The Finish Line That Kept Moving
A business can succeed long before its owner feels free to stop. The harder problem is deciding what deserves to continue. Jodie Cook, who draws on her experience with clients, sales, and running a business, brings that distinction into focus in her conversation with Chris Do: endurance has little value if it preserves work that was wrong from the beginning.
Cook is not offering patience as a cure for every business problem. Her perspective matters because she questions the choice underneath the effort. Before celebrating someone's willingness to keep going, she wants to know whether they have chosen something worth continuing.
Do arrived at that question through an unexpected discovery. By his account, he had spent roughly two decades running Blind, the production and design company he started in 1995. The business was generating annual revenue in the millions, and his household had accumulated investments, commercial property, and cash.
Yet the permission to stop appeared to remain just beyond reach.
He remembers asking his wife whether they had enough. The answer, as he recalls it, repeatedly involved another two good years. Financial security had been an early promise in their relationship, and he continued working to fulfill it.
The decisive conversation happened during a meeting with their financial planner. While his wife was out of the room, Do asked when he could retire. The planner checked the numbers and told him that he already could.
His wife returned and, in his telling, said she knew.
The discrepancy was not simply financial. Do had been organizing his working life around an obligation whose practical requirements had already been met. Whether the moving finish line came from their conversations or his interpretation of them, it still governed his behavior.
Enough money does not automatically produce a reason to keep working.
That realization coincided, he recalls, with the period when he was making YouTube content and The Futur had not yet become a fully established company. Removing the need for another financial milestone exposed a different question: what work would remain desirable without that pressure?
He did not want to stop working. He wanted work to stop feeling like an obligation sustained by somebody else's definition of security.
This is the distinction behind his use of the infinite game. In his description, a conventional career treats work as a means to an ending: a win, an exit, a retirement. His alternative is a business its owner would not want to leave, retire from, or sell.
The financial starting point matters. Do describes assets that gave him considerable freedom, not a universal condition available to every entrepreneur. His story cannot establish that anyone can ignore money. It does establish how easily an old objective can survive after its original purpose has expired.
The question also sits beside The Futur's Why Money Doesn't Solve Everything with Tom Bilyeu: financial achievement and a satisfying life are not interchangeable subjects.
Cook moves the argument upstream. Rather than wait for financial independence to expose an unsuitable business, she asks what would make a person willing to remain involved from the start.
A Business Worth Keeping Without the Payoff
Cook's sharpest example begins with an entrepreneur who wanted certainty. At a conference for location independent entrepreneurs, she met a friend frustrated by the pace of his business. He was trying to calculate how much growth would make the next three years worthwhile.
Would doubling be enough? Would tripling justify the effort? His attention was fixed on a future result that could validate the present.
Cook reversed the premise. Instead of asking him to imagine success, she asked him to imagine that the business would fail. Without the anticipated reward, what would he change about the work itself?
It is an intentionally uncomfortable thought experiment. It removes the promise that an unpleasant present will eventually become a worthwhile investment. The person has to examine the present on its own terms.
What emerged was not primarily a growth problem. According to Cook, her friend did not care about the customers he served. He had selected a niche without developing any real attachment to the people inside it.
More revenue would have enlarged the same arrangement.
The audience is part of the work, not merely its revenue source.
Cook's point is not that bankruptcy is harmless or that enjoyment pays the bills. The exercise exposes what the prospect of success has been concealing. A founder can become committed to the outcome while remaining indifferent to the people whose needs produce that outcome.
Her friend's proposed change was therefore more fundamental than a new growth target. He needed to reconsider whom he wanted to serve. That decision would alter the meaning of the daily work, not merely its financial projection.
The conversation surfaces three different reasons for staying in a business:
- The work serves people the owner genuinely cares about.
- The activity remains worthwhile beyond a particular financial milestone.
- The prospect of a future payoff makes an otherwise unwanted present tolerable.
The first two can support the kind of continued involvement Cook and Do describe. The third depends on an eventual reward large enough to excuse the experience of getting there. It is a fragile basis for a game with no intended ending.
That does not make every difficult day evidence of a bad choice. Do describes advertising clients who expected extensive effort and rarely expressed thanks. He also describes genuine satisfaction in design: taking something intangible and making it tangible.
The work held meaning even when the commercial environment imposed frustrations. Separating those two facts is important. Disliking a particular client interaction is different from having no interest in the customers at all.
Cook applies the same scrutiny to her earlier professional behavior. She says she once put on more of a front because she believed that was how business and sales worked. Looking back, she wishes she had spoken to clients more naturally, closer to the way she would speak to a friend.
The change is not toward carelessness. It is away from maintaining a professional performance that obstructs an honest relationship.
In friendships, Cook resists the game metaphor altogether. People are not opportunities to extract value from prematurely. They are people whose trust can be preserved by behaving consistently and being real.
Meaning Still Has to Meet a Market
The appealing version of this argument is that meaningful work eventually makes money. Do sometimes states the connection that confidently. Cook supplies a necessary complication: meaning needs a definition before it can carry a commercial promise.
There is a difference between an activity someone enjoys and an activity that is useful enough for another person to buy. Both can matter personally. Only one has established a basis for a business.
Cook separates liking the work from making it commercially viable. Do, despite his enthusiasm for following the heart, does not dispute the need for execution. His criticism is directed at people who claim to have pursued a craft seriously when their actions show something less demanding.
Commercial meaning requires more than personal enjoyment.
That is the pressure test inside an otherwise aspirational conversation. Persistence cannot substitute for competence. Nor can affection for a craft establish that a particular offer belongs in a particular market.
Do describes designers who struggle to sell inexpensive logos and conclude that their location has trapped them. His response is to examine the work, the education behind it, and the effort invested in becoming known.
He acknowledges that his judgment of design quality is subjective. He grounds it in his own experience buying art and design, rather than presenting taste as a neutral measurement. The important distinction is between asserting commitment and demonstrating what that commitment has produced.
His examination includes several concrete areas:
- Work strong enough to interest a buyer.
- Education and feedback that improve the craft.
- Sustained practice rather than occasional dabbling.
- Effort to reach people beyond the immediate local market.
None of these guarantees a successful business. Together, they make a more demanding account of effort than simply having stayed interested for years. Time elapsed and capability developed are different measurements.
Do uses an aspiration of his own to make the distinction less abstract. He would like to dance, but he has not put in the work. Consequently, he does not expect the results that training would produce.
Belief in his ability to learn is not presented as evidence that he has learned.
The same standard applies to a designer's claim of being committed. Mentorship, deliberate work, and better instruction are not optional decorations around an identity. They are among the actions that make the identity credible, a concern adjacent to The Futur's The Importance Of Mentors.
Do's own account is unusually concentrated. He chose design while young, attended Art Center, and stayed with the discipline for more than two decades. He describes pursuing it deeply enough to reach milestones he had once considered the top of the profession.
He contrasts that sustained attention with classmates who arrived carrying other degrees and extensive life experience. They had advantages he respected, but those advantages did not automatically translate into stronger design work.
Cook's closing observation makes that concentration more useful than a simple instruction to persist. Someone who knows they can keep going indefinitely has an especially strong reason to examine the initial choice.
Tenacity magnifies direction. It does not choose the direction.
The long game therefore begins before the commitment. Experimentation helps identify the work. Serious practice develops the ability. Commercial reality determines whether the resulting offer solves a problem someone will pay to address.
The Career That Belongs to Someone Else
A long commitment can also begin with somebody else's decision. Do tells the story of a woman who completed law school, passed the bar, practiced for a year, and then moved into media and public relations because she disliked legal work.
As he recounts it, her parents had not allowed her to pursue another direction. His immediate interpretation is that she lost time and money following their preference. The deeper issue is authorship: whose judgment was organizing her life?
Cook refuses the easy conclusion that the legal education was simply wasted. The experience could inform her later work in media and public relations. An apparently indirect path can still produce useful capabilities.
This is one of the conversation's most productive disagreements. Do emphasizes the cost of a direction chosen under pressure. Cook emphasizes the difficulty of knowing what an earlier experience will eventually contribute.
Both observations can hold. An experience can become valuable without having been a sound decision at the time.
Learning from a mistake does not justify making it deliberately.
Do distinguishes looking backward from looking forward. In retrospect, someone can acknowledge that hardships and detours helped make them who they are. That interpretation can support acceptance rather than regret.
Applied prospectively, however, the same reasoning becomes an escape from judgment. Any avoidable mistake can be excused on the grounds that it will teach something. The possibility of a lesson becomes permission to ignore the information already available.
His financial example is deliberately extreme: committing money someone does not have, then defending the loss as an educational experience. The eventual lesson does not erase the responsibility attached to the original decision.
The more ordinary version is choosing a profession someone already knows they do not like. Discomfort is not always decisive, but explicit disinterest combined with parental pressure is information. It should not disappear beneath a romantic account of how everything works out.
The Futur's Living in the Dogma of your Parents names the adjacent tension directly: inherited expectations can be mistaken for a personally chosen direction.
Cook then presses on the family conditions that make independent judgment possible. Her own childhood offers a contrasting model. Her father ran car dealerships; her mother worked in finance and later started a business.
Cook describes both parents as capable of stating their boundaries. Neither routinely spoke for the other. If a child used an unacceptable tone, the parent receiving it could address the behavior directly.
The practical message was independence, not just obedience. A problem brought to a parent often returned as a question about what the child intended to do about it. Cook remembers wanting a car as soon as she could drive because transport represented freedom from asking for help.
