John: Jon, are you prepared to ignite?

Jon: I am, indeed. Of course I am.

John: Yes, love it! Jon is the New York Times bestselling author of five books, including his most recent, Do Over; Rescue Monday, Reinvent Your Work and Never Get Stuck. He’s also a big proponent of social media with blogs that have been read by over 4 million people and more than 230,000 Twitter followers. In 2010, he used his influence with his tribe to build two kindergartens in Vietnam. Jon, say what’s up to Fire Nation and show what’s going on in your world right now.

Jon: Hey, Fire Nation. It’s awesome to be No. 953. I think that’s probably the best number I could have. I don't know who’s going to be 1,000; that’s a sweet spot.

John: It’s a secret.

Jon: I know, I know. There needs to be some buildup. So things are going well in my world. Just released a book today and so excited about kind of – you know, as an entrepreneur you go through crazy seasons and then slightly less crazy seasons. And so I'm in a crazy one right now.

John: I have to say, I understand the crazy season. I actually had the honor of shaking your hand just last week at Icon. But Fire Nation, when you're listening to this it will be about a month in the past. But got to see Jon speak on stage and actually read his book during some of the less enthralling presentations. His was definitely one where you put the book down and you just looked up and were enraptured. So loved your energy on stage, John. We’re going to get to that. We’re going to get to a lot of stuff in your journey as an entrepreneur.

But first I want to dive into what I call the one minute mindset. These are five insights into your industry. The first one being: ideally, what do the first 80 minutes of your day look like?

Jon: I'm writing. The first minutes – ideally, that’s what I'm doing. It’s me and either a notebook or a computer.

John: So a lot of people, especially writers, they say I need to use my best mental bandwidth, that will power that I have, that energy to write first thing. Are you of that same ilk?

Jon: Totally. But it’s hard because the more successful you get, the more invitations you get to not do what made you successful.

John: Yeah, we actually talked about that a little bit in the pre-interview chat. I liked your quote that you want to dance with the girl you brought to the dance. I definitely get that. John, you have a lot of strengths. I've seen them in person, live. But let’s hear about your biggest weakness as an entrepreneur?

Jon: The fear of missing out. The inability to say no to shiny things that are enticing to my ego but are out of line with what I'm trying to do long term.

John: So on the flipside, what would you say your biggest strengths are?

Jon: I would say I'm able to present intuitive ideas in counterintuitive ways that encourage you to listen and act on them.

John: So share and example of that. Because I know you have some of those in your book, but I'd love to hear one that really kind of shares why you have that as a strength.

Jon: Let’s say you have a horrible boss. Some of your audience right now don’t like what they’re doing; they’ve got a terrible boss. So there’s a lot of obvious ideas about that, but what I would say is what every horrible boss is really saying is I dare you to get a better job. I dare you to get a better job. And what I'd say to you is answer that dare. They’re daring you to work on your lunch hour on building a better career, or on becoming an entrepreneur. And so answer that dare.

Versus going: oh, it’s really hard to have a bad boss. I wish you didn’t have a bad boss. And so finding a way to say: yeah, I'm sorry you have a bad boss but they’re daring you to do something better; I dare you to answer that dare. For me, a counterintuitive idea.

John: Take that challenge, Fire Nation. Love it. Jon, what’s a habit that you wish you had?

Jon: I wish I was better organized. Email just kills me and there’s valuable opportunities that stack up in my inbox. I idolize people that are better organized. The information you sent me about this podcast, I thought: he is killing it; he’s organized. That’s so admirable to me.

John: Are there any tools you have picked up over the months and years that have helped you in any way?

Jon: Evernote’s helped a lot. There were times where I thought I need a really crazy idea system. Like 12 years ago, I would do all these ideas in binders. So I would have a catalog of automotive ideas and fashion ideas. And I would gather them and kind of it was my version of Pinterest before there was Pinterest. But once you have a certain number of ideas, you can never find them again if you don’t have a system. So having Evernote and knowing I don’t have to keep it categorized; I can just throw it in as long as I know the keyword. That’s helped me.

John: Love that. So you have a lot of things going on, Jon. You're doing some pretty serious book tours going on. Let’s be honest, a book in general. What is the one thing that has you most fired up right now?

