Stop Overthinking and Start Deciding with Derek Sivers

Summary

Podcast Summary: All the Hacks - “Stop Overthinking and Start Deciding” with Derek Sivers

Podcast: All the Hacks: Money, Points & Life
Host: Chris Hutchins
Guest: Derek Sivers, Writer and Entrepreneur
Date: April 8, 2026

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Main Theme

In this episode, Chris Hutchins sits down with Derek Sivers, author, entrepreneur, and passionate life explorer, to discuss the art of decision-making and overcoming analysis paralysis. Together, they dive into frameworks for living intentionally, the value of journaling, parenting, traveling with children, and why your actions—not your intentions—reveal your real values. The conversation is a masterclass in moving from theory to practice, learning to satisfice (not maximize), and designing a joyful, flexible life.

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Key Discussion Points & Insights

1. The Challenge of Decision-Making

• Chris opens with a personal story about agonizing over a travel points decision, stuck between what the spreadsheet told him and what he actually wanted.
• Derek’s advice helped Chris close the spreadsheet and go with his gut:

  “His decision making framework... was just one of about a dozen things that I am so glad I took away from that conversation.” (00:36, Chris Hutchins)

2. The Pendulum of Pursuit and Comfort with Change

• Derek describes being led by whatever he feels is lacking in his life—a perpetual swing between extremes.

  “The pendulum goes too far off to one end and... I wish I had a little gravity bringing me back to the center. So that’s probably driving a lot of my pursuits.” (03:35, Derek Sivers)

• He’s unafraid to make big life changes (moving cities, countries) but acknowledges sometimes those shifts take years to realize.

  “It might take a couple years for your intention to turn into reality.” (07:20, Derek Sivers)

3. Experimentation vs. Immediate Action

• Not all change happens overnight—sometimes it takes years for intentions to materialize, yet sometimes immediate action is required.
• Derek keeps his life “light” to enable flexibility.

  “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.” (09:52, Derek Sivers)

4. Expanding the Option Set & Creative Brainstorming (Journaling)

• Derek emphasizes not defaulting to binary choices. Push for at least 10-20 options, often with the best solution appearing far down the list.

  “If you think you only have two choices, you still haven’t thought enough. You have to keep thinking of other options... Many of my best ideas... have come from this pushing myself to further solutions.” (18:48, Derek Sivers)

• Journaling is key—not just a tool but “sanity.”

  “Unlike the other things where I say, hey, not everybody has to do this—everybody has to do this, everybody should do this.” (17:11, Derek Sivers)

5. Rubber Duck Debugging & Imaginary Mentors

• Journaling is likened to explaining a problem to a rubber duck, which clarifies thinking and exposes the real issue.
• Mentally consult mentors (“What would Seth Godin say?”) before reaching out.

  “If I were to call Seth right now, what would he probably say? ...And that ends up helping me get to a good solution for myself without ever having to bother Seth Godin.” (25:25, Derek Sivers)

6. Satisficing vs. Maximizing: Overcoming Analysis Paralysis

• Key concept from Barry Schwartz’s Paradox of Choice: maximize only when you enjoy it or if it’s your job to vet options for others; otherwise, satisfice (“good enough”) and move on.

  “People who satisfice feel much better about the decision they make... We should choose to satisfice, not maximize.” (40:37, Derek Sivers)

• Chris shares how he gets intense joy from the process but acknowledges it’s not for everyone.

  “You were having fun. You say that you were sweating it, but part of you was just enjoying it.” (43:08, Derek Sivers)

7. The Value of Trying Things in Practice (Theory vs. Practice)

• Theory sounds great, but you have to experience decisions to really know.

  “There are so many things in life that in theory sound good, but in practice are not, or vice versa. And so I’ve learned... you have to just try these things.” (50:38, Derek Sivers)

8. Your Actions Reveal Your Values

• Reflect on what you actually do, not what you say you want to do.

  “You keep putting it off, which to me makes it clear that you don’t really want this thing, because otherwise you would have just done it.” (64:04, Derek Sivers)

9. Hell Yeah or No: Raising the Bar (Context Matters)

• Don’t say yes or no by default—overflowing with opportunity? Raise the bar. Early in your career? Say yes as much as possible.

  “Hel Yara no, basically just means that. It just means raise the bar all the way for what you’ll accept.” (69:39, Derek Sivers)

10. Saying No (Politely)

• Use form letters to say no graciously and often. People typically respond positively, even with admiration.

  “Take 20 minutes and write a very nice generic no with a little elaboration... I do my form letter so many times a day... People respond, ‘Wow, that’s the nicest no I’ve ever received.’” (75:07, Derek Sivers)

11. Parenting and Travel with Kids

• Let the child lead. Lower expectations on “sightseeing,” and reframe a trip through their eyes; randomness and enrichment come from following their curiosity.