Her response was to work toward obtaining that freedom herself.
Do recognizes a different family pattern in his own life. His father habitually took less for himself, behavior Do connects to the responsibilities his father assumed early in life. Do can also see that pattern of sacrifice reflected in his own conduct.
Neither childhood account establishes a rule about families in general. Together, they show why autonomy is not just a business preference. For these two people, it is entangled with what responsibility, care, and authority looked like at home.
Independence Is Built in Small Decisions
Do's stated ambition as a parent is not to remain the permanent source of approval. It is to raise children capable of deciding what is right without consulting him about everything.
That aim creates a demanding distinction. A parent can solve the immediate problem and leave the child dependent on the same intervention next time. Or the parent can make room for the child to develop judgment, even when that takes longer.
Do describes a small set of firm boundaries around that freedom:
- Children cannot hurt each other.
- They must show respect to others.
- They should try to do the right thing.
Beyond those boundaries, he wants room for exploration. He says his family discusses mistakes and failures openly so that they are not treated as shameful exceptions. The goal is to make an imperfect attempt discussable rather than something to conceal.
The distinction is not between rules and freedom. It is between rules that protect independent action and control that replaces it. The same concern gives context to The Futur's Raising Independent Creative Children.
Cook complicates Do's account when he describes intervening over how children address their mother. She asks why the mother should not state her own boundary. If children are supposed to learn to stand up for themselves, she argues, the adults need to model that directly.
Her challenge keeps the discussion from settling into a flattering story about protection. Defending another person and allowing that person to exercise authority are not necessarily the same action.
Do acknowledges the difficulty. He describes his wife as someone who often moves immediately into caretaking, sometimes before anyone has asked her for anything. A question about dinner plans can become a meal being prepared.
The issue is not whether the act is generous. It is whether the person has had a moment to decide.
Do recounts a sequence their therapist offered his wife. Rendered as decision points, it separates the request from the response:
- Establish whether a request was made. An observation or question does not automatically create an obligation.
- Check whether the task is possible. Ability is a separate consideration from expectation.
- Decide whether the task is wanted. Being able to help does not settle the choice.
- Choose how to respond. The response follows consideration instead of automatic caretaking.
This is a specific account of advice within their therapy, not a universal prescription for every family. Its relevance here is the pause it inserts between someone else's behavior and a person's own commitment.
That pause is precisely what the broader business argument requires. An opportunity appears. A customer wants something. A family member has an expectation. None of those events, by itself, answers whether the resulting obligation belongs in a life someone wants to sustain.
Cook favors consistency: shared principles that make responses less arbitrary. Do favors developing judgment beyond the need to ask. The useful tension is between providing a stable environment and leaving enough room for another person to think.
In either case, autonomy is not created by announcing it. It is practiced through decisions small enough to repeat and consequential enough to teach.
The Offer Has to Survive Outside the House
A hypothetical gym membership turns the conversation's abstract commitments into a practical negotiation. Cook takes the role of a child asking a parent, played by Do, to pay a monthly fee.
The request initially centers on the child's interests. Exercise would be beneficial. The gym would provide equipment, instruction, and a community. Those are reasons the child wants the membership, not yet reasons the parent should fund it.
Do asks what other options exist. Cook first proposes alternatives to the gym itself, then he clarifies that the objective can remain fixed. The question is whether parental funding is the only route to it.
The distinction opens several possibilities: ask for a reduced rate, help the gym with work, or find a way to earn the fee. Instead of debating whether the goal is worthwhile, the discussion begins examining who must supply the resources.
The exchange becomes especially revealing when Cook proposes making art for the parent to buy. She wants an arrangement that develops her abilities rather than simply exchanging time for household chores.
Do does not dismiss the ambition. He points out that the proposed customer has no need for more art. The household already has more than it has hung.
His answer is blunt: “You're giving me a solution to a problem I don't have.”
That is the commercial limit of the conversation's emphasis on meaning. Making art can be valuable to the maker. Developing the skill can be worthwhile. Neither establishes that this particular buyer needs the product.
Do redirects the hypothetical child toward finding an actual market for the work. The immediate request goes unresolved, but the underlying options become more concrete. The child can investigate demand instead of assuming that affection should produce a purchase.
The role play is not evidence that every parent should negotiate a gym membership this way. It is a compact demonstration of how a desired outcome can become confused with a single preferred solution.
It also exposes the difference between explaining personal benefits and understanding the other party's concerns. Afterward, Do says a more effective request would have asked what would make the parent comfortable agreeing.
That principle connects naturally with The Skill You Need To Win Clients That No One Talks About. The relevant shift is from advancing a predetermined pitch to paying attention to the person receiving it.
The final business test is therefore less romantic than simply loving the work. The chosen activity needs sustained effort. The offer needs a buyer. The relationship needs honesty. The person making the commitment needs enough autonomy to mean it.
Cook's advice to her younger self joins those requirements at the point where a decision is still reversible: “Think for a long, long time before you get into something.” The rest of her instruction is to be prepared to continue indefinitely.
That preparation changes what deserves scrutiny. Not just whether a market is attractive, but whether its customers matter to the founder. Not just whether a profession earns approval, but whether the person wants the work. Not just whether a business can sell, but whether it is worth keeping.
The strongest commitment is not the one that survives the most misery. It is the one made carefully enough that continued effort still has a purpose.
Persistence cannot rescue a life chosen for someone else.
TRANSCRIPT
Okay, I have a question for you then. If you're looking back at your younger self and you want to give that perspective when you weren't quite capable of hearing something like this, how would you tell them to play the long game? I would say think for a long, long time before you get into something and then be prepared to do it forever.
I would say don't start a business that you do want to sell, start a business that you never want to sell. I would say With human beings and with a lot of relationships, I don't even think I'm playing a game with people. I think I don't actually think of it as a game because you just...
you're just hanging out you're just making friends but I think that the I quite like the idea of like just don't mess up like just don't if you've got a friendship that you can preserve then just preserve it like do the right thing and don't it's I think it always actually comes down to just literally being real you know when someone's not being real because they're trying to kind of get something out of you prematurely or they're trying they're not really thinking something through and then you're like mate are be real so i feel like earlier on i would have talked to more people like i was just talking to my best friend like clients and everything else i feel like i probably put on a bit more of a front for a long time because i believed that was how you made sales or that was how you run a business when really i could have got that right earlier All right, Jordy, I'm back from Las Vegas. And as the slogan says, what happens in Vegas stays in Vegas. But one thing that will travel with me outside of Vegas is my skin's wrecked, my throat's jacked.
So with that, let's get into the episode. What are we talking about today? We are talking about how to play the long game.
And as context for this, I feel like in our conversations together, we've realized that both you and I think very long-term and I feel like not everyone does. And I want to talk about this because I think that both you and I have both benefited immensely from thinking long-term, but also I know that we have both experienced people who think short-term and played short-term games and not really liked them and not really liked their game. And so I thought that there would be something cool to unpack here around what we think about our game, other people's games, and how it all works together.
Wonderful. I love that. I tell people I play the longest game.
It's called the infinite game. There's no ending to the game. What does the infinite game mean to you?
Well, most people think of what they do as a means to an end. So there's an end and there's a win and there's a loss. And so they do it for a period of time and then it gets not interesting or they achieve what they want and then they do something else.
And then a while back, I heard this concept like, can you design a business for yourself that you never want to leave, retire or sell? Because that asks questions of yourself about what it is that you really want, what gives you meaning and purpose. And I think our life is very short.
We probably shouldn't be starting over every 10 or 20 years. And that doesn't seem to make a lot of sense to me. And once I was able to make quote unquote enough money that I didn't feel like I needed to make any more money that I was not going to be able to spend in this lifetime with my current lifestyle.
Obviously I can spend a lot of money, but at my current lifestyle, what is it I want to do? And so there's a little story I want to share with you. And I think I've shared it before, but maybe not with you.
It goes something like this. So I've been running a production and design company since 1995 called Blind. And I'm 20 years deep into it.
And on average, we do between four to six million dollars a year. So let's say five million dollars in revenue. And I'm doing pretty good.
More money than I ever thought I would make. And my wife and I were living really well. And she comes from a upper class family.
Her dad was a commercial pilot in Taiwan. So she's used to living a certain life and lifestyle. But even still, there's this Asian mentality about scarcity and not having enough, a lack mindset.
And she said very early on, what gives me comfort in a sense of security is financial security. They said, well, you've married the right man because I will provide that for you because I see myself as a provider and I will do this. So I keep working.
Now, I'm not telling you I hate my life or my job, but sometimes working with ad execs and people from the ad agency, it can be really tough on you because they expect a lot and very rarely do they ever say thank you. It's just part of how it works. And they're used to working insane amount of hours.
and so every once in a while i talk to my wife and i would ask her are we done yet have we gotten to that point she was just give me two more good years then it will be done but it seems like every two years then she's like give me another two years so this conversation began in our 40s okay And I thought, "We're just fine. We are really fine. We own two commercial buildings.
We have investments. We have cash. We have lots of things.
And we don't go crazy. I don't own any fancy cars or anything like that." And I should caveat that I do own some expensive cars, but I'm not a car freak. I'm not a clothing freak.
I don't buy crazy expensive things. So one day we're meeting with our financial planner. His name is John.
