Roadtrip Nation Nathan Gebhard

Nathan Gebhard
Roadtrip Nation Co-Founder

Ingrid:            Welcome Nathan, it’s great to talk to you today. Nathan Gebhard is with Roadtrip Nation, and I’m talking to him today about an incredible bit of work he’s doing, and most of it is about figuring out what to do with your life and finding a satisfying career.

So Nathan, do you want to tell me a little bit about Roadtrip Nation, and what the promise is of this thing that you have started?

Nathan:          Sure, yeah. I think what the promise is, and what it was when we started, are interesting things. I think the probably first and most important thing is to say that this was not a business that we had intended to start. This was not a big plan to do something really elaborate. It was really this place of just utter confusion in graduating from college, and not quite sure the life we were leading was the one that we really felt was true to who we were.

Ingrid:            Right, something I think a lot of people can identify with at different stages of their life, but particularly outside of college.

Nathan:          Exactly. So yeah, we did a road trip in 2001, where we just thought, if we don’t know what we want to do with our lives, lets interview people that have already figured it out, and ask them how they got to where they are. That simple idea really has evolved into what Roadtrip Nation is today. Which is still very closely connected to these deep and meaningful conversations with people that have built livelihoods around the thing that are interesting to them, that matter to them, as opposed to conforming to the social cultural narrative that exists out there. I think it really centers around authenticity. So if I were to say, what is the promise of Roadtrip Nation, or what is our goal? It is to help people define their own roads in life, to build careers and livelihoods around the world of interests that they have, and to really live out a authentic life. We do that by collecting stories from people all over the world, and sharing those stories so that people can gain insight, and then create their own way forward.

Ingrid:            Well, I’ve long been an admirer of your PBS series Roadtrip Nation. What I find interesting is, I was reading your bio, and it talks about how at the beginning you were told over and over again that being an artist would leave you homeless and penniless.

What’s interesting and I would like to also explore is, what the difference is between when you started this probably in 2001 and now. Which it seems a little more acceptable to go your own way. Do you think it’s becoming more accepted to find your way in life, or do you think we still have a lot of the same barriers of: well you have to get a job outside of college, you’ve got to start all the “adult things” that are expected of you, or how do you think things have changed or not changed since you have started this?

Nathan:          Hmm. I think certainly the world has changed in terms of the way we find our work. The idea of career is very very different than it was when we started. Not the idea, but the practice, the reality of a job. I think 15-20 years ago there was still I think a large amount of the population really felt like, if you just committed to this job and made a lot of money, you could stay in that job for 30 years, retire with your gold watch, and then live your life.

The systemic problem with that, is this idea that it speaks to this phrase, that one of the gentlemen that we interviewed by the name of Randy Komisar, he said that’s kind of this idea of a deferred life plan. This idea that I will sacrifice who I am today for the promise of who I want to be in the future. The challenge there is, there’s just no guarantee. There is no guarantee we will make it to that future, or that the world will be as we expect it. So that was like the systemic problem with which we grew up in and which Roadtrip started, but I think the way the world has changed over the last 10-15 years, is that everything is just quicker. People are not staying in one job. They are having on average 6,7,8 jobs in their lifetime, and it’s not acceptable or realistic to think there is this guarantee that if you make one sacrifice here that it will pay off in the end.

So, I think we are forced to find our way through madness, through the uncertainty, in a way that is kind of unprecedented. I think some people are really succeeding. Most of the people we interview are really succeeding by finding their course though that uncertainty by being true to themselves. I think that that has been a consistent piece that we have seen, this element of authenticity, to be able to kind of block the noise of society, to resist that influence that is just not true to yourself is really really important.

I don’t want your audience to confuse what I am saying. What I’m not saying is, everybody should be in these really outlandish, wild careers. You should go be a circus performer or be a painter. I think being true and authentic to yourself is the same whether you’re a kick ass accountant, a lawyer, a doctor, or a circus performer.

Ingrid:            Right. I know I find a lot of people now are saying give it all up and travel the world, or go live on an island, but you’re right it’s not for everyone. You can also fashion your life around a lot of things that might not be considered the most exciting career in the world. I think you are absolutely right, and I love that approach because you don’t go and just find people that are doing the outlier type things. You are finding people that are true to themselves doing all kinds of careers.

