Career Crashers Episode 15: Jason Rink on the Journey Toward Your Dream Career

He spent a year in film school, working towards his dream career. But he couldn’t afford it. So he dropped out. Then he spent ten years in the financial services industry. But he wanted to make movies. So he started creating. He became resourceful. He pursued his dream career and did what he could to make it happen. And he made his dream career a reality. Now, Jason Rink is the CEO and Executive Creative Director of Simplifilm–his own film studio–and has created his dream career. On this episode of Career Crashers, Jason shares his story and how he leveraged…

He spent a year in film school, working towards his dream career. But he couldn’t afford it.

So he dropped out.

Then he spent ten years in the financial services industry.

But he wanted to make movies.

So he started creating. He became resourceful.

He pursued his dream career and did what he could to make it happen.

And he made his dream career a reality.

Now, Jason Rink is the CEO and Executive Creative Director of Simplifilm–his own film studio–and has created his dream career.

On this episode of Career Crashers, Jason shares his story and how he leveraged opportunities in other roles to launch a career he loves.

Related: Career Crashers: Leaving Wall Street Behind to Found a Startup

Also Related: Career Crashers: Building Your Career Launchpad with Projects and Apprenticeships

Topics: – The Journey Toward Your Dream Career

  • Jason’s dream career journey–from dropping out, to banking, to film
  • How creative people are often perfectionists, and why you’ve just got to launch it
  • How to look around at what types of new career opportunities your past interests and career capital would be well-suited for
  • Using a financial services role to learn highly-valuable skills
  • Why a role at a non-profit worked as an intermediate step between his career in banking and starting a film company
  • Why working for others is often the best path to working for yourself


Learn more about Jason at: jasonrink.com

Learn more about Simplifilm at: simplifilm.com


Also listen to this on iTunesSpotifyAnchorTuneIn, and Overcast.

Full Transcript: – The Journey Toward Your Dream Career

Welcome to Career Crashers, where we tell the stories of those who are not content to wait around following rules and hoping for good things to happen. Great careers aren’t found. They’re forged.

It’s time to crash the party.

Hey, Career Crash listeners, we want to take a second before the episode to let you know that we have a brand new pocket book out called Crash Your Career. You can pick it up on Amazon or at crash.co/crashyourcareer. You’ll learn how to launch your career without waiting on gatekeepers and standing in line. Applying many of the lessons you’ve heard from guests on the show. Go to Amazon or crash.co/crashyourcareer. Now onto the episode.

All right, on this episode of Career Crashers, I’m joined by Jason Rink. Jason, what what would you, I mean, what’s what’s your title? How should I introduce you you own a movie production company? Is that correct? Is that how you talk about your current role?

Yeah, that’s that’s what I am. I’m a I’m a commercial film producer, for primarily business to business type video content online. Everything from, you know, feature length documentary style stories to short brand documentaries to explainer videos and book trailers to, you know, online content for every part of a business’s sales funnel.

So lots of different types of content that I’ve done over the last several years. And I have a company right now called Simplifilm, that I’ve got four employees of. I have another production company called Dig Deep Films that we just launched, which is kind of an original content play. So a lot going on.

But yes, I’m in Austin, Texas, in the video production world.

So, my guess is you studied real hard, went to film school, got a film degree, put it on your resume, somebody hired you, right, I’m sure that’s your path?

Well, the funny thing is, is you know, I’m, I’m, I’m a little bit older than maybe the people that are going through the that you’re talking to about entering their dream career journey.

You know, I went to college, my first year in 1992. And I did go to film school for a year. But you know, that was actually back in the day, when one day a guy brought in two big suitcases with a computer in it. It was like, here’s how you do computer editing. And it was like, you know, 100,000 plus dollars for this, you know, nonlinear editing thing.

And I remember thinking, Man, real films are shot on 16 millimeter. So, you know, it was before that whole revolution, but I did spend a year in film school, couldn’t afford it, you know, dropped out, and ended up sort of just meandering down a career path of, you know, I went back to college and other time dropped out again, I’ve dropped out of multiple institutions of higher learning.

