Off The Vine with Kaitlyn Bristowe - Sahil Bloom | The 5 Types of Wealth & How to Get Unstuck in Life!

Episode Date: May 15, 2025

#841. Sahil Bloom went from private equity powerhouse to one of the internet’s most thoughtful voices—and he’s here with Kaitlyn to break down the five types of wealth. He shares the moment he realized he only had 15 visits left with his parents, and why “later” is a dangerous lie. Plus: the perspective shift every parent needs, what to do if you feel completely stuck, and why your tolerance for uncertainty might be the key to everything. Tune in—this just might be the conversation that changes how you see your life.If you’re LOVING this podcast, please follow and leave a rating and review below! PLUS, FOLLOW OUR PODCAST INSTAGRAM HERE!Thank you to our Sponsors! Check out these deals!Booking.com For the bookings you’ve dreamed of, list your property on Booking.com!Splendid: Go to Splendid.com and use code VINE for 20% off online or in store.Wayfair: Shop the best selection of home improvement online. That's  WAYFAIR.com. Wayfair. Every style. Every home.Chewy: Chewy has everything you need to keep your pet happy and healthy. And right now you can save $20 on your first order and get free shipping by going to Chewy.com/vine.Macy’s: Just head to macys.com/giftguide to shop the Macy’s day gift guide!Pretty Litter: Pretty Litter helps keep your house smelling fresh and clean. Save 20% on your first order and get a free cat toy with code VINE at www.PrettyLitter.com/VINE.Soul: Go to GetSoul.com and use the code VINE for 30% off your entire order.EPISODE HIGHLIGHTS: (3:40) – Why your mood is the most important decision you make every day(26:50) – The life-changing conversation: “You’ll only see your parents 15 more times”(39:31) – Feeling stuck? Here’s where to start when everything feels broken(49:00) – What real wealth looks like: Sahil’s definition might surprise you(58:30) – The powerful parenting moment that reminded him he’s living his answered prayersSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Hey, Vinoes, real quick, if you are listening right now, which obviously you are, you wouldn't be hearing this, can you hit the subscribe or follow button on whatever platform you're on? Please, that one simple thing helps more than you even realize it allows me to keep growing on this podcast and making these episodes the best they can possibly be obviously for you. That's the only favorite I'm going to ever ask, okay? It truly means the world to me. Thank you. Now, let's get into it. Hey, everybody, welcome to Off the Vine. I'm your host, Caitlin Bristow. I could not be more excited for you to listen to this episode. His writing will make you rethink how you spend your time, what you value, and who you are and who you love.

Sahil Bloom is an author, investor, creator, a dad. He's gone absolutely viral for breaking down life's biggest lessons in ways that are actually easy to apply. So, we talk about his book, The Five Types of Wealth, the Powerful Story that changed how he sees his parents, why he believes most of us are chasing the wrong scoreboard. This is something that all of you are going to really love and take a lot away from. This is just one of those episodes where I'm so proud of and that I will listen back on because I took so much away in the moment that I know I can re-listen to every few weeks to get inspired and feel better about what life is all about. So enjoy my conversation. Just to start off, thank you for being on the podcast. I am so hyped on this. many of my friends and family are really excited about this episode. And I just feel like you have quite the resume. You went to Stanford, played Division I baseball, vice president at a private equity fund with $3.5 billion in assets. You're also super in health and fitness. Like, you really do it all. What, like, what were you like as a child? Oh, God. What was I like as a child? Very, very insecure. Yeah, I, um, I grew up, uh, in a very academically oriented,

So like my mom is Indian. My dad is a white professor at Harvard. And so like from both sides, you get the Indian gene, which like my mom to this day still asks me if I'm sure I don't want to be a doctor. I swear to God. I'm like, mom, it's a little late. I don't think I can still do that. She still asked me. And then from the dad's side, it's like, you're a professor at Harvard. Like you have to be academically high achieving. And I have an older sister who was extraordinary academically. And so I was kind of the like idiot brother who was like, I would, get to a class the first day and they'd be like, oh, you're Sonali's brother and have all these high hopes. And then within two weeks, inevitably, they were just like looking at me rolling their

eyes because I didn't live up to it. The pressure. Yeah. And the thing with that pressure is like, the stories you start telling yourself when you're a kid impact your entire reality. Because if you tell yourself that you are not smart, which is what I did, you're very good as a human being at finding evidence that confirms the story you already believe about yourself. I do it to this day scale, knowing that. Yeah, and it's things that happened as a kid that continue and stick with you, too. So, like, those original stories are so impactful. And it's why now I talk about constantly the need to consistently, on a regular basis, think about whether those stories you were telling yourself are actually true. Or if you are just continuing to reaffirm something that is not grounded

in reality. There's no evidence for it. Here on this podcast, we call it shopping for pain. Hmm. You go shopping for pain. You look for it. You look for the, the validation of what you feel insecure about is true. And as soon as you find it, you hurt and you're, it's like you, you were looking for it. I like that phrase shopping for pain because it also implies that you can shop for joy. Totally. And you can just flip your mindset on it. You really can. I think it was, I think it was Voltaire that said that the most important decision that you make on a daily basis is to choose to be in a good mood. And I've always really like that. Like I can wake up in the morning and be really annoyed about something and then just

just as quickly choose to be in a good mood and focus on good things. I used to be so mentally strong with that. I don't know why I struggle with it more as an adult just because I guess there's more going on, more happening more to worry about. But I remember going through a phase in my 20s where I went, if that's upsetting me, don't think about it. Hi, duh. Why would do it? If that song's making me sad, why am I listening to it? I would just like completely compartmentalized shut it off, but at the same time, I'm like, is that bearing the problem? Is that just shoving the trauma down into my body? That's a good question because there's definitely a fine line to it, right? With people, I am fully on board with that approach, by the way. Like, I've gotten to the

point where if someone is just draining my energy, I'm just going to lean away from that relationship. Yeah. Or shut down around it, not allow that into my space. Because life is too short. Yeah. Like, I don't need to have. One of the greatest changes in my life has been the realization that I don't need a hundred friends. Yeah. I used to think I needed hundreds of friends. Yeah. I've got about three in Asheville.

