(upbeat music) - Hello, and welcome to another episode of All The Hacks, a show about upgrading your life, money, and travel. I'm Chris Hutchins, and today I'm talking to one of my favorite authors, Derek Sivers. He has a seemingly unlimited arsenal of incredible life advice that comes from one of the most unconventional life paths I've ever come across.

He started his career as a professional musician, ended up joining the circus for almost 10 years until he started CD Baby, which became the largest seller of independent music on the web in the early 2000s with over $100 million in sales. In 2008, he sold the company, giving away most of the proceeds to charity, and has been focused on a life of creating and learning ever since.

We're all fortunate for that path because of the amazing writing he's done since then. So today, I'm gonna try to give you a glimpse at that wisdom as it relates to decision-making, aligning your actions with your personal values, living a more satisfying life, creating meaningful experiences, and a lot more.

We'll also talk about why Derek thinks traveling with children is easier than just about any other parent I've met. It's a lot to cover, and I really hope you enjoy this episode. So let's jump in right after this. With the tax filing deadline around the corner, you're probably dreading sifting through all the paperwork to find those donation receipts, or wondering if you missed out on maximizing one of the most generous tax deductions, charitable contributions.

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So head on over to allthehacks.com/daffy if you wanna start giving today. And for a limited time, if you visit that link, you can get a free $25 to give to the charity of your choice. Again, that's allthehacks.com/daffy, D-A-F-F-Y. (upbeat music) - Derek, thanks for being here. - Thanks, Chris.

- So from the outside looking in, when I read everything you write, I'm like, "Gosh, this guy has it all figured out." And for every aspect of life, I'm always like, "Ah, there's probably a post Derek wrote. I could just search up about this thing. I'm trying to make a decision or be a better parent." Do you feel like you have everything figured out?

- I'm an explorer. So at any given moment, I might have figured out right now, or I might've figured out yesterday's exploration and what I want to do about it, but then give it a few days and I'm off to somewhere new. - I wanna make a bit of a theme of this because I think the average person listening isn't comfortable with that level of exploration in their life.

How do you get comfortable saying, "Well, maybe I don't have to have this job. Maybe I don't have to live in this place," and reframing it around what you wanna do in the moment or what you should be doing? Is there a thing, maybe a tappiness that you kind of use to guide your exploration?

- Intellectual interest, but also I'm usually led by whatever it feels I'm lacking now. And it sounds weird to put that so bluntly, but say you might be living in the middle of a city and you're too hectic and you're too booked up and you've got too many things going on and you think, "Ah, if only I could go live in the middle of nowhere in the country." And so you do that, you make some changes in your life, you make your job remote or whatever it may be, and then you move off to the middle of nowhere and you get there and you go, "Ah, I've done it." And after a week or a month, you go, "Yeah, I kind of miss a little commotion," you know?

And so you start pursuing something to put a little commotion back in your life. I think we're often driven by what we feel that we're lacking right now. And so I do that too. It's like the pendulum swinging. You know, the pendulum goes too far off to one end and it kind of goes, "Ah, I wish I had a little gravity bringing me back to the center." And so the pendulum swings back to the center, but then it keeps swinging to the other end and it goes, "Ah, yeah, I wish I had something bringing me back there again." So that's probably driving a lot of my pursuits, but let's say that combined with the intellectual curiosity drives to just try something new.

- Now, if we rewind, you said the person living in the city feels overwhelmed, so they move to the middle of nowhere. I imagine that most of those people are actually not gonna do the move. I think most of the people probably get stuck in a situation saying, "I'm living in the city.

Everything's overwhelming. Wouldn't it be nice to go just disconnect for a month, but I just can't do that." So I wanna rewind to that narrative and say, how have you been the kind of person that's been able to do that? When so many people, six months later, are still saying, "I'm still in the city.

I'm still overwhelmed. I'm still frustrated in my job." Is there some thing that you've unlocked that allows you to do what so many people can't? - Hmm, I think I've always pursued that, even since I was a teenager. Now, hold on, you said one key thing in there. You said like three months later or six months later.

It might take a couple years. When I was 25, I was a touring musician playing the college market in the Northeast, and I decided to move to Woodstock, New York. And I did it, kinda like the little scenario I just described. I had enough of New York City. I had been living right in the middle of New York City for like five years, six years, and I was just like, "I've had enough.

I wanna move to Woodstock, New York. I think that's my place." And so I just did it. I just drove up there one day. I went straight to the Century 21 real estate office, and I said, "Show me what you got. I wanna live here now." And she showed me something, and I was like, "I could afford it." So I said, "Okay, I'll take it." And got rid of my life in Queens, New York, and moved to Woodstock, New York.

And about a month later, I was at a gig in Rhode Island somewhere, and Renee, this redhead who had hired me for the gig, I had known her from before. Like she had hired me like two years earlier. And she said, "Oh my God, good to see you again.

How's it going?" And I said, "Well, I just moved to Woodstock." And she goes, "Get out. No way. Derek, oh my God, that's amazing." And I said, "What? Why do you?" She's like, "Derek, don't you remember? You told me this." I said, "No, I just moved last week." She goes, "Yeah, two years ago, you told me you wanted to move to Woodstock." I said, "I did?

I don't even remember wanting to move there two years ago." She goes, "Yeah, oh my God, two years ago, you told me you wanted to move to Woodstock. You did it. That's amazing." I went, "Oh, wow. Wow, I guess I've been wanting this a long time." So sometimes I think it goes like that.

It might take a couple of years for your intention to turn into reality. - So maybe just accepting that everything doesn't have to move as fast as we expect it to, especially in a professional setting. I know you are well-known for saying that you try not to just give your first answer if someone asks you a question, not to just quick, immediately react.

I think maybe we live in a world where that's kind of not the way we default operate. So if I'm overwhelmed and I feel like I need to move, I don't think, how could I slowly transition my life to be able to move in a year or two? I think, could I move tomorrow?

No, oh, I could never move. Okay, but there are some things in life where doing it tomorrow is the right choice. Here's a more recent example. And I know this doesn't sound like a big deal, but I'm living here in New Zealand now and I was missing social interactions.

New Zealand's quite isolated. And I used to attend a lot of conferences, like whether it was a TED conference or music conferences or tech conferences. And I kind of miss having a bunch of new random people in my life. I kind of miss that thing where you'd go to a conference and meet like 50 people in two days.

And because I missed that, I was like, I'm gonna make that happen. I'm gonna go just do that myself. So I booked a trip to India, specifically Chennai and Bangalore, two cities where I know there are a lot of people in my database that I've never met face-to-face. And I sent an email saying, all right, I'm coming to Chennai and Bangalore for 10 days.

Who should I meet? And used a little scheduling program and I booked in like nine meetings per day with strangers for six days straight, met with about 55 people. And I just got back a couple of days ago and it was intense and wonderful. And I came back and I was telling a friend about it.

And she said the same thing that you said. I'm just like, God, you just kind of have an idea and then you just go make it happen. That's amazing. And yeah, that was a sweet compliment from an old friend. And it was kind of funny to hear you just say a version of that right now.

So I guess this is something like my moving to Woodstock example that I think I've just made it a priority. Also, maybe I've always kept my life quite light, meaning I try not to get into situations that bind me to a place. I try not to own much stuff.

So it's just dead easy for me to move. I can pack up my whole house and move in a day. That's just been a priority for me. But that's not to say that everybody should be like that. Some people get deep joy out of having a home with their sofa that they love and their piano and their things.

And it would be hard for them to move, but that's fine 'cause they get deep joy out of having that deep sense of home and all of these belongings that belonged to their grandparents and all of that. I'm not saying everybody should be nomadic, but when you're asking how have I done that, that's my answer.

- I'll go back and say what you did with India was something that I think some people might think, gosh, I really miss all these people. I live in a place that's kind of remote. I don't see a lot of people. I'm pretty nomadic capable and I don't own a lot of things.

Maybe I should move somewhere. And you said, no, maybe I'll just take a trip to get that kind of fix, if you will. So I wanna talk a little bit about how you think about making decisions. The decision in someone's mind might be, oh, I'm not able to do what I want.

Obviously I need to move somewhere where I can have more of a balance, let the pendulum go back in the middle. And you said, well, maybe there's an alternative. Maybe I could go get this deep, intense fix for 10 days that'll hopefully give you a little high of human interaction for a period to come and sustain you.

When you approach decision-making, it sounds like you don't just look at what's the assumed default option of what I could do. You try to really make sure you're casting a wide net at ways to experience things. - Yes. It's one of my favorite things is to be reflective and ask yourself what you really want and not just limit yourself to a few options from what you see other people doing, but to really kind of dig deep and go like, okay, what do I really want and why do I want that?

What's the real point of that? So if I think I want to be on a beach in Thailand right now, well, why do I think that? What do I really want? What do I expect will happen when I get there? Why is it that I need a beach in Thailand?

Could it be a beach anywhere? Is it just the quiet that I want? And you may keep asking yourself these questions and get to the actual answer, which is that, yeah, my home is too noisy. I hate all the clamoring here. I live right above a train station or something and it's too noisy in my home.

Really what I'm pursuing is the silence. Well, do you need to go to Thailand to get silence? Is that the sustainable solution to that? No, maybe I need to soundproof my office. And you might come to like, yeah, actually I don't need Thailand, but the money it would take to go to Thailand, I could soundproof my office.

