BTU #52 - Chris Pestel - Transcript

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JUSTIN NASSIRI: Hey there listeners, this is Justin with a quick note before today's episode. is offering Beyond The Uniform listeners one free audio book. You can see this offer, as well as a list of every book guests have recommended on the show, at That's, Thanks, and enjoy the show. Welcome back to Beyond The Uniform. I'm Justin Nassiri and each week I interview military veterans about their civilian career. Today's episode, #43, with Chris Pestel.

CHRIS PESTEL: From the process of going through West Point and then being an officer and then deciding where you're going to go next, one of the things that's first told to you is, that once you do that you can do whatever you want. You basically can write your path. I think I took that to heart. If I can do whatever I want, this is what I want to do. Again, it was a thing where I'd picked up a camera. I started photographing a few things and really, really enjoyed it. It was very intuitive and I liked that. It was the closest thing I had found to playing sports to where it was develop the muscle memory and then just let that instinctive ability take over. You get lost in the flow of what's going on. I really, really wanted to keep doing that. If I got to choose what I could do, that's what I wanted to do. That's how I found myself in that situation and then just dove neck deep in it and tried to figure it out.

JUSTIN NASSIRI: This is my 53rd episode with Beyond The Uniform and I have to admit it's probably my favorite interview to date. Chris is an incredible human being and I found his story very inspiring. If that's not enough reason to listen, here are my top four reasons to listen to today's show. Number one, courage. Chris left the Army to become a photographer. I found it difficult to dive into entrepreneurship and that was from business school in the Bay Area where start-ups are very normal. Chris, on the other hand, took a leap of faith to follow his passion. Initially he had to tell people to ignore his background in education in order to consider him for jobs for which he seemed overqualified. And it worked. He owns his own company and has worked with both Playboy and ESPN. Two, do what you know. There was no road map for Chris. He talks about how he took baby steps to start with what he knew and then worked tirelessly to fill in the gaps. Three, Craft. Chris is a case study in honing one's craft. He talks about it in a way that could benefit a listener in any industry, how he immersed himself, surrounded himself with the community, researched in the library and more. Number four, don't panic. Chris went from earning $75,000 a year in the Army to $19,000 a year initially.

JUSTIN NASSIRI: He talks about making sacrifices to get to where you want to go and the difference between patience and panic. As always at, you'll find other great episodes and resources, including show notes to links to all the things we talk about in this episode. So let's dive in to my interview with Chris Pestel. Joining me today outside of Chicago is Chris Pestel. Chris, welcome to Beyond The Uniform.

CHRIS PESTEL: Thank you for having me.

JUSTIN NASSIRI: So quick bio for listeners. Chris is the founder of Pestel Photography. He's worked as a freelance photographer for ESPN for nearly nine years now. He started out at West Point after which he served as an Army officer for five years. After his transition he started out as a photographer at Carolina Sports before moving on to Playboy Enterprises as a junior designer and photo editor. He's also served as the Director of Public Relations for his high school Alma mater, Montini Catholic. Chris has run his company, Pestel Photography for over nine years making him on the verge of the 4% of entrepreneurs who keep their company running for 10 years. First thing I always like to ask is if you could take us back to when you knew you were going to leave the Army and how you approached that decision?

CHRIS PESTEL: It was probably about six months out, in the Fall about 2007 was when I really first picked up a camera with the intention of doing that as a career. It was a matter of just picking up a camera and not looking back. I had put my paperwork in about a year out. I knew I was getting out. For the majority of the time that I was in, I was a single father and so I knew pretty quickly that it was going to be about a five year plan to stay in the Army and then move on to something else. Like I said, within that six months was really the window with which I decided what my path was gonna be and here we are, eight plus years later and I'm still shootin.

JUSTIN NASSIRI: And that was one of the things I was really excited to learn. So you said about a year before you got out was when you picked up the camera with the thought of doing it professionally. Had you been doing photography your whole life, or when did you first get into photography?

CHRIS PESTEL: That's been an interesting re-discovery for me. The photography aspect of it was here and there, but never really a focal point at any point in time. In about 2003 I picked up a Poloroid camera and used that kind of extensively for the last year, year and a half of West Point and I actually took a creative writing class. I was a Art Philosophy and Literature Major at West Point. We had a creative writing class and in that I talked quite a bit about the desire to capture imagery from a story telling perspective. I didn't realize that until maybe about two years ago when I was going back through old papers. And so it's been this process of kind of connecting the dots to some past points in my life to where this desire to do this was springing up but not quite taking hold yet. And the photography aspect, it was a new thing basically.

JUSTIN NASSIRI: I was just really excited. So Annie Taft, who's also been on the show connected us, and I was just very excited 'cause it's such a different career path that you've chosen and I'm wondering was that difficult when you made that decision was there, were you just immediately all in or was there some inner doubt or people trying to talk you out of this or what was that decision process like when you did say, "Hey I'm gonna actually give this a go?"