  “Let your kid and circumstance lead the way. So you’re just gonna get there and then you just go out into the world with your kid and let them explore and let them lead the way.” (84:25, Derek Sivers)

• Psychological experience matters more than quantity of attractions seen.

12. Satisficing in Life and Travel: The Bike Ride Story

• Slowing down can yield 99% of the outcome while vastly increasing enjoyment.

  “I just relaxed and put in so much less effort and got almost the same result, but psychologically, you feel so much better about it.” (102:54, Derek Sivers)

• Applied to travel: It’s okay not to chase the “best” croissant—any croissant in Paris is likely to be memorable.

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Notable Quotes & Memorable Moments (with Timestamps)

On decision-making and journaling:

• “Journaling... everyone should do this. It helps so much to pause... you can stop, like every day, and ask yourself these reflective questions...” (17:11, Derek Sivers)

On maximizing vs. satisficing:

• “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 the other choices we could have made...” (40:20, Derek Sivers)

On actions and values:

• “Your actions reveal your values. And that’s been so, so useful to me.” (64:04, Derek Sivers)

On saying no:

• “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 say no to their random things.” (75:40, Derek Sivers)

On travel with kids:

• “I think travel with kids is easy and wonderful... You get to experience this place through your kid’s eyes.” (85:15, Derek Sivers)

On letting go of maximizing during travel:

• “Satisficing is the correct strategy for travel with kids. You’re just like, ‘Alright, I’m just gonna book us a trip to Paris... We’ll see what happens, but we’re gonna spend three days in Paris with no expectations.’” (99:41, Derek Sivers)

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Timestamps for Important Segments

• 00:35 – Big takeaways from Derek’s frameworks
• 02:30 – Comfort with change, following what you lack
• 07:20 – Moving to Woodstock: sometimes action takes years
• 13:40 – Choosing creative alternatives over defaults
• 17:11 – Journaling as a universal tool
• 25:25 – Rubber duck debugging and imaginary mentors
• 31:01 – The struggle of choice overload; analysis paralysis
• 40:20 – Paradox of choice: satisficing vs. maximizing
• 50:38 – Theory vs. practice: why you must try, not just plan
• 63:47 – Your actions reveal your values
• 69:23 – Hell Yeah or No: context-dependent decisiveness
• 75:07 – Saying no, and why it’s polite
• 83:40 – Travel with kids: tips, attitudes, and reframing enjoyment
• 99:41 – Satisficing vs maximizing in travel
• 102:06 – The “bike ride story” and maximizing enjoyment by slowing down

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Final Thoughts & Resources

Derek closes with travel advice (New Zealand tip: avoid cities!) and an invitation to listeners:

“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.” (112:17, Derek Sivers)

Chris recommends Derek’s books and the Paradox of Choice by Barry Schwartz.

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Further Exploration

• Derek Sivers’ website
• Relevant articles: “Actions Reveal Values” (sive.rs/arv)
• Paradox of Choice – Barry Schwartz

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This episode is for you if you want to worry less, find peace with your choices, make better decisions, and enjoy life—whether at home, at work, or on the road with your kids.

Transcript

[Chris Hutchins]

For one of the Alaska milestones, you have to pick between 15,000 miles and 10,000 status points. Now, I'd built this entire model, I'd ran the numbers, calculated the opportunity cost down to the penny, and I knew what the math said, but I also knew what I wanted the answer to be, and they weren't the same. And I just couldn't let go of the spreadsheet long enough to actually make

[Chris]

the decision I wanted to.

[Chris Hutchins]

And then I was listening to a conversation with Derek Sivers and one thing he said completely cut through all the noise in my head and it reframed the decision. So clearly I just picked the option I wanted, closed the spreadsheet, and moved

[Chris]

on with my life.

[Chris Hutchins]

And his decision making framework that I've used half a dozen times the last week was just one of about a dozen things that I am so glad

[Chris]

I took away from that conversation.

[Chris Hutchins]

We covered journaling as a way to push past your instincts. Decision making, satisficing versus maximizing. Which if you've heard me and Amy

[Chris]

go back and forth about furniture or insurance or ski lessons, you know it's

[Chris Hutchins]

a lesson I need on repeat. We also discussed traveling with kids in a way that's changed how I'm thinking about our trip to Japan and this idea that your actions reveal your values, not your intentions, which is one of those things that sounds obvious until you

[Chris]

actually hold it up against how you've been spending your time.

[Chris Hutchins]

Now, if you've listened for a while, this all might sound familiar because it's

[Chris]

the exact conversation I had in episode

[Chris Hutchins]

109 a few years ago. But I recently re listened to that episode and I picked up on things I must have completely missed the first time, even even though I was the one asking the questions and editing the episode. So whether this is your first time hearing it or you caught it years ago, I really think you're going to

[Chris]

get so much out of this episode and I hope you enjoy it.