And I really do like living here in Toronto or wherever it is. In fact, I'm gonna stay here, not go to Thailand and soundproof my office. Yes, that's what I really want. If you keep digging into yourself, you might come out with a solution that suits your problem better.

- Is there something you do, maybe it's natural for you, I have to assume it is, where someone asks you a question or you have an idea and you're able to force yourself to pause and think before kind of going all in on this thing. Someone says, oh, do you wanna go here?

And you're like, and my default is, do I wanna do this thing or not? Not, oh, what are these other options? Someone asks a question. My default is, do I know the answer or not? And if I think I know it, let's answer it right away. I don't have the natural instinct to pause and think before.

And I'm curious, is there something that you've trained yourself to do? Is it natural? Have you thought about how people who maybe don't have that instinct could adopt it? I think it would be beneficial to me, which is why I'm asking. - Well, I journal like crazy. - Okay.

- I journal so much. Unlike the other things where I say, hey, you know, not everybody has to do this. Everybody has to do this. Everybody should do this. It helps so much to pause. And it doesn't even matter what, pen, paper, text file, Google Docs, doesn't matter. Something where you can stop like every day and ask yourself these reflective questions.

Like ask yourself questions like, why am I doing this? And what am I really after? What's the point of that? And then you should doubt yourself. You should doubt the answers you give yourself. So even if you say, why do I want this? Because I've always wanted to go to Thailand.

Challenge yourself, right? Really, have I always wanted to go to Thailand? Really, always? Why do I think that Thailand is the answer? Like push back on your own answers. And it can take just an hour of your day. And it is so, so useful. And if you say that I don't have an hour in the day, well, the hell you don't, you know?

Like turn off other things and do this because where it takes you makes all the difference in the world. - And are there prompts that you use or is it just whatever's happening in the day? - Yeah, whatever's happening. Not like generic prompts that I'm gonna, you know, hey everybody, write down these five questions to ask yourself every day.

No, it's not like that. It's just based on whatever your situation is in the moment. Generally, I think use it to clarify your thinking and to think of other options. Like you said, like if you think you have no choice, you're always wrong. There's always another choice. If you think you've only got two choices, well, those aren't options, that's a dilemma.

If you think you only have two choices, you still haven't thought enough. You have to keep thinking of other options. You can always add some crazy ones in there. Like, okay, option number three, I quit everything and join a monastery. Okay, option number four, I go down to my local park and I lay on the bench and I don't leave, I become homeless.

Okay, well now you've added two more options that you don't like. Okay, you can always keep going and then get more creative. Do the brainstorming approach where you're deliberately thinking of out-of-the-box, crazy solutions for your situation, but just keep going until you've got like 10 or 20 options. And many of my best ideas in life, the ones that I've been the happiest with, the choices I've made, have come from this pushing myself to further solutions, right?

It was actually like solution number 18 that got me the most excited and that's the one I pursued. - Is there an example of, I thought I was gonna do this and this new thing came out that I never was thinking about originally? - Ooh, yeah, what's an example?

Well, like actually that trip to India that I just took, that came far down the list. At first it was like, I think I need to go to the TED conference again, which I haven't been to in 10 years. And it was like, well, I think I just need to go to any conference.

And then it was like, what about a local class here in Wellington, New Zealand, where I live? Maybe I can find like a philosophy course here so I can meet other interesting people that are into this kind of stuff I'm into. And then it was like, oh, I could go traveling.

I could go travel Europe. And I just kept going. And then yeah, way down the list was like, I could go to India. That was like, oh, India, yes. Oh my God, I haven't been to India in 12 years. I know so many people in India. And through a weird thing that I married a woman from India, I'm a citizen of India.

I have the legal right to live in India for the rest of my life. I was like, ooh, see this one works for me on many levels because this wouldn't just be a travel. This wouldn't just be a trip. This is like an investment into my future. Like it's likely I will live there someday.

And so getting to know it better now, meeting people now would be an investment into future long-term friendships, not just a quick romp at a conference. So yeah, that came way down the list. And that's one example. And again, I just got back from this trip. So it's on my mind right now, but I met so many interesting people there and had so many fascinating conversations.

It was just what I needed. And yeah, that solution did not come until I had really spent an hour in my journal thinking of different solutions. - I love it. I'm gonna propose for people who might be like me thinking, gosh, journaling. I wanna try, but I'm not sure what.

What I hear is take some decision you're thinking about making and maybe just spend an hour by yourself with a notebook, a pen, not a computer, and just kind of think of different ways that you could have a different outcome. Instead of journaling, I'm gonna call it brainstorming 'cause I think we might be more familiar with how to start doing that.

But at the end of the day, it's just writing things down and thinking about them. So you can call it whatever you want. But I like this idea. I'm not a disciplined journaling person, but I feel like I'm gonna try to take your advice after this and at least commit to it.

- I'm not disciplined either about it. It is absolutely not a discipline. To me, it's just sanity. It's like, I've been doing this since I was a teenager and I'm 53 now. So almost every day I hit some point where I need to clarify my thoughts on something. What might even be about somebody, like somebody's pissed you off and you find that you're all upset.

You need to kind of stop and clarify your thoughts instead of just sitting there and feeling angry. And like, wait, why am I feeling angry? What's this really about? And so instead of just sitting there on your sofa stewing, it's just like, open your thing, whatever it is, your paper notebook, or in my case, I just use a plain text file.

I just open up a plain text file and I just start typing. There's no discipline to it at all. It's just like, what the hell? I am so angry right now. Why am I angry? Because this person did that thing. Well, so what? Why does that matter? Well, because this.

And I'll just kind of have this dialogue with myself, like I said, and like kind of challenging and pushing back. I hear that, I don't know much about this, but I've heard that this is similar to something called cognitive behavioral therapy. And it is known to be one of the few things that works for people with depression or anxiety or other major life problems.

Cognitive behavioral therapy works wonders. I heard that a couple of times. And when I just looked into what it is, it sounds like it's what I've been doing in my journal since I was a teenager. So I could say it in my very undisciplined way that it's worked wonders for me.

And most of the major life decisions that I've made have come from that process. - It sounds a little bit also like rubber duck debugging. I don't know if you're familiar as a way to make decisions. I think you wrote a post about getting mentors advice without actually ever speaking with them.

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- Should we tell the listeners quickly, so the rubber ducking comes from, first it's from back in the day when people had those big monitors, the big CRT monitors on their desktop computers. - That you could actually put something on top. - Yeah, where you could put things on top.

And so computer programmers started a habit of putting a little rubber duck on top of their monitor. And whenever they were trying to get work through a programming problem where they're stuck, there's like, okay, tell the duck. And so you'd say to the duck, like the reason I'm stuck is because I can't figure this.

Well, then why can't you figure out that? Because what I'm trying to get is the instances table to match with the something table. Well, why can't you do that? Because it's, and so yeah, explain it to the rubber duck and it'll help you clarify your thoughts. Yeah, so that's definitely what I'm doing in my journal, then changing the subject.

You said the mentors that, yeah, I often, when journaling, I'll ask myself, like, what would Seth Godin say? Like he's a hero of mine and he's such a wise guy beyond his marketing that he talks about. He's just wise in general. Like his approach to life is very thoughtful and measured.

And he's a friend that I could call, but before calling him, I ask myself, if I were to call Seth right now, what would he probably say? Like, I know what he would say. He would say this. And I'd like write that. And then that ends up helping me get to a good solution for myself without ever having to bother Seth Godin.

So yeah, I wrote a post about that. Like how to ask your mentors for help or something like that. And I just basically described this process, like ask yourself what the mentors would say. - I love it. I'll try to find all the links to everything we talk about, put it in the show notes so people can find it.

I met someone once and I offered to help them with a challenge. And they said, no, no, no, I don't want your help yet. I have a rule. I try to spend 15 minutes at least on my own, trying to solve something before I ask for anyone to spend their time to help me out.

And I was like, oh, wow. To use one of your phrases, this person is making it easy for me to say no on my own. And so it's something I've tried to do in my own life is I feel like plenty of us are overwhelmed. We have lots of stuff going on and we could talk in a bit about how to slow down and say no and only focus on the things you care about.

But one way that I can kind of contribute to the problem or relieving the problem is just trying not to ask everyone to help me out until I've tried to do some work on my own. And my snarky reply to close friends and family members for years was always the, let me Google that for you site if you've ever been there, which was someone texts you and they're like, do you know a good Italian restaurant in Dallas?

And I'm like, yeah, Italian restaurant. Like you could just search for these things. I've never even been to Dallas. Now I'm hoping that the world will slowly adopt a practice of trying to do a little bit of homework before asking people. 'Cause it's easy for me to text back my sister or my mom.

Hey, why don't you do a Google search before asking? It's much harder to text a stranger or a business acquaintance back and be like, hey, could you actually just try before emailing me? But there were a couple of things we talked about that I wanna loop back to. So it's gonna be a bit of a zigzag conversation.

Journaling allows you to come up with lots of options. You know, you talked about decision-making. If there's one option, it's not true. If there's two, it's a dilemma, but you wanna get to a place where there's a lot. One of the challenges I have, and I think a lot of people listening have, is actually on the other direction, which is getting into this analysis paralysis.

So a few weeks ago, I did an episode about insurance and I went down this crazy rabbit hole of how do I get the best homeowners and auto and umbrella policies for my life, which led to, oh, there's all these carriers. I should go get a quote from all of them and I should analyze all these details.