CHRIS PESTEL: One of the things that gets fed to you a lot, from the process of going through West Point and then being an officer and then deciding where you're gonna go next. One of the things that's first told you is that once you do that, you can do whatever you want. You basically can write your path, and I think I took that to heart. Where it was like, if I can do whatever I want, this is what I want to do. It was again, it was a thing where I picked up a camera, I started photographing a few things. I was working as a door guy at a small, small music venue in South Carolina and once the initial rush of the door kind of subsided, I would take the camera and start photographing the acts, the musicians, and really, really enjoyed it. And it was this thing that it was very intuitive and I liked that. It was the closest thing I had found to playing sports, to where it was develop the muscle memory and then just let that instinctive ability kinda take over and you kinda get lost in the flow of what's going on. I really, really wanted to keep doing that. If I got to choose what I could do, that's what I wanted to do. And so, that's how I found myself in that situation and then just dove neck deep in it and tried to figure it out.

JUSTIN NASSIRI: That's so awesome. When you separated then, I know you went on to work at Carolina Sports, how did you navigate? Take me from when you got out of the military 'till you started at Carolina Sports, how did you find that?

CHRIS PESTEL: Okay. So, like I said I had about a six month window where I was like, "Okay, what do I do? Where do I go? Who do I talk to?" And I had come across this photography clinic and I had been an athlete my entire life and so the advice that writers always get is you write what you know, and so I just kinda transposed that over to photography and I said, "Well, I'm gonna shoot what I know." And so it wasn't a real desired outcome to be shooting sports team or the team portrait stuff, but I knew it was an arena that I was comfortable in. And so, I just went and did a little bit of research. Found a company that basically had a strangle hold on all of the athletics throughout the State of South Carolina and went on a shoot with the owner of the company, he was going up to Clemson and he had this, he had an air... He was a pilot too. And so we jumped in his plane from the little regional airport, flew up to Clemson, photographed the team, I was like, "I'm in. When can I start." And he goes, "When are you done with the army?" I'm like, "Done on April 15." He's like, "Okay, you can start on April 16." And I was like, "Okay." I had about 45 days of terminal leave saved up. And I went to work, I signed out at about 2:00 on a Monday and I went to work on a Tuesday. I made the transition from making, I don't know it was, I was probably making close to 70-75,000 as the captain with BAH to making $19,000 and didn't care.

JUSTIN NASSIRI: Man, there's so much I love about what you said. One of the things that jumps out at me as your talking is, so many people that I've interviewed have gone on much more traditional paths of business and things like that. And even for them it's such a, coming from the military it's such a jumping off point of like, what do I do and who do I talk to and who are my role models. And it seems like you made a jump even further by comparison where there's not a lot of role models and a lot of guidance and so I really like what you were saying about do what you know, you took that baby step in the direction of what was familiar enough to find your own way and I just admire the willingness to jump off to take that pay cut to have alignment of something you were just really passionate about. I think that's very rare that people have the courage to do that. So next thing I wanted to ask about, so you're at Carolina Sports, you've taken this pay cut but you're just completely passionate about this. What did your day-to-day life look like? What does it look like to be a photographer in a sports team like that?

CHRIS PESTEL: You'd show up, it's somewhere in the morning time, depending on what the shoot that day required. And you'd hop in one of the company vehicles, you drive to some corner of South Carolina usually after school because it's when the majority of the shoots would take place. And you'd be there from about 3:30 to about 5:00 maybe shooting anywhere from one team to six or seven teams in a day. And hop back in the car, head back to the office, maybe download the images right then and there or maybe you'd do it the next morning before you go out to your next shoot and kind of repeat the process. And so, it was monotonous to a certain degree, but it was very different being presented with a lot of different challenges on a daily basis, from who to coordinate it with, with the schools, is it a coach? Is the athletic director? Is the athletic director in tune with the coach? And so there's a lot of potential pitfalls there, and then on top of that, then you don't know what, you shooting inside or you shooting outside? Is the gym well lit? Is the gym poorly lit? Is there a big mural that they wanna have in the background? Is there a big parking lot you wanna avoid?

CHRIS PESTEL: And it's a process of problem-solving on that daily basis which is, even though it was a monotonous sort of process, there was enough within that to keep it... It was a really good stepping stone for somebody who had never done it before because you learned how to problem solve quickly in the presence of all these other people. Sometimes you can get into a studio situation where it's just you and a still life or you and a model or a subject or whatever, and you can slowly go through it. But when you've got a line of 75 kids that are all high school learners, all talking and then you got a coach that doesn't want practice to be interfered with, it's a different beast and it's... It doesn't sound like a lot, but when all that's thrown at you and then you got to collect the forms, and you're taking all that time, there's quite a bit to it. And it takes a little bit of time to figure all that out. So, it was a good...