And if you have three that really... Fill your cup. Yeah, and that you can call it three in the morning when there's an issue and they'll pick up. Yeah. If you have three of those people in your life, you are rich in relationships. Agreed. I totally agree. And that's a great mindset shift of just like you can choose to just avoid the things that are

draining you in whatever way in life in certain cases. Right. Like you said, it's a fun. line of being like, why are you doing this? Yeah. And is it for, you know, to protect your peace? Or are you, you know, are you just bearing something down? I think it's just about being self-aware in that setting. You know what I mean? Yes. What made you kind of step away from all that and start writing publicly? You know, I mentioned the insecurity. I spent the first seven years of my career and really my first 30 years of my life trying to mask or at least hide insecurity in some way. And the way that we do

that is by choosing the path that offers the greatest number or scale of external affirmations, right? Like you have an internal problem, which is the insecurity. And what you do is search for external solutions to that internal problem. And external solutions come in the form of money and status and popularity, all of these things that you think are going to one day make you wake up and feel good, that you're going to feel good about yourself. And we see that in society. You don't have to look far to find an insecure man who is clearly insecure and is doing. And he's doing all of the things publicly to try to make himself feel better, feel cool in whatever way. I was going down that path. I took the job that I thought was going to make me sound impressive rather than the

job that I necessarily thought was the path for me. And I was marching down that path and getting the things that I thought were going to make me happy. It's called the arrival fallacy. Like we create these mountaintops that are the point at which we are going to feel we have arrived. It's the destination where you say, like, once I get that, then I'm going to be happy. Then I'm not going to be insecure. Then I'm going to feel great about myself. And I got those things. And at every single step along that journey, I felt this familiar dread of it not being enough and that it resets to the next mountaintop, the next thing. And unfortunately, along that whole journey, all of these other areas of my life had started to suffer. So my relationships, I had lost sight of, I was living

3,000 miles away from my parents, never really seeing them. My relationship with my sister had ground to a halt. My wife and I were struggling to conceive at the time. That was causing strain in our relationship. And I started to have this sensation in kind of late 2020, early 2021, that it looked like I was winning the game. But if that was what winning felt like, I had to be playing the wrong game. And unfortunately, I didn't really know what a different game was. And the way that I went about figuring it out was leaning into energy. We talked about leaning away from bad energy just as much positive can come into your life if you lean into your good energy that you feel. And for me, writing was something that my whole life I had always really enjoyed. It was something in

my house. My mom was a creative writer growing up. And I wanted to just start doing that. And it was like COVID, I have no social life. I'm stuck inside most of the time. So why don't I just pick this up as kind of a hobby? And so I started writing. That was in 2020. And very quickly found that it was resonating with people. It was creating value for them. I was receiving value in return in the form of people's attention and followers. And so I started to have this thinking that like maybe there's something that can be created around this. Yeah. I mean, you say that your mom was a creative writer. I feel like sometimes that is just in people's blood. Do you feel like now that you found, like you found, you were chasing this, chasing this, but do you feel like you found what actually brings you joy now?

So much so. Yeah. Yeah. I am. The worst thing in the world is not being. being on a bad path. The worst thing in the world is being on a good path that isn't yours. Yeah. Oh, God. Being on a bad path screams at you every single day to get off of it. It's so obvious. You just, every morning you wake up, you're like, I'm on a bad path. I have to jump off this. But the good path that isn't yours, there are a lot of reasons to stay on it. Society pats you on the back for it. Maybe you have responsibilities that you're able to meet. There's all these reasons, all this gravity that's keeping you on that. And so it's very difficult in the situation I was in, which was a good path that wasn't mine,

to make the decision to take that leap of faith and change. And I think that only comes when you start to feel that sensation that like, oh my God, this is my thing. This is the thing that I get so much energy from that I just want to lean into it. That's how I feel about podcasting. Yeah. Podcasting for me became the thing that I was like, this fills my cup. This energizes me.

I love having these conversations. with people where it's so present. You're present. You're in the moment. I say I'm not on my phone. My notes are just here, but I usually have them printed out. But it just, it really fulfilled me and felt like my whole life I'd been trying to find my voice. What I am hearing is that it was the first time in your life that you felt this intrinsic pull towards something that was fundamentally an act of service. That's like what's interesting to me about podcasts relative to other mediums. You are creating something that is in service of a lot of other people. people. The listeners that are going to hear and benefit from these conversations you're having, you're creating an active service for the other person because you're bringing their voice to your platform. It is sort of like an inherently selfish activity because you are benefiting from these amazing conversations that you get to have, but the selfish activity gets converted into this incredible active service and millions of other people, which makes it such an amazing platform and, you know, medium to distribute information. It's interesting that you say acts of service

too, because that's totally my love language. Oh, yeah, me too. It's how I show it. It's how I like to receive it. So then that makes sense that this is a passion of mine. But I mean, sometimes I use my podcast as free therapy. I'm like, so what do you think it is in me? No, back to you, back to you. No, I love it. I love it. You found that passion. And what was the thing that you wrote that really hit that you were like, this is it for me? It's so funny because we live in this sort of like viral culture now. where most people can point to like the single thing. My experience with this entire journey that I've been on is nothing has been easy. Everything has been a byproduct of consistently showing up

over long periods of time. And it's funny to say that because people always want the hack. They're like, well, what was the thing? What was the shortcut? What was the thing? I just wrote 500,000 words over the course of four years. Yeah. Like I quite literally. I've written two newsletters a week every single week since May of 2021. I didn't miss Christmas. I didn't miss Thanksgiving. I didn't miss my birthday. I just wrote every single week.

