. It wasn’t so much the having to put in the hours for them, because I was getting compensated really well, you know. It’s like totally fine. I saw the paychecks and I was like, “that’s cool” but to be available… and I think this is common for a lot of people’s jobs where they work from home and there is like a chat client, you know, where it pops up on your screen and your boss can hit you up anytime. They kind of expected, and rightly so, that you would be available for that so you could be popped up and say, “hey, how’s it going with that project. I just wanted to check in. I had a few questions.” And being around for conference calls and stuff like that and it just kind of didn’t… I didn’t love that part. I really like, I really like to be left alone to do what I consider the creative process, which is sometimes doing laundry, sometimes it going for a 20 mile run, sometimes it's… whatever it is until I come up with the idea or whatever. Its cool. That job was great, for sure, and you know I think a lot of people would question walking away from it, for sure. I think it was the freedom that was the most… like I’m at home, ok.. but I have to stay at home and I have to be available on this computer, so I’m kind of just like.. the word “house arrest” is a little aggressive, but it kind of feels like it. Like, I can't go do that and I don’t get paid by the hour to do anything anymore, except for like, film production work or whatever. But, like most the time its like “How much money do you need to do it?” and I say a price and they say, “well, that’s a little high” and I say okay, sure. I don’t keep track of the hours I put into things because it would be sort of like, structure, that’s so difficult.

Brendan Leonard: Structure is sort of difficult for creativity in my mind and there are studies that say this. That’s bad. So I don’t want to sit down and say, “ok, now I have to do this drawing for a company and I can spend 4 hours on it or it's not worth my time, you know. Some projects you nail it in an hour and you’re like, wow I just made X amount of dollars in an hour, and sometimes it takes you 4 days and you are slapping your forehead going, “I’m getting you know, I should go work at Subway instead and make more money, you know.” Yea, like the freedom is the most important thing to me and the ability to come up with projects on my own. Most of what I do is my own idea, most of the time. Occasionally I will get someone will reach out and say “hey, we would like for you to draw a chart for us or a series of charts for our company because we like your style. Can you do that.” And I say, I can wrap my head around making something for you guys if you like the sense of humor that I exhibit on a daily basis on Instagram, then sure but you know what you are getting into already, so its not like I really have to conform to something that I don’t believe in.

Shea Oliver: Very cool. So what did it feel like those first few weeks after the computer went back to IBM and you had that sense of freedom? What was the experience like for you?

Brendan Leonard: Aww, man. You know, it was kind of gradual… this process… you know, the first day was sort of terrifying. You’re like, “Oh, I can take the day off!” But you’re not going to because you are totally worried about if you have any money coming in. Your doing the math and thinking okay, I have this much money in the bank and if I do this, this person will pay me, and on the 15th, then maybe I will have enough money. You know, I had worked in offices for like, 7 years and then started working from home and one of my first few weeks working from home as a copywriting for IBM, I went to the coffee shop by my house and used the computer. Got on the internet and sat down, and this guy sat down next to me he was kind of chatting me up and said, “so how’s it going?” and I said “I just started this job working from home and I'm just kind of figuring it out.” And he said, “Like how much time to spend?” and I said “Yea, you know it's like do I show up from 9:00 to 5:00.. I mean, I had a conference call at 7:30 this morning and like, what the deal.” And he said, “Well, think about this: When was your last office job?” and I go, “Oh, like 2 months ago.” And said, “Well how much time did you think you worked there per day?” and I go “Like 8 hours” and he scoffed and “You stand around talking at the water cooler. You walk over to your bosses desk to ask about their weekend. People coming up talking about stuff. I’d be surprised if you worked 6 hours.” And I go, “Okay… hmmm.” So he said, “So work 6 hours a night and make them good.” I go, “ok, well alright.”