JUSTIN NASSIRI: Yeah I imagine... You know when I was... Yeah, When I was thinking of your bio, I was thinking it seems like you're getting your reps in, you're getting the practice, you're building up the different muscles that you need to perfect and hone this craft. And I was wondering as we're doing this, was it a 100% on the job getting experience, or were you trying to learn Photoshop through a class or online? Or how did you go about building up all the components that you needed to be successful?

CHRIS PESTEL: Yeah, it was a full-fledged, like I said, immersion. Everything from, what you were doing that day and that day's shoot, to assessing that day's shoot and trying to learn from it, to spending the evenings going to bookstores or the library. Library was my best friend, I'd go there and I would just, anything on any subject that related to it, whether it was photography specifically, or design, or any number, anything from, everything from film... The different languages of visual storytelling, and web design and graphic design, it was pulling all these different things together, and, to create your own education for it.

JUSTIN NASSIRI: And, especially if someone's listening, and they're liking this path that you've forged, is there any particular books or resources specifically that stand out to you that you would recommended to them that would be a great resource for them in learning more about this?

CHRIS PESTEL: Yeah, there are. I've used quite a bit. There's so many different angles you can take to try to learn something there, and I know with a lot of public libraries, or community college libraries, you get that for free with it. So it's invaluable in that sense. If you gotta pay for it, it can be a little bit expensive, anywhere from like 20, 25 bucks a month or something like that. But I know it's a really great resource and there's endless topics there, but as far as a book goes, the book I always recommend is Stephen King's memoir on writing, which is a little bit... Not quite a photography manual, but if you go through that book and you substitute writing with photography, it works about 95% of the time. And it's a fantastic resource for voice and for vision and for... I've always taken a little bit more of a storytelling approach to photography, and so that was a big help for me, was that book. And it's again, also anything that has to do with visual arts I think can apply, so it's, I don't really recommend a photography book because a lot of em are manuals and technical. And I try to stay away from that, 'cause that's one of those things again, you learn by doing a lot, with a lot of that.

CHRIS PESTEL: And you can learn by doing and then supplement that with technical manuals and learning all about shutter speed and aperture and ISO and those things. But those other aspects are the ones that really... I think they're harder to come by in resources.

JUSTIN NASSIRI: I read Stephen King's on writing as well, and one of the things that stands out to me most, and I think this applies to entrepreneurship as well as arts in different fields. But he described this loft he lived in and they had this board across the roof and this inch-and-a-half thick nail, and he got his first rejection letter and slapped it up there, and he said by the time he was finally had just an article in a magazine published, that inch-and-a-half or two-and-a-half-inch nail was full, just completely full of rejection letters. And I think it's just such a powerful example for anyone who forges their own way or takes a risk of just how much rejection you need to be willing to face. And I think I grew up, I love Stephen King and I just grew up assuming he just wrote and was successful. And to realize, like the amount of adversity and challenge and rejection he faced and overcame and persisted with, is really inspiring and I think it's such a good valuable lesson for anyone to know that that's the attitude you have to go in with.

CHRIS PESTEL: Yes, I've conducted a photo-a-day project for the past almost two years now and probably within the first three weeks or so actually started reading that book in conjunction when I started it. And so day 15, 16 or 17, somewhere along that lines, it's that quote, it says, "I replace the nail with a spike and kept on writing." Or the [0:19:01.3] ____ crumbled up piece of paper. Again, it's the writing, the drawing, painting, the business you're creating, just replace whatever it is you do with what you do with writing and it makes sense. And it's about forging and forging on ahead despite all the people that say no and/or say that you're doing it wrong or that's what you're gonna do. It's not easy. A lot of people have circumstances around that doing alone to do that, but, I think a lot of us have the right circumstances for stepping off and taking that risk. And if you're looking for the perfect scenario, you might not ever find it.

JUSTIN NASSIRI: That's great. And so, you're at Carolina Sports, how do you make the transition to Playboy? It seems like in some ways it's a different subject material and then it's also going from a relatively smaller company to, I imagine, one of the more difficult organizations to get through to.

CHRIS PESTEL: Yes. I stayed at Carolina Sports for about a year. I left in May and by the time that next June rolled around, I'd already developed the relationship at ESPN. So I would commute from South Carolina every so often back home to Chicago and would shoot for the ESPN the local radio station, some of their events and what not. And came home one time and found out that the Blackhawks, the Chicago Blackhawks were hiring a team photographer. And so I put in a word with, that I was interested in that through some of the people at ESPN and whether that helped or not, I ended up getting... I got an interview and flew home just for that. And it was in the process of doing that that I realized I needed to be back home in a bigger market. There would be more photographers in that bigger market but there would also be more opportunity.

CHRIS PESTEL: And moved back home, went to that interview, didn't get it, but then tried to figure out what to do next. And so, it was a process of, "Well, if I wanna do something, you're supposed to go to school for it." And so I went to... I took a couple of classes, couple of semesters worth of classes at a community college in hopes of developing a creative community for me to be a part of. I knew that that was probably really extremely important because the communities I had previously, be it, West Point, in the Army, we're not filled, the ranks weren't filled with other creative people who had kind of done or were doing what I was doing. And so it's a little bit of a challenge and so I said, "Well, let me go see if I can create this other community."