And believe me, I did not have a dilemma or A or B. It was like, there weren't enough letters in the alphabet to define the option set I had. And then you're like, oh, well, if I go with this one, it's a little bit more expensive. But if our SUV breaks down, they guarantee that I could rent an SUV instead of just an economy car.

But this other one offers this other feature. And for me, it was a struggle. I searched to see if you'd written about this because I was like, ah, I know someone who might have some advice. Then I tried to think about what would Derek say and I couldn't really come up with it.

So I'll just ask you, how would you suggest people think about making decisions when there are too many options and they're struggling? - Oof. For me, one option usually leaps out as the one that makes me feel the best. And it's not always rational and that's okay. And then if it doesn't, I just pick one that seems to rationally work.

And then it's a mindset that picking anything is better than picking nothing. If it's something that you have to pick. Okay, so wait, what do I mean by that? There's a great value in launching, for example. I've met some people that have been working on their book for so long without launching it, without calling it complete, that they're reaping none of the benefits of having the book out there in the public, right?

So at some point with anything you're creating, whether it's a blog post or a decision, you realize, all right, well, I just have to finish this thing. I have to finish this choice. I have to finish this article that I'm working on. And once you put great value onto finishing or deciding, then what you do is you just get into a different mindset about the benefit of putting it out there, the benefit of finishing.

Like say, you can make any choice great through just deciding to make the best of it. Okay, but wait, sorry, that answer was a little mushy. - Related to this insurance thing, I'm looking back and I'm thinking there were two moments where I could have done what you suggested that would have made it a lot faster.

And I probably would have felt a lot better. One was for some reason, and I can't really explain why, maybe it's the positive reviews, maybe it's the word of mouth, the consumer reports rating, just felt like USAA as an insurance carrier was where I kind of just wanted to end up.

Every time I was about to hit the recalculate button, I was like, come on, just be really competitive so I can just be done with this. So one answer was, if you have that feeling, just own it and be like, yeah, it might be a little more expensive, let's move forward.

That was one. The alternative version, let's say you don't have that, is, well, right now the problem was that we were using one carrier and they just couldn't continue to insure the house because the house had kind of appreciated and it wasn't a good fit. So we needed to move carriers.

Instead of making it about the big decision of we have to have a new insurance carrier, so this is not a do I need this or not, we absolutely need this. But instead of trying to find the best possible thing, I could have picked the first carrier that could do what we needed and put that policy into place, be done with the policy that I have now that I know is not good, and then decided, okay, is it worth continuing to evaluate the landscape?

Because what I was doing was I actually had two problems. I had, I have something that doesn't work and I need something that works and I'm also interested in finding the best thing. And because I was solving them both at the same time, I was actually delaying getting the thing in place that I needed to do more urgently.

And if I had just picked anything, it might have been more expensive, but I would have been done with problem A and I probably could have said, is it really worth trying to solve problem B right now? But when I put the two problems together, I made it seem like they were equally as important.

So if you could just pick anything that is good and then decide whether you wanna go on the quest for great or go on to another quest for good in your life. I don't know. That's me trying to philosophize your feedback, but I could have completely butchered it. - No, you nailed it.

That was wonderful. All right, Chris, I've got three topics you just brought up. - Okay. - I'm gonna name them first so we can remember to come back to them. Number one, the coin toss. Number two, the paradox of choice. Number three, theory versus practice. Okay, coin toss. The reason to flip a coin when you're making a decision is not to let the heads or the tails actually decide it.

It's to notice how you feel when the coin is in the air. Like you just said about USAA. If you were to do the coin toss with USAA, you would have been like, oh, please land on USAA. And as soon as you notice that feeling in yourself, it's like, okay, I think I've just decided.

It isn't actually the coin that decides. It's the pressure of that like, oh God, here it comes. Here's the final decision. And then you notice which one you're actually leaning towards. Okay, that is to be valued because emotions matter. I've sometimes chosen, say like, the more expensive internet service provider because I think they're more ethical or they're cooler and I just feel better about giving my money to that company even though it's more expensive than the other choice.

Okay, so that's the coin toss. - I'm like thinking with the coin toss, I'm like, I want to create this rule around it where I have to commit to the decision of whatever lands on the coin toss unless I stop at midair and decide. So it's like, you know, I could flip the coin and if my gut says what it is, I can grab it out of midair and say, done.

I don't have to abide by the rule, I've decided. - I wonder if it loses its value if you don't commit to it being a decider. I just say, let's flip a coin and see how my gut feels. I feel like the first few times, maybe it'll work. By the end, I'm like, well, now I just know I'm just flipping a coin.

I'm trying to think of ways to make the coin toss higher stakes so it forces that kind of deep-rooted gut instinct out faster. - Well, it's a fun idea. I disagree. I think you should always go ultimately with the one that makes you feel the best. - Okay. - Your thoughts matter, your feelings matter.

You need to feel good about the choices you've made in life. You can't find yourself working at a job and every day for eight hours a day going somewhere where you're like, ugh, yeah, it's the right choice. (laughs) You know, the coin said, here I am, damn it. So you've got to feel good about your choices.

You can add rational reasons later, but the feelings are harder to adapt. Sometimes it's the reverse. Sometimes you make a choice because it's the right thing. Okay, so "Paradox of Choice." There's a wonderful book about this thing. You said that you were looking to my site to see if I'd written about this.

You need to look to the book called "Paradox of Choice" by Barry Schwartz, S-C-H-W-A-R-T-Z. Brilliant masterpiece of a book about exactly this, about having too many options and what do you do. And the gist, if you had to narrow the book down to a few sentences, is that when we consider every option, we may technically make a better choice, but we will feel worse about it because we're too aware of all of the other choices we could have made.

So the advice, and let me pause to say, the advice which is coming from a PhD psychologist who has been studying the science of decision-making for many, many, many years, the advice, after all of his studies and research into the subject, is that we should choose to satisfice, not maximize.

He said people, when they're making decisions, are either satisficing or maximizing. So maximizing is what you were just doing with the insurance where you dive deep down the rabbit hole and you look deeply into every option and you really kind of kill yourself over it and you maximize to make the best possible decision.

Satisficing is, in short, it's saying good enough. It's like, I need a new insurance policy. I'm gonna give myself one hour to pick a new one. You look at some options. You're like, okay, I'm picking this, good enough. So what he said is that people who satisfice feel much better about the decision they make, psychologically, the way our brains work.

We feel better when we just make a decision, stick with it, and don't try to make the best possible decision. - What about people who love, like get intense joy out of that process? 'Cause I think that's the crazy thing is when I was going through this, my wife was like, you have a lot of stuff to do.

Why are you still researching insurance? And I was like, I don't know. I built a new table. I built a new comparison matrix and I was loving it. And what was going through my head wasn't the $500 a year I'd save. And I don't even know if it was the joy of knowing I made the best outcome.

You know, you mentioned earlier, following your kind of intellectual curiosity. And I was just generally very excited to understand the nuance of this whole space. I get a lot of joy knowing that someone could ask me about it, I could give them a recommendation. And I'm very jealous when someone says, hey, I'm thinking about this thing.

And I'm like, oh, I did all this research. This is what I said. They're like, great, I'll do that. I'm like, that's all you need. You just needed me to talk for one sentence and now you're done and you made a decision. And I'm very jealous of those people, but I do enjoy it.

It's not totally wasted time if you enjoy the process, fair? - Right. Yeah, see, it's funny. You're talking about something different that I think was not included in that book, which is the benefit of kind of you taking one for the team. Like you doing the hard work so that others don't have to and getting like a deeper kind of community joy from how much you're sharing.

Like, yeah, it's wonderful that people like you do all the hard work like that every now and then and dive down those rabbit holes. So people like the rest of us can just say, I need new, well, Chris already figured it out. So hold on, let me just see.

All right, Chris chose this. All right, I'm just choosing that. There, problem done. It's like, because you maximized, we can satisfy. You know, we can say, all right, I'll let him choose. I do that so many times in life with say, what'd you say, the best Italian restaurant in Dallas that I'll just look, okay, what did somebody else say?

Oh, look, somebody's done an article about the seven best Italian restaurants in Dallas. Which do they choose? All right, I'm just gonna go to that one then. Problem solved. When I moved to Los Angeles years ago, I'd never really been to Los Angeles, but my girlfriend at the time had just signed up for film school down there.

I was like, I'm gonna go with her. So I emailed 10 people I knew that lived in LA and I said, hey, what neighborhood should I live in? And everybody had different answers, but Santa Monica was on nine out of the 10 people's lists. It's, oh, you know, Palisades, whatever, Pasadena, Santa Monica, somebody else would say Venice, Santa Monica, Century City, but Santa Monica was on everybody's list.

So I didn't even look at any other options. I just went straight to Santa Monica, went to the real estate office there and just said, what do you got? And I didn't look anywhere else because I deferred to my friend's choices. So yeah, other people did the hard work of living there for years and discovering every neighborhood and learning the hard way.

I just took the benefit of their work. So yes, you diving down your rabbit hole and benefiting the rest of the world by doing so is great. And I love just using other people's work for that. But also you were having fun. You say that you were sweating it, but part of you was just enjoying it.

You're like, this is fascinating. Oh my God, look at all these different options. I'm gonna make a grid. You know, this is giving me some kind of joy to lay out all my options in a spreadsheet and find out about this and wow, this is fascinating. You know, like this one won't give you an SUV replacement.

