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Chris Do

In this two-part episode, Chris is joined by therapist Nidhi Tewari and designer Stefan Bucher to discuss knowing when to quit and when to persevere.

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Knowing when to quit (Part 1)

Acclaimed NFL coach Vince Lombardi once said, "Winners never quit and quitters never win." It's a motivating and catchy sentiment, but famed marketer Seth Godin begs to differ. In his book, The Dip, he argues that quitting can be the best strategy.

In this two-part episode, Chris is joined by therapist Nidhi Tewari and designer Stefan Bucher to discuss knowing when to quit and when to persevere.

Like it or not, the free market rewards exceptionalism. Success goes to the obsessed. But where is the line between intense focus and toxic hustle? And how do you determine if what you're grinding away on is worth it?

Knowing when to quit (Part 1)

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Mar 1

Knowing when to quit (Part 1)

In this two-part episode, Chris is joined by therapist Nidhi Tewari and designer Stefan Bucher to discuss knowing when to quit and when to persevere.

In this two-part episode, Chris is joined by therapist Nidhi Tewari and designer Stefan Bucher to discuss knowing when to quit and when to persevere.

Be exceptional or quit.

Acclaimed NFL coach Vince Lombardi once said, "Winners never quit and quitters never win." It's a motivating and catchy sentiment, but famed marketer Seth Godin begs to differ. In his book, The Dip, he argues that quitting can be the best strategy.

In this two-part episode, Chris is joined by therapist Nidhi Tewari and designer Stefan Bucher to discuss knowing when to quit and when to persevere.

Like it or not, the free market rewards exceptionalism. Success goes to the obsessed. But where is the line between intense focus and toxic hustle? And how do you determine if what you're grinding away on is worth it?

Greg Gunn

Greg Gunn is an illustrator, animator and creative director in Los Angeles, CA. He loves helping passionate people communicate their big ideas in fun and exciting ways.

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Be exceptional or quit.

Episode Transcript


When should you quit? In winners, you've heard this expression before, winners never quit and quitters never win. Sometimes that idea sends us into the state of becoming workaholics and pursuing goals that are no longer worthwhile. How do we know when to quit?

So I reread the book, The Dip, by Seth Godin, and this book is very similar to other books that you might have read, like The Obstacles Away by Ryan Holiday or Mark Manson's book, The Subtle Art of Not Giving an F. There's a lot of books out there, true Grit, that talk about a similar idea about not quitting, but is it creating an unhealthy culture around work and celebrating grinders, and what's the difference between all this stuff?

Now I'm going to share with you some of the big ideas from the book, the Dip by Seth Godin. And I'm hoping that, by the time that I finish telling you some of the big ideas, I think you, too, will see that there's a big difference between the things that I believe in, and living and staying in a toxic, destructive relationship, whether it be at work or at home.

So we've all heard that expression from Vince Lombardi who once said, "Quitters never win and winners never quit." Seth says, that's a bunch of BS. Winners quit all the time, they just quit the right stuff at the right time. They quit the wrong stuff and they stick with the right stuff. You have to have the guts to do one or the other. And quitting, he says, is often a great strategy. He points out something because the market loves a winner.

There's something called Zipf's Law, Z I P F, Zipf's Law, where they have done research and studies that shows the value of being the best in the world. That number one is 10 times bigger than number 10, and number one is 100 times bigger than number 100. And they look at the sale of ice cream of all things, that the percentage of sales for vanilla is 10 times more than praline. I got to be honest, I didn't even know what praline is. That the difference between number one, number two, and number three is not just a little bit different, it's a lot different. And he says, from the market, from a buyer's perspective, if you have cancer, you're not going to want someone who's average. You want best in the world. When you're new in town and you want a restaurant, you don't want an average place, an okay place, you want to eat at the best restaurant. And when we're hiring people, we don't want to just hire an average person based on an average resume, we want the best most qualified person.

And this brings up the idea of scarcity, which is reinforced throughout the entire book. Scarcity is a good thing. Scarcity creates value because it's hard to come by. I think that's why people are trading on NFTs right now, because it's one of one, it's a non-fungible, non-exchangeable thing. That we've been lied to in school and to get this idea we're all wrong, that being well-rounded is the secret to success. The free market rewards exceptional, and if you can't be the best and you've determined you can not be the best, you don't want to be the best, you don't have the resources, the passion or the determination? Quit, but quit before you start.

So there's a big difference, and he makes this distinction between strategic quitting versus reactive quitting or serial quitting. Some of us are serial quitters. When the short-term goals don't line up, we quit even though we know the long-term goal is good. And the book is called The Dip. In The Dip, he talks about is that long slog between starting when it's really fun and you're getting a lot of results, and mastery, the difference between beginner's luck and real accomplishment.

He goes on to talk about adversity is your ally. It insulates yourself from competitors. I love this line. Success goes to those who obsess. Success goes to those who obsess. And I have to admit, I'm an obsessive person. I find a way to succeed in light of the obstacles. So before you quit, ask yourself this question, what if I could win in the marketplace that I'm already in? What would that look like? How would that make me feel? See, a lot of us get discouraged because we're not making as much progress in the time in which we've set for ourselves. And I think the culture, the marketplace, our friends, media have created an unrealistic expectation that we're supposed to be successful when we just barely try.