[Chris Hutchins]

If you're new here, I'm Chris Hutchins. If you enjoy this episode, leave a comment or share with a friend.

[Chris]

And if you want to keep upgrading

[Chris Hutchins]

your money points in life, click follow or subscribe.

[Chris]

Derek, thanks for being here.

[Derek Sivers]

Thanks Chris.

[Chris]

From the outside looking in When I read everything you write, I'm like, this guy has it all figured out. And for every aspect of life I'm always like, oh, 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.

[Derek Sivers]

I'm an explorer, so at any given moment, I might have figured out right now, or I might have 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.

[Chris]

I want to 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. You know, 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 want to do in the moment or what you should be doing. Is there a thing, maybe it's happiness, maybe that you kind of use to guide your exploration,

[Derek Sivers]

intellectual interest. But also, I'm usually led by whatever it feels I'm lacking now. Right. Like, this 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, 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, oh, 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, Yep. 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 drive to just try something new.

[Chris]

Now, if we rewind, you said the person living in the city feels overwhelmed, so they move, you know, to the middle of nowhere. I imagine that most of those people are actually not going to do the movement. I think most of the people probably get stuck in a situation saying, I'm living in the city, everything's overwhelming. And I wouldn't it be nice to go just disconnect for a month. But I just can't do that. So I'm actually. I want to rewind to that narrative and say, you know, 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?

[Derek Sivers]

I think I've always, always pursued that, even since I was a teenager, when I was. Now, hold on. You said one key thing in there. You said, like. 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 kind of like, actually kind of like the little scenario I just described. I had had enough of New York City. I had been living right in the middle of New York City for, like, six years. Five years, six years. And I was just like, I've had enough. I want to 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 want to 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, you know? That we. It might take a couple years for your intention to turn into reality.

[Chris]

So maybe just accepting that everything doesn't have to move as fast as, you know, kind of 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.

[Derek Sivers]

Okay. But there are some things in life where doing it tomorrow is the right choice, you know? So 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, you know, 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 missed 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 a lot of. 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 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 was 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, you know. Yeah, I think I've just tried it. That's just been a priority for me. But that's not to say that everybody should be like that. Some people get deep, deep joy out of having a home with their, you know, sofa that they love and their piano and their things. And it, it would be hard for them to move. But that's fine because they get deep joy out of having that deep sense of home and all of these belongings that, you know, belonged to their grandparents and, and all of that. So you. I'm not saying everybody should be nomadic, but when you're asking, how have I done that, that's my answer.

[Chris Hutchins]

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[Chris]

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. Right. 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 want to go talk a little bit about how you think about making decisions. The decision in someone's mind might be, oh, this isn't. 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.

[Derek Sivers]

Yes, that's you've written about this.

[Chris]

I can't remember the URL.

[Derek Sivers]

I don't either right now. But it's one of my favorite things is to 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? Is it? And you may keep asking yourself these questions and get to the. 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. And so, in fact, I'm going to stay here, not go to Thailand and soundproof my office. Yes, that's what I really want, you know, so if you keep digging into yourself, you might come out with a solution that, that suits your problem better.

[Chris]

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 want to go here? And you're like, and my default is, do I want to 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. 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.

[Derek Sivers]

I journal like crazy. I journal so much. And 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, you know, 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 just, you know, it can take just an hour of your day and it is so, so useful to. 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.

[Chris]

And are there prompts that you use or is it just whatever's happening in the day? Yeah, whatever's happening.

[Chris Hutchins]

Yeah, yeah.

[Derek Sivers]

They're not like generic prompts that I'm going to, you know, hey, everybody, write down these five questions to ask yourself every day. No, it's not like that. It's just use just based on whatever your situation is in the moment. Generally you could use, I think, use it to clarify your thinking and to, 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, if you think you only have two choices, you still haven't thought enough. You have to keep thinking of other options. You know, 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, 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's like, it was actually like solution number 18 that got me the most excited and that's the one I pursued.

[Chris]

Is there an example of, I thought I was going to do this and this new thing came out that I never was thinking about originally.

[Derek Sivers]

Oof. Yeah. What's an example? Well, like, actually that trip to India that I just took that was like 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, I think I need. 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. I was like, ah, 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 like, thing that I married a woman from India. I actually, 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, you know, romp at a conference. So, yeah, that came way down the list. And that's one example. And I was, yeah, 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.

[Chris]

I love it. I'm gonna propose for people who might be like me, thinking, gosh, journaling. I want to try, but I'm not sure what take a. 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. Like brain. Instead of journaling. I'm going to call it brainstorming because 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. And so, I don't know, I'm not a discipline, I'm not a disciplined journaling person. But I feel like I'm going to try to take your advice after this and at least commit to it.