You know, to my parents dismay, and what ended up happening is I, I wandered into the financial services industry, and I ended up spending about 10 years there. So I had this dream to be in the creative field and making films. And I just college wasn’t working for me, especially in the world, I just wanted to make movies.

When I dropped out, I found that I didn’t have a whole lot of other opportunities to get into the industry. And, you know, I ended up getting married, had a family early. The next thing I know, I spent 10 years in commercial banking. And I turned 35 years old. And I looked up from my cubicle, I had a nine year old son, I’d been married for almost 10 years. I said, Hmm, 10 years is probably going to pass. And if it does, I’m going to still be sitting in this cubicle, you know, making good money, by the way, have having tons of vacation time, and totally unfulfilled.

So I had this sort of dream career crisis at 35. And I was like, I got to make a change.

So, let’s back up, let’s back way up. When you were like a kid, what, what was it that made you think? When did you start to think that you would like your dream career to be something in the arts or in a creative sphere?

Yeah, you know, I remember shooting videos with my a couple of friends of mine in high school, you know, probably when I was 14, 15 years old. You know, and again, this is in the 80s right? So video cameras being accessible, like was just sort of happening. And but what I remember happening, We would shoot these little videos and skits and we would be like doing funny stuff. And we’re entertaining ourselves. We’d show them to people. And I remember thinking how easy it was to just make a film. I was like, Oh, this is fun and easy, effortless.

And people would would say to us, like, Wow, that’s really cool. I don’t know how you did that. And I was like, Oh, I don’t know. It’s just like, you just do it. And I had this realization that not everybody wanted to make movies. Like, I thought that when I was in high school, like, of course, everybody would want to make movies. Who wouldn’t want to do that? They started to realize, no, that’s not what everybody wants to do. And so, you know, I did have the freedom to just sort of choose my path in that my parents wanted me to go to college.

When I said, Look, I want to go to film school, they were like, Okay, well, that’s college, and they knew I had a passion for it. So in that way, I was definitely supported in it. But I don’t know, it just was like, sort of the next logical step. I was making movies with my buddies in high school. And I’m like, Well, I’m supposed to, I’m graduating. So what am I gonna do? Well, I guess I’m gonna go to film school. And so that’s what I did. But I did, I did have that desire for a number of years before I made that choice.

I love that realization that, oh, not everybody wants to do this.

It’s interesting, the things, often the things that we think everybody is good at. Turns out, most people stink at them and are scared of them. And like comes easy to you. But it doesn’t to them, things that you think everybody would think are fun. A lot of people hate and are terrified of.

And when you have that realization, that’s usually a good indication that there’s money to be made there. Because something that comes easy to you, and it’s exciting to you, you’ve usually got an advantage in.

Yeah, and and you know, that that insight really served me when I came back around when I was 35 years old, figuring out like, wait, I don’t want to do banking for the rest of my life. I don’t even know how I got here. By the way, what do I want to do? And I went back to those clues in my history. Like, I was like, Man, this desires never gone away.

I even like, did a few film competitions, like just kind of on the side while I was still, you know, in commercial banking. And I was like, you know, there’s really some, like, there’s piles of stones along the way that indicate, maybe I should go down this pathway. So when I decided to make that leap, I did a big, I did an inventory of like, my dream career capital at the time. And I was like, how can I make a shift into doing what I want to do.

And what I ended up doing was, I had an opportunity to just sort of get involved in a nonprofit on my dream career journey. So I pivoted to an executive director position of a new nonprofit. But that was actually kind of a secret way for me to make my movie. Because what I ended up doing was I started, it was a political Libertarian education nonprofit. And I just decided, you know what, I think I should make some video.

So I just started making videos, because I had a budget and we could tell some stories, it was part of the mission of what we’re up to. And I ended up just going down that path kind of accidentally made my first documentary. In fact, you know, I didn’t have a ton of money. So I actually used Costco’s generous return policy, to fund my camera for the for the video, like they have a 90 day return policy. So I got like a Nikon kit off of Costco and use it for 88 days, returned, it got got a Canon, you know, used it for another 88 days. And, you know, I finally kept the last one.