So when people make posts on social media and they say, "It's not working, Instagram isn't working anymore." How many posts have you made? 12. 12? I'm at 900 posts myself. Oh, YouTube, it's too late, it's too late. How many videos have you created? Four. See what I'm saying? Something's up there. Now, when we talk about the value of scarcity, we can look at magazines and how magazines are sold. In the fitness space, whenever they feature a model on the cover that has amazing abs, sales go up. This is why abs sell magazines. It's because getting great abs are difficult to attain. Scarcity. And when we look at exercise, you quit before you reach the moment. The stress causes your muscles to grow because it's human nature to quit when it hurts.

So what do we need to do? We need to anticipate The Dip as part of the journey that, that is a natural and wanted barrier to competition. No competition means what you're doing is not scarce. We can look at the jobs that command the highest dollars. If we look at the executive branch of any organization, the C-suite, they get a disproportionate amount of money, and we can make an argument later why capitalism is evil. But facts are they get a disproportionate amount of money because there are few of those roles. They do things that are hard to come by. They go through school in training, they put in, sometimes, years of working in the dark where no one knows about them to get to a position where they're able to be in a position where they can make those decisions.

So his advice is if you can't make it through the dip, do not start. Don't play the game if you can't be the best in the world. Do you want to be a superstar? It's really easy to be a superstar. Find an industry, an occupation, a job, a thing to do that has a really steep dip. Few people can do it. Doctors are paid well because it's difficult to go to school, it's difficult to go to graduate school, it's difficult to go through the residency and their practice and the supervision and the certifications to maintain your license. It's difficult. If you want to be a superstar, the goal is to eliminate your competition by creating a dip so long and so deep, the nascent competition cannot catch up. These are barriers to entry.

So yeah, we've been in this game for a while. I've been making videos, now, on YouTube, for over seven years. Over 800 videos. That sounds to me like a barrier to entry that's built on 20 plus years of making commercials and music videos, which is built on top of studying design for four years. We look at companies like Apple who've built incredible barriers to entry. Apple's got an amazing ecosystem that chains together a bunch of technologies, which makes it really hard for a company to enter. It's built on the Mac OS, running on Mac hardware, oftentimes with proprietary ports, so only those people who are licensed to make peripherals can work within the Apple ecosystem. They have iPhoto iTunes, the iPhone, the iOS, Apple TV, Apple Watch, wireless speakers, wireless earbuds, airdrop, the phone speaks to your computer, which speaks to your TV. When you update one thing, it's all connected. When I take a picture on my iPhone, it transfers my desktop. You see, these are natural barriers to entry.

So if you're in an industry and you don't like competition, and one could argue the whole point of going in business is to reduce or eliminate outright competition. The barriers to entry are your friend, adversity is an ally. So here's the decision you have to make; either quit or be exceptional, because being average is for losers. There's a study that they cite. Salespeople often quit after making the fifth contact. What they don't realize is 80% of customers buy on the seventh attempt. Here's the gem: change the tactics. Never quit the big idea. So if you set out to do something in your life, a career, make a difference, make an impact. Because you're not getting the results that you want today, don't quit that goal, change the tactics on how you get there.

The market wants to see you persist. It demands from you a signal that you're serious, determined, that you're the safe bet. What's the opposite of quitting? It's not waiting around for things to happen. The opposite of quitting is rededication. Implementing an invigorated new strategy designed to break the problem apart. Before you even think about quitting, amplify the long-term benefits of not quitting. Think about what the end result looks like, and if it still excites you, get through the dip.

Nidhi, what do you think about what you're hearing right now?


Yeah, well, it's an interesting concept because it demands that either you go all in or you just don't bother at all. And I'm just not a big fan, most of the time, about black and white thinking like that, where it's either one thing or it's completely the other. I think that there's a lot of gray area. But I will say that when it comes to developing expertise in an area, there are a number of challenges that come up along the way. And I can say that as a therapist and somebody who's building authority and thought leadership in the mental health realm, it has taken years, a decade plus, to be able to get to a place where I can even consider myself to be an expert. And there were many times and many struggles along the way, and thousands of dollars of investment in coaching or consulting and training, et cetera.

So there were many dips. I would consider those all dips, times that were quite exhausting to have to get through, and it did pay off at the end of the day. I can't deny that. So I can see it being applicable to my own life in that, I think I'm also obsessive in a lot of ways, like you are, Chris, maybe not to the same degree that I would sacrifice as much as you have to be able to get where you are. I think that, that's pretty tremendous. But I will say that I do go all in when I want to do something, and it does mean a lot to me to invest the time and energy. At some point, it's, well, I've already invested five years, let's do more. Seven years, let's do more. 10 years, let's do more. So it's that small steps principle where you've been able to push yourself to a certain point, so why not push yourself a little bit further and push yourself a little bit more beyond that in order to achieve the optimal goal there.

So I don't know, I just wonder, I guess my question is I wonder if there's any gray area. Is this too black and white? And what is the gray area, then, where it's between quit, don't even begin if you're not going to try to go all in, or the other end of the spectrum being a hundred percent all in, expert or nothing. I don't know. I don't if there's gray area there.