And at a high quality bar, like a quality bar where I would have wanted to read the thing. And that gets lost. Everyone tells you to be consistent. And everyone says like, oh, I'm going to be consistent. But no one really does it once it comes down to it. It's so difficult because it requires, you know, living by what I would say is the key to life, which is just.

show up. Yes. Show up when it doesn't feel good. Show up when it does feel good. Show up when the rewards are entirely uncertain. Yeah. And that, to me, is everything. It's like if you are on a path that you clearly get energy from, the second piece to that

is tolerance for uncertainty is the number one predictor of success in life. Say that again. Tolerance for uncertainty is the number one predictor of success. The ability to tolerate uncertainty to continue to. who show up with energy and enthusiasm when the rewards are uncertain is what is going to determine whether or not you win in the long run. The person who can tolerate the most uncertainty is the one who will eventually win because they are willing to continue to show up even when it doesn't feel good. Right. And again, many people will say that. Very few will do it. When you

get into the kind of messy middle, like people have tons of energy at the start. They get all excited to do the podcast. They get the launch momentum and everyone has the big launch and they're high on the charts. Yes. Well, how are you going to react 15 episodes in when no one's listening? Yep. And you can't see a path to anyone listening. Because the algorithm pushes it out and then they're going to, yeah. And it's the consistency. Yeah. And it is very, very difficult to navigate those valleys of stagnation when you can't see or feel any change happening into you. Breakthroughs very rarely feel like breakthroughs in the moment. You're right. They are so tiny and so invisible in the moment. It is the tiny little action that you take that creates momentum. It's the tiny thing that

you choose to let go of. It's the slight mindset shift. They're only visible with the benefit of hindsight. Yes. I always talk about the benefit of hindsight. And so you have to be willing to navigate through that period when you can't feel anything. And that is very difficult mentally to do. I agree. I think with writing, I think it's with so many things in life, consistency, they say is key for a reason because it is so easy to, no, it's not easy to put your shoes on to go to the gym, but it's easy to get that momentum once you've gone once. Once you've gone a few times, you're like, okay, but then it's so easy to drop out and then get mad at yourself and then go down that rabbit hole and give up and people do it in relationships and their jobs and, you know, everything that you're saying. And that was something that this girl Kelty, who I've known since, I was one years old. She told me when I started podcasting, which was eight years ago when podcasting wasn't what it is today, she said, you have to be consistent. You have to want to show up. Even like you said, the numbers drop. You're not getting the ads. The listeners aren't, you're going to go through phases of everything, but showing up. And for eight years, I've done two podcasts a week.

And I missed one. And it was like two weeks ago. And I still, it haunts me because something happened on the back end where we couldn't put out this episode. And I was like, I broke my string. because it is so important to me and I think you're right I've always kind of lived a life and my parents and my family will say this about me where I although I'm scared of uncertainty

I kind of lean into it and I think that's why I've been able to do the things that I have always dreamt of doing because there's a very small percentage of people who are willing to lean into that yeah leaning into fear as a recipe for success is a great one

the fact that you say you can even articulate that to say I'm kind of scared of it with consistency see the secret to this is quite simple actually it is much easier to do something every single day than it is to do something most days that sounds like a paradox yeah because it kind of is yeah the reason is every single day becomes an identity whereas most days doesn't every if you show up and decide you're going to show up every single day for something that becomes who you are I'm the type of person that shows up every single day but the key to doing that is what I say you have to

hold yourself to the fire in the act, but give yourself grace in the amount. Meaning do the thing every single day, but don't worry about how much of the thing you do. Yeah. The way that I actually think about operationalizing this is on a daily basis. Let's say it's working out. I have an A goal, a B goal, and a C goal for how much I'm going to work out. The A goal is my best case. Everything goes well. I sleep great. My daily routine is all structured. My whole life goes well. I'm going to work out for an hour. That's like my optimal case. My B goal is kind of a baseline. Everything is sort of average.

I'm going to try to go to the gym for 30 minutes. And then my C goal is like my all hell breaks loose in my life. You know, my kid keeps me up all night. Work is crazy. There's something going on. Well, my C goal might just be going for a 15 minute walk. I can do that any day. It doesn't matter how little sleep I got.

It doesn't matter what happened. I'm going to do a little bit. The rationale here is that anything above zero compounds in your life. we think, and ambitious people especially, which I know you are, we allow optimal to get in the way of beneficial over and over and over again. Yeah, we say those things, right? Like we say, oh, I don't have an hour to work out, so I'm just not going to work out today. I don't have two hours for deep work, so I'm not going to do anything.

I don't have 30 minutes to call my mom, so I'm not even going to text her. When in reality, the 15-minute walk is better than nothing, the text of the mom is better than nothing. The 15 minutes of deep work is better than nothing. Anything above zero compounds. so the ABC system allows you to make sure that even on your worst days you are doing something move the ball forward in that wow I just I want to I'm so glad this is being recorded because I just want to listen to that back so many times I was almost like thinking like I forgot this was recording I was like can you say all that again no Caitlin just go listen to it that was powerful

this shit just comes to your brain I write all of it so like I mean I um the reason I write like my version of how you feel about podcasting is writing and for me everyone now asks me like oh do you use AI for anything you're doing in writing the answer is no we can hear it in your voice this is not AI this is your reign exactly so I cannot articulate anything if I haven't thought about it yeah writing is how I think yeah like when I sit down to think about something if you ask me a question about life or anything if someone emails me a question the way that I think about it is I have to sit and write and it takes a while to like hammer out writing into a way that is understandable. That is then how I'm able to think about it,

articulate it clearly when I speak about it. And so I can't, and I also, and you can't either, like you can't podcast, you can't write about things that you don't care about. No, true, true, true. It's impossible to fake it. Like, you know when someone's authentic to the things they're talking about. It just, it comes across immediately. You can't explain why, but I can tell. Well, thank God that you can like have, you know, this version to put out because I would get so mad if somebody was thinking that AI was doing what I'm actually working hard at. Yeah. That just takes away how hard you were.