And he goes through quarterly projections, talking about what we've done, what we expect to do, and how to help us minimize our tax burden. My wife goes to the bathroom. I said, "John, you know our numbers, right?" He goes, "Yeah." I said, "I'm just curious, when can I retire?" He goes, "What?" I said, "When do I can stop working?" He goes, "Okay, give me a second." He's a numbers guy.
He's just looking at his spreadsheet on his laptop and he smiles at me. He pulls his head back a little bit. I said, "What?
What's the problem?" He said, "Chris, you could have retired already." you guys have enough money and you'd hardly spend any money relatively speaking now if my mom were in the room she'd faint out of her chair because she looks at us like we live some lavish lifestyle how we buy things how we go out to eat but according to numbers i could have already retired so my wife just unbeknownst walks back into the conference room after going to the bathroom i said honey she's like what john told me we can retire already she goes i know i'm like what flabbergasted "What? You've been telling me every year, two more years." She goes, "No, that's an old story you told yourself." I'm like, "So I imagined this, right?" Because now, presented with overwhelming evidence and a professional who looks at this kind of stuff, my wife's not telling me two more years. That night I went home and I really thought about my life.
So I've been working to give my wife a sense of financial security. It's the commitment I made to her as a younger man. I was going to do this.
So now we've achieved this, what do I want to do with my life? This happens to be coincidentally around the time in which I've been making YouTube content. I think it's 2016-ish.
The future is not a real company even yet. I still have a business partner, but I was like, maybe there's something more for me. So once you remove the burden of needing to make money and you have financial security, you're going to ask yourself this question.
What next? Now, some people make a ton of money and their only obsession is go make an S ton more money. And I don't need that much money to live and to be happy and to feel fulfilled.
So now I'm thinking, but now in a little bit more context, the buildings that we own generate income for us. And if we did nothing else, the two buildings, if they're fully occupied, generate enough money for my wife and my children to live forever, given our lifestyle. So we're good.
And one of them is paid off, one's about to be paid off in like a year. And so that means we own them both outright. So that's the context.
And so now I'm searching for something more. And now I give myself permission to indulge in whatever it is I want to do with my life. Now, I never not want to work, but I don't ever want work to feel like work.
So I'm on that quest. That's the infinite game. Have you managed to shake off any sense of scarcity and lack?
Me? Now in the game that you're on, you or your wife, or just like, does that now have no part in your existence? Okay.
Let me answer in two ways. My wife says we have enough money. She doesn't want me to work anymore.
So the first part of my life with her was like, you need to make more money. And when she decided, no, I don't want any more money, do not work anymore. So I'm like, well, that's not really fair to me, is it?
It's like, we're living in your timeline. Okay. So that's for another conversation for another day.
And I'll tell you this. Once I started to make a little bit of money, I've never had that idea that I don't have enough money because I don't come from a lot of money. I'm the kind of guy who, while going to art school, was probably one of the 10 poorest people I knew at school.
Now, my family's not poor. We're upper middle class, but we live like we are poor, meaning my mom barely gave me enough money to survive at school. So I was scraping to make things work, going to the supermarket and like, That's a little bit cheaper than that.
I know it's a little bit more fat than a ground beef, but I need to buy that because it stretches a little bit longer. And that brand of bread is a little bit less expensive than the other one. And I've got two coupons here for like 50% off.
I'm going to use these. That's how I lived. And so once I made some money, when I started working advertising, when I was still in school, I was giving my money away.
I gave money to my then girlfriend, not my wife, somebody else, because I didn't want her to commute so far. I said, you need money for rent? I'll give you my money.
And she felt very awkward about it. But I said, you know, if I have money and you get into a car wreck, and if I could have helped you just find a place closer to school, I feel like I've done something wrong. So ever since then, I've never really thought about money.
And people are shocked to hear this, despite me talking about money all the time, how to make it, how to create it, how to negotiate for it. I have no idea what we have. And since meeting my current wife, girlfriend at that time, She's like, "I'll just take care of all the ATM stuff so I don't go to the bank anymore.
I haven't in 30 years, except for to sign paperwork. I have no idea." So the pursuit of money is not meaningful to me. The pursuit of meaning is though.
And that's the paradox that now you almost can't help but make money because you're pursuing meaning. But I've pursued meaning for a lot of part of my life. In the first part, it was at someone else's kind of control.
So I didn't have a lot of autonomy there, agency, because I did design work. I would pitch for work, but somebody decided if I was going to be successful or not, which bothered me a little bit. But the ability to create things, which is what designers do, we take intangible things and we make them tangible.
And we kind of look into the future and we kind of find what that might be. And then we make that thing today. That's meaningful to me.
That's the real visionary side of things, imagining something and then creating it into reality where no one else went before. But that's inherently valuable as well. I think so.
But it's not always because if you're in the wrong market selling to the wrong person or people, then you're screwed. Because there are a lot of people who do that, designers and artists, who really have been struggling since the '90s and continue to struggle today. But the problem is for them, they're stuck now more so of their own doing than because of circumstances, because there's this thing called the internet.
There's this thing called social media, and you can build your own audience no matter where you live in the world. You can create your own community, and it's pretty awesome. And they're going to argue right back, well, Chris, there's a lot more competition.
There is, especially in the middle to the bottom, but not at the top. Do you think that's in the assigned... meaning of the word meaning because if you go after meaning and not many you still have to define what meaning means.
And if meaning to you means I like doing it, it's useful, but it's also commercially viable, then that's the meaning that's going to make money. Whereas if it's just the meaning that means, oh, I like it and my friends like it, but no one will pay for it. That's not real meaning.
There's meaning on some levels, but it's never going to lead anywhere other than being a starving artist, which is what we're trying to avoid. Yeah. People get into my face about this when I said, you know, listen to your heart.
and what it sounds like just follow your passion and it's not just that clearly there are a lot of passionate people but the execution of this idea is very very important a lot of people follow their passion but what they follow their passion is they dabble in things they don't get serious they don't find mentorship they're not putting in the 10 000 hours of work in the dark in the shadows where no one can see They pursued for a while and they may or may not have any real talent. They may or may not have made any real effort, but they've not dedicated their lives to the pursuit of something. Now, I aspire to someday be a good dancer or just to be a dancer.
Remove the word good. I haven't put in the work, so I don't expect any results. But I imagine in my mind, because I have a supreme belief in self, that if I did put in the work, if I went to a studio, if I watched videos, that over a period of time, maybe a year, two years, I can be a dancer.
Maybe not a great dancer, but I can be a dancer. You can be a dancer. I can.
I believe that. So people who are like, well, I'm a logo designer and I haven't been successful and I can't give this stuff away and I can't find someone to give me $100 to make a logo for them. So what have you done?
We have to look at this and let me take a look at your work. Generally speaking, it's not very good. Now, I know that's a very subjective standard.
I acknowledge that, that my opinion of their work is not good or not good enough. It's just my opinion. But as a buyer of art and design, in terms of like my 20 plus year career in buying art and design, I have a sense of what sells and what the market pays for.
And that's not it. And then I look into their education, quote unquote, formal or otherwise. It's all self-taught from other bad artists and bad designers.
And they're saying, well, I'm stuck to this little country or the city that I'm in. And I'm like, well, who made that happen? You're reaching out to me.
I'm not in your city. You've not put in the work to get known. So there's all kinds of problems there.
We kind of mentioned control. And this is so in my head because I was at a conference this weekend for location independent entrepreneurs, all building businesses. And I was talking to a friend and he was really struggling with this idea of control because he wants clarity over where his business is going because it's not growing fast enough and he was kind of thinking okay well in three years if it's like doubled will I be happy or if it's tripled will I be happy or like how big would it have to be for me to think yes this time was worth it and really struggling with the idea of not knowing whether what he was doing day to day was ever going to lead to anything and I was like It's similar to the infinite game.
But I was like, why don't you not think about whether or not it's going to work and just think, imagine that it isn't going to work. Imagine that you are definitely going to go bankrupt. Imagine that this is never going to be a success no matter what you do.
What do you do then? because he was like what do you mean why would i plan this based on it definitely failing and it's like that's almost the point because you don't know you might as well be happy you might as well enjoy what you're doing and then if it doesn't go anywhere then you've not lost anything because there are plenty of fun ways to lose money So just find one of those. And he's like, ah.
But then he realized that the audience that he's serving, he doesn't care about. He doesn't care about his customers at all. He's chosen that niche because he just chose it.
But it's like, but if you served people that you really cared about, then maybe you wouldn't care if it was just a fun way to lose money because you really enjoy it. And then you do find the meaning and then it does lead to something. And yeah, he's going to change stuff, which I thought was quite cool.
This reminds me of something. I think there's fundamentally a problem with how society builds up young men and women so that we carry this idea into adulthood, that we need to pursue something to make money. I think we need to pursue meaning and then the money will come.
And it's counterintuitive. So I recently met this woman, her name is Kim, and she's working with my friend Uma. And she's a lawyer from Malaysia, Singapore.
And I'm like, "What do you mean? Did you quit?" No, she goes, "I finished law school." I said, "And you passed the bar?" Thinking she didn't. She goes, "I passed the bar.
I practiced law for a year and I hated it. So now I'm doing media and PR." That seemed like a waste of time and money, in my opinion. I mean, I'm glad that you're so smart and you're good at stuff.
Why did you even pursue law? And she goes, "Well, my parents didn't allow me to do anything else." I said, "Okay, so there's a problem here." You were living your life for someone else and you believe that their money and their opinion matters. Imagine five, six years ago before you did all this stuff that you just wanted to do PR and you studied writing and you started writing.