So what would you say are some of the points in how to determine that? I know you just wrote a book called, Roadmap: The Get-It-Together Guide for Figuring Out What To Do with Your Life, which is amazing. It sounds like it has exercises and things to help you figure out what your true compass is. Do you have any advice on that?

Nathan:          Yeah, absolutely. More specifically, your question was what is the advice on finding your true compass?

Ingrid:            Yeah.

Nathan:          The history behind the book was that for the first 12-13 years of Roadtrip Nation, before this book came along, we really were taking a very hands off approach. We were basically saying, here’s a bunch of stories of how people figured it out. Listen to those stories, and good luck, we hope it works for you.

Ingrid:            Right.

Nathan:          But we weren’t really sitting there and saying, well what have we learned? We have interviewed over 1,000 people for the last 15 years all across the world. We’ve certainly learned something. We’ve seen the consistent trends. We’ve seen what people have done and not done. So, with this book we really forced ourselves to say, do we have our own philosophy, and if we do, what is that? It turned out we did. I think what took so long, is we didn’t want to become the noise for somebody else. We didn’t want to say, well here’s the prescription, you need to do A, B, and C, and then you’ll make it work.

So what we created in the book is something that we feel is really true and representative in the real world. We created an open framework so that the reader can really use this book as a tool to guide them on their own path, but it’s not a prescription, it’s not a guarantee of do these things and you will have a perfect happy life. I think life is really tricky and messy. So what we have seen and what we have teased out, is this open framework that is consistent with all of these people we have interviewed, and we encapsulate that framework in the book as this idea of self construction.

It’s this circular loop of this process that we break down into: let go, define, become. The idea is that you let go of the noise of society, that cultural narrative that is inconsistent with your own authentic self. You define who you are, and what you want to be in this next iteration, and then you go out to become that thing. The follow up to that, is that we all change and we evolve, and so we go through this process again. This is something we have seen very very consistently with everybody that we have interviewed. That you are evolving and continuing to become yourself.

I think one of the most shocking things we had on the Roadtrips is sitting down with somebody like the founder of Starbucks, or the director of Saturday Night Live, or Wanda Sykes. You expect them to all say, “Well I always knew I wanted to do this, and this is how I figured it out.” What you’re more surprised by more often than not, is that they feel the need to give us this disclaimer that they’re still figuring it out. So we really wanted to create a book and a guide that was true to both the process of figuring it, but didn’t sell this short sided idea that you figure it out once and you’re done. So, the book is really representative of that.

Ingrid:            Yeah. You know, one of your quotes was “figuring out how you fit into the world isn’t an equation you solve once.” I think that is so true, and it’s so funny a lot of times. I have a friend who calls it chapters of your life because each chapter is distinct but connected. It’s funny how a lot of people, like you said, even if they are incredibly successful and seem very grounded in whatever they are doing, it was a curvy road to get there.

Nathan:          Mm-hmm.

Ingrid:            What’s interesting, is to give yourself the leeway I think to try some things, and like you said, work through sort of what fits for you. One of the things I think is the biggest problem is getting rid of the noise because I think now more than ever, you’re just bombarded with the noise of either what other people are doing, what makes them happy, what you feel should make you happy. Do you have any advice on cutting through that?

Nathan:          Yeah, absolutely. I think if I were to reflect back on my own story, and then come up to this piece, the noise was so corrosive to my own self that I started telling family members a lie. It was kind of those family barbecue conversations where the uncle comes up and is like, “so what are you going to do with your life?”

Ingrid:            Right.

Nathan:          Those stressed me out so much. So what I started to do was, I realized that if I said “I’m going to be a business major, and I am going to become a management consultant.” That was like the perfect answer for what that uncle or aunt wanted to hear. The awkward conversation ended there and they said “Oh, that’s really cool. Will you pass the ketchup?”

Ingrid:            Right.

Nathan:          So I quickly learned that if I just said this thing, it got me out of these difficult places. I didn’t have to resist the noise. If I truly said what I was feeling, “Oh, I want to be an artist, but I don’t really know how to get there.” I think I would have gotten a bunch of noise about, well you’re a pretty bad artist, which was true, you should abandon that to go be a doctor or a lawyer.