That must be so frustrating. And obviously, you have such a large audience now. Like, what is something that people still misunderstand about you, would you say? I would say that I am a pretty normal guy that still struggles with all of these things. I mean, I think the parisocial relationships are quite a weird thing. Like, a lot of people out there feel like they know you. but you haven't met them yet. And the most common thing when I spend time with people is this reaction of like,

oh, you're still figuring these things out too. And what I try to get across is that everything I write about, I kind of think of as like notes to self in some way. You know, you talk about like live therapy when you're having a conversation. You said it somewhat jokingly, but I really think that. Yeah, I do. Normally when I write something, it is that I have been wrestling with it in some way. And my book is like my own transfer.

it's not about me, but it's a manifestation of my own journey and the things that I've struggled with. And so I think that that gets lost in this assumption that the people that you see on social media are like so perfect and have it all figured out. There's certainly things that I've figured out in my life and I'm trending in the right direction. But I don't believe that you ever figure it out when it comes to life. No. No, no, no one. Spend time with some of the most incredible business people, billionaires, whatever, all of these success, they're all in a process of figuring it out. Even the people you admire have no idea what they're doing. They're just stumbling along. And some people are just better at stumbling forward into things that feel

magical. What is the Curiosity Chronicle and how did it evolve from a personal project into something so widely followed? The Curiosity Chronicle is my newsletter that originally started as a way to send out these longer tweets that I was writing to people's inboxes. A lot of people came to me and were like, oh, I would prefer to read this in my email than on Twitter. And I didn't know what a newsletter was, full disclosure. It was like, this is kind of early in the creator thing. It was like 20, 21 in COVID. And so I just set it up. It was super easy. And I was like, I'm just going to copy and paste from Twitter into there. And then the newsletter ended up being the thing that unlocked my entire brain to think about there being a path outside of what I was doing because it grew to like 15,000

people that were just reading my tweets. And I went to a company that I had invested in and asked like, hey, would you pay to put a sponsor slot at the top? I'd seen that and some emails that I would get. And they paid me like 500 bucks to send it out. And so I remember thinking to myself like, hmm, okay, right now I send one thing a week and someone just paid me 500 bucks. That's, you know, let's say $2,000 a month that I'm making off this newsletter now. And it's just like a little side project. What if I send two a week and I get 500 for each one? Now I'm making $4,000 a month. I was like, huh, maybe if it grows, I can get paid more than 500 per newsletter. It just like started my brain on this idea that there was a business that could be built alongside this

thing that I really loved doing. And maybe there was a passion in life. Yeah, it's a dream. Yeah. The dark side to pursuing your passion always is like the second you monetize something, it no longer, it can lose some of the sort of passion that you have for it. There's science around this. The Stanford Marker Experiment is the most famous one. They gave a bunch of kids who love drawing markers. And then they told half of them they were going to get paid for the drawing and half of them didn't. And they came back a few weeks later.

And the ones who had been paid for drawing no longer enjoyed drawing as much as the one who hadn't. Crazy? Crazy. So you like monetize a passion and it is no longer a passion was what the science showed around it. And what is the science of why? I mean, the science around it is like basically you sap some intrinsic joy. when you attach a reward to an activity. It becomes a job.

You turn something that was intrinsic into something. I felt that in so many different areas of life, but yeah. And it's why, by the way, the person who pursues podcasting because they're trying to make a certain amount of money off of it is going to, in the long term, produce a worse podcast than the person who is doing it out of this intrinsic love. And maybe it's making money. When you go look at and study the most successful people in history in any domain, they would have done it whether or not they were making money. Steve Jobs would not have stopped making

amazing products if you paid him less. Right. He wouldn't have stopped and gone and done some in like a carpenter because he could make more money as a carpenter. He would have continued making amazing products because that was his life's work. Yeah. And that is true for anyone who has achieved 0.01% outcomes in a domain. It has to be driven by something more than just the financial gain. Yeah. I mean, your book dropped in February, right? Called the Five Types of Wealth. It's broken down into five parts. There's time, physical, mental, social, and financial. So most people chase financial wealth, as we know, above all. When did you realize that that wasn't enough? Was it because you had done it and you, that's kind of it right there? Yeah, I mean,

that path that I said that I was on of making money and seeing these other areas of my life deteriorate all came to a head at a single conversation in May of 2021. I went out for a drink with an old friend and we sat down and he asked how I was doing. And I told him that it had started to get difficult living so far away from my parents who were on the East Coast. I was in California at the time. It was the first time in my life I had noticed them slowing down that they were getting older. And he asked how old they were. And I said mid-60s and he asked how often I saw them. And I admitted that it was down to about once a year. And he just looked at me and said, okay, so you're going to see your parents 15 more times before they die. I hate that, but yes.

And I just remember feeling like I'd been punched in the gun. I mean, the idea that the amount of time you have left with the people you care about most in the world is that finite and countable that you can put it onto a few hands, that just shook me to the core. And in that moment, I realized that my entire definition of success of what it meant to build a wealthy life had been incomplete, that I was missing this fundamentally so beautiful and important thing. And in the aftermath of that conversation, my wife and I made a, a dramatic leap. Within 45 days, I had left my job. We had sold her house in California and we'd moved 3,000 miles to live closer to both of our sets of parents. And in that one decision was a very important realization, which is you are in much more control of your time than you think. We had taken an action and created time. That number 15, it's now in the hundreds. I mean, I see my parents multiple times a month. They're a huge part of our son, their grandson's life. We had taken an action and created time, prioritize the things that matter to us. That was the spark.

That was the catalyst that led to this book, all of the work that I've done, to create a new scoreboard, to figure out what are the things that really contribute to a good life so that we can measure them and work towards them. And is that what you mean when you say like you invest in like social wealth? What do you do to build that? The idea with all of this is that when it comes to financial wealth, you know. that a small amount of investment today is going to stack and compound in your future. You'd rather put away $50 today than zero because it's going to grow.

