Chris Cole is one of the best skateboarders on the planet. He’s also taken more shit than most skaters on the planet – from his peers, from the skateboard community, from the Internet. In a culture where image and playing it “cool” are often more important than your actual ability on a skateboard, not many pros have had to prove themselves to the extent that Cole has. To the point of second-hand embarrassment at times, Motivation 2: The Chris Cole Story pulls you into the center of his struggle.

Directed by Adam Lough, Motivation 2 (iTunes, June 23) is the story of an East Coast underdog who made his way to the top, battling self-discovery, industry politics, and the void of a father he never knew along the way. The following is a conversation with a man who’s been put through the ringer and become one of the most comfortable-in-his-own-skin people I’ve ever met.

ROBERT BRINK: Is it challenging being under the microscope for a year to film a documentary?
CHRIS COLE: Yeah, you have to let somebody in pretty deeply. But the hardest part was really figuring out what needs to be told versus what is me trying to give you 100 percent of what happened. I’m very nostalgic and want to take you down each road and tell you why certain people and stories are so important to me. But you don’t need every story from my life; you just need the ones that matter.

What gets stirred up emotionally in the process?
The only thing that’s ever really a tough subject is talking about the fact that I didn’t have a father. And then watching my mother and my brother talk about it. I can talk about my life skating and the stories that go along with that – even tough stories, because that’s a path that I’ve chosen. But when you have to talk about feelings and things from when you were too young to control – that’s when it’s difficult.

I feel like a project like this would bring me closer to my family. There’s stuff that comes out in these interviews that I wouldn’t necessarily bring up to them.
Totally. You don’t just walk up and say, “Tell me about this painful memory.” When I see their commentary and see them on camera, it brings a magnifying glass over the fact that I don’t live there and I’m losing valuable days I could be spending with my family. It makes me wish I were closer to them. But I love hearing their take on how things were.

As I get older, I’m reaching out to members of my family asking them about things, just through this process of trying to understand myself. Maybe it’s a mid-life crisis.
No, it makes sense. Skateboarding keeps us like Peter Pan for a very long time. We play, we go out with our friends, we have recess all the time. It’s not that you’re getting old, it’s just that now you’re maturing and inquisitive. You’re really not always sure who your parents are because their job isn’t to be your homeboy – their job is to prepare you for the world and prevent you from becoming an asshole. Certain parents take that job really seriously and leave themselves shrouded in mystery to get that job done.

In the time this documentary was being made, you won the Street League Championship in 2013, but you didn’t even make the finals in 2014. You quit Zero, which you co-owned, and did the free agent thing for a while. Then you got on Plan B. It seems you inadvertently added the task of a documentary during one of the busiest transitional stages of your life and career…
Yeah, and the funniest part is that none of that stuff is really in the film. It shows primarily what got me here rather than what I’m doing here. Because what got me here is what you can’t Google. You can’t find my sponsor-me tape anywhere, for example. And that’s where this documentary really comes in.

I’ve always admired that you’re the first to admit you aren’t “cool.” And some of this film almost painful to watch – the bad outfits, people making fun of you behind your back. At a point you said, “I’m still figuring out the script.” Does that lack of script come from your father being absent, to a degree?
Yes. You’re essentially learning from scratch. There are a billion things you miss out on when your dad is gone. For example, there’s the right way to measure and cut wood. The correct way to use tools or change oil in your car. How you carry yourself when speaking to other people – people of authority, people that are older. You miss all that shit.

Did you realize at the time you were riding for them, that Jamie Thomas and Rodney Mullen were both becoming very paternal for you?
I didn’t realize it actually. My wife pointed it out. It wasn’t a conscious thing. But tough decisions came up – times I had to disappoint them. With Rodney, I wanted to ride for Zero and I had to quit enjoi. It was really difficult to make that call. Then disappointing Jamie when I had to leave Fallen. Making those calls is like disappointing your dad.

People say, “Skateboarding saved my life.” Often times it literally got them off the streets or away from drugs. But for some, it’s because it gives you the family you didn’t have. I realize now that, aside from skateboarding, this bagel bakery I worked at for eight years was my family to a degree – my coming of age. They took me to my first bar. They taught me how to dress a wound when I cut half my finger off. They gave me a work ethic. They took me to my first strip club. Some of my co-workers there even died.
That’s super true. Like being on the road with people on a skate tour: the guy you always room with or the position you have in the van; the dude that rallies the troops at the skate spot to move on. Those roles, when you start young, they define who you are for a very long time until you choose the next role in your life.

In the film, Stevie Williams says you were “Weird but good – definitely weird.” Bam Margera and Jamie Thomas added similar commentary. Are you watching these interviews about the younger you and thinking, Wow, maybe I was weirder than I thought!
I’ve self-reflected and looked at it a whole bunch of different ways. I knew how they felt back then, but I never heard any of them ever say it. I thought it was rad that they finally came out and said it, because skateboarding used to be pretty goddamn rough around the edges. But now, since everyone’s all so connected and polished, people usually bite their tongues. So it was cool to hear them say, “This dude was kookin’ it.”