[Derek Sivers]

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 and you need to kind of stop and clarify your thoughts instead of just sitting there and feeling angry. Like, wait, why am I feeling angry? What's this really about? And so instead of just sitting there on your sofa stewing, 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? You know, 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, 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 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.

[Chris]

It sounds a little bit also like rubber duck. Duck debugging. I don't know if you're familiar, as a way to make decisions. Just, you know, I think you wrote a post about getting mentors advice without actually ever speaking with them.

[Derek Sivers]

Yeah. Should we just 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

[Chris]

you can actually put something on top of.

[Derek Sivers]

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. They were trying to get work through A programming problem where they're stuck. They was like, okay, tell the duck. And so you'd say to the duck, like, like, like the reason I'm stuck is because I can't figure out this. Well, then why can't you figure out that? Because what I'm trying to get is the. The instances table to match with the something table. Well, why can't you do that? Because there's. And so, yeah, explain it to the 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? I'm like, I know what he would say. He would say this and I'd 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 describe this process. Like, ask yourself what the mentors would say.

[Chris]

Yeah, 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. It's something. 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 need to spend. I have a rule. I try to spend 15 minutes at least on my own trying to solve something. But before I ask for anyone to spend their time to help me out, oh, wow. This person is, you know, to use one of your phrases, this person is saying making it easy for me to say no on, you know, 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 text 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. And I've never even been to Dallas or uh. And so now, now I've, I'm hoping that the world will slowly adopt a pro, a practice of trying to do a little bit of homework before asking people. Cause it's, you know, it's easy for me to text back my, my sister, my mom, hey, why don't you do a Google search before asking? It's much harder to text a stranger, a business acquaintance back and be like, hey, could you actually just try before. Before emailing me.

[Chris Hutchins]

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[Chris]

don't have to think about any of it.

[Chris Hutchins]

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[Chris]

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[Chris Hutchins]

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[Chris]

a couple things we talked about that I want to loop back to. So it's going to 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. But you want to 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 the A dilemma or one or A or B. It was like, you know, there weren't enough letters in the Alphabet to define the. The option set I had. And then you're like, oh, well, if

[Chris Hutchins]

I go with this one, it's a

[Chris]

little bit more expensive. But they have this, you know, if. 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, 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, what do you think going the other direction with decision making? How do people, or how would you suggest people think about making decisions when there are too many options and they're struggling?

[Derek Sivers]

For me, one option usually leaps out as the. 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 of 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 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, this article that I'm working on. And once you put great value onto finishing, were 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 just through just deciding to make the best of it. Okay, but wait, sorry, that answer was a little mushy, I think.

[Chris]

Can I take a stab at the answer that I think I'm going to interpret what you said. You, you tell me whether you want to go this path, but I want to. I have an idea of interpreting what you said, which I actually think would have made what I did much easier. So I can turn your, your feedback into very concrete tactic which was 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. Where like I kind of just wanted to end up. You know, you're always like, when I. Every time I was about to hit the recalculate button, I was like, come on, just be really competitive so I could just be done with this.

[Derek Sivers]

Yes.

[Chris]

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 making them, I was solving them both at the same time. I. 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. They were equally as important. So if you could just pick something, decide whether you actually pick anything that is good, and then decide whether you want to 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. I could have completely butchered it.

[Derek Sivers]

No, you nailed it. That was wonderful. All right, Chris, I've got three topics you just brought up.

[Chris]

Okay?

[Derek Sivers]

I'm going to 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, you 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. And 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.

[Chris]

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. So I'm trying to find a fun way to kind of make the coin toss. Not something, 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 I might 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. And so 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.

[Derek Sivers]

It's a fun idea. I. I disagree. I think you should always go ultimately with the one that makes you feel the best. Like we, I think feelings. Yeah, your emotions 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, yeah, it's the right choice. You know, the coin said, here I am, damn it. You know, so you got to feel good about your choices, even if it's maybe wasn't the rat. You could add rational reasons later, but the feelings are harder to adapt. Although, you know, sometimes it's the reverse. Sometimes you make a choice because it's the right thing. Okay, wait. Okay, so Paradox of Choice. There's a wonderful book about this thing you said that you were looking for. 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 going to 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.

[Chris]

What about people who love, like, get intense joy out of that process? Because 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, you know, comparison matrix. And I was. 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. The joy of knowing I made the best outcome. But I really just. 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 we 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. So I don't. It's not totally wasted time if you enjoy the process, Bear.

[Derek Sivers]

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 in a way, 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. 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, would you say the best Italian restaurant in Dallas that I'll just look. What did. 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 going to 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. They'd say, 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 friends 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 were. 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 going to 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 like the. 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 it's. 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 hundred percent 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 in the morning I'd set it up for, you know, at somebody's desk and 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 want to 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 because you enjoy it.