They'll just give you a car. This one won't do this. Wow, there are so many parameters here I hadn't noticed before. So computer programmers do this a lot, of course, when you're looking for a tech solution to something and you look out to the world of open source software and you're like, okay, oh my God, there are like nine different calendar apps that I could use.

Okay, let me dive into the pros and cons of each one. And then you might find this less popular one that serves your needs exactly. But boy, it was kind of interesting to learn about all the different features that you hadn't even considered in these. And we might just enjoy that process.

And somebody might say it's a stupid use of your time, but if you're finding it fascinating, well then you're kind of like choosing this over watching a movie, right? Like other people would just sit there and stare at a TV screen. You're engaging with the world and getting entertainment out of doing this.

And lastly, my example that I got made fun of a lot for was when I was running my company CD Baby for 10 years, I was the 100% owner, I was the CEO, and yet whenever we needed a new computer for the office, which happened about 50 times, I had 85 employees and we had about 50 computers in the office, I would build the computer myself.

I would go down to the electronics store, get the motherboard, pick out the CPU, the graphics card, the hard drive, the case, the power supply. And I would thoroughly enjoy being in the office at night after everybody had left, building a computer while listening to music. And once it was all put together, I would install Linux onto it and get it working.

And then the morning I'd set it up at somebody's desk and be like, ah, that was fun. And somebody teased me years later saying sarcastically, like, yeah, that was a good use of the CEO's time. And I said, it fucking was. It was a great use of my time because I loved doing it.

Like, I wouldn't wanna outsource that joy to somebody else. Like, I really loved those evenings at the office putting a computer together. I find it very peaceful. Some people do crossword puzzles for that same joy, right? You don't outsource the crossword puzzle to have somebody else solve it for you.

You do it yourself 'cause you enjoy it. - I think it's a message that we probably haven't shared enough in this show is that if you really enjoy that process, sometimes it's stressful. I've had moments where I'm like an hour into comparing the distribution of one to five ratings on Korean restaurants in LA, and I should have stopped and flipped a coin.

It wouldn't have mattered. And sometimes I think it's too much, but there are times where it's really enjoyable. And even when it's a lot, it can be fun. And I like the fact that you've been able to prioritize pursuing things that make you happy and that you enjoy and stimulate you intellectually.

And I think we probably don't do that enough as an average person in society. - Hey, wait, Chris. So remember when I like named those three things, the coin toss, the paradox of choice, there was a third one. - Theory versus practice. - Yes, we haven't done that yet.

So many times I've found myself in my journal thinking maybe this, maybe that. And you realize there's so many things in life that in theory sound good, but in practice are not or vice versa. And so I've learned the hard way that you have to just try these things.

You have to just go do it. And it even comes with choices like yours about insurance. I'm really glad that you gave that example of like, maybe I'll just pick one now just to get out of my situation and then if I don't like it, I'll change again. That to me is a beautiful little example of trying something in practice instead of just in theory.

So there have been a major life decisions I've made, like moving here to New Zealand. That came from the similar kind of dilemma. I was sitting in Singapore with my ex who said, I hate it here. And I was like, okay, so where else can we go? New Zealand seems nice.

We've never actually lived there, but it seems like a nice place to be like, let's try it. Like we'll never know what New Zealand is like unless we just try it. And it took a few months of paperwork to become a resident in order to stay long enough to really try living here.

But you have to do these things in practice, not just in theory, just to see what it's really like with the understanding that I'm still just trying it. This isn't like a final decision. This is still just, I'm going to try this option, but I need to try it in practice, not just in theory.

- Has that changed? You talk about moving and living different places. You have a family or you have a child. How does that affect your ability to live this kind of nomadic lifestyle or put these theories into practice or has it not? - It has. We let the tangent go earlier, but you said something about the fact that I went to India for only 10 days instead of deciding to move there.

Dude, if my kid wasn't in school in New Zealand right now, and if his mother didn't work for the New Zealand government and needs to be here, I would be living in India right now. I loved that trip so much. I just wanted to cancel my return flight home.

I met so many wonderful people there. It was one of those moments in my life. And I've had a few of these where you go somewhere and it just like, everything in you is just a yes. You're like, oh my God, yes, this is where I need to be.

And so a few times in my life, I've done this, where I just was visiting somewhere and I just canceled my return flight and stayed. I was living in Santa Monica, California, when I went to New York City for a friend's wedding. And it was a three-day trip. And I went there with just basically three days of clothes, attended the wedding.

But just something about like getting out of the train in Penn Station and walking out into Manhattan, it was like (growls) the energy of the place. I was just like, oh, hell yeah, this is what I need right now. I was like, I could fly back to Santa Monica to get my clothes, but that would put a lot of pollution into the air.

And I think my clothes aren't even worth that much. So I just canceled my return flight and bought some new clothes and stayed. And I lived in New York for a year. And so, yeah, I just had that moment last week in India of just like, damn, I just wanna stay here.

This is where I need to be now. But yeah, I've got a kid who's 11 and in school now and his mom works for the government and here we are. So instead, I'm just going to use that restriction in my life, that creative restriction to work within that. So I'll just go visit more often.

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Again, that's allthehacks.com/deleteme. I just wanna thank you, Quick, for listening to and supporting the show. Your support is what keeps this show going. To get all of the URLs, codes, deals, and discounts from our partners, you can go to allthehacks.com/deals. So please consider supporting those who support us. So I wanna come back to parenting at some point.

A lot of these tangents, you said something earlier about heroes, and I know you have some perspective on how thinking about heroes can be valuable to thinking about what you wanna do. Maybe we could touch on that a little because I think it kind of ties together. Who are we?

What do we care about? What do we wanna do with our lives and our careers? How do you think about that? You're in a place where you've both had success. It's given you a lot of creative flexibility with work and life and where you live. Maybe not everyone has that.

Maybe people need to work towards that. But you've been fortunate to find the thing you love doing. And I don't think it was the thing you always thought. You've said that you feel like you most associate with a writer now, but I don't think it started like that. You didn't know that for many years.

How did you come to that, and how might you have come to that sooner with the wisdom you have now? - Well, it's funny. People sometimes say, "Oh, well, dude, you're lucky. "You can just get up and go." I'm like, "But that's not luck. "That was, the life I'm living is the culmination "of like 180 little decisions along the way "since I was a teenager." Like at every little point, starting from when I was like 17 years old, I over and over again made the choice that gave me more freedom because I knew this was important to me.

So even if I was, say, like offered a job that was going to pay more but give me less freedom, I said no. I chose the choice with more freedom even though it paid less money. I chose the romantic partner that also wanted to travel the world instead of getting romantically tangled with somebody who is bound to living next door to her parents.

Even when I set up my company, the way that I set up like the organization and how it was run, I chose the choice that would give me more freedom. And God, so many things. Even like when I decided to sell my company, my number one criteria was like, "This is going to be a cash sale.

You're going to pay me for this and then I'm gone. I'm not going to consult with you. I'm not going to stay around because I want the freedom." Everything along the way, every choice I made was to get me to this point. And so when somebody goes like, "Oh, you're just lucky." (laughs) I'm like, no, this is very deliberate.

In fact, let's rewind even further. A friend gave me a really good example of this when he said he doesn't believe in luck. And I said, "Yeah, says the guy that was lucky to be born in a first world country, 'cause he was born in America." I said, "Yeah, easy for the American to say he doesn't believe in luck, right?

Tell that to somebody in South Sudan." And he's just like, "Dude," he said, "I was born in America because my grandparents left everything they know in Poland and got on a ship for four months and sailed all the way to this country where they didn't speak the language. And it was incredibly hard, but they did it because they felt that would give their children a better future." And then even their children were like children of Polish immigrants that lived in a bad neighborhood, but worked really hard to save their money and spend nothing on pleasures so that they could save it for their kids.

And then, yes, I grew up in Chicago or whatever with a nice life, but it took two generations, he said. So I think that's insulting to call that luck. He said, "My nice life is the result of like 80 years of sacrifice." I was like, "Okay, all right, very good point." So I still believe in luck, like crazy.

I still think that most of my success was luck, but a lot of little decisions that you make on a day-to-day level can have huge impacts on the direction of the rest of your life. - You knew freedom was something you wanted to optimize for over years. I meet lots of people that maybe don't know that thing.

The job comes, it offers to pay them more, it doesn't have the flexibility to travel, they don't know what they want in life. Is the answer to always optimize for freedom because it gives you more options in the future? Or is there a time where more financial resources can add more value?

Or is there a framework you have for thinking about what do I want right now in my life? What do I look up to? Who do I wanna be? - Well, like we said at the very beginning, sometimes you need to ask yourself, what is my life lacking right now?

And I need to steer that direction to get my balance back. But more often it helps to look at the common thread in your life so far, like your life choices so far. In reality, what has been something that through all the choices has made you the happiest? And maybe it's money.

Maybe it's choosing the option that binds you tighter to people. Like maybe you're one of those lucky people that at the age of 19 found the love of your life. And ever since then, like your friends had crazy dating adventures, but you've been happy to be with one person since the age of 19.

And you know that like that's given you such a deep happiness in life that can't compare to all these little digital nomads bragging about their freedom. And they're just like, yeah, but guess what? I've got something better than that. You need to just look back at your life to notice what continuously makes you the happiest and use that when making your future decisions as well.