CHRIS PESTEL: So took two semesters worth of classes. And in the summer of, it would have been 2010, I had decided to stop the community college route and took what would have been an internship, 'cause I wasn't taking classes, I was just volunteering basically at a local newspaper, a suburban newspaper. And after about a week of doing that, I found a listing for a job opening at Playboy. And I had been shooting my high school's football team on that previous fall and had come across a guy who actually graduated from the high school on the sideline of the State championship game, and he was a senior photo editor at Playboy. Now, we shared the commonality of both being photographers. We shared the commonality of both graduated from a catholic high school.

CHRIS PESTEL: And within a moment, after meeting him and then seeing that job opening, we then shared the distinction of both working at Playboy which was kinda interesting. And it was a matter of forging that relationship by being out and shooting. It was that act of being on the sideline of a football game and putting a project together that he became aware of me. And then, the stars aligned and then I was able to get my foot in the door there. So simultaneously, I was taking basically two... I was doing basically two internships. The job at Playboy was, I was making $8.25 an hour working three days a week in conjunction with volunteering at this suburban newspaper. So that's what my career looked like at that point in time. The work I was doing for ESPN was far and few between and maybe once a month. Maybe at that time, it was once every other month. It wasn't like that was a big pay day there. It was just some consistent work that I had come across.

CHRIS PESTEL: And so, at one point in time I was working for free at one hand and then making $8.25 an hour working at Playboy. And I came in as a photo editor and it was a really interesting interview there because they looked at my resume and they said, "Why are you applying for this?" And I basically had to tell them, "Can you please ignore where I went to school and ignore my job history in the army and don't tell me what I want, cause I want to get my foot in the door here." And yeah you're right, the subject matter... Subject material was not... It was... I wasn't in glamour photography. I had no interest in that sort of output, but getting a foot in the door at a company like that was of very much... That was a lot of interest to me.

CHRIS PESTEL: And it was through that process of being a photo editor, being on the other side of the camera then that it opened my eyes to the idea that as a photographer your creative process stops when you take a picture for the most part. Your process is over. And then for me at the photo editor side or for the layout designers that were in our department. Our process just began. And so, there was this really interesting realization of how the creative process works from start to finish. And I was able to turn that three day a week into four days a week pretty quickly. And was able to... I got a promotion within the first few months of being there, and then I was working as an image technician doing retouching. And then, through the process of them downsizing, they let go of one of their layout designers and they asked me to fill in the void.

CHRIS PESTEL: And so again, right place right time, but also the ability to take that chance and... Yeah, I know how to do that or I can learn it. And that was probably the biggest thing was that they took a chance that he can learn how to do it, and I did. I ended up getting... I was there for about two years and in those two years I actually... While people were getting laid off and the art was getting taken off the walls and the office was getting boxed up I was... I managed to squeak out two promotions. So that was kinda interesting. And so I ended up walking away with not only a photo credit in a Playboy magazine but also as a layout designer. And I never... I don't know I was... It was... And that still kind of baffles me that that happened that way, but it doesn't make any sense because the next job I took was at my Catholic high school as a communications director, so that's a lot of different 180s there that you pull...

CHRIS PESTEL: It's that flexibility that kind of figure out what the common thread is through all that. And that can be tough especially when you're changing jobs and you've got these full-time to part-time positions that are in the same world as being a photographer but not maybe not fully being a photographer. And that's what Playboy was. I wasn't a photographer there. It was an interesting dynamic. But I shot still, I was able to photograph some freelance jobs in conjunction with that being a part time position.

JUSTIN NASSIRI: And I love this theme of immersion though. Where you immerse yourself and you're at your high school and you're immersing yourself in this field, in this community, and because of that it seems like these connections form where you're just living and breathing this so you find these connections that lead from one opportunity to the next. What was day-to-day life like at Playboy? What would be a typical day?

CHRIS PESTEL: So I worked in the department called Special Editions. And we had... We were an autonomous unit under the Playboy umbrella. And we weren't the main magazine, we were a subset magazine, and it was nothing but pictorials. So it was very much like a... We completed, I think it was, two sometimes three magazines a month, we would have put together. They were about... They were 96 page magazines and we did everything from start to finish. And so, those magazines were filled... The pages were filled through a casting call. And so, part of our department would go out to a new city once a month and conduct a casting call. Images would come back, that's what my initial job was, was to help our editors, our executive editors, help them get all those images together so that they could process them and figure out who they would then give a call back to, and then setup a photo shoot with one of the freelance photographers.