I did that three times over a year. And I was like, so any means necessary to get me to get this film made? And again, that was another indicator. It’s like, what when would I What else would I have done this with? I would never have done this in banking to like, get the job done, you know, but here I am being totally resourceful. Trying to figure out, didn’t know what I was doing. totally clueless.

I look back on that first film, and I and I cringe. And yet, like it was my calling card that opened doors up for me. Because I also realized something was that by creating and finishing a film, I had joined a club. That’s called launching, making something and putting it out in the world. And that is like an elite club in many ways compared to the people who actually think about doing it or want to do it or talk about it. And one of the things that came from that process was me, turning into a creator, who honors other creators, and it’s made me way less of a critic, because I’m like, man, there’s so few people out there actually creating stuff, that it’s just a honorable thing when somebody actually launches something. So anyway, man, that experience was really transformative for me.

That’s really powerful words, like, give me somebody who’s made a crappy movie over somebody who’s talked about making a brilliant movie any day. You know. And that’s hard for creative types. Especially because it’s tend to be you have a vision of what you want to be able to do. And you kind of are perfectionistic about it. And like, you don’t want to put something out into the world that you’re embarrassed of.

But at some point, you got to just, you know, click publish, or whatever, whatever the right terminology is.

Yeah, and, and on that note, like, at this point, I’ve, you know, me and my team, we’ve produced, you know, hundreds and hundreds and hundreds of videos, conducted over 100 interviews, you know, like, hundreds of animated videos, all sorts of stuff. And I can’t think of a time where what we launched didn’t, in some way, fall short of what the perfect version was, in my mind. And the more I talked to people who are creative, especially, like, that just is always the case.

I mean, it’s never done, you can tweak these things forever, you get diminishing returns, so you’ve got to launch it. And the thing is, is you get improvement every time you start to discover your voice. And it really is incredible.

Well, the the money that Costco did not get from those videos, maybe it’ll be made up for by this plug for Costco. Yeah, in the episodes free advertising, my wife and I used to go on dates at Sam’s Club for the free samples, and we’re really poor, and we first got married. So…

That’s terrific.

There’s always a way.

I want to come back in a minute to the whole sort of parlaying the nonprofit thing into a film thing, which I think is interesting. But first, let’s go back before that, was the was the quitting film school and/or the going into banking? Was that was that selling out? Were you giving up on something and you should have done something else? How do you look back at that time? You say, Man, I really sold out and just went into banking and got a quick job? Or what do you what do you look at those years, as you know?

Well, frankly, I think there’s a lot of mindset work that I had to do over that time, because I just didn’t even see that it was possible.

Like, it’s only in retrospect, now that I recognize how strong the entrepreneurial drive is in me, now that I’ve been in business for myself for a number of years during my dream career. I recognize, I can’t do anything else. Like that is just how I’m designed.

It kind of ruins you as an employee, doesn’t it?

Yeah, Yeah, it does. And I want to say, I don’t think that everybody’s supposed to be an entrepreneur, like, I don’t know what it is, all I can speak to is like, this has been with me my whole life. It wasn’t until I exercised it, I actually started my first business. When I was in high school, I had a band, I opened up a business banking, accounting, like at 14. So it’s kind of always been a part of my story.

But it always seemed like it was super far away. Like, or I just, I just believed that there was a path that you wander, or you went through in life that was like, get a degree, get a job, rise in the ranks. And then, but I don’t know how business owners or entrepreneurs were born, like, I couldn’t figure that out. I started to see that rising in the ranks and banking, I saw what the top of that was. And I was like, I’m not interested in that in my dream career.

So something had to happen in me where I was like, wait a minute, I can start a business, I can create, go out and be on my own and create value and do it in that way. And so that was, that was what had to happen for me.