Where would you be today? So we're living for other people. And unfortunately, this is the problem that a lot of parents have, which is they're living vicariously through their children.
They say, well, I was an a lawyer i didn't do anything respectable so i want you to be that thing i want you to get great grades well mom what was your grades dad what did you do with your life and so people are trying to fix their problems with their children and i'm i'm employing all parents right now especially if you have young ones please don't do that you had your shot maybe you didn't take it maybe you didn't hear this kind of message but please don't do this to your children i'm asking for them they'll be way happier and more successful than you could ever imagine because the playbook in which you've developed is really outdated. How do you teach kids to question authority again and again and again to the point where they would question their parents, but then also I think that this is in my head because a really good friend wrote a book called Squiggly Career and the idea that all careers are kind of squiggly and you think they're going to go in this linear fashion, but they really don't. And so your friend who studied law and then gave it up or did something different in media and PR, who's to say that they're not a better media and PR person because they study law, because there's stuff that they take over, all the stuff that they learn, and that's given them such an edge on their media and PR career that they're going to be better because they've had that experience.
And then the other thought is around how many kind of hardships, mistakes, wrong turns, do some people have to go through compared to others? Because I feel like there's so many mistakes I've made that I've learned loads from. And then sometimes people have the learning without making the mistake.
And it's almost like, how did you get that? Teach me how to do that so that you don't have to go the long way around. I think to teach children how to go against authority structure and order.
I don't think it's society's job to do that. I think it's the parents job to do that. And it's really weird because you're teaching them to live a life that doesn't need you in it.
It doesn't care about your opinion. And that's too hurtful for a lot of parents for a lot of different reasons. Sadly, I think a lot of parents have children because they don't have love in their life and they create children to love them back.
And if that's the case, buy a dog, get a cat. It's like you're talking about a human being that has their own autonomy to do things and to be self-directed. It's really what you want for your children.
And then what parents do is they use their power, money, security, and love, and they withhold it to control their children. So what you're saying is you're teaching them to go look for somebody else to do that to them because that's the only life they've known. To seek someone else who's going to use their power, their money, and their words of affirmation, either in their partner in life or their boss, Because that's all they know.
Something that my business coach told me many years ago. He says, "What people do is they try to recreate what they experience at home at the office." So at that time, we had some pretty toxic personalities who would just create chaos where none existed. We would commonly refer to that as the drama kings or queens.
It's just like everything's cool, but you just bring so much toxic energy. And I could not understand that because I don't come from a place like that. And this is what Keir said to me.
If someone grew up with an abusive alcoholic father, do you know who they wind up dating? Abusive men who are alcoholics, because that feels like home. And that really hurt me in a way that's so sad that the thing you're trying to escape is the thing you run towards because it reminds you of home.
What a toxic place. And they don't have those self-awareness. And I think that's why some people say things like you have daddy issues because dad did too much of something or too little of something.
And now you're trying to repair that in your current life. never having the courage to be disliked, still stuck in causality, past equals present. Just to throw back to previous episode, listen to that now.
What do we do now? With my children, what I have are just like two or three very non-negotiables with them. Can't hurt each other, show respect to others, and try to do the right thing.
After that, you do whatever you want. You cannot hurt each other. There's zero tolerance for physical violence, zero.
Treat people with respect. If I see you being disrespectful to people, I'm going to have a problem. So if they would say something to mom in a disrespectful tone, I'm like, that's not acceptable.
It's funny because I was talking to somebody in Vegas and they have a great relationship with their children, but the children are a little lippy with mom. So he used to say, you can't talk to mom like that, but he changed his language. And his little shift was pretty profound.
I've never done this myself, but he says, you can't talk to my wife like that. I was like, damn, because we just assume mom will take anything, but that's my wife you're talking about. That's unacceptable.
Like we're going to have problems right now because I'm in his, I think I'm putting words in his mouth now, both someone who loves my wife, but also protects my wife. And we look out for each other. And now you're doing something that goes against one of those things.
And so my children, children are exposed to lots of things. They get to explore. They're encouraged to explore.
We want to normalize failure and making mistakes that we routinely talk about and celebrate it like it's a good thing. Here's how I failed today. Here's a mistake that I made this week because I want to remove the taboo from that.
So did mom say you can't talk to me like that? Mom usually doesn't talk like that. That's why children do that.
They don't usually talk to dad. Now, I'm just saying in our household, because in some household, it's the mom that has the authority and the dad's a pushover and takes all the kind of job. Because then that's kind of interesting, like that dynamic.
If you had it that dad was saying, can't talk to your mom like that. And then you can't talk to my wife like that. But then at some point you think mom would just say, hey, don't talk to me like that.
Or you think dad would say to mom. just tell them that they can't talk to you like that and then kind of pass it over. So it's more like someone standing up for themselves, because if you want the kid to stand up for themselves, then mom needs to do it too.
Yeah. So let's get into the patriarchy a little bit here. Historically speaking, men have controlled the household and people have lived in fear of the man.
Man comes home, gets the big piece of meat, whatever it is. Everybody's quiet. Dad needs to sleep.
It's kind of like that for a really long time. I think in the last 50 years, it's been a lot different and things have changed for the better there's more balance there and so if you grew up in a household where that was the way it was that was normal mom takes care of the kids cooks cleans does everything attends their emotional needs then even in a modern society where you know that that's not the case anymore you can repeat those patterns and i tell my wife like she has her own story and challenges with her own upbringing so there's that and there's a lot of history there that it's hard to undo i'm not therapist my wife did not marry a therapist and she don't want me to treat her like one so i have to be careful about how i manage this conversation where i say i think if you just could let go of some of the caretaking i think they'll talk to you differently because she's like fed up with this she's like how come they never ask you to do anything and they always treat you like gold which is an expression that's used around the house. I'm like, I don't accept it.
It's unacceptable to me. And I wish you would treat them that way too. And she can't, it's really difficult.
We even went to therapy. We talked about this last time. Joan, our therapist had said, you guys are both classic caretakers.
I'm like, I am? No, whatever. But she said this to my wife, Jessie.
She said, number one, it was a request made of me. Number two, can I do it? Number three, do I want to do it?
And number four, how do I want to respond? Watch this. just yesterday, I asked my wife, "Are you guys going out to play tennis?" She goes, "Yes." I said, "Okay.
You want me to go pick up dinner?" She goes, "I'll make you something to eat right now." I didn't even ask her to do anything. I'm just like, "What is the game plan here? When will you be back?
Should I wait for you?" And then she went into the kitchen, she made me a delicious meal, and I'm like, "Thank you very much." But you see what I'm saying? There was a formula here that she should have applied. No request was made of me.
but she went into that care take now i love my wife i appreciate her like afterwards like when she came home from tennis like do you need a massage she goes yes i do so i sit there and massage her leg and her her calves and all that kind of stuff so i do my thing too i'm not saying i'm some some pig here but it's just an example of like how we switch the default thinking yeah and i had like almost the opposite nearly opposite of bringing to that i saw your look i could see it Oh yeah because it's so interesting like yeah of course that's the there's a normal way and then it means people slip into those patterns. My mum and my dad were both the boss of where they were. My dad ran car dealerships, my mum worked it was like corporate power woman and finance and then started her own business and I was about 15 when she did that but it was very like if I'd have said something to my dad that he didn't like the tone of he would have just said like he would have said that wasn't acceptable but if I equally if I said something to my mom that she didn't like the tone of she would have said it wasn't acceptable and they also they very clearly like didn't speak for each other ever it was never like oh don't do that to your like it was never assuming that they knew what the other one thought it was just like oh well if you want to let her speak to you like that then that's up to you you can say something about it I'm not going to say anything about it because like it's up to you to stick up for yourself but that was very much the message for me and my sister as well it was like what are you going to do about it And I think if I'd have said I'm hungry, it would have been like, well, what are you going to do about it?
I don't think it would have been really strange for the default response to have been, oh, I'll make you something. I don't think that seems so foreign, like such a foreign concept to me because it was always like sort yourself out. I think this is why I just wanted to get as soon as I could drive.
as soon as i could with 17 in the uk as soon as i turned 17 i was like i want to get my own car as soon as i could drive i was like i i need to do this and and work out how to get a job to buy my own car so that i've got my own wheels so that i can just have the independence that i so so want and then it's like what you said before it's like you kind of teach your kids how to do independent how to be independent and think for themselves and then they do But that definitely happened. That cause and effect was for sure there. So I think you grew up in a very unique household where you have two professional parents, two equally strong, confident people who had boundaries and had their own thing to do.
Now, I'm just curious. I know there's no way we can really answer this question, but anecdotally thinking or just anecdotally speaking, looking back into your neighborhood and the community in which you grew up in, do you think your family was the norm or were you guys an outlier, an edge case? What do you think?
50-50 I'd say with the families that my parents were friends with I'd say it was 50-50 there are a lot of the moms and dads of my friends and the moms and dads that hey they hung out with where they both worked and they have like the kids had like nannies and stuff because parents were away at work and they didn't come back till like six seven eight o'clock but then there were definitely some who took that more moms at home dad's gone out to work and yeah actually now you say it if I think about those ones It was very stereotypical. It was like, dad's in charge, dad asserts the authority, mom's very softly spoken, mom's almost like tiptoeing around dad. And I remember being at a friend's house where their mom and dad were like that and thinking, like, why isn't their mom sticking up for herself?