CHRIS PESTEL: They would shoot those... They would do those shoots, and those images would come back and then they would go to the layout designers and the image technicians. And so, you would prepare those images and then all the while you're... There's a theme in mind for each issue and so it was just from one month to the next, that process kind of repeated itself. And it was great because like I said, I was able to be a part of just about every step of that process, and never really picking up a camera. But bringing all of the photographic knowledge that I had to the table of being a photo editor or a designer. Again that's worth... And I talked before about how when I would go to the library and you would just gather things that looked interesting to you. Not necessarily, I wanna learn how to be a photographer, looking at a photography book. It's about learning visual language and that's what that job also taught me, was that the visual language, there's more of it beyond the actual task of taking a photo.

JUSTIN NASSIRI: I'm just trying to put myself in your shoes. You're going down this path initially of photography. You're always taking photos, then this incredible opportunity of Playboy pops up, and it's more on the editing side. Was there a part of you that was like, "Oh, I want to stay behind the camera, and therefore, this might be not what I want." Or was there more excitement of like, "Yes, I get to build out another skill set and build up another muscle I haven't used." I'm just wondering if there's that hesitation of doing something that wasn't a 100% in the direction you were originally going?

CHRIS PESTEL: Yeah. At first, my initial response was, no, there was no concern at all. But then as I started to be there a little bit longer, my day-to-day was not photographing, that's when I decided that I might commute. I daily commute. I would take a train into the city every day. And I'd have a two-mile walk to more offices. That's when I started doing street photography. It was this process of, again, supplementing the day-to-day work, with basically a personal project, because I wasn't obligated to anybody, and any of those images. It was all just for me. It became an outlet. And the really great thing about doing street photography, especially in a bustling city like Chicago is that, it was never sit around in a place and photograph. It was always just on my walk. People were coming one way, and I was going the other, and it was a matter of just kind of trying to capture something out of the chaos of those movements everyday. And it's not all that much different than shooting sports photography, because there's this thing that's happening, and it's gonna happen whether you're there or not, and it was about timing.

CHRIS PESTEL: It was about knowing what the camera's gonna see. Most of the street photography that I did was shooting from the hip. It wasn't with the camera up to my eye. And it was a really, again, it was a really great lesson to learn, because I was able to shoot, and learn what my camera was seeing, without the obligation of what the output needed to look like. I could shoot for two, three week and not get a single image, but it didn't matter. But I was getting those reps in, those being like, we did talk of for getting those repetitions in. And it was about building muscle memory. So then if I was ever in a situation shooting a game or an event or whatever, and I know that I need to get that shot, but I can't have my camera to my eye, I know what it's gonna give me. You will see, those sporting events where a photographer is holding the camera up above their head, and people are like, "They don't even know what they're getting." Yeah, they do. They know what they're getting.


CHRIS PESTEL: They actually do know what they're getting. If their good, they know what they're getting.

JUSTIN NASSIRI: Do you have mentors or role models in photography? I'm just kind of trying to construct this image of going from the army and choosing a career that is just... It has so little in common, at least from my perspective. It seems like so little in common, and I'm just very impressed with this immersion that is in the library, on the walk to work, just constantly finding ways to hone this craft. And I'm curious if mentors or role models, have in some way, influenced you as well, or other ways, you've kind of sought to forge this path through this unknown territory.

CHRIS PESTEL: Yeah. That was one of the things that actually peaked my interest initially about photography, was that I... There was this concept of, "The Apprentice and The Mentor." And when I first started getting into it, there were a lot of people that were kinda like, "This is on its way out." Probably, like the old guard was kind of, "Well, digital's gonna take over and ruin it." I never really... I kind of got that like, "Old cranky man," feeling from a lot of people that I first originally kind of reached out to, and that wasn't the attitude I had. I had a very green, excited attitude. And for the most part, that hasn't really left. I still kind of feel that way. I still feel pretty good about... I don't get worried about those aspects of it. But I find that, more than anything, it's other art forms that I look to. More so, than another person. I'll look to other visual medium. Film, or maybe more the language of film. Or the language of comic books.

CHRIS PESTEL: The language of graphic design. I look to those things, be it for inspiration. I think maybe because the idea that I had that opportunity of being behind a camera, and then working at a magazine where I wasn't behind the camera. And it was more like a directorial approach, and understanding that big, wide realm of a film maker, is more of what I was more interested in, rather than how to get a specific photograph. Pretty early on, when I was making the decision to be a photographer, I had some people that would ask, "Oh, what's that mean, five, 10 years down the road? What's the big picture?" And everything. I remember saying very specifically that, "There's a chance that I won't always be a photographer, but right now I feel like that's gonna get me to the next thing." I've always had kind of an openness with it. I kind of fought the idea of labelling myself as something specific. Just because people make a lot of preconceived notions about that.