So, and I and I also really honor my journey. Like, there’s so much that I got out of my experience in commercial banking, frankly, when it comes to how to talk to clients how to how to operate at a higher level of thinking, I learned a lot about writing and communicating myself, and teaching other people in that environment. And so I really think I can’t speak to why the road went the way that it did. But I can see how I just gleaned all of these different tools and things and experiences that created the toolbox that when I finally did start my own business on my dream career, I had all of this equipment that I wouldn’t have had otherwise. So…

Yeah, no, I, it’s funny, I can relate to that so much. I had a, you know, 10 years span of working in different places before I launched a company, even though I had a very vague idea for something kinda like it, way back then 10 years ago, but I just didn’t really know what to do with it.

On the one hand, it’s like, man would have been great if I had the confidence to start earlier? Who knows where I could be. On the other hand, it’s like, I look at what what happened in that 10 years, and the things that I learned and gained and the person I became, and I think, man, I wouldn’t have been able to it would have been impossible. If I didn’t have those things. You know, like I had to have those things they were necessary to get here. So I like the way you put it. You want to honor your your journey.

So when you went to the nonprofit, you see this opportunity to get out of banking, you realize this isn’t where I want to be long term. There’s a sort of a cause or a nonprofit that I believe in, I’m interested in, they’ve got a role here, I can fill it. And you kind of, what made you see that as a potential side door into film production, because I think that’s a pretty cool, that’s a pretty cool way to see it. Because to not say, well, this isn’t a film opportunity, which is what I really want. So I’m going to turn it down, but to say, No, no, this gets me closer. And maybe I can parlay it. I think that’s pretty cool. Tell me about that.

Yeah, so one thing I would say is, you know, being where I was at stage in life, where 10 years, married nine year old son, like, the decision to like, go off and pursue this other path. That was a challenge to make it because you know, mortgage, all that stuff.

One thing my wife told me, though, she knew I was itching, she was like, like, she knew I was itching to go forge my own path. She’s like, you’ll never be able to tell our son to pursue his dreams if you don’t actually do it and start you dream career. And you got to do it. I was like, You’re so right. And so what happened was this opportunity, I at the time, I had been involved in some political activity in Ron Paul’s 2007 2008 campaign. I was doing that on the side. And I was building up a little bit of a capital out there, I had been in organizing and speaking and I was starting to make some relationships. So I didn’t realize I was kind of building a side gig. It was unpaid.

But I was, I was building a platform out in this other space. And so when I had an opportunity to sort of leverage that platform, into this other direction, all I had to think about was, is this guy, does this have the potential to move me closer or further away from where I’m trying to go? And I was like, I’m going to be running it. I’ll have a board of directors. And I’m interested in the ideas like, that was the thing I was doing in my spare time at the time. And I didn’t think I want to make political videos my whole life. No, but I said like, Well, I became really interested. And I have an opportunity.

And here’s a way that I can actually get a paycheck, less money, big sacrifice, but I just saw that it was a pathway that could set me on a course that could eventually take me there, I think it’s super important to look at the opportunities before you be clear about your alignment, like where’s it I want to go in my dream career? What do I want to create my life? And then look at opportunities and say, does this move me further away or closer to my dream career, because that’s where the opportunity to sell out is.

I think we sell out when we take something and we say, this is moving me further away from my dream. But it’s a temporary, like, that’s where I think the selling out actually happens, at least for me. That’s where I’ve seen it.

Yeah. And I think that’s really, that’s really cool that to just break it down to doesn’t move me closer. Even if it’s only a little bit closer. It’s easy to get stuck in Well, this is slightly closer, but it’s not the big thing. Like if it’s a real opportunity, and it moves you a little closer, Don’t be afraid to take it. And it’s pretty cool.

I also love in your in your story that you mentioned, this nonprofit opportunity arose because of stuff you were doing in your free time with your interests and politics and whatnot. And I and I think sometimes it’s easy to underestimate how you operationalize your interests. Okay, I’m interested in this, I want to do something with it. Let me get involved in some activities, do some, you know, let it Let it be known that I’m interested in this. And let me bring my skill set, maybe a skill set that I can’t usually use in my day job to bear in this interest. It’s often that that’s the very type of stuff that spins up the next opportunity.