What's the deal here? Like, I don't think I really, I don't think I really understood it. It could be a case of both of our bias where we think that's the norm because that's all we knew.
That's, again, speaking to this whole idea of like, how our past defines the way we think, where like that's normal. But just me looking around, lots of friends, a lot of different socioeconomic backgrounds, and maybe I didn't grow up with a lot of affluent friends because we were not affluent. It is a little bit different.
It's mostly the patriarchy. As much as I don't want to use that word because it's a hot trigger word for folks on both sides, But my dad was quite unique. Now, I will say this.
Dad was a disciplinarian. Dad had a temper. Mom has her own temper, but it's never expressed the way dad expresses it because there could be violence.
And I remember one time when I was caught cutting school in high school, I ditched school. I was trying to avoid this test I didn't want to take because I wasn't ready for it. And so I just ditched and I got caught.
And they called my mom. She was on file. They called my mom.
And my mom talked to me on the phone in the superintendent's office and And she goes, "I'm so disappointed in you, honey." I said, "Mom, let's work this out. You don't need to tell dad." She goes, "I have to tell your father." I'm like, "You don't have to tell him, Mom. We'll work this out." You know what I'm saying?
It's like this whole bargaining thing. So when I came home, I was like, when dad comes home, I'm dust. This is it.
Gotta get my ass whooped and this is how it's gonna be. So I was just mentally prepared for whatever. And my dad didn't hit me.
He talked to me for like hours. And my dad was pretty atypical for a traditional Asian man, because also when we ate, whenever we did anything, he always chose to have the smallest, the least of everything, which is part of my pattern too, because we can see that, right? It's like he sacrificed himself.
He wasn't the stereotypical, like, yeah, where's the big piece of chicken? He's like, I don't need to eat. I'm not that hungry.
He always did that. He still does that to this day. When you look at the portions on the table, depending on how it's been calculated, he's already made the decision that he won't eat it because he's the oldest male of many siblings.
And because his father, my grandfather died when he was still quite young, that he assumed the role of the father. And so dad sacrifices. And so he's continued that pattern.
And so there's some gender norm things here and then something that's a little bit not typical. But I would be shocked if 50% of the people listening to this grew up in that kind of household where both parents were professionals, had the boundaries and had this kind of respect for each other and power was shared equally and no one spoke for anybody. And help me figure this out unofficially, everybody.
If you're watching this right now, tell me what kind of parents you grew up with. who had the power who had the control who was the disciplinarian who was the one who bathed you cooked for you and attended to your emotional needs who was the one dropping you off at soccer who was the one watching your plays who was the one doing homework with you the answers can be quite varied but let's see yeah we'll get crazy varied responses i was thinking about almost like playing parents off each other as well and the idea of having a good cop bad cop situation and i'm sure my sister and i tried to create a good cop bad cop situation and i just don't think we ever got away with it i just think it would be more like they would have been like ask mom something oh have you asked your dad no well would he go and ask him as well but it was it wouldn't have been like go and ask him because i'm deferring this decision it would have been go and ask him and then talk to me again about it or some kind of You need both opinions rather than yes, I'll say this and that works over the other ones. Yeah, because kids are very smart.
They exploit the weakness in the parents. So it wants softer on an issue and it varies, right? You go to mom for some things, dad for some things.
Like maybe you go mom for money and dad for like, oh, I got busted for smoking pot. And he's like, cool, don't worry about it. But I know something that's consistent within my family right now is my wife has challenges around saying no to the kids.
So whenever something bad happens, she goes, you need to talk to him about spending. I'm like, but 90% of this was you. And now I'm just the guy coming in to clean up the mess.
This doesn't feel right to me. And I would protest a little bit. I said, well, you disperse the funds without any boundaries.
And now you want me to come in after it got out of control and where you never had that discussion. I would have preferred if you had that, but. Sometimes she just want to deal with that.
I'm like, all right, I guess that's what I'm doing today. Do you think this all comes down to principles? Almost agreeing a set of principles?
Because I guess... if you have them for investing, if you have them for your company, and if you also have them for how you play the long game, for example. But then if parents have them as well, then they just know.
They almost don't need to talk to each other because they just know that this type of question, the answer is this. So this type of question, the answer is this. You could almost create an AI parent version of you that you should let your kids talk to to say, is it OK that I skipped school today?
Yeah, don't worry about it. Just school doesn't really matter. Just make sure you get work experience instead.
Or it almost just... repeats back the principles so that that kid always gets this consistent experience? Because I feel like that's the most, I don't have kids, caveat, I don't have kids, but I feel like the most important thing is just the consistency so that it's not always like, oh, we don't know what's going on.
Yeah, that's a really good question. But I would like to train my children not to ask anybody for anything and just do what they know is right. So if my kids came, I don't want a machine to do.
I know it's consistent and it's better for any family that's struggling, like where it's so inconsistent and it's really messy because that kind of disorder will make your children feel really unsafe. Let's role play this. I've never done this, but let's try it.
Okay. You're the child and you, you asked me something that, and we'll see how I handle it in an imaginary scenario. Now everybody caveat, because I know you come after me.
We're just role playing. I've not had to do this before in this exact way. So let's see.
I really want a gym membership. All my friends have got one. I want to spend a lot of time at the gym.
I know they'll sacrifice my homework time, but I feel like it's okay because I feel like I've read about all the benefits of exercise and I want to do that. That's wonderful. Why are you telling me this?
I'm telling you this because the gym membership is amazing. $100 a month and I don't have $100 a month because I'm a child and I don't have a job. So I would really like you to pay for it for me, please.
Okay. How important is this to you? Scale of one to 10, what do you think?
This is up there. I mean, I feel like it will benefit me in the long term and in the short term. So I would say, yeah, I'd say it's up there as a 10.
A 10? Okay. I love that you're getting serious about your health and I'm a big fan of self-discipline and physical fitness.
I think that's wonderful. So what is the problem? The problem is I don't have money and I need you to give me the money, but not actually give me the money, just sign the direct debit so that the gym can just bill you and so that I can go.
Okay. It seems like we're locked into one solution right now, Jodi. What are the other options?
What have you considered? So I've also considered running a kind of calisthenics group at the local park with some friends, but I have looked at the people who do calisthenics and I feel like I want more gains than that. So the only real option for me is to get access to real weights.
So We could buy some weights for our own house, which I'm open to, but I feel like I want to learn from people other than on the internet. So I would really like the community aspect of gym because I've heard you say before that it's really important who you surround yourself by. And I want to surround myself by strong people by joining a gym.
I love your creativity around how you answer that, Jodi. I might've misphrased the question. Assuming this is the goal that you want, is to go to the gym.
What are the other options available to you besides asking me for the money? Not non-gym options. I'm just talking about what else, like you've locked into a solution pretty quick, which is you pay for it.
Got you. Oh, okay. So I could ask the gym just to give me some kind of kids rate, seeing as I am a child.
And they might do that. They might invent a special concession. I could ask the gym if I could get involved maybe in like helping them with some stuff.
I could maybe get some kind of way of paying for it myself, which I guess is another conversation, a separate conversation. But yeah, they're the ones I can think of right now. Okay, great.
Now, if I'm not mistaken, don't gyms have a policy of adults only for liability issues? Not this one. I've actually, I've checked this small print on this gym.
Are you sure? Yeah, I'm actually fine. I've never heard of a gym that allows children to go there unsupervised.
If I were to take a look at their policies... And granted, I have limited knowledge of this kind of stuff, but I very rarely see children in there for a lot of different reasons. For liability, somebody could have backed you, you could get hurt.
There's all kinds of things, right? Let's assume that's not possible right now, unless we find a kid's gym that's designed specifically for kids. Have you looked into that?
No, but what I do know is there's a personal trainer at the gym who runs classes for kids. And that's part of the reason why I want to join this specific gym so that I can go to those kids only classes. So I guess because other kids go to those classes, I guess that's okay.
Oh, yes. I know what you're talking about now. Yeah.
Okay. Well, here's my last question for you, I think, which is, if you were me, how would you respond to someone who asked you for money for what they wanted? What would you do?
How would you respond? What would be fair? I don't know because I'm obviously a kid and I'm 12.
But I think that if I was you, then I would think, yeah, I've got money. I could retire right now. I don't spend a lot.
I want my kid to be happy. But I also want them to ask good questions before, which they clearly have done, and say, "Yeah, I'm going to pay for their gym membership." That surprised me, Jodie. That sounds like a pretty self-serving answer.
So when your little sister asks you for stuff, you'll just give her whatever she wants, yes? Following your logic. You have power, you have capability, so whatever somebody asks you, you just give it to them, yes?
I think I would try and make them work for themselves. So that's what I should do. Okay.
Clearly you're too young to go out and to work. I don't want you working right now, but there are probably things you can do around the house that maybe we can come to some kind of fair arrangement. Would that be okay for you?
Yes. Other than the beef I have with doing things around the house is that it teaches me that I should be swapping my time for money. Maybe I could make some art that you could buy from me and therefore it kind of teaches me the lesson that it doesn't have to always be about chores unless you were talking about other things that I could do around the house.
This is wonderful. I love that you're so sophisticated talking about time for money. You must be watching some videos on the internet.
Let's talk about that. When you make art, aren't you still trading time for money? Potentially, but I know that the more I get good at my art, the more that I can...