For me, it was freedom, but for somebody else, it might be money. They might say, you know what? The kind of life I want, I really want a swimming pool and I really want a Ferrari. I really want three houses. It's like, all right, then for what you really want, especially if that's in practice, not just in theory, if you've actually rented a Ferrari for a week and you know that owning that Ferrari will make you so much happier.

If you know that in practice, not just in theory, then all right, you know, this is gonna help shape your decisions that you need to go for the option that pays more versus the freedom option. You shouldn't be a digital nomad if a Ferrari is super important to you because it's harder to bring that Ferrari to Thailand and Columbia.

Not everybody should choose what I've chosen. That would be stupid. You should choose what you've noticed in practice makes you the happiest. - For anyone who doesn't know Derek's full story, you had the option when you sold your company to take all the money and live the life of Ferraris and swimming pools and wanted to kind of take that off the table as a future path that you could even be tempted by and gave it all away.

So I thought that was kind of an ultimate hack in my mind of you didn't want the chance to ever be kind of turned towards a life that you weren't actually interested in, you just gave it away. - Yeah, yeah. I noticed from the past, I knew that choice would make me happier.

It was really obvious when I was looking at all the different options of what to do when selling my company. And when I looked at the option of giving the money away, but in a way where I do continue to get a trickle paid out to me for the rest of my life, that option made me way happier because that made it so I couldn't get into this scenario where I had $20 million just sitting in the bank to do something stupid with.

I didn't want that option. I knew that option would make me unhappy because that's too much money. But having half a million in the bank, that makes me happy, that gives me freedom, but that's not too much. It's not stupid money, just very nice. - And you mentioned to look back at who you've been and what you've done.

There's something that I took away from you that I think has been really valuable is not just looking at the thoughts and the opinions you've had, but what you've done. Like looking at your actual actions. You've said, I think, that your actions actually reveal your values. Maybe we could talk on this just for a minute is, you know, it's interesting.

Some people I know say, "Oh, I'm the person that does this." But if you're not actually doing it, are you really that person? So... - Right. You know, it's funny. I had to read that post again. I had almost forgotten about that one. I'll tell the little tale quickly.

The article is at sive.rs/arv, A-R-V meaning actions reveal values. So I remember that short URL I gave it and I should revisit it now. Almost forgotten. So the story is, I was talking to an old friend of mine and I had been putting off starting this company called Muckwork.

I had this idea, like literally the day after I sold Seedy Baby, I had this idea for my next company called Muckwork. And I got four months into it and then I paused to go explore the world instead. And here we are 10 years later. And I said to my friend, "Oh, I really want to do Muckwork.

I really want to make this happen." And my friend goes, "No, you don't." What do you mean, no, I don't? I'm telling you. Yes, I do. And he goes, "No, you don't." I said, "Dude, you can't just tell me I don't. I'm telling you, I really want to do this." And he said, "No, you don't.

You don't really want to do this. If you really wanted to do this, you would have made it happen right now." He said, "You keep putting it off, which to me makes it clear that you don't really want this thing. 'Cause otherwise you would have just done it. You wouldn't be saying I want to do it.

You would do it if you really wanted to do it." Went, "Oh, wow." And he said, "Yeah, your actions reveal your values." And that's been so, so useful to me. Wow, actually, Chris, thanks for bringing this up because that is kind of in theory versus in practice revealed, put into action, right?

It's don't think about what you want in theory. Look at what you've chosen in the past or look at what your actions have revealed your values to be. Ever since I read that post, I've just been reflecting it. I've been sharing it with people. Someone I talked to was like, "I really want to lose weight.

I've wanted to lose weight for the last two years." And I'm like, "Do you know how?" And they're like, "Yeah, I know I need to exercise." And it's like, "Well, I don't think you really want to." Which is fine. I'm not trying to cast judgment. I'm just saying, you know how to do something.

You say you really want to do it and you haven't done it. Maybe you don't want to do it and that's okay. And so it's made me reflect on my own life. Oh, if I say I really want to do this, I should either do it or stop saying it.

Like there's no point in continuing to say you want to do something if you're not willing to do it. And that simple phrase of your actions revealing your values has made it easy for me to make one of two decisions. Either, yes, let's do it or let's stop and let's not put it at the top of the priority list and just continue to push it down.

So that's been really helpful, thank you. - Yeah, I'm just thinking about how you could use that to do tests of something you think you want. See if you actually want it in practice. Like if somebody says, "I really want to lose weight." It's like, all right, well, let's spend at least one week where you eat nothing but protein twice a day and that's all you eat.

Let's make sure that's what you really want. Or, "I really want a Ferrari." Okay, rent one for a week and see if it really makes you so much happier. Or, "I want to be a minimalist." Like, all right, well, leave everything behind and go spend a year living in Lithuania with nothing.

And if you like it in practice, not just in theory, you got to try these things. - Sometimes it reveals itself to be a lot easier. Starting this podcast for me was one where I was like, I'd always wanted to do something. I tried a blog, I tried a newsletter and I'd never really found the thing.

And once I put the podcast out there, I was like, oh, it's actually, it's not as hard as I had thought, but it wasn't until I realized that if I didn't do it, then I didn't really want to do it in the first place. So why not just force yourself to try?

And you're like, oh, it's actually, I'm more capable of doing this, it's easier. So for me, I think it's just that framework has helped make it easier for me to do things that probably would have been harder before thinking with that perspective. And there's two things we haven't hit on that I think are really important lessons.

One, you've written an entire book that I would encourage people to read about when to say yes and no. And I think someone might look at the title, which is hell yeah or no, and say, oh, you should always either be fervently excited or say no to everything. I actually know that your perspective is, it really depends on where you are in life.

And if you are very overwhelmed with things, a philosophy of hell yeah now or no is great. But if you're earlier in your career, maybe you just say yes to everything. And I've written posts in the past about earlier in my career, why saying yes is just this magical thing that opens all these doors and lets you have new experiences.

Is there any kind of clarifying things you wanna say on the kind of spectrum of say no to lots of things versus say yes to everything that might help people overwhelmed right now? - I'm really glad that you said that. Yeah, in fact, you might be the first person that's ever introduced that book by also giving that clarifier right away.

'Cause yeah, you're right. Almost everybody looks at that and says, yeah, man, hell yeah or no. I'm just gonna follow that from now on. And I get these emails from people that are like straight out of college going, yeah, thanks for saying that, man. I'm just saying no to everything I don't feel hell yeah about.

And I'm like, wait a second, hold on. It's a tool for a specific situation. It's in the toolbox. It's that really unique wrench in case you need to get into the hole and do a Phillips head screw. In general, I think it's better to switch strategies for your correct situation.

So yeah, straight out of college, or if you're young and say you want more opportunities than you have right now, you want more success than you have right now. Yeah, very often the best solution is to go say yes to everything. Take on as much as you can take on, try it all, overcommit yourself and say yes to everything because it's a little bit like lottery tickets.

You never know which of these 12 things you're doing at once is going to reward you. And then when one of those 12 things you're doing simultaneously rewards you, then you can like double down on that, get rid of the other 11 and throw everything you've got into this one thing.

And then that's when you should raise the bar 'cause hell yeah I know basically just means that. It just means raise the bar all the way for what you'll accept. So you wanna do that if you're overwhelmed with opportunities and everybody wants a piece of you and you've got so much success coming your way, then that's when you need hell yeah or no as a reminder to raise the bar to let go of these other options because you've got so much going on.

So yeah, so thanks for mentioning that. It's the very first sentence of the article but it often gets lost in that point. - It could also apply to just so much going on in life. You have two young kids, you have a job, you have a family and it wasn't that there were new business opportunities or financial opportunities, it's just life got so busy that to maintain sanity, you have to raise the bar.

And I found that as a 20 something single person, people say, "Hey, you wanna go to this thing?" "Yeah, I wanna go to this thing." "Yeah, I wanna do this thing." It's easy. And then we have two kids, my wife and I can't go out to every dinner. We can't go to every concert.

Some of our friends without children are like, "Oh, do you guys wanna go to Belize for the weekend?" We're like, "No, that's not a thing "we can just do on a whim." And we've created an intentional life that we're happy with, but it just means we can't do those things.

So I think right now, this year is a little bit more of the year of the hell yeah or no than the say yes to everything. But it's not necessarily because of opportunity, it's just because the overwhelming nature of life with young children. - Thanks for mentioning that because sometimes I think in terms of like business career choices with hell yeah or no, but you're right.

It's when you've got a kid, that's your hell yeah or your kids. And so that helps you say no to everything else. It helps to remember that you'd be better off putting more attention into your kids instead of spreading yourself thin with other things. In fact, I feel like I've unfairly mentioned moving too much in this conversation, but I was living in Singapore when my kid was born.

And Singapore is a very exciting, distracting place. I knew a lot of people there. I was super social there. There's so much going on. And even its location within Asia is just a short hop to so many interesting places. And I noticed that the first few months of my kid's life, I was too distracted and I was being pulled different directions.

So a big part of the choice to move to the middle of nowhere in New Zealand was to create an environment where I've just by side effect of my location, I've said no to everything else. So for my kid from age zero to 10 here in New Zealand, I was basically a full-time dad.

I was in the middle of an island in the Pacific Ocean where just everything else in life became a no because I'm here with my kid and this is my hell yeah. - So I wanna get to children, but I have one quick question, which is can you talk about the saying no part?