The exact same principle applies to these other areas of life. Doing the one tiny thing in your relationships today, sending the text to the friend when you're thinking about them, calling your mom, getting the old group of friends together for the annual trip, these small investments stack and compound into your future. But when it comes to relationships, when it comes to health, those are the first things that fall by the wayside when you get busy. Yeah. You stop texting the friends.

You stop getting the group together. You stop investing in relationships. And fundamentally, relationships are the single greatest predictor of a happy, healthy life. Again, scientifically, the Harvard study of adult development, they followed the lives of 1,300 original participants and 700 of their descendants over the course of 85 years. They found that the single greatest predictor of physical health at age 80 was relationship satisfaction at age 50. It wasn't your blood pressure, it wasn't your cholesterol, it wasn't your smoking or drinking habits. It was how you felt about your people, your relationships that determined your outcomes.

What better reason to invest in your relationships on a daily basis? I mean, it seems so simple. Why do we make it so complicated? I really think it's because we don't have awareness in the moment. So what I mean by that is life is basically a game of awareness and action. It is awareness to know something is important and then action to act against that important. But importantly, when it comes to awareness, the awareness has to be there in the moment when it counts. It's not enough to just know something in the abstract. You have to know it in the moment when it's being tested. So you have to know it when, you know, you have the decision to stay later at work on some silly project or get together with your partner for that date night that you've always had on the calendar.

You have to know in that moment, well, what's going to matter more in five or 10 years? it's probably leaving this work and doing it tomorrow morning early and going and having this date night that we've set out for a while. But we don't think that way. If you don't have that awareness right then, you probably just prioritize the thing that you've always defaulted to prioritizing, which is probably going to be the career in financial wealth. Right. So creating triggers, creating sparks to have awareness of the things that you really hold dear, the values that matter most to you, so that you have that when it counts, yeah, it really allows you to act. So in your

current season of life, what type of wealth feels the most fragile or at risk? Time and social wealth are probably the one that I am most focused on now simply because I got out of whack with them during the book and the book launch. I bet. You know, look, you said season. It's a perfect word. Life has seasons. What you prioritize or focus on during any one season will change. the other realization here is that you are going to have seasons of unbalance. This book is not about saying, oh, my life is going to be perfectly in balance at all times. I'm going to have all five perfectly balanced in perpetuity. It's not how life works. You were going to have seasons when you're very unbalanced. But you need to realize that you can zoom out and have that season of unbalanced

be in service of a future season of balance. I went through that when it came to the book launch, right? I was really pushing on this project that was really important to me. and impactful to me in many ways, recognizing that I need to then zoom out and kind of pull back into a season of balance, make sure that the spring, this summer, that I'm able to be really present with my son, really enjoy it. He's three years old. Like, you know, he's not going to be three forever. The things that he's doing that bring so much joy to our lives are going to be things that I look back on and miss. Yeah, yeah. So yeah. Yeah, that makes a lot of time. Three is such a precious age, too. It's terrorist age, too, but, you know,

I'm not the terrible twos. It's the threes. Yeah. I mean, I like, my wife is the most amazing person in the world for having the energy level to keep up with him at all times. I mean, I'm like completely blown away by her in so many different ways for that. But it is, it is pretty remarkable seeing him grow up. I love that. If somebody feels broke in every category, where would they start? You have to start with financial wealth. Nothing in the business. Nothing in the book. book is to say that money doesn't matter, right? Like, that you should give up all your possessions and go, like, live off in the mountains drinking warm broth and meditating for 12 hours a day. Like, if you want to do that by all means, but I'm not going to be joining you. I like having money. Money isn't nothing. It simply can't be the only thing. You know, your wealthy life may be enabled by money. It'll be defined by everything else. But you need to get to that

baseline level of financial wealth in order to start to benefit from and start using money as a tool to accumulate these others. So that is sort of the first prerequisite is like to say Maslow's hierarchy of needs is real. Until you have your basic needs met, food, shelter, taking care of the people around you, maybe some basic pleasures, money directly buys happiness at that level. Above that, you need to start making sure you are investing in these other things. You need to design them into your life. Because what happens is we get into this mindset of using the word later. We say, I'll spend more time with my kids later. I'll invest in my partner and my relationship with my friends later. I'll focus on my health later. I'll find freedom and

purpose later. Mine's not even later. Mine's tomorrow. Tomorrow, later, someday. All of these words are so dangerous because realistically, all you are saying is never. Because those things are not going to exist in the same way later. They're not going to exist in the same way someday or tomorrow. Your kids are not going to be five years old later. Your partner, your friends won't be there for you later. If you're not there for them now, your health certainly won't be. You won't magically wake up with freedom and purpose later. So either we find a way to design these things into our life in some tiny way right now,

or we're going to end up regretting it later. My grandfather used to say later we'll be dead. It's sad. It's morbid, but it's true. Yeah. Now, sometimes the morbid things, there is this app called We Croke. Have you ever heard of it? And it's like literally morbid talking about how you're going to die.

But it's a reminder all the time. One of my friends, do you know who Ben Nempton is? Yes. Yeah, you do? Yeah. So I've known Ben since I was 21. Oh, wow. And I'm 39.

So I've known him for a very long time. He's the one that got me on the We Croke app because he's, you know, he's done the thing of what do you want to do before you die. That's his whole purpose in life is trying to inspire people. Like kind of the same idea that later you're going to die. So what are you going to do now? Yeah, I mean, you get 4,000 weeks on this earth. Oh, that's crazy.

Four thousand weeks. How many of them are already gone? I have this chart in the book of visualizing your life in weeks. So you have 52 columns across and 80 rows down. And looking at it and realizing how many of those are shaded in. So I'm 34. So 34 of them are shaded. You can see what the remainder of your life looks like.