[Chris]

Yeah, 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. Don't you know, 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 like, they're all gonna like anyone. I could have just picked. 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, and even when it's a lot, it's. 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.

[Chris Hutchins]

This episode is brought to you by Copilot Money. I've tried basically every personal finance app out there to track spending. Not just looked at them. I mean, fully onboarded, imported. My accounts gave them a real shot. And I keep coming back to Copilot Money because for me, it's just the best one out there. Copilot Money connects to all of your accounts and gives you a clear picture of where your money is going. You get spending by category, cash flow, subscriptions, and even investments and net worth all in one place. With beautiful design and the best AI powered categorization I've seen. Honestly, having that picture has led to some real meaningful conversations with my wife, Amy, about how we actually want to spend our money. And the decisions we've made wouldn't have been possible without a really clear understanding of where our money is going. And I get that from Copilot Money. Copilot works on iPhone, iPad, Mac, and to anyone on the web. And right now, new users can get 26% off their first year when you sign up on the web. Plus two more months free with the code [e-mail] copilot that's allthehacks.com copilot and the code hacks2.

[Chris]

Thank you so much for being here today.

[Chris Hutchins]

You can find all the links, promo codes and discounts from our [e-mail] deals. These are brands I love and use, so please consider supporting those who support us.

[Derek Sivers]

So remember when I, like named those three things? The coin toss, the paradox of choice, There was a Third 1.

[Chris]

Theory versus practice.

[Derek Sivers]

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. Like, 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 major life decisions I've made, like moving here to New Zealand, that came from this 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 could we go? New Zealand seems nice. We've never actually lived there, but 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.

[Chris]

Has that changed? You talk about moving and living different places. You now 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?

[Derek Sivers]

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 need 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's 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, you know, 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 and be like, the energy of the place 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 want to 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, use that restriction in my life, that creative restriction to work within that. So I'll just go visit more often.

[Chris]

So I want to come back to parenting at some point. I have 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 want to do. Maybe we could touch on that a little because I think it kind of ties together. Who, who are we? Who, what do we care about, you know, what do we want to do with our lives and our careers? How do you, how do you think about that? I mean, you're, 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 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?

[Derek Sivers]

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. 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. I chose the. 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. You're going to. 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, 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, yes, says the guy that was lucky to be born in a first world country because 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 that would give their children a better future. And then even their children were like, you know, 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 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. Sorry, I think I got off on.

[Chris]

No, I mean, you knew freedom was something you wanted to optimize for over years. I meet lots of people that maybe don't know that thing. You know, the job comes, it offers to pay them more, it doesn't have the flexibility to travel. They don't know if they want to. 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, 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? What, who do I want to be?

[Derek Sivers]

Right? It's. 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, 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 know, you need to just look back at your life to notice what's make what continuously makes you the happiest and use that when making your future decisions as well. So, yeah, maybe 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 and I really want three houses. It's like, all right, then you 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've, if you know that in practice, not just in theory, then all right, you know, this this is going to help shape your decisions that you need to go for the. 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 Colombia. So, no, I think it's. 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.

[Chris]

Yeah. And I think 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 know, 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.

[Derek Sivers]

Yeah, I just. I noticed from the past that I'm. I knew that 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 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 kn. That option would make me unhappy because that's too much money. But, you know, 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. It's just very nice.

[Chris]

And you mentioned to look back at, 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 and that, you know, you've said. I think that your actions actually reveal your values. So. So maybe, maybe we could talk on this. About this just for a minute is, you know, it's interesting. Some people I know say I'm the person that does this, but if you're not actually doing it, are you really that person? Right.

[Derek Sivers]

God. Thanks for. You know, it's funny I need to read that post again. I had almost forgotten about that one. And I'll tell the little tale quickly. The article is at SIVE RS arv. Arv 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 Muck Work. I had this idea, like, literally the day after I sold cd, Baby, I had this idea from my next company called Muck Work. And I got four months into it, and then I paused to go explore the world instead. And here we are ten years later, and I said to my friend, oh, I really want to do Muck Work. 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. 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, because 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. Oh, wow. He said, yeah, your actions reveal your values. And that's been so, so useful to me.

[Chris]

Wow.

[Derek Sivers]

Yeah. 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.

[Chris]

Yeah, I've been. 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 really. I've wanted to lose weight for the last two years. 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, 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. And that simple phrase of, you know, 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 kind of put it at the top of the priority list and just continue to. To push it down. So that's been really helpful. Thank you.

[Derek Sivers]

Yeah. You know, 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. You know, let's make sure that that's what you really want. Or I really want a Ferrari. Okay, well, rent one. 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 see if you like it in practice, not just in theory. And, yeah, you got to. Got to try these things, and it's.