I think to be able to answer that question, what we do, what we need to do is we need to study people who don't go all in and are super successful because that will give us some information. As Jim Ronan said, success leaves clues. I can only cite my own life, and you're citing your own experiences. We can study the people who we admire and look up to, and we can ask ourselves some questions. What did they quit, what did they stick with? Because I think being successful is about quitting the things that you need to quit, and sticking with the things that are difficult that you want to have and to push through the pain.

So another line from the book, never quit something with great long-term potential just because you can't deal with the stress of the moment. And I have two boys, and watching them grow up, there are things that suck. When my son, Otto, was taking Latin, he did terrible at the beginning, up until the point where he did really, really well. Both kids know how to speak Mandarin. They hated it for a while, until they got better at it. And so I think we can see in children it's, you know what? There are things that suck for a little while, and then you get really good. Both boys studied and played the piano for a long time. One person after putting in, I think, the amount of time, decided this is not for him. We respect that. He stopped. The other one continues to play piano with a great deal of passion and actually composes music now, and is experimenting around with avant garde music compositions.

So I want you to think about that. Nidhi, help me out. Help me out, and I'm going to come back to you where you can say, here's a couple of people. And so I just look for data. I think history is filled with people who try and are serial quitters. And if we look at the bell curve, if you guys can imagine a bell curve, the bell curve is high in the middle and thick in the middle like a bell, and it tapers off on both the left and the right edge. So if we look at that in almost every application, it seems like the majority of the people are stuck in the middle. There's a few people starting, there's few people who achieve that level of mastery, master chef, master architect, master therapist, master public speaker. And there's a lot of middle of the road average people. And maybe that's okay.

And in a little while I'm going to talk about all the ways when you know should quit because it's begging this question, how do you know you're doing something that you shouldn't quit?


I have an example, Chris, of somebody who became really good at one thing, but it was by happenstance, I think. So I'm thinking about Thomas Edison. All right, so this is a man that tried out a million different inventions. I'm literally looking at his list of inventions. We've got the kinetoscope, we've got the electric pen, we've got something called the pastometer, we've got something called the phonometer, we've got something called a carbon microphone, which I guess, went into phones, we have a vitascope, things, mimeograph, things that nobody has ever heard of. So at some point, this man had to have tried all of these different inventions out with the hope that they were going to be successful. And at some point made the determination that I'm going to quit, and that's not the one, it's not taking off. Until he stumbled upon, or maybe not stumbled, but discovered or created or invented the incandescent light bulb, the phonograph film, movie cameras.

So I wonder if we take this example of somebody who everybody knows, Thomas Edison, someone who was a serial inventor and probably failed quite a few times, and it wasn't for lack of going all in, I would think. It just wasn't, maybe, the right idea or just didn't take off. So I'm curious what your thoughts are about an example like that.


I don't know if that's a great example to make your case, Nidhi, because this is the person that never quit. They didn't quit the long-term plan, which is to make something and contribute to society. They would try one tactic, that didn't work, they would try another, and they just kept trying different things until they were successful. This is the kind of thing I'm championing, so I want to be clear about this.

So if we can refer back to our friend, Mo, he was having some success with his new business and all the measurements seemed to be pointing in the right direction, which was he was growing, he was growing his company, he had better leads, better clients, he was getting more referrals, his sales numbers were moving up, and then he wanted to try something else in addition to this. So this is the opposite of what I'm talking about because in most books that I've read, they pretty much say the same thing. Mark Manson's book, The Subtle Art of Not Giving an F says, don't give an F about a lot of things, but give an F about something. So in essence, he's saying quit a lot of things that don't matter, focus on the thing that matters.

And I think that's the problem that a lot of people have. They start too many different threads, they try to acquire too many well-rounded skills, and they never get through the dip of achieving mastery. Remember that part at the beginning? The dip is the gap between beginner's luck and true achievement. And I'm going to go through a whole list of reasons why you should quit so that we can get some clarity around this. Stefan, welcome to the stage.


This whole discussion is so interesting to me because you are, obviously, such a prime example of a tenacious and flexible person with a goal that you're just, you are not letting go of it and you are pursuing that relentlessly. And I think what I would really like to know from you, also, is how you measure success. Because where this all came from for me, and what started the discussion between you and me, was that you shared this anecdote of going hiking with your son, and you went up the hill and just, I don't know if it was five minutes or 500 feet or something below the summit, your son said, "You know what, that's it for me, dad. I'm turning around." Which, first of all, I thought was a really funny line and I'm going to steal that.

But then you said, this is what you see in your colleagues and what you've touched on already of people that, they get almost to the point where they're going to get to their goal or they're breaking through and then at the last minute, they pull back. And what struck me about it is, do you have a correct reading on your position in your journey? Because on a hillside, it's fairly easy to see, okay, well I'm 500 feet from the summit, the weather is good, I just have to push through. But then in career settings, it's very hard to see, am I actually on the hill that I think I'm on, is what looks like the summit, the summit, and are there, what are the forces that are helping me and that are pulling me back? And so, in your call with or in your space with Nidhi one or two weeks ago, you talked a little bit about the metrics that you applied to your work. And I don't know if you want to recap any of that.