Yeah. And you realize when you look at something like that, a wasted week is meaningful. Yeah. A week when you got stressed about stupid stuff, when you had anxiety about the future, when you were like stressed about some silly thing, it's a week you're never going to get back. And that, while a bit morbid, does have a clarifying effect on most of these things. If they're not going to matter in six months, I'm just going to let them fall out of my mind. I just, I cannot say that strongly enough that your life improves when you just stop worrying about these silly things. When you recognize that fundamentally stress and anxiety feed on idleness. If you start moving, if you just take action, if you stop scrolling on your phone, you literally starve them of the oxygen that they need to breathe.

Right. The answer is found in the action. What is your thought if somebody needs a bed rot day? Like my mental health in the toilet, I'm, I'm going to allow myself two days to be a piece of shit. Are you in for that? Are you, okay. Yeah.

You have to find what works for you. Yeah. Look, I, um, I'm looking for validation. No, no, I always, I stop short in any area of life of being prescriptive because that might feel like action to you. Yeah. That might feel like, oh, the action that I need to take is to just allow myself to be lazy and eat some ice cream.

Yes. Uh, or go for a long walk and listen to my face. favorite music or audio book or something like that and just be off in some way. And if that is the action that you need in that moment, then I think that's great. What I wouldn't say is generally good or healthy is spending that day scrolling on Instagram feeling bad about yourself. God. But what about being the, I always talk about being the curator of your own media intake. What if you are following accounts that actually like yourself are inspiring others? What do you feel about scrolling then? I think it's fantastic if you're able to do that. Very few people.

have done that. I mean, I don't. I preach it and I don't do it. I mean, I went through a very deliberate exercise on this because I found that my sort of unhappiness, if I mapped it during the day, was entirely mapped to social media usage. And it was all driven by the fact that I would see things that made me feel like I was not enough in some way, that I wasn't doing enough, that I wasn't a good enough dad, that I wasn't good enough at business, that I wasn't a good enough creator, whatever thing. And I just started saying, uh, not interested in this thing, whatever the app allows you to do. Now it's amazing. Or I would just unfollow people. Yeah. Or block them or mute them or do whatever I had to do. And now my feed is like, uh, running stuff,

working out stuff and like crazy food videos. And I love Instagram. It's great. It's like, you know, inspiring things. Yeah. Kind of lift me up. Plus like just like fun things that are sort of light. Yeah. And I don't feel that same negativity. My life has improved. The same goes for news. consumption for me. My life improved dramatically when I reduced my news consumption by 95%. I'm trying to get my mom on that train. Gosh. It's hard with parents. Oh, my mom falls asleep to it. She puts headphones on and falls asleep to political news. Yeah. And then wonders why she has anxiety. Yeah. anxiety, you know, a, I mean, you can go look at this. It's very, very clear data. But like if you look at, they've done a chart, side by side chart of, it's like a pie chart of the

proportion of deaths in the United States by cause in reality versus like the proportion reported by the media and the one reported by the media is basically like if you were to just track deaths in the media it would be like terrorism is an enormous bucket and homicide is an enormous bucket and those are like basically the two things yeah and then if you look at reality it's like heart disease and cancer right right no one's reporting on that they're just reporting on terrorism so you would literally think that you were going to walk outside and just get killed by a terrorist or just otherwise. Yeah, and your body is literally consuming this kind of like fight or flight information

at all times. At all times. And then stress is like the number one killer of so many things too. But we're all punishing ourselves. Yeah. Going back to shopping for pain, if you will. Shopping for pain. You know?

It's entirely shopping for pain. You've told the story of the fisherman and the investment banker. Can you please recap that quickly for us? This is the best encapsulation of some of the ideas from the book. An investment banker goes down to this Mexican fishing village. And he's walking along the docks. He comes across this old fishing boat. And he asks the fisherman, how long did it take you to catch these fish?

The fisherman says, only a little while. The banker says, why didn't you fish for longer? The fisherman says, well, I have everything I need. In the morning, I fish for a little while. Then I go home, have lunch with my wife. Then I take a nap. Then in the evening, I go into town, drink wine, play music, and laugh with my friends. and the bankers like, you got this all wrong.

Here's what you got to do. You got to fish for longer so you can catch more fish. Then you use the extra money to buy a second boat, then that boat fishes. Then you buy a third boat, a fourth boat, a fifth boat, a six boat. You move to the big city. You take your company public and then you're going to make millions. And the fisherman says, and then what?

And the banker's like, and then what? Then you can retire and move to a small fishing town. You can fish for a little while in the morning. And you go home, have lunch with your wife, take a nap. Then in the evening, you can drink. drink wine, play music, and laugh with your friends. And the fisherman just smiles and walks off into the distance. That story is commonly interpreted as saying that the banker is wrong and the fisherman is right. I think it's more nuanced than that. It is about the fact that the two have a

fundamentally different definition of what it means to have enough. Yes. It is perfectly okay and reasonable for the banker's definition of enough to be building something big, creating jobs, chasing this grand ambition and purpose. But for him to apply that map of reality to the the fisherman's terrain makes no sense. The fisherman is already living his version of enough. And yet, that is what we do when we take out our phones and compare our lives to other people. We are allowing their maps of reality to impact how we feel about our terrain. We all need to decide where we exist on that spectrum from fishermen to banker in our own lives. What our version of that enough life looks like, because then we can take actions to build

towards that ideal state. God, that thought alone, I think, just changed my life. I'm serious. Because I do this to myself all the time. I mean, we all do, I guess. And it is. It's defining what enough looks like depending on each person, because everyone is so different. And we do, I mean, all you're doing all day long when people scrolls comparing. So how do you personally define enough today? My wealthy life is being able to take my son in the pool at 1 p.m. on a Tuesday. That basically captures everything that I want out of life. Like, I want to be healthy enough to do it. I want to have the relationship with him.