CHRIS PESTEL: You tell me you're a photographer. They almost immediately think I take family photographs, family portraits, or shoot weddings. I have nothing against those things but that's just not what I'm really all that interested in. It becomes this process of once you get into that world, then you have to defeat that stigma. It's, "Well, that's not what I do." and it's like, "Oh, okay, what do you do?" And then you can't even explain that. It can be difficult. So I've always taken an open approach to what it is I'm gonna be. Like I said, the photography led me to a magazine. So that's kinda why I was okay with it. But with that comes not a real strong sense of a specific mentor. I've reach out to people. I've built up a bit of a community of people I will reach out to if I'm trying to figure something out and there's a... That's been a little bit tough but they're out there and you just have to find them and find the right people. It's something I'm always still looking for. It's never too late to have one of those and that's how I look at it.

JUSTIN NASSIRI: That's awesome. How did you go about starting Pastel Photography then? At what point in the story do you decide to create your own organization?

CHRIS PESTEL: It was when I moved back to Chicago. And it was when I decided to go back to school. That's when that materialized. One of the first things I did, one of the books that I came across was some entrepreneur books. The more and more I dug in the idea of being an entrepreneur, the less I wanted to be that. There's the general census, "Automate as much as you possibly can. Scale, scale, scale." I wasn't interested in that. That was a tough thing to come to grips with trying to find your footing because you're a business but... I think Steven Pressfield wrote a book called "The War of Art." It's a little play on "The Art of War." It's a pretty good breakdown of some of the hang-ups you can get yourself into by trying to do something creative and have it be a business because you have to put...

CHRIS PESTEL: You gotta make money but you also... There's a weird thing that happens when you try to create stuff. When you're creating it and you're not being held obligated, there's no obligation, you create nice things. They're for yourself and then suddenly someone pays you for it. This weird collision that somehow stifles the... Or can stifle the process. It's a weird thing and I haven't figured it out totally but everyday I hopefully get a little better at walking that line. But I knew early on that taking myself seriously with what I was doing, be it at a small level, be it at a part time level. It was important to have that distinction if nothing else to have separate bank accounts. That was the driving force with it. It was really nothing more than that.

JUSTIN NASSIRI: I think that's so interesting. I do think about creativity a lot. I like what you said with a lot of entrepreneurship, there is this pressure to scale and monetize and it becomes a process and it starts to distance you from the active creation that I think attracts a lot of people initially. I don't know if you've ever read... Elizabeth Gilbert has this book called "Big Magic." And I just have found it. It's one of the few books that I've read multiple times but she talks about creativity and like you had said about Stephen King, it's mainly for writers but you can insert different art forms in there. Just all of these different ideas she has on how you feed creativity and how you can also kill creativity and a lot of that comes when you're putting pressure on your inspiration to generate money rather than just doing what it sounds like you've tried to align your life with, of enjoying the craft and creating for the sense of creating. And I think that's just the fascinating topic in general. I wanted to also ask about how you started with ESPN and it sounds like that preceded actually your work with Playboy. It sounds like it started a little bit slower and then ramped up. How did that initially take hold?

CHRIS PESTEL: My brother had been working as a part-time in their promotions department right out of college. So he was working there. They had a golf outing. They needed a photographer. I had just started doing that so they called me up, or he called me up and said, "Hey, can you come shoot this golf outing?" That golf outing led to another job later in the fall which led to something else. And then it started to... It was a good fit for everybody. It just took hold and like I said, I was able to photograph for them maybe once a month or so, maybe 10 times a year over the course of a few years. It's not as sexy as it sounds. It was a lot of just live broadcasts and I was able to get... Through that though, there were several situations that were kind of interesting, I was able to photograph ESPN's Mike and Mike, the morning show guys, as they threw out the first pitch at Wrigley. Was up in the booth with them when they sang the seventh inning stretch, and I did that for two or three years in a row. That was kind of cool, because when I was a kid, growing up in Chicago, being a Cubs fan, I remember I heard a story about Jim Abbott and he had written on a piece of paper, that one day, he'll play in the major leagues. And he had put it underneath his pillow every night. And I did that as a kid, as an 11, 12, 13, 14-year-old, whatever. And I had, "I'll one day play at Wrigley Field." And that was under my pillow.

CHRIS PESTEL: And I didn't play as a baseball player, but I got to go play as a photographer. That was one of those moments where it was kinda like, "Okay, cool." Like, this is, "Not everybody gets to go do that. The camera is starting to open up doors for me, to places I have wanted to go." And so, that was really cool. And the relationship with ESPN has stopped now, at this point. I moved on from those jobs, and so it's... It was a good thing to have, back in those days when I was working, either full-time or part-time, at a photo-centric job. And that became a job I would go and shoot every so often. And so, it was, again, even when I was working at... There was one day at Playboy where I worked at Playboy all day, and then, went to Wrigley Field, and shot there, and I was like, "Awesome! That's what my life is." [chuckle] It's like, "I'm every day at Playboy, and then I go to the field, go shoot at Wrigley Field." That was pretty cool, so...

JUSTIN NASSIRI: Looking back, in what ways do you think that your military service has helped you in this direction? And in what ways have you had to break habits from the military, in order to be successful in this?