First of all, Stefan, I just want to say it's so good to hear your voice and to hear the way you phrase questions and sum things up, and just remind me a little bit of the context for our discussion today. You're absolutely right, in this very clear example where we can see the top, and it's a matter of a couple hundred steps, it's not even that much where he can see it and he's just like, I'm done, dad. But in real life, things are not that clear. We don't know what the top looks like, we can't see it, we don't know where there is. And I think I picked this up from the book where we asked ourselves this question, under what circumstances are you willing to quit, and by when?

So I think a lot of times when we read books on goal setting and vision planning, I think most of us get really vague about what done is, what success looks like. So we don't know if we've crossed it, we don't know how far we are because life doesn't seem to be that easy to measure. And that's why I think we need to make this decision with great intention. This is what we want. So in the very clear example of the hike, we know what the top is. I know, literally, on a map, what it is. I've seen it before and even if I didn't, it's the end of a cul-de-sac and you could go further, but you don't need to because that's it. It's the end of the paved road.

And if we say, when would I quit, under what circumstance? Well, if it's really cold, it's freezing cold and we're both shivering, if it's dumping rain on us, or if the sun is scorching, searing hot and we don't have a hat, I'm just feeling I'm baking and the sun is not good for me, I would quit. If my legs cramp up, because my legs do cramp up from time to time, and then I have to hobble back. So if I'm feeling that cramp, if I feel the tingly, I'm going to be very mindful, I might stretch out a little bit, but obviously, I don't want to cause any long-term problems. If, for whatever reason, we're completely dehydrated and suffering from dehydration, we would quit. If I got a call from my wife, my mom, my dad, someone's in the hospital and we need to attend to this, I would turn around. If my wife says, I'm locked out of the house, can you let me in? I would turn around. I already know these conditions before starting, so I'm 100% committed to seeing it through.

Obviously, my son is still a young person, he's still thinking about other things. Most likely, he's just motivated to go home and play video games again. And so he's like, dad, I'm done. This is good enough. But for me, it's really clear. So when we're talking about in business, I'm pretty clear my mind to what the goalpost looks like and it's super ambitious. I'm clear about my physical health goals like, why do I need to work out, why do I need to watch what I'm eating? Because I'm clear on that, too. And I'll do everything I can because I do have that single-minded obsessive determination to get there.


I'm really happy to hear you talk about these things and because you're very clear about it and you're very intentional and I think that's why you're here. And I think I'm here to bring up the wishy washy, what the hell am I doing side of things, where I think what you are doing is exactly right and is something that I certainly, in my career, have never done enough of, which is to be very precise. What does success actually look like and what does failure look like, or what does an unacceptable condition look like. For me, I also have, I think, a similar obsessive energy to you, but I think I have, maybe, a comparable engine to you, but a shitty nav system.

And so I think there was a lot for me, there's always been a lot of, oh, wait a second. Well, this is not what I set out to do, but that's really interesting. Let me run after that for a little bit. Or, oh, well this is really cool, let me play with this for a little bit. And also have been very suggestible where people were like, oh, have you thought about doing this with that thing that you do? And I go, oh, well sure. And I've not had the clear compass that you've had. So I've, then, started a lot of different things with great vigor and great dedication, but without any metrics to guide me.

And then I've had multiple burnouts. I've done a ton of therapy over the last 10 years, and that's also brought me to a point of seeing and setting goals outside of business that, then, led me to reevaluate a lot of the things that I had set as business goals where I was like, oh, I want to have, I do this series called The Daily Monster, and I was like, oh, I want to have that be a TV show. That suddenly became the overarching goal of it. I have to make that happen. I invested a lot of money, I invested a lot of time, but I had no metrics, and I also put myself in a situation where success wasn't solely, or even 50% determined by my effort, but also by submitting myself to the judgment of others. And then, as I've gone through therapy more, I've figured out, oh, my goal isn't to have a TV show, or my goal isn't to have a design award or whatever. It's, I want to connect with people and I want to feel like I have a family in this world.

And so then, that changed a lot. And so I think when we set out to start this conversation, what was very much in my mind is, how do we figure out what those metrics are, and what are meaningful metrics, and what are things that are metrics that are under our control?


Time for a quick break. But we'll be right back.

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Welcome back to our conversation.

If you guys don't know Stefan, he does this thing called Daily Monsters where, the ones I've seen, you put a little ink on a piece of paper and you blow it and create some weird blob. And then through creativity and imagination, he's able to create a little character out of it and they're wonderful to look at, and he's been doing this for a really long time. And I would encourage you guys to check out his work just to see what the heck we're talking about.

Now, let's just take, for example, and I love that you say, and I know this about you, too, because we went through the same school, we survived and have shared trauma over going to the same school. And I know hard work is, you're not allergic to hard work, so that's not the problem. You said you have a really good engine, but maybe not the best nav system. You mentioned about being easily distracted about other fun, creative, interesting ideas that you create for yourself or when other people suggest things to you, you're easily suggestful, as you say. And so you might have a little case of the old ADHD, shiny object syndrome thing like, that looks fun, let me explore that.