I want the time freedom to do that. And I want to have enough money to have a pool. If I can do that, my life is incredible. And I can do that right now. And so I have to remind myself of that regularly. It doesn't mean that I stop chasing ambition, but it means that I recognize that that ambition has to be grounded in something more meaningful than just money. Yeah, it's because when you first heard that fisherman banker's story,

what part of you, did part of you get uncomfortable? Who were you in that situation? Because I hear it and I go, I'm team fishermen. My first interpretation of it was to just say like, oh, yeah, the fishermen figured it all out, the banker's just wrong. And I just think that that's not necessarily right. Because if you want that, if that's what you want out of life to go and chase and create some lasting legacy in big company. I think that that's great. But the point is that we get

to run our own race in life. And so often, we are so busy worrying about everyone else's race, looking around us constantly, what race is that person running? What are they doing? What's this person doing? That we forget that we get to run our own. And we get to choose what race we want to run in life. That is what my entire book is about it. It's like to say, you get to decide. And no matter what the world tells you, no matter what your parents tell you, your friends, social media, you actually get to decide you are in the driver's seat of your own life. You can choose the life that you want to build and then go take actions to go and build it. And it doesn't have to be the approval of other people. It is perfectly okay to live a life that looks confusing

to other people. Yes. Even advice. What practices do you have in place with either money, time, energy to keep you from chasing the wrong things? regularly ask myself these kind of big picture questions. So I have this practice that I call the Think Day, which is once a month, I try to take an hour, maybe two hours, go to like a coffee shop or go on a walk, bring a journal and a pen, no social media, no technology. And I ask myself some bigger picture questions about life. One of my favorite ones is this kind of, I call it like the main character question, which is to ask, if you were the main character in a movie of your life,

what would the audience be screaming at you right now? We've all been there. You watch a movie or television show and you just want to jump through the screen and grab the main character and shake them and say, don't go down in that basement, look out behind you, chase the girl to the airport. Literally what I'm doing right now. I'm rewatching my season of the bats right. I'm yelling at myself through the screen telling her what to do. A perfect example. You are that main character in the movie of your life right now.

And the audience would be screaming something at you. What is it? What is that thing that is so blindingly obvious from the outside looking in that you are either choosing to ignore or that you have not yet created the perspective to see? Those kind of questions when you ask that, when you create that perspective, when you zoom out on your own life, often inform whether you are running the right race or whether you were doing something for the wrong reasons. Wow, which leads me to my next point. You've said that you're more focused on anti-goals than goals. What does that mean? Charlie Munger is this famous investor, late investor, who had this quote, all I want to know is where I'm going to die, so I'll never go there.

That idea is basically anti-goals in a nutshell. It is to say, we all know what goals are. It's the summit of the mountain. Anti-goals are the things that we are not willing to sacrifice while pursuing those goals. So your goal might be to become CEO of a company. Your anti-goal along with that could be not spending 300 nights out of the year. year away from your family or allowing your health and sanity to really suffer from all of the travel and work. You want to achieve the goal, but not if it means having these anti-goals become real.

It sort of provides the guardrails on your journey. The reason that's so important is because what often happens to people is that they achieve the goal. They achieve the thing that they think they wanted and find that they won the battle but lost the much bigger picture war. We don't have to look far in society to find examples of this. It is, the guy who went and made hundreds of millions of dollars, maybe billions of dollars, who we pat on the back, we celebrate, we admire, and we ignore the fact that they have three ex-wives and four kids that don't talk to them. And we write books about these people. We celebrate them as success stories. We tell them that they won the game. But in your own life, you have to

ask yourself, is that actually a game that I care to win? The Forbes top 10, richest people in the world, have 13 divorces among them. Yes. Yeah. That, to me, is a Pyrick victory. It is winning the battle but losing the war. And so having anti-goals establishing those on your journey to set those guardrails as you pursue these goals is really important because it is possible to do both. It is possible to win the battle and the war. What is the thing you said? The what victory? It's called the Pyrick victory. It is a phrase that means a victory that takes such a steep toll on the victor that it might as well have been a defeat. Have you had one of those? I was the path that I was on in my own life was, you know,

marching down this path towards what would have been a Pyrick victory. I would have made a bunch of money, but really come to regret it. What is the one thing that you used to want so bad that you actively avoid now? That's a good question. Thank you. What is the one thing that I used to want so bad? I would say like bot status. So what I mean by bot status is like things that you can buy that you think confer, like respect and admiration upon you. Like fancy cars, jewelry, club memberships, like all these things that we think are going to make other people look at us and be like, wow, you're so cool. When in reality, it is a race to nowhere.

Yeah. The truth is that real status has to be earned. It cannot be bought. You know, otherwise, lottery winners would be the highest status people in society because they have a lot of money. But that's not what it's about. Jeff Bezos doesn't respect a lottery winner because they have a lot of. of money. You have to earn it. You have to go build something. I used to really chase and want that

bot status, try to signal that I was a high status person versus realizing that real status is earned. That is a really great answer. I knew you. What's yours? Honestly, that kind of brought up something for me that I'm actively working on. I think, I think I have really truly gotten to a place where I'm like, why am I not more grateful for all the things that I have achieved that have been dreams of mine? And I'm still doing the what's next. And I still go, why am I not approved to the Soho house? And this, knowing that that's just for status. And I'm, I'm like, You're speaking my love language. I, a few weeks ago, just before the book launch, I was in my office and I was working on something, really focused on something. And my son came and barged in

and started like jumping around, throwing things around my office, just terrorizing it. And I started having this very annoyed train of thought. Why is he doing this? This is so annoying. Doesn't he know I'm working? And I looked on my desk and I have this picture of me holding him when he was born. And it snapped me back to four years ago when my wife and I were in the middle of this two year struggle with infertility. And I had prayed every single night that we would one day have a healthy child. And here I was in this moment complaining about the exact thing that I had prayed for. And it was a reminder to me of that fact that sometimes in life the things you pray for become the things that you complain about if you let them. If you don't have the presence to pull