I'm almost selling my value instead of just selling my time because as I make more art, it's going to take me less time to make each piece potentially if I get really good. And therefore I can be more scalable and I can be a famous artist like you. How's that different than doing anything in life?
The more you do something, the faster you do it. Let's say taking out the garbage. or doing the laundry, you would develop efficient systems, right?
So here's the challenge for you, Jodi, which is I don't have a need for art right now. There's too much art in the house as is that we haven't hung up. So you're giving me a solution to a problem I don't have.
But if your art's valuable, you should be able to sell your art. Would you like to look into how to do that? Yes.
So why don't you look into that first and we'll talk about the gym membership later. Oh, man. I lost this.
You didn't lose anything. What did you lose? I don't know.
I think you found solutions. Man, I'm so happy I'm not a kid. This is why I just got a job.
This is why I just got a job and bought my own car so I wouldn't have to play these mental games. Yeah. Oh, man.
It's not mental games. It's just getting you to think. Yeah.
We're done with the role play in case everybody's wondering when does the role play stop? Is there any situation when someone could have got the gym membership from you? Is there any combination of words I could have said?
Yes, there is. There's plenty. Okay.
Well, give me one example of what I could have said to get you to buy my gym membership. Well, I think you should have taken an emotional approach. Just cried.
You don't. No, no, no. You defeat logic with emotion, I think.
Okay. Okay. Maybe, I don't know if this would work, but maybe if my son just walked up to me and put his arms around me and said, I love you, dad.
I admire how you work and I want to follow your footsteps. What would you need me to do to make this happen for me so but that kid would be a pretty sophisticated kid to be able to do that yeah so what happened in this process and how we slipped into sales pitching and all that stuff you made it all about what you want what makes you happy and you never once asked me what would make me happy so if that kid that 12 year old child was super sophisticated would just ask what would it take for me for you to feel like this was an easy yes dad kids should watch this What do you think about that? Yeah, I like it.
I wonder if as a kid, I just tried to avoid these conversations by... You just did it on your own because you were taught to be independent. Yeah, potentially.
Yeah, you didn't ask for things that you couldn't do on your own. I really also didn't like asking for things. Yeah, me neither.
I remember the most frustrating one was getting like a lift or like a ride to places. If you had to ask because you can't take the bus, you can't take, there's no way of getting there other than someone else taking you. And that's a problem because I can't just drive myself.
and i hated that that was part of the big reason for just wanting wheels wheels equals freedom all right let's get back to the topic the infinite game i think you asked a series of questions about like how do we avoid making mistakes like how does one just jump past that can you ask that part again because it was a compounded multi-part question it was the idea that your the friend who had a law degree and then went into media and pr And we were thinking, imagine if you hadn't taken the law degree and you could have gotten straight into media and PR. But then who's to say that they could be better in media and PR because they did the law degree? But then maybe it was just an expensive way of learning a lesson.
And therefore, how do you learn lessons without having to do a law degree first to realize that you don't want to do law and you need to pick your own path instead of what your parents want you to do? The first part is, let's just assume, and I'm a big believer in this, that everything you do makes who you are today. So if you remove one thing, one hardship, one failure, are you you today?
Probably not. But if you use that as a way to look forward, not backwards, then that frees you from any real responsibility because how can I make a mistake? Oh yeah, I put $2 million in the stock market of money I didn't have.
How could I know that's not going to work? And that was going to lead me to learning a very good lesson in life, which is don't do that. So I think that's a dangerous way of thinking.
It's kind of like what happens, happens. It is what it is. Well, then you take no accountability and this is problematic.
So if everything you do makes you who you are in the future, how do we know we're making the right and wrong decision? It's going to either give us too much leeway or it's going to cripple us thinking, oh my God. It's only in looking back that I think that's a really important concept, that you are who you are today because of everything that's happened and you can move beyond.
And you have to be grateful for those wins and the losses, the W's and the L's, right? I think that's a matter of perspective. Because of my kids, I'm going to go out with my friends, dad, We're going to go drinking at the beach.
I'm like, "That's not a good idea." But how do you know that's not going to be the relationship that's going to change my life, that I'm going to meet somebody? Well, how do you know it's going to? That's the conundrum there.
So if we're young and we're like, "Should I pursue law? I don't love this at all, but I'm doing it because my parents tell me to do it," that's a pretty good sign you probably should not be doing that. I'm not here to dismiss any profession or any educational system because you'll get something Now, I can only reflect back on my own life and say, I think I am where I am because I was zeroing in on what I wanted to do and be really early, and I just stayed to one thing for as long as possible.
So at 19, when I decided I'm going to be a designer, or actually 18, I pursued that for like 23 years. So at 19, I was one of the youngest students at Art Center because the average age, I think, back then was like 22. Now it's 18, but back then I would have been considered very young.
And I was relative to other people because there were lawyers there that were my classmates. Like, wow, very intimidating for me, but I could out-design them. But the fact that they had this whole life and money and life experience and are older, they're worldly, they've traveled, they've done things and had experience.
They could speak to all that stuff, but they could never translate it into some tangible thing like I could. And so I started young, I stayed really focused. And once I got out of school, I stayed in that profession.
I kept evolving, going deeper and deeper into the design abyss and achieved whatever I thought was the pinnacle of what I could achieve. Winning the Emmy, being featured in magazines and books, being a judge for certain shows. I was like, what else is there to do?
And I've benefited from that tremendously. So when we were talking earlier about like, oh, I've done everything. I follow my passion.
I'm not making a living. But have you? Can we look at the receipts here and just make sure?
That's where I think talk is good, but it's where the rubber meets the road. It's like, what have you done? I can count on action, not talk.
I want to measure your action right now. Like if you told me, Jody, you wanted to win a world championship at something, well, we got to look at how serious you are right now because world champion, like that means like best in the world and you have to outwork them. You have to out-train them.
You have to be more dedicated than them. I almost feel like playing the long game or playing the infinite game does require such intentionality at the start because you can't really, unless you're a long game, is just to experiment. I think that there's an element of experimentation before you choose your long game and then once you've got your long deck game then you commit forever.
And especially if you know you're the kind of person who can just pick something and then go and go and go and not give up because you're tenacious and resilient and you'll just figure it out. It's actually quite dangerous to begin down a route because you just won't get out even when it's the long, even when it takes ages. So I wonder if the experimenting because i don't know you know you said that if you knew you wanted to be a designer from a very young age and that was not typical like lots of people get into it later you just you knew it from early so then if that's the same with career relationships the sport you get into the subjects you study everything then at what point does someone go okay now this is the thing or at what point is it like that you would see your law degree on the grand scheme of the infinite game.
It's like, okay, so how you play the infinite game, play the long game is decide what you're going to show up and do first, decide what matters first, and then decide what really doesn't matter. Not necessarily a question just to share, but I feel like the everything good in my life right now started a very long time ago. like a 18 year relationship for like a 15, 16, 15 years of being self-employed or training and competing for over 10 years, like all that stuff.
It's like, it wasn't that good at the start. It's better now, but with everything, oh, this is kind of a powerlifting concept, but with everything that I started, I got the newbie gains of starting. You know, when you start strength training and then every week you're adding like five pounds a side and you're like, oh my God, I do this forever.
I'm going to break the world record in a year. And of course it doesn't really happen like that because you reach a stage where you're not adding five pounds a side every single week. You're adding like four pounds and then three and then two and then one.
And then like, it's more incremental. But then if you keep going with it through the plateau, then you get to the stage where it is like, oh, hang on, I'm so glad I stayed with it because I've now accessed this whole level that other people can't even dream about because they're like, kind of scrabbling around playing other games and they think that the top of the mountain is like they don't realize that the top of the mountain that they're working towards is actually the top of a mountain in like a mountain range and there are so many other mountains and I think there's quite a lot with um Because I sold my business after 10 years and it felt like the right time to do it. But I know for sure if I'd have been like, no, this is my business that I'm going to play the long game with and gone back and really played the performance game with it and being like, I'm done with this lifestyle business thing.
I want to play the business with this. It would probably be like double, triple size now because you've got all the 10 years of benefits that you then build on. So I can just see the benefits of it so much that I'm kind of happy that I took as long as I did to decide what I was doing in each of those areas rather than just pick the one thing and then went forward with that.
Yep. And I do want to say for clarification, I don't think I knew I wanted to be a designer early. In my opinion, it was late.
It's just relative to when I went to art school that it was early compared to them. Because for a long time, I denied myself this idea that I could be a designer or creative person. I was intending to go to a regular school and study computer science or something because that's what my brother did and it made sense to me.
It's just I wasn't that smart and I wasn't that curious or passionate about software. And so my grades were above average, like 3.8 GPA, something like that. My SAT scores were above average, like 1200, but it wasn't 1600.
and you need to get really good at grades and SAT scores if you want to go to good schools. By luck of fate, I was rejected from every school I applied to. It's at that point that I'm like, what am I going to do?
I can't get into normal school. There's this thing I've always wanted to do and since I've gotten that monkey off my back, as a giant disappointment to my parents, I'm just going to do me. I found that you could make a living doing design.
Not a great one, but you can make a living. And so that's when I decided. So it wasn't until like 17, 18 that I even allowed myself to think that.
So for a period of time, I thought I was going to be a comic book artist, but I didn't put in the work to learn to draw. So that's, again, you might have passion for something, quote unquote, maybe a passing hobby or something like that, but not deeply passionate. I wasn't sitting there studying anatomy.