So the most important thing I would say, is be really careful about how you internalize that noise because the noise told me that I wasn’t good enough to be an artist. So I created this lie that was about business management, that everybody liked, and then literally I became that lie. I was a senior in college handing out my resume to a consultant at, I think Arthur Andersen, or something at the time, and realized that I was about to become that lie that I was telling. I think the point there, is to be really careful about when you start to let the noise really affect your own sense.

Noise external is one thing, but when it becomes internal and becomes part of your own conversation, that becomes self doubt.

Ingrid:            Right.

Nathan:          For me, the most important way in which to block that noise was to get exposure. I grew up with the idea that I liked being creative, that I liked the arts, but the only exposure I had to that was the occupation of a painter. So when I told people that I wanted to become a painter, everybody laughed at it, and they should. I was a really bad painter. I just didn’t know that there were all these other ways…

Ingrid:            To be involved as a creative person.

Nathan:          Exactly. The interesting thing about who I am as a person, I like making stuff, but I’m actually not an expert at making any one thing. I couldn’t get around photoshop very well. My 6 year old daughter can paint a flower better than I can.

I do have this deep understanding about how things could or should look better, and it wasn’t until probably a month into our first road trip where I met a creative director. He was a creative director, and did all the design work for Burton snowboards. It was just this eye opening experience where I saw a different application to being creative that matched my strengths and avoided the weaknesses that I had. Also, combined this interest that I had in snowboarding. It was just this magical moment of seeing that as possible.

Had I had this example of Michael Jagger before those family barbecues, I could have said, “You know what, I’m really interested in the action sports industry. I like the creative pursuits. I’m not a very good designer, but I know I can contribute in this role as a creative director.” That’s a totally profoundly different path my life would have gone had I had that exposure. So I think so much of the first bit of advice I would say is, watch the noise and get exposure to validate the things that you are interested in so that you don’t accept the noise as fact.

Ingrid:            Well, I think it’s also, don’t you think important to be careful who you share that dream with because a lot of people will just crush you. Then there is the self doubt. It’s kind of a careful walk you have to do in that, you stop the noise but you also don’t share it with people that are just going to say, “oh forget about it” you know.

Nathan:          Right.

Ingrid:            You’re done because that can be … When you are starting out you still haven’t gotten those little bits of affirmation, I think it’s really tough. I was also curious, when you tell someone to explore things, have you learned anything from all of your interviews about what are the best ways to explore what makes you happy, what might fulfill you?

Nathan:          Well, obviously from our experience talking to real people doing that thing, is like the absolute best way, but often you don’t know what that thing is.

Ingrid:            Right.

Nathan:          So we really think in terms of baby steps. We interviewed this woman from Google. She had this beautiful analogy, the road trippers were asking her, how did you get there, you’re so successful. She really kind of put this beautiful analogy together where she said, “What you see in me now is this person who has been successful, who could get up on stage and speak to 20,000 people and not flinch, but that is the equivalent of looking at someone swimming in the ocean and fully comfortable. She’s like, when I go to the beach, I dip my toe in and it’s freezing so I run back to the sand. Then I get in to my knees, and I run back to the sand.

What she was really saying, was you have to find these little ways to keep getting exposure to that interest. Sometimes the little ways are: if you like art, follow some artists on Twitter. Instagram is an amazing thing because people are really sharing these viewpoints with what it is like to do that thing they like to do.

I would say start really small. Think about the top 5 interests that you have and find people on Twitter that are doing those things and follow them. Do the same thing on Instagram, and see which visuals, what conversations really captivate you. Go to a magazine stand. A magazine stand is the most beautiful example of a way to explore interests. It’s ultimately one of the greatest ways we find people to interview. Because you can say, “Hmm, we have got a road tripper that is really interested in sports. Let’s grab a magazine.” When you have a sport’s magazine it’s the world of that interest, but it’s not just the athlete’s, it’s the statisticians, it’s the bloggers, it’s the writers, it’s the designers. It is a beautiful representation of what an interest can manifest to.

So, I would say that the dipping the toe in the water is social media, the getting to your calf is like magazine subscriptions, internships, and then actually cold calling people and asking them to share their story is insanely powerful. Not only are you getting the ability to explore something, but you are making deep personal relationships in the types of conversations we have. I’m still in contact with a number of people that we interviewed 15 years earlier, and instead of them being my idols now, they are my mentors and peers, and it’s really really exciting.