But from the book, I got these questions and one of the things that it asked you to do is to be honest with yourself and say, are you making progress? Are you making progress towards this goal of turning Daily Monsters into an animated TV show? So what we want to do is we're in one of three states always when we're asking ourselves this question about making progress.

One, am I moving forward? Am I falling behind or am I standing still? This is very important for us to ask ourselves so that we know, man, I've been doing this for 10, 15, however many years, I feel like I'm regressing or I'm standing still, and it's either I need to change the tactic or to ask myself if this all works out, I'm actually able to create this show and I'm the executive producer or the creative director or something, of a cartoon and I can select, yes, that was my life's work, and that's still worth pursuing, then I suggest you find a different tactic.

So I think a lot of this, too, is setting the intention that this is one of my life and not being shy about it and putting it out into the universe, this is what I want, in many places as you can, and just keep saying this until someone you know can connect you to someone that you need to know.


You talked about meeting a person at E who really helped you out where you were doing pitches, and it was not coming together and this person started helping you do pitches or write contracts. Am I summarizing that about right?


Sort of, not a hundred percent. It was just through a chance encounter that I'm like, I need a producer to help me. And someone connected me to someone at E and she did one bid for me and left the Excel spreadsheet. That's all I need. I'm a fast learner. And based on that one spreadsheet, I was able to figure out how to start bidding projects and it changed the trajectory of my company.


I thought that, that was so massive and so generous of you to mention at the time, and to mention it again, now, because the thing that I always talk about is that if you're really talented and which is just an accumulation of work and reinforcement and training over years and years and years and years, and if you pair that with grit and effort, what it does is it buys you a ticket to the lottery. It doesn't guarantee a lottery win. And I think it doesn't, necessarily, have to be this huge lottery win the way we're shown, sometimes, in the movies where it's like, oh, all of a sudden you're discovered as you're in the right place at the right time, and all of a sudden, all the doors open. Sometimes it is just, you meet a key person at the exact right time.

And I think that was, I was very impressed and I was really gratified that you mentioned that at the time, because I think it also demystifies it a little bit. Because what I think, what I sometimes react to a little bit in these discussions that are being had all over the place about how do you get there and what are the obstacles that you remove and how do you stick it out and everything, is that the element of placing yourself in the path of good fortune, but then, also, intersecting with that good fortune, isn't always addressed and it's very easy to get to a point of success, and then erase your tracks a little bit, and I'm so grateful that, that's not something you do. And I try to do the same in the stuff where I've been successful in my design practice and the good stuff that's happened has been me working really, really hard, but then having somebody come along, somebody who was in a position to, I guess, what do they call it, a force multiplier? Somebody who comes along and goes, oh, I see you're working really hard. I like what you're doing. Let me introduce you to this person. Let me give you this opportunity.

And that's where it gets a little bit tricky with the whole grit discussion is that, for me, it's the way I sometimes perceive the presentation of it is, it's all about your grit. If you work hard enough and if you stick with it long enough, it will for sure happen. And I think in reality, my perception, at least, is that if you work really hard and you stick it out and you bring all your grit to it, as long as you stick it out, there is a chance that you will find opportunity. And as soon as you remove yourself, you will not find that opportunity anymore, which is a different thing, I think.


One of the things that I think, and I appreciate you mentioning this, is I have a pretty decent memory. I'm terrible at faces and names. I've run into former students and I stare in their face. I'm like, have we met before? Dude, I was in your class for two semesters. I'm like, oh, I'm so sorry. I'm just so bad at that. But I do remember certain things because I find that capacity to remember, I prioritize certain pieces of information. And one of the things that I can see so clearly as is, this event happens because this thing happened, and making the decision to do that and show up here, and they all seem very clearly interconnected, and I am not so delusional that I think all of this was some God-given magical gift that I'm able to float above the air and not have to work through things.

And I also believe in this, that everyone who's successful has had good fortune or luck happen in their life. And I also believe that when luck keeps happening to you, it's no longer called luck, it's just working hard, being open to opportunities so that the opportunities can present themselves to you. And being brave enough, sometimes, to walk through the door into the unknown that you can receive this gift. And this is really important. And I'm also strangely obsessed about certain things, and I can forget about everything else.

So this goes back to the whole, in school we're taught to be well-rounded. Everything in moderation. We've heard this a thousand times, you might have said it a couple times, yourself, everything in moderation. Oh, you, that's toxic, being so focused on something. But in a lot of the books that I read about really hyper successful people, it's that they have this singular obsession. They might be horrible human beings, sometimes. Steve Jobs, not known to be the best human on earth, but his obsession with some things made him great in very specific areas. I wish it were possible that Steve was an amazing inventor, but also a kind human being who took care of the people in his life, including his daughter and his ex-wife. I wish that were the case. I don't think these are mutually exclusive, but sometimes, people who are singularly obsessed tend to be bad at lots of other things. And so when we say you need to quit lots of things and focus on the thing that really matters to you, that's what I'm referring to.