[Chris]

It. Sometimes it reveals itself to be a lot easier. So thinking about it's really hard. 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 never really found the thing. And once I put the podcast out there. Oh, it's actually. It's not as hard as I had thought. So. 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 hear, oh, it's actually, you know, I'm more capable of doing this. It's easier. It's. You know, 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 that with that perspective. And then I think there are two things that are to come back to on parenting and travel. But there's one. There's two things that 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, you know, when. 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, 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, Is there any kind of clarifying things you want to say on the, on the kind of spectrum of say no to lots of things versus say yes to everything that might help people overwhelmed right now.

[Derek Sivers]

I'm really glad that you said that. In fact, you might be the first person that's ever introduced that book by also giving that clarifier right away. Because, yeah, you're right. Almost everybody looks at that and says, yeah, man, hell yeah. I know. I'm just going to 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. I'm just saying no to everything. I don't feel hell yeah about. I'm like, wait a second, hold on. Like, it's, it's a tool for a specific situation. You know, 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 you're safe, 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. Go, like, take on as much as you can take on, try it all over, commit yourself and say yes to everything. Because it's a little bit like lottery tickets, right? Like, 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 if, like, that's when you should raise the bar. Because Hel Yara no, basically just means that. It just means raise the bar all the way for what you'll accept. So you want to 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.

[Chris]

It could also apply to just so much going on in life. Right. You have two young kids, you have a job, you have a family, and you kind of never. 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, you know, 20 something single person, you know, people say, hey, you want to go to this thing? Yeah, I want to go to this thing. Yeah, I want to do this. It's easy. And then now, you know, we have two kids. We can't. 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 want to go to, you know, Belize for the weekend? We're like, no, that's not a thing we could 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. And so I think right now this year is a little bit more 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.

[Derek Sivers]

Yeah, and thanks for mentioning that because I sometimes I think in terms of business career choices with Helyara. No, but you're right. When you've got a kid that's a big, big, like that's your Helya or your kids. And so that helps you say no to everything else and helps to remember that you'd be better off putting more attention into your kids instead of spreading yourself thin with other things. Like that's. In fact, that's. Sorry, 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, distracted place or 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 from age, for my kid, from age 0 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 just, I'm here with my kid and this is my hell yeah.

[Chris]

So I want to 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. You know, do you want to grab a coffee? And I think saying no is something people find very hard and they almost feel like I'm going to look bad by saying no. It's going to make me, you know, people are going to think that I don't care. And you've said a few things that have given me perspective there and so that I think it would just be helpful for people to understand why saying no might be, you know, in some weird way polite or a better way to do it.

[Derek Sivers]

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, 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, you know, 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? Yeah, you just, you're keeping your head down in your work. Man, I should be more like that. Like you think people are going to be mad, but actually people often get inspired by how you say no to their random things.

[Chris]

Yeah. The other. I wouldn't necessarily put this in a form letter, but I heard you say once that, you know, you say no so that you leave your calendar open to say yes. And if, if someone's calendar is always full, it's almost like, oh man, this person isn't leaving enough time for, for exciting things.

[Derek Sivers]

When, 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. Like, I didn't. There was like literally nothing on my calendar. I mean, maybe like once a year we would take a flight to go see his parents or grandparents. But yeah, for 10 years I had nothing on my calendar app. And when somebody would want to schedule, they're like, hey, can I call you next Thursday at 3? And I'd go, eh, I'm not going to like 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 want to call, just call. I'm not going to schedule. I don't do scheduling. I mean, now I do. I'm just, you know, 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 last 10 years. But yeah, for 10 years that was fun. To just say no to all of it and, 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.

[Chris]

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. We were both like, wow. Because a lot, you know, 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're. You're just. It can feel like work, but if you. 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 think, makes the task of, you know, I know plenty of people like, oh, my partner's gone, and I've got. You know, I've got. I'm on 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.

[Derek Sivers]

And, yeah, whenever I was on daddy duty, because his mom and I always split it 50, 50, you know, 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 live, you know, far, far away from family. So there was nobody else to help. So it was either her on duty or me on duty. And so whenever it was my time, okay, so she had her own way, right? So she. 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. 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. And so 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 today. We're going there. And so we would go to that green patch, get out of the car, and just kind of, like, hang out there for the day. And we would spend, like, you know, two hours, six hours in this green patch I'd never been to. And so I got to know my city really, really well, or I got to know the area really, really well by. 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, you know, Hotel Transylvania 3 kind of entertainment. I'd go and like, I do a little work to like find some like beautifully award some 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, this German animated thing and subtitles. And 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 common, the lowest common denominator kind of. 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. Yeah, 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, yeah, 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, you know, 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.