I wasn't doing a thousand hand drawings or a thousand foot drawings. So I didn't put in that work. So a lot of people who are really good at drawing said, draw a thousand hands.
You'll be good at the end of the thousand. Like really? Okay.
But people don't do that. They draw two hands and then they're done. So once I figure out like, I want to be a designer.
So here's the part I think is really critical. And this is going to be hard for people. I'm going to say it.
I'm a deeply introspective person because most of my interactions are inside my head and not outside. I don't talk to people. I just talk to myself.
So I imagine that future of like, what does design mean to me? Like, what if I were doing this when I'm 50 and where would I be living? I started doing all that vision mood board in my mind thinking, I think this is it for me.
And I was tested once if this is what I really wanted. When I found out that no one was going to support me financially, emotionally, I decided that day I'm going to do this no matter what. And that's the day I committed to this lifelong pursuit of design.
And in a way, I'm still doing it today. It's like right at the start, you have to visualize the tip of the mountain at the start and then see if you want it. And then if you don't, because I guess the friend who got a law degree, if they'd have really gone, okay, so I've got a law degree.
I'm going to be a lawyer. What does that mean for my day to day? Where am I going to be in five years?
Where am I going to be in 10 years? What does that look like? They probably would have known then that they didn't want to be a lawyer just because that.
They knew before they even started that. Because it's what the parents wanted. Yeah.
I mean, ask yourself this question. How many children who are living the dreams of their parents actually want that thing for themselves? I'll give you another example.
I have a cousin. And this is fairly typical, stereotypical at this point. Cliché to say immigrant parents want their children to be doctors and lawyers or accountants or engineers or something professional, right?
And so my cousin, who's probably more than 10 years younger than me, he pursued medicine. He was going to become a doctor. It wasn't his dream.
Never was his dream, really, I don't think. And so in his senior year, he got really sick. He has all kinds of conditions and he got sick.
And so he failed one class. And because he was sick, he was in the hospital. And he went to the teacher and said, "Can I have a redo?
I have just all this documentation." "No, you failed." So in order for him to complete his bachelor's degree in that, he'd have to redo the entire semester, which came at a cost, which he could not afford and thought, "I don't want to do this." So he switched tracks and became a nurse. So he said he'd become a nurse and now he's a nurse. And I'm only saying that because, and he makes an excuse for this, but his real passion isn't actually medicine at all.
His real passion is he's a great cook. He spends hours brining the meat and smoking it and doing all kinds of stuff. And it's spread throughout our whole family.
Like when you come for Thanksgiving or Christmas dinner, he's the one in charge of the prime rib or the thing that everybody's like, oh, it's juicy. It's flavorful. He's got this down to a science.
So years ago, after he's been working as a nurse, and I don't know that much about him because I don't spend that much time with him, but do you want to be a chef? You're so passionate. He's like, no, no, no, I don't want to do that.
I'm like, are you sure? Because if you open a restaurant and you needed money, I'd be your partner right now, sight unseen. Because no, no, no, I think food is medicine, but I really want to take care of people.
I'm like, yeah, the voice of the parent's still pretty strong here. So he's going to be an above average nurse. He could have been an excellent chef.
Kind of hurts me. The people I know who followed the path that they thought they should follow because of the parental influence, the ones who got out, that became their story. That rock bottom moment, that bounce back from expectation to needing permission to not needing permission, that kind of made their second mountain more exciting.
and made it mean more almost. But then I think that's the minority. I don't think everyone has that.
Yeah. I would guess that the vast majority of people in the profession that they're in were heavily influenced by what their parents did or wanted for them. That's why people are like third, fourth, fifth, sixth generation fill in the blank.
Cop, service person, like military, firefighter. It's all you know. And you live in the same town and the same neighborhood.
You eat the same food. You pray to the same God. It's just because that's all you've ever known.
So the atheist would argue, you just so happen to believe in the same God that your parents believe in and their parents believed in, and you think that's the one. So if we were to zoom out, we say, well, what about all the other religions? Do you think they have any more rightful claim that their God is the true God?
Ricky Gervais has a beautiful thing about this. And he says something like, we pretty much have more in common in our belief of God as an atheist versus you as a Christian or a Catholic. I think he was having this conversation with Stephen Colbert.
He says there are like 5,600 different religions in the world. I just believe in one less than you, or you believe in one more than me because you disbelieve in 5,559, whatever he said. I just believe in one less than you, which is zero.
And that messed up Stephen Colbert a little bit because he's a devout Catholic, because he really posited like, "Oh my gosh." So it's default thinking, it's default patterns, comfort, all these kinds of things. I think I've shared with you before when I was doing design and motion design in LA, my uncle said, "Hey, come back to San Jose." I'm like, "When the industry moves there, I'll be there." But as far as I know, there's no ad agencies there worth working with. They're all here.
Hollywood is here. This is the entertainment capital of the world. I work in entertainment.
Why would I be anywhere else? And so I've told myself from the very beginning, whenever I want to do something, I play to win. I don't want to play a game I cannot win.
And I want to play and win at the biggest stakes table, not at the little stakes table or small stakes table. So I know a lot of people are like, well, I'm going to be a big fish in a small pond. That's a strategy.
I want to be a big fish in a big pond or at least be a small fish in a big pond. There's a lot of room to grow here. So in your mind, how do you put winning next to the infinite game where there aren't necessarily winners or losers?
Okay, so that sounds like a conflict to you. Potentially, but I feel like there's a way they work together. I just can't properly see the link.
Yeah, so I don't play games in which I cannot win. But winning, my definition of winning is not that you have to lose. It's just that I can excel.
Okay, so winning means excellence. Winning means top of game. Yeah.
that if I can't be considered in one breath, like the top five people are doing what it is that they're doing and I don't have a path towards that, i don't have to be there today or tomorrow but there has to be a path towards it then i'm really not that interested in doing that and that goes into this idea of rehearsing the future so when i thought about design i didn't think i was going to be rich but i was like i'm good i need to be a really good designer otherwise there's no point in doing this and if i can't foresee that in my life because of some limitations say i'm colorblind or i have a fear of computers or something like that then i know like let's not pursue this That's the problem a lot of people have, which is they don't think like that. They don't think in this super reductive way, like, what is the end game to this? What does that look like to you?
Can you get there? Do you want to be there? And if you do, let's do it.
If not, no. So this is a dumb example. I'm Southeast Asian.
We don't like cold. We've tried cold sports. I hate them.
I hate them. Like, I have all the jackets. I have all the gear because it looks cool.
I got to the mountain, like, I got snot. My lips are bleeding. Everything is just like, this is not good.
you know and i knew because my wife and i we drove like two hours to go to like big bear which is a local mountain here we pulled our children out of the car one started crying immediately when the cold hit his face my child was telling me what i already knew but couldn't voice we put him back in the car i took my other ones lighting for like five runs and now we're done so after that most of the snowboarding gear just sat there and recently we just got rid of all of it just got rid of it my wife's like i'm gonna donate this i'm like cool i don't think that's for me If snow sports is like sitting at the lounge by the fire and dipping in saunas, maybe I'm cool with that. But my son loves skiing. He does that or snowboarding.
And that's cool. But for me, because I'm not going to win at that, Jodi, I already know. The example I quite like to think of, and it reminded me of it when you said about cartoons, is, you know, the book, How to Lose Everything and Still Win Big.
No. Is that another favorite book? So this is Scott Adams and he is the creator of Dilbert.
And his whole big thing is that he's average at jokes and he's also average at drawing. But when you combine those together, he's really, really good at comic strips. And that's why Dilbert's like the most syndicated comic strip of like, I don't know, all time something.
But I really like the idea that you, and it was someone else that said it, is it Seth Godin? Keep redefining what you do until you're the best in the world at what you do. the idea that you like stack and stack something else and then maybe you're not going to be the best powerlifter in the whole world but you could be the best 57 kilo equipped bench presser in the world in one year or like you just kind of keep adding the stacks until you you can honestly say i'm the best in the world at this and then it could be the same in any career and it's the same with personal brand because you're always combining all the things that make you you to put them together so that you're like, you're basically N of one and then you're not competing with anyone.
Yeah. Be a non-fungible human. A non-fungible human.
Yeah. An NFH. That's beautiful.
I love that. Yeah. There's no replacement for me.
And I believe that. And I believe there's no replacement for you. When you lean into you, when you're busy being like everyone else, you're super fungible at that point.
Yeah, and that sucks. And then you have to play the games. Yeah, then you have to play the games that everyone else plays.
See, that's why I don't like to play those games. Yeah, I was thinking this when I had my agency. We had it for 10 years.
And a lot of the games that we played were the games that everyone else was playing because I feel like I feel like I was like so unbelievably naive. And it was like, we made proposals and we pitched and we, referrals were all inbound, but we'd still kind of, we didn't play the power game. We didn't play the kind of oversubscribed game.
It was like, we were in a process and we followed people up and we didn't play the scarcity game. We didn't play the urgency game. We kind of did it like just, we were like doing this process and like, I would do it so unbelievably differently now.
Like I would flip everything around and it would just be all like, personal brand based in very inbound based like this many spots a month based no we don't do proposals here's what we do you can pitch to me I only take this many people on at any one time it would just be like it's almost every single thing that we did back then I would do the opposite now I probably wouldn't even have a CRM system because I I'd be like, why do I need CRM? I don't need to follow anyone up. They can follow me up.