I think that's absolutely right. And Steve Jobs is a cautionary tale always, to me, where I'm like, oh, change the world massively. What device am I calling you on, at the moment? And at the same time, I want to take, if you'll allow me, I want to see if there's a little detour here because there is absolutely, I agree, you have to be single-minded. And certainly, if you're [inaudible 00:36:53], and to wrap your head around that level of impact, like what you said, you want to teach a billion people and the single-minded focus that Jobs had and that some of the other titans have, is something that I don't even know if my brain is wired for. And I think that takes a special kind of just makeup, like a self-contained fusion reactor of motivation and giving yourself permission.

I worry a little bit, and this was also at the root of let's have this conversation, is when you're only hearing from the people that succeed in the way that is shown as this is what success looks like, is Steve Jobs as a success, Christo as a success, that's the level. Then it's easy to take that on into your psyche and measure yourself against that. And as I get older and as certain things that I've done have worked out and certain things have not worked out in the way that, maybe, I would've enjoyed, and others have worked out much better than I ever thought, I'm basically, my entire career, I'm also interested in how can you forgive yourself, successfully, for how can you live with yourself and go, you know what? I'm pretty happy with what I'm doing, I'm pretty happy with the stuff that's coming out of me, I'm pretty happy with the way that I am interacting with people.

When you've had that dream, if you've never had the dream and you're just like, oh, I like a sandwich, then that's great. But if, like you and I both, as you mentioned, went through the art center thing and we went into this whole, how big shall my private jet be, thing, and then you come to the point where you go, I don't think the jet's coming. And possibly, as I'm getting older, I'm like, do I need the jet? I think I'm okay. I feel almost heretical saying it in this space is, how do you create a kind off-ramp for yourself, should you choose to go off?


The thing I enjoy really talking to you about, Stefan, is you have these deep thoughts and you also create different sparks in my brain, and so I'm like, oh, let me think about that, too. And so I'm going to tell you about a couple different things that may or may not relate, exactly, to what you just said, but I'm going to use this opportunity to speak about things I normally don't speak about.

One thing is that my wife and I, we both went to art center, and she has lived most of her life supporting others, supporting her mom, her sisters, and then her boyfriends, and then her husband, me, the business, everything. And so she's now in her fifties and waking up one day and saying, when do I get to prioritize my life? And I've been saying to for years, now, "the only job I want you to have is to find your own happiness, to find your own voice and to find your own way." So for her, that's success. That's the goal in life right now, to live for herself and not to think of others always before her, to always to take the passenger seat to make the compromise because the kids want to eat X or they want to go to some other place that she doesn't want to go to. And so there's a lot of reprogramming and unpacking that we have to do.

She's also a middle child and didn't have the ideal childhood either, but nobody does. And so that's a goal for her. I think it's worthwhile goal. So in the last five years, she's reupped and rededicate herself to find her spiritual voice and a connection to higher purpose and belonging and developing friends that she can connect with on a deeper level. And I think, for me, that is the thing of beauty. And so you're right, I think in our culture and our society, we can put certain people on a pedestal and who become titans of industry, but there's a heavy price to pay for that. And then we look and reflect back on our own lives, as well, I'm pretty far away from that, and now I feel bad. And then we start making decisions not for ourselves, but to please someone else. And I think that's the wrong decision to make.

So each and every single person gets to define, for themselves, what success looks like, what your big idea is, and also to give yourself permission to change that big idea when it's no longer in alignment with what you know and feel. Because the whole point of growing and living is to change and evolve our thinking over time. And the danger to this is sometimes, we tell ourselves, oh, it's no longer in alignment, when that's not the case at all, we're just avoiding certain kinds of work to get there, which is the thing that the lesson I was trying to share with my son, which is, "You know what? You just need to get there, son." And he's like, "Dad, how long do we have to go on these hikes? How often do we need to do this?" And I say to him, "I'm more than three times your age, boy. When you can keep up with your old man, we will stop. That's your goal. If you can beat me, I will stop."


I love the fact that you talk to him like a civil war veteran. I see you, now, with a gray beard, I'm sorry.


I'm a hairless Asian. There's no beard here.


When you beat me up this hill, boy. That's fantastic.


I just tell him, I said to him, "I'm double your age." He goes, "No, you're not, dad. You're three times my age." I'm like, "See what I'm saying?"


Oh, god.


See what I'm saying? These are old bones, my knees hurt, and you still can't keep up with me. Come on, boy. We can do this together.


If your kid ever plays a full set at The Comedy Store, I will be there because he's got a good line, that kid.

First of all, so much power to your wife. That's such a great journey to go on. And it takes so many people so long to get to that. And I have, I see it all through my life. I have this discussion with my mom, who's 74, of what's just for you and what's not in the service of somebody else? And at the same time, she's like, "Oh, but I loved doing it for you and for your dad." It's a big shift to go, okay, what do I want? And I think one of the things to think about is, can you bring as much creativity to your life goals and what you value, identifying what you value, even, as you do to the work?

Because what I've found in my life, in the year, I spent, easily, 30 years, I'm 48 now, I spent good 30 years just being obsessed with, I want to make this business thrive. I want to do the best possible design I can possibly do. My first book, I hand curned every word on every page. Absolutely ludicrous endeavors because I was like, that's what it takes. That's what it takes, as you said, to create this barrier for entry, to create this, to distance yourself from the pack. And I'm glad I did it because I don't want to ever look back and go, well, I didn't really try to your point, but I also created great harm, I think, in relationships I had where I wasn't present. And where, in fact, used the work to not face my relationships because that, the work, wasn't nearly as scary, because I knew how to make the work yield positive reinforcement of how I saw myself. And the relationship was much more of a mirror that was, sometimes, not that pleasant.

