Are You Playing It Safe? | How to Have No Regrets w/ Chase Jarvis

0:00There's so many kids right now who are about to become a lawyer because they want to make their parents proud. that's a nice thing. But if that kills you inside, eventually you will tip and you will resent your parents. They don't realize is if they went for the micro pain of telling them now and dealing with the three, six, 12 months of transition of everybody calibrating, it will save them potentially decades of resentment and anger in both directions. My personal story is that I had a very clear path to play professional soccer. So when I bailed on that, everybody in my world was like, yo, what's up?

0:31And then I said, well, I'm going to go to medical school. And then again, And everybody was like, oh, okay, that's cool. I get it. But both of those were living a lie. Count$300 ,000,$400 ,000 in student loans, a decade off track. I mean, how painful is that? So this is me learning exactly. If you are off track by a couple of degrees and you walk for 10 years, you're a thousand miles from home. To try and not make that mistake up front is really valuable. And yet the cool thing is wherever you are right now, it doesn't matter how you got where you are, that right now you're in the driver's seat.

1:02And when that happens, the world starts happening for you rather than to you. Losing in front of others is crippling to people. Yep. And, you know, it's funny. I've had a revelation. I definitely, you know, not diagnosed when I was in school, but I have a reading comprehension issue. And just even a reading issue. I'm not a good reader. and I can give a public speech as you know in front of a 8 billion people all of them very pretty makes me feel very zen makes me want to read it I can give a speech literally actually if you're like Gary surprise you're not interviewing me for my book by the way never play it safe go to Amazon right now open another tab, order it I know this audience is a big book buying crew So I'm excited for chase on this.

1:56Thanks for the support, brother. Yeah. Look, I mean, I know you, so I know that there's going to be stuff and I know this audience. So this felt very natural, but if you were like surprise, Gary, I tricked you. You're not interviewing me for never play it safe. I'm about to press a button. You're giving a keynote to the world, the world. Yeah. You'd be on. Right. Like I would be brother. It would be so simple. Now, if you said right now, and we're recording this, there's nobody, just me, you and a couple people back you said and i'll go to a page i'll do it actually in real life read page 81 strategic renewal is simply strategy that i like already i'm as i just read that i'm already getting those feelings that i felt weird that i'm like like it's i'm not me yeah that that is what like so this one place of like knowing my reading isn't great i would do anything but i would never read class ever.

2:51Of course. And even at 40, not 48, soon to be 49, I just started reading the first sentence of page 81. And I could, I did it because I wanted to see what happened. The chemicals started to go defense in a world where very rarely do my chemicals go defense. Chase, why don't you let everybody know who you are and why we're here? Of course. I'm Chase Jarvis, lifelong artist and entrepreneur. I think most people know me as a photographer where for, man, two decades, I was one of the top commercial photographers in the world. And in the process of doing that and teaching myself along the way, not dissimilar to Gary, I started telling stories about that process and was the first photographer to really, there was no such term behind the scenes video.

3:37It didn't exist back in 2005 when you and I were recording on Viddler before YouTube. It was called Google Video. And it was that process of telling stories about my journey that really helped my footprint to expand. And I think one of the reasons that you're hosting me on your show today is because I got a great new book out called Never Play It Safe, Practical Guide to Freedom, Creativity and a Life You Love. And one of the reasons that I'm grateful to be here, aside from the others that I've listed, is because you exemplify this, my man. And this is not about seatbelts and sunscreen. It's not about going all in on, you know, put it all on red.

4:14This is how all the best stuff in life is on the other side of our comfort zone. And it requires that we take practical risk. Yeah, absolutely. And I don't think, you know, that's the funny thing. As I sat down to write this book, I was like, where's all the best stuff in life? How can I help people get there? Well, it's all on the other side of risk. It's all on the other side of fear. And the reality is that we don't have a good blueprint culturally. Our parents, our career counselors, everybody I know tells us to choose the safe thing, right to do the same things that our parents did become the you know get the nine to five and that's not a diss on the nine to five but that's not for everybody and for most people um getting that advice is really confusing and if they all the best stuff in life is on the other side of fear in a comfort zone how do we get there so that's the book that i wrote so for the people listening that really resonate with that opening line let's go a little bit more tangible because obviously so many of them hear that from me.