yourself back into the moment and recognize that sometimes you are quite literally living out your prayers. Yes. I, I, that is very much me. It's like I'm so aware that I'm doing it, but I can't be stopped on the downward spiral of it. And it's like, part of it's PMS. I'll come out of it next week. But like that really is a struggle for me where I have, I dreamt of the life that I'm living. And instead of reaping it all in and being so proud, I'm doing the what's next. Why am I not here? Why am I not doing? While also being aware of how silly. that is. You should write down like one thing every night before going to bed. I should. Just like a tiny practice. I'm a big fan of creating these really tiny, impossible to skip

rituals because they're so easy that will create some slight improvement. And that's one that might really help. I do, I call it my one-one one method in the evening right before going to bed. I write down one win from the day. That's something that went well. One point of stress, tension, or anxiety. So something I'm stressed about. Get it off my head onto the paper. And then one point of gratitude, something that I am very grateful for. It takes like two minutes and I immediately go to sleep with much more clarity and happiness. But that one one method is in your book. Yes. It's one of the tactics in the book. Yes. You were speaking of like your wife and how you've prayed for everything and now you have it. I want to know how you knew that this woman was for you. What was the moment?

The thing you have to understand about my wife and my relationship is we met and started dating when I was, she was 15. I was 16. Stop it. Yeah. So we're high school sweethearts. We've been dating the entire time. Very rare these days, obviously. Yeah. But we grew up together and grew together through different seasons of life in a really meaningful way where she has actually been remarkably consistently an incredible person. I have had various phases of insecurity and ups and downs and needing to find myself on that journey. And the fact that we grew together through that has been incredible. Before I got married, my mom asked me how I knew Elizabeth, my wife, was the one. And I told her that it was because I loved doing nothing with her. And my mom looked

so confused. And what I meant by that was I had come to this realization that life is not about the glamorous, perfect, filtered moments, like the honeymoon moments, the Instagram photos, the fancy date nights, all of those things. Life is mostly just sitting around doing nothing. In your pajamas, watching television, your favorite shows, at home for dinner. When you find someone that you love doing nothing with, that is your person. Yeah. And I had found that. And I still, to this day, like my favorite nights are not fancy nights out. It is the normal nights at home when we're literally doing nothing. Yeah. I actually really like this question. I am such part of thinking about feeling rich in life and what, you know, that means to me is

my listener community. When I'm having a bad day, I will go on the Facebook page and I see the connection that is being built where moms are asking other moms for advice. People are giving trigger warnings and talking about infertility. People are talking about depression and what's help them. I find so much connection in that Facebook group that is like my favorite thing in the whole world. How do you build real community in an online world? Because I think a lot of people want to do that. I think a lot of people in careers forget about that aspect of it. How do you do it? I try to spend as much time with people in real life as possible. I mean, I do not do remote podcasts for this reason. Like I just, I at any point in time, if there's an option,

to just spend time with someone in person, I'll get on a plane. Yeah. Like, I have always had a very low bar for getting on a plane because I fundamentally believe that real human connection is built face to face. Oh, my. Then how hard was the pandemic for you? Very, especially in California, where it was very locked down. I mean, the first, you know, nine to 12 months in California were really tough, although

the being stuck at home was what contributed to me spending enough time writing that it created this life on the back end. So there was a benefit to it. I mean, I just think that, uh, you've, I've never. in my life built a relationship with someone over Zoom or over a phone call. It just doesn't happen. God, that's podcasting for me. I'm like, I'll fly wherever to do it in person over over Zoom because everyone's zoomed out. You're never friends with someone after doing a Zoom podcast, right? Like, it never happens. But in person, like, if you like the person, you always are

friends. I know, I'm going to call you later. Totally. Yeah, like, let's do the live therapy session later. It's great. It's perfect. Yeah, it is. That is, that's an important aspect. That's why I love doing podcast tours. I love being able to meet these people that I'm like, I feel connected to and I've never met them in my life or seeing their faces. And then to see them all in one room and feel the energy and then talk to them after and hear their laugh, them actually laughing at my stupid jokes. Like I'm like, live events are the best for that reason. It's the best. The best energy. And I find it, I find it actually, do you ever do a live? I did a whole like book tour for the launch and I ended up extending it. Now we're doing more events. I was like, I got so much energy from seeing

people in person and getting to talk about these things and hear their stories that I want to spend a significantly larger chunk of my time doing that. Yeah, isn't it? It's one of those things where I go, I'm already exhausted before doing it. And then I get there and it lights me up and I walk away from it being drained but in the best way possible because I had really put everything into it. And I poured everything out to this audience and I feel all of their interactions and I take it home with me and I'm like drained in the best way. Yeah, you just got to lean into those things that make you feel that way. Yeah, you really do. And unfortunately, we don't do it enough. But anyways, I could talk to you forever. Thank you so much. Where can people find you, your book, all the

things. You can find the book on Amazon or anywhere books are sold. And you can find me at Sawhill Bloom on any of the platforms. Yeah, you're so inspiring and real. And just, I always tell people like, I wish, because what you say, I think in my head, but cannot articulate. the way that you do. I think you're doing pretty great. Oh, thanks. I just needed some validation there. Thanks for giving that to me. Thank you so much for being on the podcast. This was honestly so one of my favorite conversations I've ever had. So thank you. Thank you. And everyone go follow. They probably already are. My name is Amanda. I work with women who are trying to quit smoking. And I have some tips for you

in case you're pregnant or thinking about having a baby. First thing is, keep trying to quit. Or better yet, don't start smoking. It can cause premature birth, which can then increase the risk of your baby having developmental delays, problems with eyesight, breathing, and more. So don't give up. There are people like me who are here to support you, because I know what can happen if you don't quit. Your baby could be born two months early and weigh only three pounds. She could be in the NICU for almost a month, put in an incubator and fed to a feeding tube that goes through her nose down into her little stomach. I know that because I smoked while I was pregnant, and that's what happened to my little baby.

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