Jon: The one thing is interacting with people who are turning the ideas into actions. It’s one thing to write a book. It’s one thing to have a podcast. It’s completely different to help people use it to do something different in their own life. So I've been doing meet-ups around the country where I'll go: “I'm going to be here at 7 a.m. and if I'll be brave to show up, you’ll be brave too and we’ll get together.” And I'll hear the most amazing stories of entrepreneurs that are working on things. And to get to see real people doing real things is fantastic.

John: Can you share a story of one of those meet-ups and something that really impacted you from being there and just seeing the impact that you're having?

Jon: I think what’s interesting – you’ve experienced this. You do a podcast for entrepreneurs but I guarantee people have come up to you and said: hey, I lost 20 pounds with some of the ideas you taught me. Or: I worked on my marriage. Because good content and good ideas go viral. Change is contagious. And so when you change one part of your life, it changes other parts. So one story I remember a woman in Austin at the meet-up stood up. And she said: “I’m from Seattle and I flew here to tell my parents I was going to adopt a child. Because I always promised myself if I got to a certain age and I hadn’t gotten married yet, I was going to adopt.

And I'm 38 now and I've just always wanted to give a teenager from the foster care system a home.” And everybody starts crying. It wasn’t a “here’s how I changed my job;” it was a “I’m going to be brave. And this is a room where I get to brave and so I'm going to share this before I have to share it with my parents.” And that’s the kind of stuff where you go: that’s what’s amazing.

John: And what’s crazy is that it’s not always completely related to the messages that you're sharing. It can sometimes just be something that comes out of that. Like I had an email six, eight months ago from a guy that said, “John, I don't want this to sound too weird but you are the person that saved my marriage. Because my wife and I, we could never talk. We would get in the car and we’d just put on music and we’d just zone out. But then when I started listening to Entrepreneurs on Fire in the car, we started talking about it and we built ourselves back by having these conversations; getting excited again about stuff.

And now we’re considering launching a business together.” And so it’s crazy, Fire Nation, what happens when you just put stuff out in the world that you know that you're meant to be putting out there and bringing people like Jon on the show, and like all the other 952 entrepreneurs that I've brought on and just sharing that. Because you just never, never k now.

Jon: Well, it does two things. It gives you hope because you're right, the business you're going to start, you don’t really know who it’s going to help, yet. You didn’t sit down with that episode and go: there’s a guy who he and his wife are headed to divorce, and maybe if I do this episode right, it will help. You didn’t know that. I don’t know the books that – you know, who’s going to actually use. And the second thing is it keeps you humble. Because I'll give a speech sometimes and somebody will come up after and go: “That line you said changed my life.”

And I'll go, “Which one was it?” And they’ll say something I didn’t say. Because when you hear somebody speak on a podcast, when you hear somebody in a speech, you internalize it with your own vocabulary and the experiences you’ve had in life. That’s part of the creative process.

John: I love that. And Jon, you have a story yourself. You’ve been on this journey of an entrepreneur. I've gotten some glimpses of it from the books that I've read and from hearing you on stage. But what I really want you to do now is pick one story. And that story is going to encompass what you consider your worst entrepreneurial moment. So take us to that moment in time and tell us that story.

Jon: I did a meet-up in 2008. I had a blog, I had some momentum. I thought: okay, I'm gonna do a meet-up and all these people will come. And so I got 1,000 stickers printed up from my blog and I brought all this candy – these Skittles – because I'd done a joke about Skittles. And I announced it and did all this stuff. I printed up all these quizzes because I thought: oh, people won’t be able to see me all at once; there’ll be a line. And I went to a room and I sat there for 90 minutes and two people came.

One person was a friend who came to encourage me and the other one was some dad that said: “Hey, my daughter likes your blog. Here, call her on the phone.” And we had an awkward, 30 second conversation and that was it. And it was really humbling but what I did in the moment, even as it hurt, I had a friend take a photo of me sitting by all these empty chairs. And I shared it and it became one of my most popular blog posts ever. Because entrepreneurs are tempted to only share the after, and we create this false world for people. And if you’ll be brave and share the moments where it doesn’t work.