So so you get in, you’re running a nonprofit, and you’re like, Hey, we could tell stories with film. Let me let me turn this into one of our projects. And it was sort of from there, you realized you had something special?

I mean, in a way, I mean, I ended up you know, the film made its money back, we didn’t spend much on it. And it built relationships, and it gave me a calling card. And what’s really interesting about this, the way that this story goes for me is that I was the executive director of this nonprofit. I became my own boss, I actually became a terrible executive director of that nonprofit, let me just say something honest, you know, and but as my own boss, but what ended up happening was so so this is 2012.

Well, a company called Emergent Order, production company that was putting out content that I really loved. They were up in New York City, they decided to relocate down to Austin and I had made a film, I’d put something out into the world, it wasn’t great. It wasn’t even close to the quality of what they were doing. But it gave me an opportunity to introduce myself to John Popolo, who ran that company. And they hired me on there.

That was also really interesting, because I actually went to work for somebody else for about three years. And I ended up transitioning out of that nonprofit in a bit in a big way. And I was like, wait a minute, I’m going to work for somebody else. But what I what I did was I looked at it, and I said, Okay, I can spend the next several years bootstrapping another project, learning the hard way. Or I can go take this really paid apprenticeship at a production company that I really admire world class talent. And it was through that I was like, one of the first people hired.

When I left a few years later, there was only four of us. And then when I left, there was 24, people, I had had the chance to write, produce, direct, do all sorts of stuff, like I just, I was able to just 10X, my own ability. And by the time I left there, I was confident in my ability to produce and direct the kind of product projects I wanted to do, versus if I would have stayed in my entrepreneurial role working in this smaller way. It would have taken me so much longer to learn all that stuff.

So even in the way that that journey came together, I want to highlight like, Hey, I had to go out there and be a creator, for that opportunity to have opened itself up for me. If I hadn’t been creating, just waiting, and then like, Hey, can I come work for you guys? It’s been like, no, because you haven’t? Who are you? Yeah, add something to show. It was my signal in the marketplace, right?

And then I went back to work for somebody to get equipped in a, in a more robust way for the next level, which was then to launch my company, which has been now for about four years, totally on my own. It’s been around for about six years. So you know, I would say that too. Like, there could be an opportunity where working for somebody else in an organization might be exactly where you’re at and where you need to go. And that it can actually supercharge your journey towards your dreams as well.

Oh, man. Yeah, I often say that. Working in fundraising for a couple years, was the best training I had before I started a company and I kind of went into it deliberately, for that reason, like, I’m not interested in just fundraising for its own sake, but I saw a lot of skill sets that I could build. So it’s like, Alright, let’s take this opportunity, because I think I can parlay that if I can. If I can raise money for a nonprofit, then I’ll know how to how to get customers and investors for a company or whatever.

And just being able to see that there’s a maybe an indirect route to something that you’re not ready for is really key skill. I can’t I’m keep seeing your story and comparing it to my story. Because I keep seeing parallels. I’m not trying to hijack your story, Jason, where can people find out more about you and what you’re working on?

Yeah, just check out JasonRink.com is my website and find me on Facebook or Facebook’s where I’m at, you know, so find me. I’m friends with you, Isaac on Facebook. So if you find Jason Rink, friends with Isaac Morehouse on Facebook is probably the right guy.

And, man, I just want to salute you for what you’re doing. I want to encourage anybody who might listen to this, like, just take advantage of the time and season you are in your life to get clear on what you want to create in the world. And then just move forward.

Start creating today in a way that will produce what it is that you want to want to make and what you want your legacy to be in the world. That’s what I would encourage anybody to do. And I think what you guys are doing is amazing. So…

Man, we got to turn that last little bit into a little clip for social media sharing.

Hey, thanks so much, Jason, for joining us.

Yeah, I appreciate it, man.

Like what you hear? Go to crash.co and join the career revolution. Do you want to share your own career crash story? Send it directly to me at isaac@crash.co.

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