Ingrid:            Well, you know it’s interesting because a lot of people are afraid to do that, but if someone is truly happy and excited about their career, they want to share that with people. They love talking about it. That’s why they are in it. So, I agree you have to really reach out, and it’s surprising how much help you’ll get or the amount of people that will just say, “yes, I would love to talk to you about that.”

Nathan:          It’s crazy, we interviewed Michael Dell, who started Dell computers obviously. I got to him from dialing the 1-800 number that was on the commercial that I was watching 5 minutes earlier.

Ingrid:            Right.

Nathan:          There’s no reason Michael Dell would have wanted to interview me. I was a broke college student with no credentials, but you are exactly right, he cared about being in that moment. He remembered what it was like to tell his parents that he didn’t want to be a doctor.

The same thing with Sandra Day O’Connor. I cold called Sandra Day O’Connor from the US Supreme Court’s website, and I dialed the tour and information number.

Ingrid:            I love that. You know what- people forget about that old fashioned way of calling people.

Nathan:          Mm-hmm

Ingrid:            Because email can be ignored, but there is something about a call with a real human on the other line if you can get through, somehow roundabout and not give up. I love that.

Nathan:          It’s the scariest way to ask, but it is also the hardest way to say no for the person on the other end of the phone. It is easier to ignore a tweet or delete an email. When you are talking to someone live it is very different.

Ingrid:            The other thing you talked about is if you look at somebody that is really successful, and you say, “oh I want to do that”, and what they’ve accomplished scares you to death, or what they had to go through. Like she said, you have to look at all their stops and starts that they went through to get it. Now when you interview people do you usually go back into all the false starts or the failures that it took to get where they are? Because a lot of times people don’t think about that.

Nathan:          Oh absolutely. That is where we start. Our conversations are not the typical. We are anything other than journalists. We actually – in terms of the road trippers that we want to join us on the road, we typically don’t select journalists because they think that you are supposed to sound smart.

Our most successful cold callers and our most successful, I would say conversationalists-, are those who are just deeply interested about learning. So, we always start our conversations with sharing where we are at, and asking them where were they at when they were our age. It’s a kind of reciprocity that the more open you are, the more open they are. It’s amazing.

I think it’s really easy to assume that people always had it figured out. To say, “Oh, Howard Schultz always knew he wanted to be in coffee, and Wanda Sykes was probably the funniest person ever and just breezed right in to comedy, and David Neeleman from Jet Blue, he knew from day one that he wanted to start his own airline.” What we have found in having these deep and open conversations, was that Howard Schultz was the first in his family to go to college, and he was so poor in college that he was donating blood to eat. You have Wanda Sykes who loved and was interested in comedy, but was so nervous about it, that she was working at the NSA for like 7 or 8 years before …

Ingrid:            What?

Nathan:          Yeah, she spent like 7 or 8 years at the NSA before she fully committed to comedy. She was doing night clubs at night and then going back and diving in to national security. Then you have David Neeleman, who started Jet Blue Airlines. He was a vice president at Southwest Airlines, and was fired. He worked his own kind of sense of self doubt and confusion back up to then start his own airline.

Ingrid:            Amazing. Well now, since we don’t have much time left, could you just give us a little round up of what people can go to your website and find to help them make these next steps into finding a fulfilling career.

Nathan:          Yeah, absolutely. The website is, and what we have there is a really extensive collection of our work over the last 15 years. We have a television series on public television that we are currently filming season 13 right now. So there are about 116 episodes online. The biggest piece is what we call our interview archive. So every interview that we have done on the TV show on other road trips, we put up online for people to explore. Probably the most important tool I would encourage people to go use is the road map. It is the center to our website, and it is also deeply tied into the book. The road map is this application of combining your interests with the thing that you are fundamentally drawn to, and in selecting an interest in the foundation you get to see the personification of all these different people that have made livelihoods around similar interests. That would be the place I would start, and the book is another great way to dive into it.

Ingrid:            Well this is just fantastic. Thank you so much, Nathan. I know that I’ll continue to watch. You’ve not only started a business, but an incredible service to people who are really asking for more in their lives. So thank you so much.

Nathan:          Well Ingrid, thank you very much for the time. I very much appreciated it, and enjoyed the conversation.


Contact Us

We'd love to hear from you so send us an email.

Not readable? Change text. captcha txt