5:09Give me a, for instance, or a chapter or a line or a detail, like give me something that you're excited to share with this audience that puts a little more color or depth into that. Happy to do it. So just like it's easy to see how our creativity gets trained out of us, right? We go to school and if you ask first graders to come up, who wants to come to the front of the room and draw a picture, every single hand goes up. And then you ask that again by 10th grade and again when we're 20 and a lot of people, maybe half the audience might not identify as creative. But as you and I know, building a business is wildly creative.

5:44And our creativity is one of the things that separates us from all the other species on the planet. Well, just like that characteristic, our natural creativity is trained out of us, so are so many other things. like our ability, our willingness to trust our intuition, our ability to direct our attention and focus on the things that matter and ignore the things that don't, our willingness to fail and fail in public and not just in lightweight like stupid internet meme fails, but I mean fail like take the L in Gary V language. And there's a handful of those. Those are all natural states within us, our intuition, our attention, our willingness and ability to fail and get up gracefully.

6:28Those are all things that are naturally within us and have been trained out of us. And so this book is about specifically how to get back on track with that stuff. Is that trained out of us, Chase, in your research and your subjective opinion and your gut feeling. Do you believe that we all are willing to go there out the womb and then our family, our parents, our society, our microcultures, our religions, our cultural cultures, the moment we're in in society and what's going on in the macro, they become the things that suck us out of it? 100%. And I mean, you can just watch a baby. The first time a baby starts to learn to pay attention.

7:14You can tell it's naturally their eyes follow mom and dad around the room. Now, I don't have kids, but I'm enough of an uncle to know that I've seen that happen. And that is our natural state. The same is watch. I mean, someone like so many kids that I know, if they didn't have the adults in their life to tell them to not jump off the, you know, the banister or not do all sorts. And I'm talking about physical, but the same thing is true emotionally, just like that idea like, hey, who wants to come up to the front of the room and draw a picture for me? Every hand goes up in first, second, third grade.

7:47And yet all that cultural conditioning. And here's the scary part. The world does it to us, but we also do it to ourselves. That organ between our ears, our brain starts adopting some of these fears and traumas that happen to us. And we do the dirty work to ourselves. And so my goal with this book, I mean, it could not be more in line with you and your message is how to basically go on offense to stop playing defense because it's in playing defense that we live the life that everybody else wants for us rather than what we want for our own precious life. Do you touch on or do you think about regret?

8:26Because I think when I hear you speak, what drives me, no question, is whether it was DNA wisdom, instilled wisdom, the circumstances of a very interesting first five years on earth, the Soviet Union, the immigration, spending time with my great-grandfather a lot of my day.

8:50I just always knew that if I didn't, that when I was older, I would be sad. Like, and then that word sad, that was me talking as a kid. In my older age, I'm like, I'm mitigating regret. I'm passionate about sharing what I'm sharing right now because I'm curious about regret. Yeah, it's a big deal. And insecurity. It's a big deal. And that's one of the reasons that I was at a good time in my life to write this book because my company had just been acquired. I thought I was ready to just jump right in and do the next thing and you know I the company was acquired in October I did a year with the with the public company that bought it and then cool I'm I'm out on my own I'm thinking cool I'm gonna rest through the holidays in January I'm just gonna jump into all these projects and the reality is is I need to rest and I was like wait a minute what's what's going on here and when I really excavated in there I it was important to me to do a little research and realize, man, what do I want to do?

9:54Because my biggest fear is regret. And I had gotten sucked into, I mean, you know me, I'm an artist and an entrepreneur. And the fact that I put myself in a position as the CEO of a venture-backed firm to get acquired and have to do time in somebody else's big public company. I'm not a public company executive. And I was like, man, so many tiny betrayals. And yet, I've recovered from all of them. So there's simultaneously this awareness like, man, I just keep putting myself in positions where I don't know how I got here. And then all of a sudden realizing it doesn't matter how I got here. I've got the tools to get out and to live a life that I love, that I'm proud of, that I'm excited about.