Brendan Leonard: I think about that and I don’t have anybody coming up to me to interrupt me at home, so this gradual loosing of the idea of work where creative work becomes, especially when you are doing your own thing, its like, it’s like whatever I need to do to create stories. So figuring that out those first few weeks was like... I was pitching pretty hardcore. I was like, I got to sit down and come up with 5 ideas for these people, and 3 idea’s for these people, and if one of them says yes to one of them and the other says yes to one, I can probably buy people presents for the holidays this year. So your kind of at the beginning of your creative career your kind of pitching a lot, your kind of putting in a lot of time into finding new ideas. I had started to realize pretty early that going.. there is a quote, a Thoreau quote where he says ‘how vain it is of man to sit down to write when we have not yet stood up to live’ and I think about that a lot. You have to have something to say first, right? And I still, I write a lot from the first-person perspective because its more efficient and it's also my best thinking time. I need to go out and do things so I have experiences so I can then share them with people and write about, you know, the funny things we do, or the hard things we do, whatever it is that I’m going to write about that week. So there’s this combination of “Ah, I should say yes to this trip and I should go for this thing and that thing.” I think the first year of work I said, “ I have to say yes to everything, like literally everything. If someone says, “hey do you want to write this piece, I have to say yes to it. And, making some sort-of smart business decisions helps but I don’t go back to see how much money I made that first year. I don’t think it was very good, but it always changed, and if you want to be able to maintain the freedom, you have to be flexible in today's media environment. You can say, “Oh, I just do this, or I don’t do X, I don’t do Y.” You just have to be open to it and say, people aren’t consuming that type of media anymore, I need to pivot and try to make this media.

Brendan Leonard: I remember, I think it was the first.. I guess it was like four months before… it wasn’t even four months.. it was three months, and I then I got sort of a good contract from your company, outdoor gear company, and sort of made a little bit of my worry go away. At least every month that’ll be there, no matter what. It ended up being a very… you know, you look on Instagram and you see people doing the #vanlife, and it looks kind of fun, and I was not doing that, I was trying to run a business so it would be, I lived in a van, but it was more like I was trying to find Wifi at coffee shops and libraries around the west and you know, using my Wifi hotspot, and sitting in the back of my van typing things at like 10:00pm… you were just more like functionally homeless, you know, for lack of a better word, you know, and it kind of felt ridiculous at times, like this really… like are we really doing anything, but you could go, you could be in Zion National Park on a Tuesday and go for a day hike, and then work for two days, and then drive to the Grand Canyon or whatever so it really was cool, but nerve-wracking at first, which is partly due to not having health insurance and I was like, I got a really cheap policy that I bought and was like, okay, hopefully nothing goes wrong.

Shea Oliver: Certainly, certainly. So, making this change and deciding to live this life full time, what’s the coolest thing.. or your favorite thing that it’s enabled you to do?

Brendan Leonard: Oh boy… honestly, I can go out for breakfast on a Thursday, and that’s cool. I can like… my girlfriend’s also a writer, we live together, you know we both are self-employed, and its so cool to be like, lets just go and have breakfast at this joint we like and it won't be crowded because it's not Saturday, and then we’ll start our work day after that. And like, that’s… it's so pedestrian it's not even… you know, I’ve done a lot of really cool stuff. I’ve gotten to ski, climb and ski volcanos, I’m going to Switzerland next week for the fourth or fifth time for work, you know, and if I balance the books on the trip, I will probably lose money on it, but come on, what am I gonna do, it's fine, that’s cool, I’m gonna go do it. It's been…

Brendan Leonard: you know as I said earlier, the amount of vacations I’ve gotten to take, you know, I have twice in my life taken more than a month off work to do something and once was a raft trip in the Grand Canyon and the other was riding my bike across America because it was when I still had a full time job but I couldn’t convince them to let me have two months off un-paid. Those are incredible opportunities, and hopefully I can do that stuff again. But yeah, its just, you know, to be able to go climb a mountain on a Tuesday or a Wednesday or go skiing on a weekday when its not crowded is such a cool thing, and you know, it's partly because you do this adventure lifestyle and you acquire those skills to learn how to do those things so you can write about them, but then on your quote-unquote you can go.. there have been a lot of days I’ve gotten up super early and skied a 14er, or gone for a 20-mile trail run and then come back into the office and work for four hours, you know. So, that’s probably the best part, to be honest. I always say going out for breakfast on a Tuesday is probably the best thing, you know. It's kind of cool. It's like, A: we have enough money that we can pay someone to make eggs for us, and B: we can go whenever we want. It’s cool.

Shea Oliver: Very cool. So, if you had an opportunity to go back and talk to your younger self, maybe while at IMB, or maybe even before that, what would you tell him? Would you tell him anything to try to hustle him onto this path, to get going, to make the change that you made? And if you would tell him… what would you tell him?