Every real estate agent I've ever talked to has had that – and they’re all entrepreneurs – has had that moment where you bring 80 cookies to an open house and one person shows up and you have to do the cookie walk of shame back to the car. Everybody has that moment. So that’s what I'd say to entrepreneurs is don’t do the internet thing where you only show the positive self on Instagram and you create this fake idea of what it means to be an entrepreneur. Be honest.

John: I love that story and I love the fact that the picture that you took actually sparked a blog post that a lot of people commented on and resonated with. Can we just stay here for one second? Because I kind of want to talk to Fire Nation because we’re so nervous about putting ourselves out there like you did. You put yourself out there. You said we’re gonna get together and then you were all fired up about it and you got there and obviously not that much happens. But where I really kind of want to go with this is: is that part of the journey? Is that okay? What do you want to tell to Fire Nation and other listeners that are just saying: I want to build a movement; I want to build an audience but I'm scared to start.

Jon: That is 100 percent part of the journey. And that part doesn’t stop. I did have a meet-up two weeks ago in Gilbert, Arizona. We had 70 people sign up and the first time I did it there in December, it was an empty restaurant so I thought it would be perfect for the second time. I showed up at the door and there were 100 people out the door for the barbecue, and the barbecue place got popular in the meantime. And so I thought, this is going to be so awkward. People won’t be able to get their food, they won’t be able to find me. I'm going to be standing up in a crowded barbecue restaurant trying to encourage entrepreneurs.

And it ended up working really well. But the thing you have to remember is that as an entrepreneur, as you keep trying bigger things, as you keep building it bit by bit, you can’t act like you’ve arrived. Like you can’t try to think you’ll be done with those awkward moments. What I always tell entrepreneurs is if you want less awkwardness in your life, don’t become an entrepreneur. Have a boring job. Accept that okay, this I just what I'm gonna do for 40 hours a week for 40 years. But if you want more awkwardness and you want to be braver and be called into more situations like that, become an entrepreneur. Because you just keep having those and you gotta push through those. So that’s 100 percent part of the process.

John: So Jon, let’s do a shift now and stay with the story format but move to one of your aha moments that you’ve had; one that you really thing that our listeners, Fire Nation, will resonate with. Again, just like you did with that worst moment, take us to that moment in time and tell us that story.

Jon: Somebody asked me a clarifying question once. And the question was: are you a writer who speaks or a speaker who writes? And I'd never thought about it that way. Because they’re very different from a business point of view. A writer who speaks is somebody who spends months of their year and time working on ideas, writing ideas, the solitary of that. And then they go speak about them. A speaker who writes is somebody who travels around the world 100 times a year doing speeches, and then occasionally releases a book. And so what I'd say to the audience is that you need to clarify what are you really doing? What business are you really in? And that’s a hard question to ask sometimes.

Because sometimes in the midst of all the hustle and the motion, you start chasing down paths and opportunities you're not supposed to chase. And they distract you from the thing you're really supposed to do. So if you’ve got two things you're doing right now, I'd ask you that question. Are you a business owner who does this one thing, or are you a business owner who does this other thing? And which one is going to win? Because one of them is going to win. That’s why, before we got on the air, I asked you how many times are you speaking right now?

Because I know that the more successful you get at this podcast – and it’s already a huge success – the more operations you’ll get to speak. And the reality is, that takes time and energy and effort and so you have to be smart about what you say yes to.

John: Man. Now, when you had that question asked to you, what was your answer?

Jon: My answer was I'm a writer who speaks. And that’s scary because that’s a longer term kind of process. You know, the way a writer works, at least a published writer with a publishing company, is that it’s a two year process. Because if it’s a good book for me, it takes me about a year to write it. So now I'm saying no to opportunities that would give me initial short term gain but they might not help me create the best book possible. And so that’s – you feel some clarity but you also feel some fear. That’s what I'd say to your audience, too. When you make the right decision, don’t expect there to be no fear.

The bigger the story, the bigger the dragon. The bigger the purpose, the bigger the fear. The lie that entrepreneurs tell each other is that when you make the right decision, you just feel constant peace. And that’s not true at all. Even when you make the right decision, there will be a loud, deep fear that you jump into. That’s not an indication you made the wrong decision. That’s often an indication you need to keep going and keep pushing.