Because I think it's very easy for a lot of people to say, "This is the hell yeah thing." And then they get an email from someone's like, "Hey, I'd love to pick your brain about this thing. Do you wanna grab a coffee?" And I think saying no is something people find very hard.

And they almost feel like I'm gonna look bad by saying no. People are gonna think that I don't care. And you've said a few things that have given me perspective there that I think would just be helpful for people to understand why saying no might be in some weird way polite or a better way to do it.

- Yeah, my number one tip is write a form letter. Take 20 minutes and write a very nice generic no with a little elaboration like, "Hey, I'm so sorry. I'm completely focused on what I'm doing right now. My new book isn't finished yet and I need to put everything I've got into finishing this.

I hope you'll understand. This isn't a permanent no, maybe at some point in the future. I really appreciate that you thought of me for this. I'm honored that you invited me." Whatever, like take 20 minutes and write a nice form letter response and then keep it handy in a word file or a text file or whatever you use, so that it might even be five times a day when you get people wanting to pick your brain or come to this thing or, "Hey dude, you got a minute to jump on a Zoom call." You could just copy paste, select all, Alt + Tab, Control + V, send.

I do my form letter so many times a day. I just have a generic no. And what's nice is that people respond to it every now and then going, "Wow, that's the nicest no I've ever received. And dude, you're actually kind of inspiring how you're keeping your head down in your work.

Man, I should be more like that." Like you think people are gonna be mad, but actually people often get inspired by how you say no to their random things. - I wouldn't necessarily put this in a form letter, but I heard you say once that you say no so that you leave your calendar open to say yes.

And if someone's calendar is always full, it's almost like, "Oh man, this person isn't leaving enough time for exciting things." - When I just said that like for 10 years, I was basically a full-time dad. Dude, for 10 years, I didn't even have a calendar. There was like literally nothing on my calendar.

Maybe like once a year we would take a flight to go see his grandparents. But yeah, for 10 years, I had nothing on my calendar app. And when somebody would wanna schedule, they're like, "Hey, can I call you next Thursday at three?" I'd go, "Eh, I'm not gonna bust open the calendar app.

You'll be like the only thing in 2018 on my entire calendar for the year." Like, no, just call. Whenever you wanna call, just call. I'm not gonna schedule. I don't do scheduling. I mean, now I do. My kid's 11 now and he's playing with friends. He doesn't need me around so much.

So I'm not as much of a full-time dad as I was the last 10 years. But yeah, for 10 years, that was fun to just say no to all of it. And to have this completely empty calendar is such a good feeling. To wake up, God, that's one of my deepest joys, to wake up every day or to wake up any day and have nothing on my calendar for that whole day.

Like the whole day is mine. It's such a nice feeling. - Let's talk about some of the perspective you had for parenting. Because I think right before we jumped in, I was sharing your post about parenting with my wife. And we were both like, "Wow." You kind of talk in it and I'll put it in the show notes.

You can talk about it as much as you want. It's not very long. But how it seems like sometimes by focusing so much on your child, you're just completely selfless and you just can feel like work. But if you present it in a perspective, that's like, "Oh." By doing these things that many of us wish that we could do more for or with our children, you're actually doing things that will help you.

And that perspective, I know plenty of people are like, "Oh, my partner's gone "and I've got childcare duty for the whole day." And I think there's a different perspective of ways that you could enrich your own life, not just by spending time with someone, but by teaching lessons and acting a different way.

I'm curious how you thought of that, how long it took you to come to those realizations. - Remind me, where do you live now? - I live in the Bay Area. - Okay, so yeah, whenever I was on daddy duty, 'cause his mom and I always split it 50/50, every day or every week, we'd make sure that it was always 50/50.

We didn't have a nanny or anything like that. It was always just the two of us. And we'd live far away from family. So there was nobody else to help. So it was either her on duty or me on duty. So she had her own way, right? So she likes watching things and she likes being inside.

Like that's how she grew up. She's more indoorsy. So then I found it my duty, whenever I was on daddy duty, to take him out. No matter what the weather, even if it's raining, that was like my number one thing. Like, let's just get out. To satisfy my own curiosity, I would pick somewhere on the map that we had never been.

I'd like look at the map and I'd see this green patch. I'm like, I don't know what's there. Like today we're going there. So we would go to that green patch, get out of the car and just hang out there for the day. And we would spend like two hours, six hours in this green patch I'd never been to.

So I got to know the area really, really well by doing that. And now let's say like, if it's really bad weather, there's some days where I'd say like, all right, let's watch a movie. But instead of just picking the dumbest Hotel Transylvania 3 kind of entertainment, I do a little work to find some like beautiful award-winning animated movie from somewhere, ideally in another language or another culture that I would find really interesting.

And I'd find this kind of like, I don't know, this German animated thing and subtitles. So my kid who doesn't read is just watching this in German, but I'm like, cool. The German language is getting into his ears a little bit today. And I'm watching an animated movie that I find interesting, not just like the lowest common denominator.

So I would make choices like that to enrich his experience by often going somewhere new, watching something new. Sometimes we just listen to music. We'd kind of like cuddle and listen to say like Indian classical music while making Lego. Actually, that was a good way. He calls it Lego music.

Indian classical music, he considers Lego music because I just thought like, all right, as long as we're just making Lego, let's open his ears a bit and put on a different kind of music. And it had like speakers in the living room so he could really kind of hear it, not just coming out of a tinny little one inch speaker.

So yeah, choices like that, I just found to me made being a full-time dad, it made it a joy because I would keep choosing these decisions that were good for both of us. - And I think one of the big ones that you've read about is travel. And you wrote a post that says travels best with young children.

And I was telling my wife about it. She's like, "How old are this guy's kids?" I don't think I said young. I said, "Oh, he wrote this great post "about travel with children." She's like, "Yeah, but are they 15?" So I think there's this idea of traveling with young children being horrible and it being the worst experience.

And you write the exact opposite. And I've gotten so many emails from listeners saying, "Oh, can you talk more about travel with children "and how to make it enjoyable?" And as early as this morning, someone emailed me saying, "I'm going on this trip. "I can't remember where they're going." She's like, "I have a six-year-old and a one-year-old "and we're nervous.

"How do you have a good trip traveling with children?" Very few people I know have a perspective of positive experience. So I'd love to wrap up a little bit and talk about that because we talk about travel a lot on this show and so many people are interested. How do you travel with your child and have a great experience when doing it?

And what advice do you have for people about to go on a trip with their children? - I love this subject. I wrote that post because I got so frustrated at people acting like it was just a truism, like traveling with kids is hard or once you have kids, you can't travel anymore.

I was like, "Damn." Like the difference between in theory and in practice, some people just decide in advance in theory, "Well, can't travel anymore. "Got kids now. "Just gonna have to stay put. "No more dreaming for me." But in practice, it's wonderful. Maybe you need to just change your mindset about it in advance, but I just find that for one, you don't need to pack hardly anything because anywhere you go has stuff for kids.

I started traveling with our kid when he was three months old and in diapers. And you realize you don't need to pack 50 diapers. You need to pack like six diapers, maybe to get you through the first day 'cause anywhere you're gonna go has diapers. You don't need to pack toys because anywhere you go is gonna have toys.

And if he's really stuck for entertainment and really needs a physical thing beyond just the one or two things that you bring with, then there are new physical things wherever you go. And I don't mean like things to buy. It may just be like random items found in the grass or on the street corner can be fascinating.

God, he got so much joy out of this like rusty spring he found once in the gutter. We went to Wales and he found this rusty spring in the gutter that he just held onto for a week and just loved this spring. And it was like his favorite toy for the whole week while we were traveling in England that he found in literally in the gutter in Wales.

So you don't need to pack much. That's a big one. As long as you leave early, like don't forget that the airport itself is a fascinating destination for kids. Like, oh my God, it might as well practically be Disneyland. There is so much there. So you get to the airport way early, like four hours early.

There's no rush, there's no stress because your kids love to explore the airport. Even when he's just a little choo-choo crawling baby, he loved the attention from so many strangers. Like suddenly there's like hundreds of faces looking at him and he'd be like, ah, you know, like so many strangers wanna play with him.

He loved hanging out at the airport. So then the flight itself, my number one advice for kids under the age of two or three is, I know this is gonna sound radical, but I actually got this from a great book called "Brain Rules for Baby" by John Medina. University of Washington, a neuroscientist has been studying brain development in babies for years.

And his number one bit of advice, oh, sorry, number two bit of advice. Number one bit of advice was help your kids feel safe. Like number one, kids need to feel safe so they can flourish. But number two was, he said, no screens before the age of two. And in fact, the longer they can go without screens in front of them, the better.

But he said like, absolutely do not let your kid stare at a screen before the age of two. So I heeded his advice and we had no screens in the house, no iPads, no movies, whatever, before the age of two. But the one exception is when we would get on a flight.

And because he'd had no screens at all in his life, you wonder how to keep a kid still in a seat, like let them watch the screen. Suddenly he was just hypnotized and he would be absolutely still on a flight to the point where many different times when the flight was done, we'd be getting up, exiting the plane, and somebody in front of us or behind us would go, whoa, there was a kid here that whole time.

And they didn't even know because their kid was so hypnotized by the screen. So I don't know, that was a good hack. And hey, that's why we're here, right? All the hacks. So that was a good hack. And then when you get to a place, you don't try to force your kid into your adult schedule.