And so I think part of my purpose is to just instill the idea of bring creativity and curiosity to, what can success look like? Because for myself, part of where my real core laziness comes in is to just take off the rack ideas of success and go, oh yeah, what that person's doing, let me do that, that seems fun. Instead of really being still within myself and going, okay, well that looks good for them. Is that what I want? Does that feel good? How does it sit in my body? All that kind of stuff. And that's just very hard to do when the media narrative tends to be geared very much towards a Jobs via model of success, and where the model of success that is, well, I want to have a life of dignity and integrity, and I want to see nature, and I want to see, and I want to just take a walk for an hour every day. It's not very camera friendly.

And this was, I'll tell you, this is in my last relationship, this was a real issue where I was at the height of my chugging along on the courier and trying to really get to, I always called it, escape velocity. I wanted to get to escape velocity. I wanted to break orbit. And my partner at the time said, "Well, I want to work a job that pays me enough so that I can see my friends and I can travel and I can just have a quiet life." And I looked at her and I was just horrified because it was just so anathema to what I was trying to do, and it was frightening to me, in a way. It was physically, I recoiled from it because it's so invalidated, in some ways, what I was holding up as the end all be all. And now I'm like, oh, I see what her point was. But at the time I couldn't, possibly.

And so I think, again, what I'm hoping for is to create space, certainly for myself, and maybe, hopefully, for one or two other people, to say, oh, there are really substantially different models of success that aren't as frequently seen.


I want to throw this over to Nidhi to weigh in on what she's heard so far. She's a mental health professional therapist. And so Nidhi, over to you.


Yeah, I really appreciate what Stefan brought into this conversation about the shift in priorities that happens. And I think that, ultimately, at the end of the day, no amount of money is going to buy you peace and connection and all of those things that are really important. And something that you had said, Stefan, about sometimes work being the modality of avoidance. I think it's rings so true, and I think for so many of us, because we pour ourselves into our work, it's almost as though we're sabotaging other areas of our lives or avoiding something in other areas of our lives that we just, I don't know. I know I've done that before in my own life, where I've overworked to the point of burning out or exhaustion and sickness out of avoidance of things. And so I just think it's really important to look at that alignment.

And I was reading an interesting article that was this compilation of feedback that these palliative nurses had gotten. These are people that are with people at end of life, and they've compiled over thousands of different patients, what the top five regrets are for individuals. And these are all people that had businesses or were successful in some way or the other. And these are the top five, and some may surprise you.

One was that I wish I had had the courage to live a life true to myself, not the life others expected of me. So really speaking to the societal pressures and family pressure, whatever the case may be to achieve a certain thing or do it a certain way.

Two, I wish I hadn't worked so hard. So there it is. The underscoring of what you had said, Stefan.

Three, I wish I had had the courage to express my feelings.

Four, I wish I had stayed in touch with my friends. So getting to what you were saying, Chris, about how your wife is developing these friendships and really finding meaning in relationship with others.

And then five, that I wish I had let myself be happier.

And so I just think it's so interesting that so many of the things that we end up regretting, at the end of the day, are goals that really, we could be attaining throughout the course of our lives. Yet, I think we're taught to prioritize certain things over others. And now we're finally, I hope the tide is shifting, through, people are seeing that you don't take money with you to the grave. You don't take any of the material possessions with you at end of life. It's who is by your side, and who did you feel connected to, and how much love did you experience, and did you feel like you made an impact and had meaning and purpose in some way? And that is separate, I think, in a lot of ways from just our work identities.

And we have to be able to find that integration, as you would call it, Chris, the work-life integration that allows us to, yes, of course, attain material success. I think we'd be dumb to think that, that's not important, but to also, simultaneously alongside that, set those goals that are going to complement that, that help to create that integration and that balance. So those were just some initial thoughts, but I'm just loving this conversation.


Nidhi, you were talking about Bronnie Ware, right? The Regrets of the Dying?




Yeah. There's a famous story about Grandma Moses. Have you heard about this story before, Nidhi?


I haven't.






Okay. I'm going to share this story about when you should quit and when you shouldn't quit. This was in the book, The Power of Self-Confidence by Brian Tracy, towards the end of the book. And he shares this story about Grandma Moses, and that's her nickname. So Grandma Moses grew up on the East coast, I think, on the farm, and when she was a young girl, like 13 years old or something, she had aspirations to be a painter, had shown some talent. But when they took her to the art supply store, even back in the old days, the cost, the canvas, she grew up in a traditional family. This is crazy.

So Grandma Moses gave up on this dream. So she did what many women were expected to do in this era. She got married when she was young, and she had lots of kids. And she and her husband worked a lot of different things. They would clean homes, they would take care of things, they would work on their farm, all kinds of stuff to make ends meet. And then her husband dies and she has this panic attack. She's like, what am I going to do? And I think she's in her seventies or eighties at this point, and she has pain in her wrist, she's suffering from early signs of arthritis, and she was having a conversation with her sister, and I think her sister said, "Didn't you always want to be an artist?" So she's like, "You're right."