John: Loud, deep fear, Fire Nation. Embrace it. So Jon, you are a New York Times bestselling author of five books. Now, what made you to say: you know what? I'm gonna do it again. I'm gonna write Do Over. What was the thought process behind it and what was the finished result?

Jon: I realized I was an entrepreneur. I had been at companies for 15 years. I've been with corporate America – at great companies. The Home Depot, Bose, Staples, the Dave Ramsey team. And in that last role I had with Dave Ramsey, it was such an entrepreneur’s environment. It was hard to be there and not want to be an entrepreneur. It was a greenhouse for entrepreneurs. And so eventually I came to a place where I realized there’s a lot of things that this big company offers, but I want to try it on my own.

And I think we have an opportunity right now with the tools we have available to do that. I don't know how people wrote motivational books in the ‘60s and said “you can do anything.” No, you couldn’t. Like where would you go to connect with other nurses? Say you wanted to go to nursing school. You couldn’t even find other nurses. You’d go to the library, I guess, and look around for nurses. Now we have so many tools. And so that was for me where Do Over started, was that I had a massive do-over. And I needed the book myself.

And then I said the question of do other people need it too? Let me travel around the country; let me spend a lot of time online having real conversations with real people and see if they’re experiencing the same kind of career transitions I am. That’s how it came to be.

John: Jon, right now we have Fire Nation listeners who are driving to work. They’re going to be sitting in a cubicle once they get there for the next nine hours. I'll be honest; this is going to be the best 25 minutes of their day in a lot of ways, as it was for me when I was doing the same thing back in 2010, 2011 listening to Andrew Warner of Mixergy and other great podcasts. Some people are going to be on their commute home.

Some people are going to be in the gym just sweating out the stress of the day and not looking forward to tomorrow at all because again, they’re going to be doing it all over again. They want a do-over. So what is this book gonna do for them that’s going to bring them closer to where you and I are?

Jon: Here’s what I'd say. There’s two things I know about your audience. They’re capable of more than they think and it’s going to be harder work than they think. And that’s the challenge. That first part’s about hope and permission. That everyone listening right now has the permission to change their life; to change their career. We have that ability. You having a good job isn’t your company’s job. That’s your job. You enjoying your work isn’t your company’s job. That’s your job. So you have the ability.

The second part is it’s going to take hard work. And so what the book does is it maps that out. There’s a lot of great books, to be honest with you, that do a good job with the first part and they get you excited and inspired. But they don’t have a plan because they haven’t spent 15 years working on work. And there’s a lot of books that you read that have a lot about the hard work part but they don’t have any hope. They don’t have any life, they don’t have any energy. They’re not fun. Jim Gaffigan endorsed my book because it’s funny. Jim Gaffigan doesn’t endorse nonfiction books about being an entrepreneur and working. But it’s funny. And so it’s got that mix.

And so if you read the book, that’s what you're going to find: very interesting, honest stories about my own experience but also practical steps. Here’s how you figure out what your scales are using note cards. Here’s how you build more relationships. Here’s how you get boomerang relationships that you don’t know when they’re going to come back but they’re going to come back and here’s how you build more of them, because casual relationships matter. So they’re going to get a ton of information. It’s 70,000 words. I don't like when somebody creates a 400 word book and there’s 90 pages of pictures. So it’s a mix of those two things: lots of hope but lots of practical action.

John: I have some really probing questions that are coming up within the Lightning Rounds. But before we get there, let’s take a minute to thank our sponsors.

Jon, welcome to the Lightning Round, where you get to share incredible resources and mind blowing answers. Sound like a plan?

Jon: I love it. Lightning Rounds are the best.

John: What was holding you back from becoming an entrepreneur?

Jon: The simple fear of saying those words out loud. Just saying I am an entrepreneur. There’s a lot of fear and power when you actually do that.

John: What’s the best advice you’ve ever received?

Jon: The best advice was when my father-in-law said: “If you trust somebody, the contract doesn’t matter. If you don’t trust somebody, the contract doesn’t matter.”

John: What is a personal habit that you do have that you believe contributes to your success?