Brendan Leonard: You know, I think about that sometimes and it’s a good interview question and it's sort of a way of asking, “Do you like the way your life has turned out?” Right? “And is there a way you could have improved it?” I think about it because, I didn’t start getting my stuff out there until I was 32..33..34… and I mean, a lot of people are more mature, smarter when they are in their 20’s but I was an idiot and I am really glad that I wasn’t putting stuff out on the internet that was getting seen at that point. I had some stupid ideas. And, it unfolded at a rate that was fine. So, I think that maybe the lesson would be to be patient. Just keep doing what you’re doing, keep grinding away, it will happen. Because it seems like, you know I wanted to be a writer when I grew up, I was probably 20… or 21 when I thought, “I’m going to be a writer” like that’s what I’m gonna do and in my head it was I’ll write a best-selling book and I’ll be famous and it will be great and that totally hasn’t happened. I actually give a talk about this on You Tube. It’s called “The Joy of Making It Small” and it's about having books that sell 10,000 copies and that’s it. You’re connecting with that many people, or your connecting with a few thousand of those or whatever. Some of them write to you or you run into them in person. That’s a really cool way to make a living and I can’t actually imagine being famous. That would suck, you know, like I love to be able to walk around the city, and people aren’t like “Hey, you’re that guy with the blog, you’re famous!” You know, like, everybody wants to be YouTube famous and have millions of subscribers and I think that a nightmare! You know. Like, I can run out to the grocery store at 5pm and go pick up stuff and nobody notices me, you know, I'm just another person in the city and its wonderful. You know, I can sit in a coffee shop and read the New Yorker and not get bothered. Somewhere, in some Western city, people will say, “Hey are you Brendan” and I can say “Yea” and I can hang and chat with them for 10 minutes and that it. It's like this level of success that cool. Im making a living, there are a few people that the work is meaningful to them but you’re not… God, I don’t want to say, Thank God Im not a best-selling author. That would be pretty great. But it’s been pretty great not to be recognized.

Shea Oliver: That’s a cool perspective! So maybe you’ve done this, but if you had an opportunity to come across somebody who was thinking to quit their job, to make a major change of quitting their job and following their dream whether it was writing or whatever it was, what’s the one thing you would tell them?

Brendan Leonard: You know, I was actually getting divorced in 2008 and one of my buddies from high school that I still hang out with, you know I was talking to every friend of mine about it, like I don’t know if it’s the right thing, and he said, “Well, one way or another, buddy, it will work itself out.” And there are psychological studies that prove that your happiness levels will not change no matter what decision you make if you decide to get divorced if you decide to stay married, if you take the job, if you quit the job… your brain returns to the same level of happiness, so you know, I think you might as well make the thing that your curious about.. make that move so you stop being curious about it. You’re wondering about it for a reason. What is the absolute worst-case scenario: Okay so you quit that good job. I mean, are you going to end up in a really bad situation because of it? Potentially. But if you have any sort of grit, you’ll probably get through it in a really good way, in a transformative way. I don’t know if working for yourself is for everyone. I hear from a lot of people “Oh, I have to go into an office.” Even friends of mine who might work freelance like to go into an office where other people are working. Some people are unable to focus at all, like I’d just be doing laundry all day, you know, going through Facebook and stuff. And I think, “yea I do a fair bit of that too, but I just consider it part of the process.” So, I don’t know, it works out. It always works out. It's not a worst-case scenario, just get some health insurance, you know, I guess.

Shea Oliver: Sure, very cool. Well this has been really interesting listening to your story. It sounds like you took a really brave leap to actually quit that job, even if it didn’t feel that way to you in the moment.

Brendan Leonard: Yea, thanks.

Shea Oliver: I think the world's a better place now they’ve not your books to read, they’ve got your blog to read, they’ve got your various productions you’ve worked on in film which is fantastic. So, if somebody wanted to learn a little bit more about you, or get ahold of you, what are the best methods to reach you?

Brendan Leonard: My website is and I’m on twitter @semi_rad and Instagram. So those are the best ways to find my work. My back information is pretty obvious from there if you have ever browsed the internet before, you can find it.

Shea Oliver: Very cool. Well I always like to wrap up with one last question, and the last question is: What question did I forget to ask you?

Brendan Leonard: Yea, that’s a good one. I think what I’m glad you didn’t ask is what is a typical day like because well, there is no typical day so it's pretty random, yea so no answer for that either.

Shea Oliver: What would it be like if you got stuck in a typical day?

Brendan Leonard: Oh man, I don’t know, I don’t know. I’m not even in the same place for 15 years, so I can't really say. I would probably work for about 9 hours and then go for a run afterwards.

Shea Oliver: Go for a run to escape it?

Brendan Leonard: Yea, exactly!

Shea Oliver: Cool. Well, Brendan, thank you so much for spending this time with me today. This has been really enjoyable today to learn about your stories and I’m actually going to go and check out your blog a little bit more. I’ve actually read a few of your stories but I want to go read a few more. So, thank you very much for spending time with me today.

Brendan Leonard: Yea, thanks for having me!

Shea Oliver: Absolutely

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