[Chris]

And I think one of the big ones that you've written about is travel. And you wrote a post that says travel's best with young children. And I was telling my wife about it, she's like, how old are this guy's kid? I, I don't think I said young. I said he, oh, he wrote this great post about travel with children. He's like, yeah, but are they 15? Like, like. 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 you know, and I would. 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 kind of 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?

[Derek Sivers]

All right, I love this subject. I mean, 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, you're 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. I mean, maybe you need to just change your mindset about 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. Because anywhere you're going to go has diapers. You don't need to pack toys because anywhere you go is going to 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. 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. Forget where 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 that was like his favorite toy for the whole week while we were traveling in England, that he found it literally in the gutter in Wales. So, okay, 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, you know, like, so many strangers want to 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 going to sound radical, but I actually got this from a great book called Brain Rules for Baby by John Medina, University of Washington neuroscientist, has been studying brain development in babies for years. And his number one bit of advice. Well, sorry, number two bit 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 wouldn't let. 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. If you let them watch the screens. 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 our 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, yeah. 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 one 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. So you're just gonna get there and then you just go out into the world with your kid and, like, let them explore and let them lead the way. Isn't that a Whitney Houston song? Yeah, you just Let them lead and be on their schedule. And what I love about that is then you get to experience this place through your kid's eyes, right? So I remember taking my kid to Thailand when he was like, six months old. And, yeah, 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. And just let him crawl around. And he would just be crawling around this temple, and everybody's giving him attention. He'd play with strangers. Monk, Buddhist monk picks him up and holds him, and he's loving this attention. And people take his picture and he crawls around. And the whole time we're just laid back, kind of like enjoying the temple and our baby crawling around. And same thing with, like, just going out to a park and he's seeing different things. He sees monkeys. Oh, my God. You know, like, it's all so easy when you let your kid lead the way. Yeah, locals connect with you more. Everybody wants to come up and interact with the baby. So all these locals that you like don't speak English, and we can't communicate through language. But, you know, the sweet old ladies come up and just. They want to play with your baby. And I just. I absolutely love it. I just thought, I kind of don't want to travel without my kid. I think traveling with my kid at any age. And even now, like, 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, like, I kept myself out of it. I just booked a few AKA 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, like, a real hot springs resort. And other than that, like, just day to day. We'd, like. 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. And yeah, he's like my favorite travel partner and has been since he was born. So, yeah, I think travel with kids is easy and wonderful.

[Chris]

We went to London and Paris in December with two kids, six months and two and a half. We didn't try to cram in the Louvre. We didn't. You know, fortunately we picked places that, at least in Paris's case, we'd both been to before. I think one of the challenges that I. I'm curious to hear your perspective on was, you know, maybe this, this gets better after multiple times. So the first, 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. And so I think if we wanted to have an enjoyable trip each day, the goal was, what's what? What's the one thing we're going to do today? What are, you know, our list, you know, pre kids was like, here's the eight things we'll do now it's one. And I wonder now if we went back and I think we weren't, 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, you know, 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 something a. 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. Will give people that feeling far greater than, than the way I would. So I'm curious how, 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 know, you're not going to have the kind of trip that will make it worth it.

[Derek Sivers]

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, okay. And so I took us to Paris, and once we got out of the train station at the Gare du Nord. Is that at 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 just like, go that way. I said, okay. 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. Like, I made a little, you know, 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, and everybody doing these double takes, like, what the hell? And me just cracking up at the. The juxtaposition of not only is my kid taking up the sidewalk, walking in a huge cardbox, 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, like, you know, walking in a cardboard box. And then at some point, he sees a huge staircase. It's, like, starting to get dark. It's dusk. And he's like, whoa. He said, 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 get. 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, one of the most top five beautiful things I've ever seen in my life. He accidentally led us to Sacre Coeur, the big, giant cathedral, which, just because it was dusk, was, like, being lit up by floodlights, but the sky was, like, dark blue. And we just. And it's at the top of the stairs, but you don't expect it. Like, you turn up the stairs, and suddenly it's just staring at you, and it's like, oh, my God, it looked so surreal and was. One of my favorite things on that whole trip was us accidentally discovering Sacre Coeur, which I had only seen in postcards or, you know, photos at that point. I'd never seen it in person. And it was only because he led the way. I don't think like 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.

[Chris]

Yeah. I think it's just about reframing what makes a good trip. Right. In another year or you know, in earlier life, a great trip to Paris might have involved ticking off a few restaurants your friends had recommended, seen a few museums. And as you were talking, what really clicked for me was I thought, okay, well if we're not going to go do all those things and we're just going to kind of 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, and the memories are why you're doing 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 kids, so.

[Derek Sivers]

Right.