10:37And to be fair, on paper, everything looks magic. What I'm afraid of is at the end of my life, And if you do the research, most people at the end of their life say the one thing that they would change is they would do less of what the world expected of them and more of what they wanted for themselves. 100%. That's why I wrote this book. Literally, I was in that position myself. I get it. I will say this. I believe that so many people do things that are well intended. There's so many kids right now who are about to become a lawyer because they want to make their parents proud. that's a nice thing totally that's not bad yeah um what i keep desperately trying to communicate is but if that kills you inside eventually you will tip yep and you will resent your parents and then you are actually creating a more likelihood of you and your folks not having a good relationship then the reverse so many kids right now don't want to tell their parents i don't want to go into family business i don't want a lawyer i don't want to be a doctor i don't want to be an entrepreneur because they want it to be good because they love their parents.

11:45It's good. They don't realize is if they went for the micro pain of telling them now and dealing with the three, six, 12 months of transition of everybody calibrating, it will save them potentially decades of resentment and anger in both directions. You just nailed it. And I'll tell you my personal story is that I had a very clear path to play professional soccer and pretty much everybody in the world that I know, if you can play pro sports, yeah, you do it. Right. And I was aware professional soccer in the US wasn't that developed at the time. I would have gone overseas and there were some pluses and minuses about that.

12:19And so when I bailed on that, everybody in my world was like, yo, what's up? And then I said, well, I'm going to go to medical school. And then again, everybody was like, oh, okay, that's cool. I get it. But both of those were living a lie. I didn't want to play professional soccer. It took me years to tell the world that. And then I also didn't want to be a doctor, but I was terrified. And the people that I was running around with, if you're a smart, hardworking, talented person, go be a doctor or a lawyer. It's hard to, you know, you know, that's a good thing. And yet I was immediately terrified of that.

12:50And I knew instantly that I didn't want to do it. And yet count three,$400 ,000 in student loans, a decade off track. I mean, how painful is that? So this is me learning exactly those lessons. And two things are what's important that your listeners pay attention to right now. Two things. One, that if you are off track by a couple degrees and you walk for 10 years, you're a thousand miles from home. So to me, you know, to try and not make that mistake up front is really valuable. And yet number two is also true. When you do betray yourself and you will, we all do. We do it all. It's the human flight.

13:27Totally. It is. That word betray, you know, words matter. Like it's a funny, you know, it's funny how that's landing with me. It's an interesting, like, I'm, it's, I like it because it's giving it power. Yeah. They're tiny betrayals, to be fair. And the cool part is, what did you say? They're tiny betrayals. Yeah. And that's the, that's the cool part is like, I had, I had done that many times and we all have, but the cool thing is wherever you are right now, it doesn't matter how you got where you are that right now you're in the driver's seat and to me that made all the difference rather than beating myself up it's like cool it doesn't matter pull myself up by the boots by the bootstraps and start walking in the direction of who you want to be and what you want to become and when that happens the world starts happening for you rather than to you that more than anything more than anything to me that's the punchline it's not that we're not going to screw up because all again, I've cited I'm hundreds of thousands of dollars in student debt.

14:30I'm years off track. I also had all kinds of, you know, Instagram beat me to the company that Facebook acquired instead of my photo app, which beat Instagram to a million users was the first photo app. Like, and so technically I lost a billion dollars that day. And yet is the most valuable experience of my professional career. And it changed a lot of my behavior. So this is why we resonate when we're hanging out. Let me go a different route because that's a story of luxuries. Like you're epic and you almost got there. Let me give you a different version. Sure. It's the Julio Cesar Chavez, Meldrick Taylor story of life.

15:08I'm going very nerdy, especially if you're not a boxing fan. You have no idea what I just said. If you're a casual boxing fan, you have no idea what I said. If you're a boxing fan like I am, you know exactly what I said, which is there was an undefeated Mexican fighter named Julio Cesar Chavez. He was like 77 and 0, or I don't know what his record was at the time. But he was huge. And he fought this kid, Meldrick Taylor, great fighter in the US. And he lost 11 rounds and 2 minutes and 40 seconds of the fight. And I was pumped. I actually wanted Meldrick Taylor to win. And I watched with my great uncle, Misha who passed away since I miss him a lot.