CHRIS PESTEL: Yeah. Yeah, it's a question, that comes up in different ways. Usually, when I see somebody I haven't seen for awhile, and they've been following what I've doing, and they're like, "Do you feel like you've made right decisions?" The way that you took the long way to get where you are, and... " I don't look at it that way. You hear people say like, "It's the journey that matters, not the destination." And it's like, it's all those experiences that I've gathered along the way, that have helped inform me as a photographer. So when you Google a photographer, or something like that, or you're searching for somebody, and you're gonna pick between one and the next, like, everybody's got good cameras. If you're, I would hope that most people that are presenting themselves as a professional are somewhat technically competent. So what's gonna be the differentiating factor? It's you as a person, and so, I get to bring all those past experiences with me to every shoot that I go on. And whether it comes up in small talk before the shoot, what my past was, or if it comes up after the fact, all of those things, they inform it, they help me produce. They help me forge those relationships.

CHRIS PESTEL: So the people skills that you're able to develop in the Army, the tenacity that you're able to develop, the work ethic, all of those things help differentiate you from being a flighty creative person. A lot of it, the biggest one is, for me, that through four years at an academy, and then, five years in the Army, you develop a sense of confidence. And you can't turn away from that path, unless you're confident. And so, I know that I made the right decisions, because I don't know if I would be where I'm at today, if I had gone to an art school, if I would have had the confidence to believe in myself to do it. So, going through those worlds, and developing a sense of confidence of who I am, it allowed me to take that path out of the military that was a little weird, or eyebrow-raising. Conversely, the things that haven't, the things I've had to break, that's also an interesting concept, in terms of... It's funny, because a lot of the things that would make me a competent creative person, such as the desire to be different, or an urge to buck a trend, those are the things that would not necessarily provide the best, "Oh, we are" bullet. So that's an interesting aspect, too, because, I was that way as an officer. And it didn't always, that outward appearance of that, didn't always play well.

CHRIS PESTEL: But I didn't necessarily believe in that part of me yet, when I was an officer. And so, it didn't play well. But I'm the same thing today was I was then, but now I'm, that same quality is a good thing today. But then it wasn't. That's a weird thing to have to learn about yourself, and that self-awareness of, "I need to be who I am, and frame it properly," and then it's gonna be a positive quality. Also, one I think that comes not so, that's something that's kind of defeated a lot, especially in a military environment, is the idea of being the loudest person in the room. The alpha-male, the aggressive kind of mentality that's kind of required in that world, and counter to that is, when you [0:47:52.8] ____ something, you're hoping that it connects with people.

CHRIS PESTEL: And sometimes, the best way to connect with people is not by being the loudest in the room, or being real aggressive. It's about being vulnerable, because people connect with vulnerability. But that's not really a great trait. Not that it's not a great trait, but it's a misunderstood trait, probably as an officer or someone who's supposed to be a leader is this idea of vulnerability, that's something that I've had to not necessarily defeat, but kind of just understand that's more of who I am, is putting myself out there in a way that's going to be vulnerable. You create something and put it out there, you're making yourself vulnerable, and that's not an easy transaction, no matter what it is. Sometimes you just have to embrace that. I just can't imagine that conversation happening in a professional development in the Army, being more vulnerable. That's a big difference between those worlds.

JUSTIN NASSIRI: Man, I've asked this question now, I think this is the 47th interview. I think that's by far the best answer I've gotten. I think it's just so true. I think that there's so much of what you said that is so spot on and so good for any veteran or person in general to listen to. I personally believe the biggest gift any person can offer the world is just to know who they are and find a way to just own it absolutely. As you're saying that, it makes me realize I can see the way in which so many traits that will make us all successful in our civilian life, which is being who we are. In some ways, that can be suppressed in the military where there's this sense of uniformity and there's a very... There's just reasons for that, of being in extreme circumstances and having to lead in life or death situations. That liberating feeling when you're outside of that environment, to really just dig deep and figure out who you are and just really be that person. So I appreciate the way you put that. One more question before I turn things over to you for just any catch-all or anything we missed. If you were able to go back to when you just got out of the Army, knowing what you do now, what's one piece of advice you would give to yourself at that age about the career that you've set out on?

CHRIS PESTEL: I think it's about a realization of, there's a really fine line between patience and panic. And as you decide to make a jump, no matter what the jump is or how far the jump is away from what you were doing, there's that tendency that we have to get right back to the level we were at. So for instance, when you leave the military, you're trying to find a job that's gonna pay about the same or more than what you were making. It wasn't designed that way, but I had the opportunity to make a lot less, and that's a head scratcher for a lot of people. Then I took a job where I made 8.25 an hour, and that's a head scratcher to a lot of people. I don't know if those things are sustainable over the long-haul, but I'm still doing it almost a decade later. So I think I've been able to at least somewhat successfully walk that line of being patient without panicking, but at the same time too, whether it's a day-to-day thing, it teeters back and forth, aggressively sometimes. And so, I think I would try to find a way to tell myself about patience and panic.