You don't say, all right, we're going to Paris, we're going to see the Louvre, we're going to see the Eiffel Tower, we're going to look at the Arc de Triomphe at 1 o'clock, and we're going to get it. You just let go of all that. Traveling with kids is so nice to just get to a destination and let go of your expectations to basically let your kid and circumstance lead the way.

You're just going to get there, and then you just go out into the world with your kid and let them explore and let them lead the way. Isn't that a Whitney Houston song? You just let them lead and be on their schedule. What I love about that is then you get to experience this place through your kid's eyes.

So I remember taking my kid to Thailand when he was like six months old. He was a crawling baby. He wasn't even walking. He was just crawling. And we would just go someplace like a temple that was gorgeous with the big golden stupas and just let him crawl around.

And he would just be crawling around the temple, and everybody's giving him attention. He'd play with strangers. A Buddhist monk picks him up and holds him, and he's loving this attention. And people take his picture, and he crawls around the whole time. We're just laid back, kind of like enjoying the temple and our baby crawling around.

And same thing with just going out to a park, and he's seeing different things. He sees monkeys. Oh my god. It's all so easy when you let your kid lead the way. Locals connect with you more. Everybody wants to come up and interact with the baby. So all these locals that don't speak English, and we can't communicate through language, but sweet old ladies come up, and they want to play with your baby.

I absolutely love it. I kind of don't want to travel without my kid, I think, traveling with my kid at any age. And even now, he just turned 11. I just took him to Japan for two weeks. His mom had to work, so it was just me and him.

And it was amazing to go see Japan through his eyes. I've been to Japan a few times. In my life, but I kept myself out of it. I just took us to Kanazawa on the West Coast, and we just stayed there for four days, and down to Kyoto for four days, then up to Tokyo for four days.

Stopped at one hot springs resort town on the way so I could experience a real hot springs resort. And other than that, just day to day, we'd wake up, and I'd say, all right, dude, what do you want to do? You lead. I'll follow you. And it was so unexpected.

I thought he'd be overwhelmed by Tokyo, but he loved it. In fact, sometimes when I was kind of tired, he's like, let's go out again. He said, let's go down this alley. And I just let him lead the way. He's like, let's go see what's upstairs. All right, sure.

And it was great. It introduced so much randomness. He chose things I wouldn't have chosen. He's like my favorite travel partner and has been since he was born. So I think travel with kids is easy and wonderful. We went to London and Paris in December with two kids, six months and 2 and 1/2.

We didn't try to cram in the Louvre. We picked places that, at least in Paris's case, we'd both been to before. One of the challenges that I'm curious to hear your perspective on, maybe this gets better after multiple times. This is our first kind of trip to a city with kids.

A part of it was like, oh, we're so used to how much we try to accomplish on a trip. With children, you just have to cut your expectations way back. So I think if we wanted to have an enjoyable trip each day, the goal was, what's the one thing we're going to do today?

Our list pre-kids was like, here's the eight things we'll do. Now it's one. And I wonder now if we went back-- we weren't going in with eight. Maybe we had two and we realized one was more sustainable. But if you go all the way, halfway across the world, not everyone has months at a time.

So let's say you're there for a week and you're only doing one thing a day. You might feel like you didn't get as much value out of the trip because you spent all this money to travel and stay and eat, but you didn't get to do that much. I have a feeling that you have a way to rephrase the perspective that will make anyone listening realize that they got just as much of a trip even though it was different.

But I feel like the way you'll say it will give people that feeling far greater than the way I would. So I'm curious how you would kind of rebut the idea that if you're not doing a lot because you can't have as much on your agenda, you're not going to have the kind of trip that will make it worth it.

I figure that if I've decided I want to go to Paris, and I've got that specific example too, I'm just choosing the where. I'm just saying, we're going to Paris. And I'll say, OK. So I took us to Paris. And once we got out of the train station at the Gare du Nord, is that it, the north one, I think, I just let him choose.

I was like, well, we're in Paris now. Which way do you want to go? And he was like, go that way. I said, OK. And I just followed him. And I'm so glad I did. Because at every turn, he just decided where he wanted to go. He led the way.

And at one point, he found this huge cardboard box that was as big as he is. And he's like, dad, check out this box. And he got inside this cardboard box. And for the next half an hour, he walked the streets of Paris inside a big cardboard box. And I got such joy out of that.

I made a little phone movie of it, of the streets of Paris, in a busy center part of town, with him taking up the whole sidewalk, walking inside this big cardboard box. Everybody doing these double takes, like, what the hell? And me just cracking up at the juxtaposition of, not only is my kid taking up the sidewalk, walking in a huge cardboard box, but OMFG Paris.

Like, to be doing this in Paris. And oh my god, there's the Eiffel Tower in the background, as my kid is walking in a cardboard box. And then at some point, he sees a huge staircase. It's starting to get dark. It's dusk. And he's like, whoa. He's like, look at all those stairs.

He said, let's go this way. I said, all right. He's out of the box at this point. And we go up, and up, and up, and up, and up these steps. And we get to the top. And we take this turn. And it's like, oh, one of the most top five beautiful things I've ever seen in my life.

He accidentally led us to Sacré-Cœur, the big, giant cathedral, which, just because it was dusk, was being lit up by floodlights. But the sky was dark blue. And it's at the top of the stairs, but you don't expect it. You turn up the stairs, and suddenly, it's just staring at you.

And it's like, oh my god, it looks so surreal. And it was one of my favorite things on that whole trip, was us accidentally discovering Sacré-Cœur, which I'd only seen in postcards or photos at that point. I'd never seen it in person. And it was only because he led the way.

That wasn't on my itinerary. And I wouldn't have put it on my itinerary. I didn't even really know what it was called. I had just seen pictures of it before. But yeah, letting your kids lead the way makes them happy. And it leads to so many wonderful random encounters.

Yeah, I think it's just about reframing what makes a good trip, right? In an earlier life, a great trip to Paris might have involved ticking off a few restaurants your friends had recommended, seeing a few museums. As you were talking, what really clicked for me was I thought, OK, well, if we're not going to go do all those things, and we're just going to walk around, then we could just do that here.

Why do we need to go all the way to Paris? But there's something about being in Paris, doing that, that makes the memories different. And the memories are why you're doing it in the first place. So I want to challenge myself on the next trip to just kind of let go, do whatever, see where it goes, and see if we have just a totally different type of memory that's equally or potentially even better than we used to.

It's just uncomfortable, right? Because it's not a type of thing I'm familiar with, because that's not how we would travel pre-kid. So we found the travel logistics to not be as overwhelming as much as the trying to find the balance between-- I don't know, my wife and I, when we're in new cities, we're like, let's go find a cool bar and have a good cocktail, or let's go eat whatever the local food is.

And so it's like, OK, well, we got to get to this restaurant. But in London, nothing opens early enough to eat before kids' nap time. But if we reframed it and just said, we're not going to have the trip we wanted to have when we were 10 years younger.

We're going to have a different style trip where our children experience things, and we get to watch that unfold, I think it would have been different. And I think we maybe had the wrong expectations. We still had a great trip, but I think we could have had a better trip.

I find it really important-- this is just my values. Nobody listening has to adopt my values. But a lot of the reason I was traveling was for him as much as me because I wanted him to know that Paris is a place that he's been and has a connection to.

So the trip was-- when you say like, why not just stay home? Yeah, the trip was for him as much as me to know-- he can identify so many countries on a map now at age 11. And he's got a little connection to so many of them, even some that he hasn't been to.

But I want him to feel a connection to the world. So when somebody says France, he's like, oh, yeah, I've been there. And if somebody says Spain, he's like, oh, yeah, I've been there. I wanted that for his self-identity. I want him to feel that the world is his home, not just this one country where we're in right now, but all of it, like the more of it, the better.

So I generally would take him on trips to places we've never been. Let him lead the way. He gets to feel the sense of autonomy. You never have to worry about him being happy. Because if your kid is leading the way-- I wouldn't know how to do it with two kids.

I don't know. But if your kid's leading the way, then he's happy. And you get the randomness. But it's more about just your kid feeling a connection to this place on Earth. That was most important to me. I didn't really care what we did in the place. But the reason I gasped while you were saying that is-- Chris, satisficing and maximizing, it comes back full circle to earlier in the conversation of you just described a way of travel that was trying to maximize.

You're like, all right, we've got 72 hours in Paris. We are going to go to the best restaurants, the best sites, the best museum. That's maximizing. And I think that's the wrong strategy. I think satisficing is the correct strategy for travel with kids. You're just like, all right, I'm just going to book us a trip to Paris.

And we're going to get off. And we're going to spend a few days in Paris. I don't know what's going to happen while we're there. We'll see what happens. But we're going to spend three days in Paris with no expectations. That's probably a better recipe for happiness. It's my eternal struggle, is to satisfice.

But I will continue to try to make gains towards more satisficing. You should read that book. You should read "Hyperoxygen." It's going to stack up a bunch of reasons why you should. I already have it written down. I try not to be distracted and write things down. But every now and then in a conversation, I'm like, well, that deserves to be written down.

OK, so there's two final things. One is around satisficing. There is a story I've somehow managed to hear you tell twice. I've picked random things. And sometimes I read it. And sometimes I'm like, oh, let's just play. And on your site, you read some of your posts. And it's a perspective that sometimes taking a different path, taking the not perfect optimal maximizing path might actually not result in as worse of an outcome as you seem.