Jon: Using note cards. When I need to figure out a difficult idea, I map it out with note cards; one idea per card. And I put it up on the wall so that I can visually see it all. There are so many studies that talk about the difference between physically writing something down and typing it into your phone. Writing something down is still a powerful, powerful act. It’s not sexy. A note card isn’t sexy. There’s no pixels, there’s no app. But it still crushes.

John: Do you have an internet resource like Evernote that you can share with our listeners?

Jon: One of my favorite that I've talked about a lot is FutureMe. If you look up FutureMe, you can send yourself an email in the future. And so it forces you to say where do I want to be in a year from now and what do I want to be true of my life? And so then you can have yourself get an email a year from now and kind of go: wow, did any of that happen? Or if you go through a bad situation as a bad entrepreneur; say you signed a client that was just horrible. You can write yourself a warning and go: hey, you took this client because there was a lot of money. It was the worst.

Never just take a client for a lot of money because it sucks. And then six months later when you're in that same position and you're about to sign a new client, this message in a bottle from your past will come and go: no, don’t do it.

John: FutureMe. So what’s the longest in the future that you’ve sent one of these emails that you’ve actually received at this point in your life?

Jon: Two years.

John: Two years.

Jon: And you always forget. We forget what happened a week from now. So it’s a really crystal clear way to remind you of something that’s true.

John: So if you could recommend just one book for our listeners to join Do Over on our show notes page, what would it be and why?

Jon: Orbiting the Giant Hairball by Gordon MacKenzie. It’s one of my favorite books on creativity. And the idea is that organizations become hairballs. And as an entrepreneur, as a creative type, you need to orbit it close enough to benefit from the system and the size but far enough away that you don’t get stuck in the hairball. So it’s a great book about how do you balance that tension.

John: And just the title alone, I mean Fire Nation, I know that you love audio. So I teamed up with Audible, and if you haven’t already, you can get an amazing audio book for free at eofirebook.com. And Jon, is Do Over available in the Audible bookstore?

Jon: Not only is it available, I read it and I added extras. I went off the cuff during the reading of it.

John: I like to call out people on my show who don’t read their own books. Because I'm like: come on, this is your book; it should be in your voice. And I love that you can do extras like that. Another person who does that great is James Altucher. He adds great extras during his audio books. He’s cool stuff.

Jon: He’s brilliant. His vocabulary; I just want to listen to him describe things that he sees.

John: So Jon, this next question is the last of the Lightening Rounds but it’s a doozey. Imagine you woke up tomorrow morning in a brand new world identical to Earth but you knew no one. You still have all the experience and knowledge you currently have. Your food and shelter is taken care of. But all you have is a laptop and $500. What would you do in the next seven days?

Jon: I would find people that were already having a conversation about the things I'm interested in. I would understand that the things I'm good at, somebody else is interested in. And I would go find those people. Because it’s not whether or not they’re having a conversation; it’s whether you’ll be part of it. So I would figure out what am I good at and who’s interested in that.

John: So Jon, I want to end it today on fire, with you sharing just one parting piece of guidance, the best way that we can connect with you, and then we’ll say goodbye.

Jon: Sure. The piece of guidance is bravery is a choice, not a feeling. You’ll never have enough bravery to do the thing you think you're supposed to do. The market will never be safe enough, it will never be perfect enough, it will never be good enough to do that. So you get to choose bravery every day. So bravery is a choice, not a feeling. If you want to connect with me I'm on Twitter at Jon Acuff, J-O-N A-C-U-F-F and then my blog is acuff.me. And you can find my new book, Do Over, anywhere books are sold; on Amazon, everywhere.

John: Choose to be brave Fire Nation. And you're the average of the five people that you spend the most time with, and you’ve been hanging out with Jon A. and JLD today so keep up the heat and head over to eofire.com and just type “Jon” in the search bar, J-O-N. His show notes page will pop right up with everything that we’ve been talking about. Again, his website link: acuf.me, @jonacuff for Twitter. Do Over is available anywhere. The click of a button, Fire Nation, Amazon. And Jon, thank you for sharing your journey with us today. For that, my friends, we salute you and we’ll catch you on the flip side.