15:49He was a father figure for me. And fucking Julio Cesar Chavez knocked out in a very controversial call. He knocked him down. The kid got up, Taylor. The fight should have not been waved off but Richard Steele, the ref waved it off. But he won the fight in the last 10 seconds. That's how I think about what you're talking about. If you're listening right now and you're 61 years old and you've been a fucking failure. relationships, professionally, friendships, like by all objective standards of the 8 billion people on earth, you have not won. You're lonely, you're financially in a bad spot, you're not happy, you're not enjoying.

16:35The fact that you could listen to this, decide to take on accountability and put in work, whether that's therapy, exercise, diet, the information all of it no shit uh who you surround yourself with and change the course and enjoy the last 30 years of your life chase that drives me every day that's true that is literally why i wrote the book because i realized that and the cool again to me the best part about this whole thing is this is not an outside game you don't have to move to france you don't have to change your clothes. You don't have to do anything. All of this, it's an inside game. And you can start immediately with very, very basic tools.

17:21And that's what I tried to create in Never Play It Safe was a little bit of a blueprint. It's called the practical guide because it's ruthlessly practical. You can't read it and not actually make progress on the things that are important to you in your life. For the people that won't be able to get the book, which hopefully is a small group. Give us a practical one, two or three, like give us a little deeper to give them a little preview. Sure. Well, let me ask you a question. Please. And there's a lot of people, you know, myself included that may be struggle with paying attention. And yet that is a superpower, right?

17:55Because the same thing that makes you have whatever your diagnosis of attention deficit is when you do focus on something and it's usually something that you love and it's important and matters to you, how deep can you go? Well, I'll go with you on that one. Let's talk about, actually, let's talk about that completely. I believe that my paying attention skillset is the greatest. I would say in a world where I have a lot of things, I'm an F. I think it's A plus. There you go. To your point though. The world might not have you think that. Correct. Because I really spend no time paying attention to things I'm not interested in.

18:31Yep. I'm sorry, science teacher, fifth grade, Mr. Molnar. Big shout out. I'm going to assume you're not still alive. But if you are, please email me. But if you're the child or grandchild of Mr. Molnar, who taught in Martin Luther King Elementary School in Edison, New Jersey, please send me an email to say hello because I'd love to know you. And also, please let me apologize to what I'm going to say. But I didn't give a fuck about what Mr. Molnar was talking about because I did not give a shit about Saturn or Jupiter. Jonathan Cazadoi, who I know is still alive. I've seen him on Facebook. Big shout out to you.

19:06He was a nerdy science kid and he did give a fuck. Like I, you know, to me, the concept of paying attention to something that's not important to you or you're interested in, like cool, you'll get bad grades, but what did that really mean? Nothing. And like, I'm willing to fight this fight till the cows come home. I don't see that as a weakness. I think lack of candor is a weakness for me. For sure. Not being able to tell the people around me what I actually feel because I don't want to disappoint them because I like rainbows and sunshine. That's been a big detriment for me. Fair enough. Let's stay focused on that attention thing for just a second.

19:41I'm sorry. I got excited because I've been on this, but let's go to yours. No, no, but here's the punchline to that is, let's just take your attention. So the world will have you believe one thing, right? The world will say that, that fifth grade, that's a real predictor of your life, and it will start to program you. And this is the kind of conditioning that I'm talking about when the creativity gets conditioned out of us, our belief in ourselves gets conditioned out of us, unless you have the family, the parents, the mom that you had, who can help you realize that no, the thing that the world is telling you, you that is a weakness that that can be an absolute strength and that's this is why the chapter starts out with our ability to pay attention it's not pay attention in school it's not pay attention to what your mom or dad says it's pay attention to what you love because your ability to direct your attention toward the things that matter to you is going to save you hundreds of thousands of dollars in student debt it's going to save you years of walking down the path that somebody else chopped out for you instead of the one that you want.

20:44So that's an example. That's the first chapter in the book about so practical, but how do we do that? Well, it's a little, it's an inside game, right? You have to be able to ask yourself, what do you care about? And I'm telling you, if you can look closely there and it's not that hard, you can do this in a weekend and then you start to follow that thing. The world, again, as I said before, the world starts happening for you rather than to you. In a real, in like a real, real way, Yeah, you this is one of the reasons that I, you know, we had to have this conversation is you literally epitomize this, there's so many aspects of you that you have articulated very clearly for a long time, that the world would have you believe one thing about yourself, whether that was because you were an immigrant, whether that was because you didn't pay attention to Mr.