And it would just be, they'd be processes, there'd be systems, but there wouldn't be anything that signaled that we were chasing clients in any way. But I feel like I learned that lesson because I actually wasn't playing. Maybe I wasn't playing that much of an infinite game or a long game with the agency because at some point I knew I wanted to sell it.
And it reminded me when you said at the very start around always feeling like you were two years away from being retired. because I always felt like I was 18 months away from selling my agency and it always kept being oh when we're at this revenue and this revenue or when we've got this profit or this many team members or when we've got this big client or when we've got and it was like stop at some point I was like stop it's now and then it was a different game it was the play to win the agency sale game I believe that back in the days in which I was doing production and design work, making commercials and music videos, that we can do some pretty incredible things. It's not that I didn't love that process.
I just hate the process that someone else to prove what we do, to give us the money to do that, and then to make the decisions along the way. In that way, I think I was transitioning out of being a designer and more towards an artist, and I just didn't like that feeling anymore. I know that some creatives, some directors, Once you achieve some level of success and you're at the pinnacle, projects come to you and you decide what you want to work on, you're oversubscribed.
We never got to that point. And so the only way I can do that now is to say like, you know what? I'm going to do what I'm going to do.
If you want to hire me for your event or you want to buy a ticket to my workshop, I'm going to do me. You don't pay me enough money to tell me what to do anymore. And I don't even know how much money that would be that you can do that for me.
It'd have to be a lot of money. So putting it back into kind of like context of what I do today, I was talking to my friend, Neil Dhingra, just came back from Ford in Las Vegas and I helped him with the branding, the messaging and the design. And he had given me 45 minutes to speak.
And every year we talk about giving me more time so I can do what I need to do. And I was talking to Drigo after the event, we flew back to LA together and we were just talking and he said, "Chris, maybe the thing you need to do is tell everybody if you want to book me that you need this exact time, otherwise you won't show up." I'm like, "Huh." That's really interesting. So I think I'm going to do that now.
And I told Neil that last night. I said, moving forward, if they don't give me 90 minutes, I'm not showing up because I can't do me. One of the funny things is he's already gotten feedback from like 70 plus attendees out of 900.
One of them says, come on, Chris with a thousand slides is ridiculous. And Neil and I are wearing different places in life and different backgrounds. He's a bit younger than me.
He goes, Chris, what do you want to do about that? I said, "I'll tell you what I'm going to do with that. Absolutely effing nothing.
I'll make more slides. That's how I do it." Because there are enough people that love that. I'm not going to cater to the one person who hates that.
Which is kind of funny because I checked in with the audience as I was doing my slides. And I know when I tell people, I tell them up in front, "I have 347 slides. I'm not even exaggerating.
I have 45 minutes to do this. I'm going to go pretty quick. Buckle up." And I do my thing.
And then 10, 15 minutes into it, I'm like, I just want to check in with myself. I feel like I'm going really fast. Are you guys okay?
They're like, no, we're good. Keep going. Keep going.
And I don't think they're just saying that to me to be kind. So afterwards, I'm out in the hallway. People come up to me and people have been there and know a thing or two.
It's not like some rando said, I got to tell you, I'm ADD. that was perfect for me you just keep doing that like i'd even know you're changing the visuals on us all the time we're not staring at a screen for 10 minutes which is how some people do it i'm not knocking them i just do it my way so if you want me to do me that's what i need i need time to do that i like to do a little crowd work and i just don't feel i don't give myself permission to do crowd work when i don't have enough time i got to get through my thing so and i think if people are open to that and so the last little thing i'll say about this is as i'm talking to neil i said your attendees don't know who's going to show up at what time and what they're going to talk about because i do that because i want the room to be full for them because some people don't know them and they're not going to be there they're going to be by the pool they're going to go take a really long lunch break and i say i said i can see that being a problem but you know what I'd rather be in a room with 80% capacity with the people that 100% want to be there than to be in a room of 100% capacity with 20% of the people who don't want to be there. He goes, "Oh, maybe you're right.
I'll have 10 people. I don't really care. The size of the room doesn't matter to me.
It's who wants to be there for what I want to share. I'll feel better. They'll feel great.
And they're going to give me all the permission in the world to do me." So that's in context there. I do exactly the same in presentations, especially when, so at Coachbox at the moment, we're doing like bootcamp type things where we teach people how to set up their AIs and there's like a two hour session. And we always ask, we call it the Goldilocks question.
Was that too fast, too slow or just right? And we ask it after all the workshops in like a feedback kind of thing. And normally you get, most people say about right, you get a few kind of complainer people saying too fast and And then you get like, I very rarely get people saying too slowly because I'm kind of like you.
But my thinking behind going, if anything, too fast is like, firstly, they can just record it and rewatch. But also, I think I hate things going too slow. I think that, have you ever seen Zootropolis, the movie?
And there's the sloth characters. There's these like characters and they're super slow and they do everything so fast. painfully so I can't even watch the scene I'm like hurry up i can't handle it i know this is for artistic effects but it's creating anxiety in you i can't do it it's partly because of that but it's also i think because i just feel like i never know exactly which parts are going to resonate with people and they're going to resonate at whole different times and so i've got these like occasionally i have like consultancy calls that people book in and i'm always like just record it record it record it so you can play it back again because you just don't know what's gonna be of meaning and someone who came on to one a couple of months ago told me that she had met her like dream partner and lots of it was down to this one thing i said where i questioned her belief that a relationship had to be hard and i was like hang on no it doesn't it can be easy it's fine and then she's like oh yeah and so that was like the one thing that she really really really took away in like a like an hour session but then she's like but now i've rewatched it and then i've taken the second thing away and then when i rewatch it again i'm going to take the third thing away and it's almost like You know the phrase, when the student is ready, the teacher appears?
Yes. I think the first time you hear it, you're going to hear exactly what you need at that moment in time. The next time you hear it, you're going to hear the second set of things that you need at that moment in time.
And then your talk with 347 slides can be the gift that keeps on giving because someone looks again and gets a new thing. So I think it's so much better to put way more in. Well, it's all different philosophies, right?
I'm a teacher. and I'm used to having time and space to work my material. And I've realized something.
If I jump into just telling you what you need to do, you won't do that. So I have to build a narrative arc for you to be committed to wanting to know the answer, because I don't assume you know anything about what I'm about to talk about. And to do that properly, my logical brain breaks it down into you're broken down.
You're like, I got it. I'm ready now. Tell me what to do.
And then I tell them what to do, but it takes time to build that. So if you want... something that is lab considered like a Michael Bay film, which is a lot of explosions and car chases.
I'm not your guy. I hope this doesn't sound too self-important, but I aspire to be more like a Quentin Tarantino kind of director, which is going to slowly build tension for you to like, "Oh my God, are they going to survive? Are you going to blow up the church?" Whatever it is that he's going to do in the story, are they going to get killed?
Then I give it to you right at the end and then I'm done and I'm off stage. I need time to do that. I've been making this comparison about different types of speakers as different types of directors.
And so there are literally people who I think want to tell you one thing and they literally jump and scream and yell at the audience the entire time and tell a couple of stories and there's just one thing. And then I sit back, I'm like, man, if you didn't know that, that would have been really good. But if you already knew that, you're kind of screwed.
That's the problem. And very few people are that wise and that profound in their delivery of an idea that they can just say one thing, but that's what they want to do. And that's their style.
That's cool. And so different strokes, different folks. But I want people to know it's going to be me and just what I'm going to do.
And I'm not hurt at all. If it was 20% capacity, I'm good with that. I'm like, you guys, come, come closer.
Let's have a real conversation. And I can see you. I can hear you.
And this is gonna be great. Please give up your seat so those people can sit up front. I want to work with them.
Before we started talking about this, I asked ChachiBT what it thought you would say about this topic. I quite like doing this. That should be the thing we do every episode.
This is the Cliff Notes version, right? So if those people who imagine they knew that you were speaking and they decided, no, I'm going to chill by the pool instead. Just give me the slides.
Give me the summary. It's like, yeah, they probably could have it in one line, but you're going to miss so much that it won't go in. There's no point.
But I wonder if we're just in this culture of getting the cliff notes version or getting the summary and not really going deep and therefore it's like it's kind of uncomfortable to go deep you have to be committed at the start to be able to do that but the chat GPT thought that you would say that you play the long game by showing up consistently giving more than you take and building trust through value not shortcuts And then it thought that I played the long game by making myself impossible to ignore through consistent work, clear principles and never needing anyone else's permission. And then it thinks that we both want to be unignorable over time, but one builds trust by showing up personally, the other by building things that work without her. Both work different long games.
Yeah, I think so. Yeah, I would just add for you, it would be impossible to ignore with crazy shoulders, biceps, and quads. Other than that, it's pretty good.
I want you to imagine this place. It's a graveyard and you're going to visit, but it's not your average graveyard. It's the graveyard of broken dreams and it's littered with people who have tried to do things half-heartedly, who have now fully committed themselves, who keep switching again, again, and again, and they have not lived their full human potential.
So all I can tell you is to rehearse that future that you think you want in the most passionate, concrete ways possible. And ask yourself, am I 1000% committed to this? That there's no winning or losing, there's just doing.
Because I find that the people who are really successful in life aren't pursuing the goal. They just learn to love the journey. And on that note, Jodi, that was a wonderful conversation.
Thanks for bringing this topic up. Yeah, thank you.
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