CHRIS PESTEL: Sometimes you can tell somebody that the stove is hot, but they actually have to touch it in order to know that it is, and I think you need to allow yourself to be in some of those, if you have the ability, if you have the circumstances that allow you to do those things. Is to take that chance and don't be so worried about success coming in the form of a dollar sign. And to go out there and make something for yourself. That doesn't necessarily mean something creative. You could be building a company, you could be building an idea. But to make it for yourself, not for somebody else, not for an amount of money, and see where that takes you. I don't like that whole, "Oh, do what you love and the money will follow." You can do that, but that's kind of a recipe for a disaster.

CHRIS PESTEL: You've got to be a little bit more careful. Again, you've got to make sure that the circumstances that you have, or you have securities built in place. But I didn't either. I wasn't saving up to start a photography company coming out. And so, I was kind of forced into that world of dealing with that patience and that panic simultaneously. Yeah, I think that's a really hard thing to do because you wanna be real productive, you wanna get right back into it, you wanna go and get the MBA real quick and get this real quick and get that and get on to the next thing. I said it before about the journey being more important than the destination. I think that's kind of what helps you balance the patience with the panic, is that the moment you're in is the moment you're in and that's all you can really handle and take care of. And so having that mindfulness of the moment and that moment, if approached properly, can lead to another moment down the road. You start to piece together those things and you look back a couple years down the road and go, "Hey, I've made some steps." I might not be exactly where I wanna be, but I've made some steps in the right direction."

JUSTIN NASSIRI: That's awesome. Well, I know we're running short on time and I always like to leave the last word and the last chunk just to turn it over to you. And I know we've covered a lot about your history and your career, but anything we didn't cover that you wanted to share and just knowing you have this community of active duty and veterans listening, either about personal life or professional life, anything that we haven't covered that you'd wanna say?

CHRIS PESTEL: I don't know. I think we hit a lot of touch points along the way there, so there's nothing really standing out with it. Just take a chance, I think, is really the biggest takeaway is... If there's something you like doing, go try it. It is... Another cliche is it's never too late. Just 'cause you're reaching 30 or because you're reaching 35 or because you've already put time and effort into something doesn't mean you can't start over again. And I think there's a lot that can come from taking that chance and starting over. It's humbling, sure, but you never know until you start exploring those things, what things you wanted to do when you were 17, 18 and they come back and they smack you in the face and being like, "I guess I should have believed in that back then." 'Cause here it is again right in front of me. 'Cause when I left high school, I wanted to be a graphic designer. I wanted to go play division one football and I chose playing football at West Point. And that got me back to something very close to being a graphic designer.

CHRIS PESTEL: And again, like I said, along the way, I found these little things as I dug in my past that showed I was on the right... Not necessarily that I was on the right path, but this was something that was speaking to me my whole life. And so, it's now just a matter of time of me now believing in it, and going out there and trying to figure out how to make it happen.

JUSTIN NASSIRI: Well, I have so much respect for the path that you've taken. In hearing your story, I hear so many echoes of my own decision to pursue entrepreneurship, but in comparison, I realize how much more... How many more people go down the entrepreneurship path than the path that you went down. And so I'm just replaying as you're talking, all these conversations I had of people doubting my decisions and kind of second-guessing me and just imagining how much more you've had to deal with on that. So I just have tremendous amount of respect for your willingness to kind of answer that call and that vocation. And it does seem like what you're doing is a calling. It's not just a job. It is something that just clearly lights you up as a person and it's so refreshing to hear your perspective on your journey and to see...

JUSTIN NASSIRI: You almost see this string of fate weave throughout your story of starting with graphic design and then things coming back full circle and it makes... It seems like the universe has just supported you in this decision that you've made and you've had the courage to continuously make decisions to go down that path when I'm sure it was far from clear in every step of the way. And so, I appreciate your time in the interview, but I also appreciate the example and role model you are to other veterans of being able to take that leap, and whether that's after 20 years of service or after five years of service, knowing it's never too late to identify that passion and to go after it and you can make that... You can make that happen, and so thank you for both of those.

CHRIS PESTEL: Yeah, you're welcome. Thank you.

S3: Surface, surface, surface.

JUSTIN NASSIRI: Thanks for listening. Before you go, three important announcements. First, if you believe in what I'm doing and believe in supporting veterans in their careers, please, please, please help me spread the word. The best way I know to do that right now is by taking 18 seconds to write a review on iTunes. It would mean a lot. Second, based on my interviews, I'd advise any and all veterans to look at and the American corporate partners. Both are completely free for veterans and give you a lot of great resources for your education or professional life, respectively. Third, there are a ton of other great interviews, resources, and data at Check it out. Share it with your friends and drop me a line if you have any feedback, because I'd love to hear from you. Thanks and see you on the next interview.