[Chris]

But 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 love 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, okay, well we gotta get to this restaurant. But you know, in London, nothing opens early enough to eat before kids nap time. So it's, you know. 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.

[Derek Sivers]

I find it really important. This is just my values. Nobody listening has to, you know, adopt my values. But a lot of the reason I was traveling was for him as much as me, because I wanted to 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. Like, 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 yeah, when he. 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 this 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. 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. Like, 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 gonna book us a trip to Paris and we're gonna get off and we're gonna spend a few days in Paris. I don't know what's gonna happen while we're there. We'll see what happens. But we're gonna spend three days in Paris with no expectations. That's probably a better recipe for happiness.

[Chris]

Yeah, I think it's my eternal struggle is. Is dissatisfice. But I. I will continue to try to make. Make gains towards more satisficing, especially in areas book. Yeah, sorry.

[Derek Sivers]

You should read. It's going to stack up. Why you should. Cool.

[Chris]

I try not to be distracted and write things down. But every now and then in a conversation, I'm like, well, that, that. That deserves to be written down. Okay, so there's two final things. One is around satisfy scene. There is a story I've. I've somehow managed to hear you tell twice. I. I've picked random things and sometimes I read it, and sometimes I'm like,

[Derek Sivers]

oh, let's just play.

[Chris]

And you know, on your site, you re. You read some of your posts and it let. It's a perspective that sometimes taking a different path, taking the. The not. 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, you know, we. 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 stopped 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.

[Derek Sivers]

Okay, so first the story and then how it ties back into what we've been talking about, because the story's about what happened, and then how it ties back in is about the psychological experience in your mind, not just the physical experience. Okay, 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 it's. 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. Like, you know, really like, head down and kind of like, you know, pushing as hard as I could to like, do this in the name of exercise. Like, I'm gonna do this track. And I would do the 15 miles back and forth. And again, sorry, 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'd have to take, like, a cold shower. And even then I would, like, continue sweating even after a cold shower, you know, so. So one day I was just like, I just need to chill. I'm just gonna relax and do the same ride, but at, like, half my normal pace. So I get on my bike and I'm just like, huh, Just going like a granny, you know, sitting more upright, you know, looking around. And I was just like, on my same path, but this time I was looking. And there were dolphins jumping in the ocean that day. I was like, 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. I was like, whoa, pelicans. And then, like, one of them shit in my mouth, and there was, like, the taste of, like, digested oyster. Michelle's like. So that was a really unique experience. And 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, like, 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, this is the. It says that this has the best, you know, creme brulee in Paris. And I could make him do this. And objectively, I could say that that might cram in more experiences and technically make a better holiday. But guess what? It would. 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. So, yeah, I think I definitely value and prioritize the psychological. The inner experience of something.

[Chris]

To me, you kind of satisfy 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 80%, you know, not even 99% of the. The output in terms of pure, you know, 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, yes, you know, 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.

[Derek Sivers]

They have the best. This.

[Chris]

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

[Derek Sivers]

Yeah, 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's 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 at the menu. 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. 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 going to eat something and it's going to be fine. 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? You know, what do you, what do you recommend? What's your most popular dish? And I'll say, oh, the, whatever the chili, 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.

[Chris]

Well, I'm going to 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, 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 things. I don't, we don't need to give them eight things per day on an itinerary, but a couple of places that are your favorite anywhere in the world.

[Derek Sivers]

Well, the first thing, 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 this 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 Tri Stretch 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.

[Chris]

Um

[Derek Sivers]

hmm. 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 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 says, oh, 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 going to 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 yeah, the whole country is so safe and the people are so nice and there are plenty of motels. And yeah, that's more than telling you one destination to go to. It's that.

[Chris]

But okay.

[Derek Sivers]

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 Staglands. 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 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, go to my website, click contact, and there's my email address. I really enjoy my open inbox. And you know, 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 because I've been here for 10 years now and I know most of the secret places.

[Chris]

It's on our list. We have kids, Stagland, Staglands 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?

[Derek Sivers]

Oh, you don't mean physical place it. No, no.

[Chris]

I just mean I know you're not

[Derek Sivers]

promoting a new thing, but never promoting I'm post agenda. Anybody actually just 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, S I V E R S and you don't even have to ask me a question. Just introduce yourself and say hi.

[Chris]

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.

[Derek Sivers]

Thanks, Chris.

[Chris]

I really hope you enjoyed this episode.

[Chris Hutchins]

Derek's advice to think about the outcome you want during the coin flip and knowing that it's okay that it might not be the rational decision was so valuable to me. It's why I ended up picking the Alaska status points, even though my spreadsheet said the miles were a better deal. And I feel so good about that decision. I hope you took away as much

[Chris]

from this episode as I did. If you want to get in touch podcastllthehacks.com that is it for this week. I will see you next week.