So one of the reasons I think a lot of us maximize is that we're like, we want the best. We want the optimal outcome. And if you don't get it, in our minds, it feels like you'll be spending so much more money. But it might actually only be $10.

Could you talk about this bike ride where you stop to slow down? Because I think it's a good way to wrap up the conversation. Because sometimes just taking a different path, it doesn't actually mean that you're getting a much worse outcome in terms of, in your case, how long it took.

Right. OK, so first the story. And then how it ties back into what we've been talking about. OK. Because the story is about what happened. And then how it ties back in is about the psychological experience in your mind, not just the physical experience. OK, so the story of what actually happened is when I was living in Santa Monica, California on the beach, there is a bike path that goes through the sand there.

And I think it's 15 miles or something like that. And for exercise, almost every day, I would at some point stop what I was doing. And I'd get on my bike. And I would do that bike path as fast as I could, really head down and kind of pushing as hard as I could to do this in the name of exercise.

I'm going to do this track. And I would do the 15 miles back and forth. I don't remember if it was exactly 15 miles. But I do remember that after the first or second time, the time it would take me was almost always exactly 43 minutes. If it was a really windy day, maybe a little more, but almost never less than 43 minutes.

So 43 minutes every time. But after doing this for a few months, I realized I was getting less motivated to do it. It's like, it's not so much fun, this kind of-- I always get really red-faced. It would take me like an hour to cool down afterwards. I have to take a cold shower.

And even then, I would continue sweating even after a cold shower. So one day, I was just like, I just need to chill. I'm just going to relax and do the same ride, but at half my normal pace. So I get on my bike. And I'm just like, ah, da-da-da-da-da.

Just going like a granny, sitting more upright, looking around. And I was just on my same path. And there were dolphins jumping in the ocean that day. I was like, oh, wow, dolphins. That's so badass. I grew up in Chicago. I'm looking at dolphins. And yes, in the Marina Del Rey, I went to-- under Marina Del Rey, there were a whole bunch of pelicans that were perching on the breakwater thing.

And at one point, when I rode my bike near them, the pelicans all went, pfft, pfft, pfft, pfft. I was like, whoa, pelicans. And then like, ah, one of them shit in my mouth. It was like the taste of digested oyster. The shells were like, pfft, pfft, pfft, pfft.

So that was a really unique experience. So then I get back to my starting point, where I would always time myself. And I looked at my watch. And it had been 45 minutes. I was like, wait a minute. No way. Like, I'm usually doing it in 43 minutes. I thought it would be like an hour and a half.

I felt like I was going half speed. But I guess just because of the strength of my legs or whatever, I was going about the same pace, even though it felt like half the effort. So that just blew my mind. And yeah, I double checked. Yeah, 45 minutes. Oh, my god.

So that became a metaphor for how you can just relax and put in so much less effort and get almost the same result, objectively. But psychologically, you feel so much better about it. So yeah, full circle to what we're talking about, whether it's travel or decision making. To me, the psychological experience matters more than anything.

So yes, I could force my kid to go to the eight things I want to see in Paris and force him to sit next to me at a fancy restaurant that he doesn't like. Because damn it, it says that this has the best creme brulee in Paris. And I could make him do this.

And objectively, I could say that might cram in more experiences and technically make a better holiday. But guess what? The psychological experience of it would be worse than if I just book the flight, get there, and just let my kid lead the way. I might see less stuff, but the psychological experience of it will be better.

I definitely value and prioritize the psychological, the inner experience of something. To me, you kind of satisfies the bike ride, which is you didn't try to get the ultimate maximum output from riding it. And in return, you actually got the maximum output. You did. You actually were able to get 99% of the output in terms of physical output.

But then you also got to enjoy the bike ride and all that. And to the Paris example, the funniest part is to the average untrained American palate, I am fairly confident that the average creme brulee in Paris is going to be better than any creme brulee you've had. So does it need to be the best croissant or the best creme brulee?

And I say this as someone who just recently searched for, oh, let's go to this bakery. They have the best this. We did have one terrible croissant in Paris. But for the most part, the random croissant at any bakery is so good that I would tell you, even though I find it hard to take my own advice, that don't track to the best one in the world.

Just track to a good one. And enjoy that, and it will probably be a better experience than schlepping the whole family on the metro to go seven stops early in the morning so you don't have to wait too long of a line. And I say this as advice it's hard for me to take myself, but hopefully the pain I've endured to say it can save people some misery.

I have internalized satisficing so much that when I go to a restaurant, and I don't even really care what restaurant I go to, I don't even maximize that. Whatever is nearby, it's fine. I'm sure it's fine, as long as it doesn't completely suck. If I see the one with the little flies and the broken fluorescent light, all right, maybe not that one.

Maybe that one across the street instead. I can walk into almost any restaurant, and my friends tease me for this. Here's how I order. I flip open the menu, and basically the first thing I see in the first three seconds, I'm like, there. I just close the menu. I'm like, that's what I'm having.

And they're just like, you didn't look at everything. I'm like, I don't need to look at everything. I'm just gonna eat something, and it's gonna be fine. Like, I don't even need to order the best thing on the menu. Just whatever. Or if I don't even feel like looking at the menu, and the waiter comes by early, I'll just say, what's your best thing?

Or, what do you recommend? What's your most popular dish? And they'll say, oh, the, whatever, the chili. I'm like, yeah, give me that then. Like, I don't even look at the menu sometimes. I really, really deeply internalized the lessons from "The Paradox of Choice" book. - Well, I'm gonna recommend everyone check out both the writings you've had, the books you've written, and that book.

The one thing, I haven't done this as frequently as I wanted to, but I ask people, because everyone here likes to travel, is there a place, and I'm hoping that you use somewhere in New Zealand, since I've been dying for an excuse to go, that you're familiar with enough, feel free to choose anywhere in the world, that if someone were heading there, you'd recommend a couple places that are your favorite anywhere in the world.

- Let me start with a do not do in New Zealand. If you come to New Zealand, do not spend a single minute in any city. New Zealand is not Europe. In Europe, the cities contain the culture of the place. In New Zealand, the cities are just dumb, generic cities.

There is nothing special about any city in New Zealand. Everything that's wonderful about New Zealand is contained in the rural nature countryside, or in the cute, small, little towns. So what you must do when you come to New Zealand is just rent a car, whether you rent a car at the Auckland Airport and drive south, or connect to Christchurch and just rent a car at the Christchurch Airport and drive west.

Just drive away from the city. Don't spend a single minute in any city in New Zealand. Okay, so that's number one. What to do, honestly, I'm just gonna leave this open. I think the best thing to do then is rent a car, install the booking.com app on your phone, because every single motel in New Zealand, and there are hundreds, maybe thousands of these cute little motels, they're all on this app, and it will show you your immediate availability.

So you can just be impulsive. You don't even need to book everything in advance. You can just go on a drive and see what looks appealing and say like, what's that over there? Let's just go there. And then when it's getting late afternoon and you're feeling like it's time to pick where you're gonna stay, you just open the app with the GPS and it says like, okay, here's the six motels in your area that have availability, and you just pick one.

And they're all good. My favorite road trips in New Zealand have been through this method with no plan. I just go to a certain direction and the whole country is so safe and the people are so nice and there are plenty of motels. And that's more than telling you one destination to go to.

It's that. But lastly, if I had to pick just one, if you've got little kids, one hour north of Wellington, there is a very special place called Stag Lands. S-T-A-G, L-A-N-D-S. It is an open like petting zoo kind of thing. The animals are not in cages, they're just roaming around.

And all of the animals will eat out of your hand and you can just go up to whether it's like deer or birds or peacocks, geese, little pigs. Yeah, everything will eat out of your hand and you just like pet them and you're just surrounded in this wonderful like valley full of animals.

And especially if you get to go on a weekday, you'll be one of the only people there. It's just, it's a really, really, really special place. So there's my secret hidden recommendation. But actually, you know what? Anybody, if you're coming to New Zealand, email me and I'll give you more examples.

Go to my website, you click contact and there's my email address. I really enjoy my open inbox. The reason I do interviews like this is because of the people I meet, the people who listen to these things. And come on, if you've heard my voice for an hour and a half, then send me an email, say hello, introduce yourself.

And if you're coming to New Zealand, definitely let me know and I'll give you more detailed tips. 'Cause I've been here for 10 years now and I know most of the secret places. - It's on our list. We have kids. Stag lands will be on the list as well.

This has been so much fun. I'm sure we could go longer, but I would love to wrap up and just say, is there any final place you'd like people to check out or anywhere you'd like to send them before we go? - I really like hearing from strangers. I really enjoy it when people introduce themselves.

It's like a deepest sense of joy to me to know people from around the world. So yeah, any fans of Chris's all the hacks, go send me an email, go to my website, sive.rs. And you don't even have to ask me a question, just introduce yourself and say hi.

- That's awesome. Well, I know you enjoy email and you respond because that's how this all started. So I'm so glad we got to do it. Thank you so much for being here. - Thanks Chris. - I really hope you enjoyed this episode. Thank you so much for listening.

If you haven't already left a rating and a review for the show in Apple podcasts or Spotify, I would really appreciate it. And if you have any feedback on the show, questions for me, or just want to say hi, I'm Chris@allthehacks.com or @hutchins on Twitter. That's it for this week.

I'll see you next week. (upbeat music) (bubbles popping) (bubbles popping) (bubbles popping)