21:31Molnar in fifth grade, whether there's a half a dozen, you know, easy examples. To your point, I wonder if you touched on this thematically, like the world told me I was going to lose and I didn't believe them. This is, this is a really, really important point, right? What you choose, what you chose to pay attention to, what you choose to now, if you're listening to this, it matters. And you can start today. You can literally start today. If, for example, you had a framework in the relationship that you had with your mom who believed deeply. It was two things in me. it was positive reinforcement to your point about my, with my mom.

22:09And it was the other one that really tipped it. Cause I think we're all a little cynical to our parents being like, you know, there's always a little like, of course my mom loves me. It was the success at the baseball card shows, the limited state. Like it, you know, it's so funny. I sit here as a 40, almost a 50 year old man. Now I'm only fucking 14 months away. And the two things that gave me positive reinforcement, the market business, my mom around my kindness and my soul. That's who I ended up being. I ended up being a nice businessman mogul. Yeah. And this is the system working, right? But so many other people, they will find themselves in, they're trying to participate in the system and then they find, they find themselves in a position where they're disconnected and it doesn't work for them.

22:57And then they're pissed off. And then that has a really negative cycle. And what I'm suggesting, what I wrote this book about. I did my own stunts, by the way, on the audio book. So if you want to listen to it, that's just fine too. But when you get disenfranchised and you get frustrated at the world letting you down, you have to remember Gary's story. Like there are things in your life that if you direct your attention to them and you trust, that's another big part of this book is learning to trust your intuition, that voice that we all have inside of us that we're told to ignore, we're told to not pay attention to.

23:29but that was actually the part of you, the baseball card lemonade stand part of you was like, wow, this is fun. I am good at that. I want to do more of it. Even in a world that says lemonade stands, you're like, hey, I'm a money machine. I'm a money factory. And when you paid attention to your parents, you paid attention to what your mom, for example, who reinforced you, you paid attention to what you loved and what the market told you you were good at. It was at the confluence to those things that you found a life that you, I mean, you couldn't imagine this. You sat on my couch in 2010 and you were wide eyed and you couldn't, you're like, you know, I simultaneously can't believe this.

24:07And you know what I was planning for it. I knew it was going to happen. I will tell you like the form factor that it took was surprising. The internet being famous was like having famous in your parents' liquor store. Yeah. I never in my mind did I think the general world would have awareness of me. I always thought, because this was an 80s, 90s businessman talk, I always thought my industry of choice, like for example, at 15, I knew that I was going to be wine spectators, retailer of the year, and that I would be famous in the liquor store industry. So I always thought I'd be businessman famous, because I knew I was going to be fucking unstoppable and crush.

24:49But selfies at the airport all the time in my life? No, that was that was for actors, That was for athletes. That was for musicians. That was wildly surprising when we first met because at that point I knew, oh, shit, that's coming. And that's the kind of – this is one of the reasons I love this conversation is because that's how far back we go. Yep. I was the first person that I knew who had a video person following me around in 2005. And I remember you walking in going like, these are employees. And I'm like, yeah, these four video people right here, we're doing this show. This is – and you're like, yeah, uh-huh.

25:23And you know what? Your ability, this is like another example. You felt that in your core because you were attuned to that moment plus 100 others. I'm not saying that's responsible. I can give you one right now that I want you to do. I want you personally to go on TikTok shop and on a platform called Whatnot. Get your books into Shopify. Tap it into Whatnot. And I want you to sell books on live shopping because social shopping is real now. Done. I go way back with live internet. You know that about me. Yeah, no, I know that, which is huge. Anyway, I need to run. Listen, very simply, never play it safe.

26:00I wanted to sneak this in as a live podcast. I'm so glad I did because shit, I just know. And honestly, I'm looking at it physically. It reminds me, I actually have it here. Yeah, it is so crazy how similar. Yeah, it's the same size. It is so similar to Crush It in size, which is obviously the breakthrough book for me. And so I really think this will be a breakthrough for a lot of you. Chase, thank you for being on the internet nation. Go grab a copy or actually grab two, buy one for somebody for the holidays who needs a 2025 in a happier way. Thanks Chase. Much respect brother. Thanks for spending time together.