Now, towards the end of her life and her career, and hopefully I'm getting the story right, but this is the essence of it. She goes out and buys those canvases and paints and just mostly a self-taught person, and she's painting this rural life in America. And then she has her work in a gallery, and it just so happens some New York City bigwig person was driving through town, went into the gallery and had this idea that she should exhibit and he wanted to buy one of her paintings. Buys the painting, and one thing leads to the other. Next thing you know, Grandma Moses is exhibiting in major museums at the age of like 84 or something like that. She continues to paint into over 100 years old, and she sells paintings and was declared, by prominent publications, one of the 10 most interesting women in America.

And throughout her childhood, she was told not to pursue this because these are flights of fancy and that she would be poor as an artist. And they have estimated, now, adjust it for inflation, had she started painting when she was 13, when she said she wanted to do this and had the career that she had, she would've been one of the richest women in America.

And so there's a couple things to glean from this story. This is a true story, if you guys look up Grandma Moses, you'll see her paintings. If you're not familiar with the name, you're most definitely familiar with her work because it's everywhere. You'll see. Okay? One of these things is one, if you have a dream of hope, this courage to live your true life, be true to yourself and not the life others expect of you, and you don't get deterred by impediments that are put in your way. Other people who supposedly know better, or constraints, or people telling you this is not possible, and you have that single-minded focus and you're willing to make certain sacrifices that you can achieve what it is that you want in your life.

I don't think she set out to be a rich and powerful, most interesting person in America. I think she just wanted to express her creativity and had denied that of herself. And it wasn't until she lost her husband and felt the pain in her arms, because she continued to work on the farm many years after her husband died. When she felt that pain, she was like, this is it. My life is about to be over. She still had this big idea that, I want to be a painter, I want to be an artist, and she pursued it.

The second lesson besides the living a life true to yourself is, it's never too late to start. If you have oxygen in your lungs, if you still have that burning passion to do something, go do it. And I tell people this all the time, I made my first YouTube video when I was 42 years old. By most standards, already too old to be making YouTube videos. But I knew this was something that I wanted to do. I wanted to be a teacher who could teach at scale, and I was willing to do just about anything to get there. So I wanted to share that story in conjunction with the Bronnie Ware story, Regrets of the Dying.

Now, as I promise, there's a couple things I want to talk to you about, in terms of when you should quit. Now, here's the thing about successful people that I've learned, and I don't know if it's true, but I read lots of books on goal setting, achievement, how to find focus, all that kind of stuff. They almost all say the exact same thing; from The Dip by Seth Godin, The Obstacles, The Way, to Mark Manson's book, The Subtle Art of Not Giving an F, Zig Ziegler's book Goals, Brian Tracy's books, pretty much they all say, the one thing all. They say basically this, focus on this one thing that you want in your life, whatever it is. If it's about finding your voice, playing an instrument, having a great relationship with your parents or your children, being a good teacher at grade school, being the best mathematician, whatever it is that you want in your life, focus on that, marshal all of your resources because it will require everything you've got, and then quit everything else that doesn't matter, and don't quit what does matter. Stick with it.

Now, three questions to ask yourself, or a couple of questions to ask yourself. One, when you're thinking about quitting, am I panicking, is this a temporary emotion that's coming over me because it's no longer fun, or I'm distracted by something else? And just pause and reflect on that. The other thing that I mentioned before, are you making progress, are you moving forward, falling behind, or standing still? Be honest with yourself there. And if at all possible, set up beforehand and answer this question, under what circumstances am I willing to quit and by when? And then measure your progress, the referrals that you're getting, your personal growth, your sales growth, and use that to help you decide if you should continue or not.

Now, when should you quit? Well, when it's a dead end path, you should quit. When the reward isn't worth it in the end and you can see the end clearly, it's not worth it. You'll want to quit the wrong projects and stick with the right one. If the best that you can do is to be average or mediocre, quit. You should quit before something gets comfortable and slip into complacency to challenge yourself. Things are becoming too easy, quit. Quitting is better than coping because quitting frees you up to excel at something else. Don't just cope. Coping is not virtuous. Quit short-term bad ideas, but don't quit long-term excellent ideas. Don't do something because you're letting pride decide because you're afraid of other people judging you. That's not the right reason to stick to something. And as I said before, never quit something with great long-term potential just because you can't deal with the stress at the moment.


Thanks for joining us this time. If you haven't already, subscribe to our show on your favorite podcasting app and get a new insightful episode from us every week. The Future Podcast is hosted by Christo and produced by me, Greg. Thank you to Anthony Barrow for editing and mixing this episode, and thank you to Adam Sandborn for our intro music.

If you enjoyed this episode, then do us a favor by rating and reviewing our show on Apple Podcasts. It'll help us grow the show and make future episodes that much better. Have a question for Chris or me? Head over to the, and ask away. We read every submission and we just might answer yours in a later episode. If you'd like to support the show and invest in yourself while you're at it, visit You'll find video courses, digital products, and a bunch of helpful resources about design and creative business. Thanks again for listening, and we'll see you next time.

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