The film gets into the brutally honest sit-downs you got from Jamie Thomas. The unwritten “rules” of skateboarding, your wardrobe, you fishing for compliments – all these things are part of being a kid. You’re not trying to be arrogant, you’re just excited and trying to connect with people. At some point you cross this line from being an excited kid who’s trying to share yourself with your idols to being someone who’s a kook and talks too much. To me there’s something sad about that transition into adulthood and “professionalism.”
I didn’t really think about it that way, but yeah, that’s probably what hurt the most. Here I am just being me and I’m told, “Hey, you can be you, but be you behind closed doors with your close friends only.” That was terrible for me. At that age you’re a teenager; you’re an idiot but it’s a good thing because if you’re cool as a cucumber then, are you gonna be cool as a cucumber when you’re older? I feel like everybody goes through some crappy wacky phase in their teens. Like they need to do that in order to not be 25 and watching 8 Mile once a day, convinced that they’re gonna be the rapping scientist or something. I wanna make sure that kids know that it’s all right to be a dork.

How did that hazing from all the skaters back then not cripple you? Some of what happened to me as a kid still affects me to this day.
It’s still one of the most crippling things that we have as grown ups. It’s something that affects you as a human being in general, regardless of age. If you don’t have your defenses up and someone hurts you, it will still crush you as if you were a little kid. It’s definitely still affecting me for sure. It always will.

But I’m not scared to go to a therapist. I sing that praise to everybody. A lot of dudes won’t do marriage counseling; they won’t do individual counseling; they won’t go see a therapist because in their mind that’s admitting you’re broken. Even a person who doesn’t need it at all still benefits from going to see a therapist.

The first time I walked into therapy, I had to coach myself through the door. By the end I felt completely relieved. It was the best hour of my life in a long time.
Totally. It’s like, you can play guitar, you can be self-taught, you can get good. But take guitar lessons and you’ll get there a lot faster. Therapy is your guitar lesson – your life lesson. When you leave, even if you can’t implement everything that was said to you, that knowledge went into your brain. And if you find it once or twice over time, that’s better than if you didn’t go.

What do you hope people watching the story of your life get out of it?
I want them to feel motivated to go out and live their dream. Everybody has a passion and the opportunity to change their lives. If you’re really great at math and you’re being groomed to be an accountant by your parents or whatever, but your real passion is tennis, you can be someone who plays tennis for a living. Maybe you won’t be a professional tennis player, but I want you to go for it because you can always fall back into a secondary dream. You could be a tennis instructor, for example, instead of just being like, “I guess I’ll just be an accountant.” Or you can be an accountant for the racquet company. You can work in the industry that you love. We need you.

I was sponsored but was never gonna be pro. So the next best thing was to be a writer in skateboarding...
And that’s the thing. I feel like for a lot of people, that’s not something that comes as normal; they don’t think of that. It’s basically like, I’m not good enough to be a professional skater. I’m screwed. And they just bail. And that’s not how it works. You could be a photographer; you could be a videographer; you could be a team manager. You travel the world with us, you get stamps on your passport with us and you’re in the van. You’re living that life. It’s a great life.

Sometimes just sitting there shooting photos seems way better, actually. I’ve seen the stuff you guys have to deal with on the business end of things. Or watching you guys juggle things at a big contest: press stuff, obligations. I’m like, “Why does he have to do this right before he jumps down a four-block?”
Dude, totally. We’re stressing out about our line, stressing out about a couple bad contests in a row. These sponsors expect a lot. It’s pretty crazy and people are like, “Oh stop complaining, the rest of us have it like this.” I get that all the time.

If somebody thinks that, they don’t understand that level of skating. Or haven’t skated at all. It’s hard to switch mindsets from being the celebrity skater guy to trying a trick down a gnarly fucking rail in front of an arena full of people.
That’s beautifully stated because that is the biggest issue in my entire life. It’s not juggling like, I don’t have any time as much as it’s juggling going from this brain to that brain and it’s a different dude each time. When I’m planning my contest run, you can’t hit me with, “Hey can you look at this credit card statement, make sure that everything’s charged by you?”

I watch you guys switching back and forth at these events. I just can’t believe it because I know you’re worrying about your legs locking up, but you don’t want to turn a kid down for an autograph or a person for an interview.
Well, it’s funny because it’s the “mo’ money mo’ problems” thing. The bigger your sponsors get and the better you’re compensated, the more obligations you have. When all these kids are like, “I wanna make it to Street League one day! I wanna be like this dude and be sponsored by that company.” You might wanna be careful what you wish for because I’ll tell you what – Mikey Taylor or P-Rod or myself – we’re doing a lot more than the average Joe. We wear a whole bunch of different hats all the time.

Actually, I’m gonna go on a tirade right now: When the “core” dudes try to clown, and I’m sure you’ve fucking heard it – it’s a defense mechanism – they say stuff like, “It’s just skateboarding, man.” Implying that you’re taking it too seriously.

A. You’re telling me what skateboarding is? Get the fuck out of my face. And B., Street League is a contest with a lot of money on the line and this is actually what I do for a living. This is my job. I love the hell out of skating; I love it more than anyone. But it’s not “Just skating, maaaaan.” That’s throwing what I love and what I’ve dedicated my life to, into some hobby that you kind of fuck around with. They love to throw that one around.

I know plenty of those people. I feel like that comes from a place of, I don’t know if “jealousy” is the word?
It’s a good word.

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Motivation 2: The Chris Cole Story on iTunes. Follow Chris at chriscobracole.com and on Instagram at @chriscobracole. Portrait of Chris by Mike Blabac.