Why Finding Love Starts With Redefining Success (Feat. Sahil Bloom)
9 Jul 2025 · 69 min
Sahil Bloom and Matthew Hussey argue that wealth means time, health, purpose, and relationships, not just money. They explore why your actions reveal your real values, how safety habits sabotage connection, and why treating relationships as your highest-return investment matters more than you think.
Questions this episode answers
July 15 (kickoff call where five missions are given).
Progressive Insurance (Progressive Casualty Insurance Company and affiliates).
lovelife (10% off).
On Amazon and at local bookstores ("anywhere books are sold").
He says he "walked away from eight figures" of money when leaving his prior job.
Chapters
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Welcome back to the Love Life Podcast. In today's episode, we dive deep into the heart of what it really means to live a truly wealthy life. Not just in dollars, but in time, relationships, purpose and health. With my guest, best selling author of the Five Types of Wealth, Sahil Bloom, we explore the tension between chasing external success and cultivating internal fulfillment.
Especially in the age of social media.
We talk about navigating the creative grind.
And redefining success on your own terms.
Sahil shares invaluable insights about embracing the seasons of life, choosing environments and people that are align with your values and the underrated power of time wealth. Whether you are building a career, a relationship, or simply trying to live more meaningfully. This conversation is for anyone who is ready to rethink what wealth really means. A quick note before we start. I am bringing back a massively popular free event that I do every couple of years called the 30 Day Confidence Challenge. This is so unique because it's me giving you five missions to increase your confidence over 30 days and we're going to do them all together. I'm going I truly believe that confidence is a superpower in this Life. And the 30 day confidence challenge begs a simple question. Who are you and what are you capable of when you don't have your.
Foot on the brakes?
We will begin with a kickoff call on July 15th where I'm going to be giving you the five missions and then the 30 days will begin. This entire 30 day confidence challenge is free to be a part of, so join the thousands who have registered and Register yourself@mhchallenge.com and now I give you Sahil Break.
Say Hill, it's good to be with you man.
I'm thrilled to be here. Thank you.
I, I, I love you. The concept of your book the Five Types of Wealth, I am really fascinated. You said something before we started just now about the kind of mimetic nature of how, why we go after certain things, certain types of wealth, how we define ourselves, how we know that we're living a good life. And you hinted at this idea that we really need to decide for ourselves what's valuable to us. And I spend a lot of my time helping people in their love lives and that's one of those big areas that is incredibly mimetic, because we're looking at people online who seem to have these amazing relationships. Building families have the thing that we want more than anything else in the world when we're single and we feel like love is the answer to. To this loneliness that we feel or this wanting that we feel when it comes to our romantic lives. Do you think that there are some areas of, quote, wealth that are not simply mimetic? They're just intrinsic in terms of our desire for them, and they're never going to go away?
It's an interesting question to contemplate whether we have anything that is uniquely our own or if we are just mimetic creatures. I think that studying and observing children gives you some insight into this. Like the things that they seek when they're young, when they haven't been patterned through school or through any of these other sort of belief sets that you come into, gives you a decent lens into, like, what is innately human. And I really do feel like the longing for connection and love and support and affirmation is uniquely human and innate. I mean, I see my son, from the time he was six months old would, like, respond really positively to being cheered for on something like that. Feels innately human at some point. He didn't learn that from being around people, but responds to these feelings of support, of love, of connection in such a meaningful way that there are things that now I look at and say, there's a version of that thing that is innately my own. And over time, I've gotten indoctrinated into this culture that has told me that, you know, X, Y and Z really matter. So you got to measure those things and really focus on those. If I want to build a successful life. And my fundamental belief is that you will never feel successful unless you create your own definition of success. And that is really the journey that we should all be on, is to say, what are the things that actually matter to me? What is the life that I actually want to build? Not the life that social media tells me I should want or that my family tells me or that my friends tell me, but what I actually want, and then go and take actions to build that life.
And when you've looked into this and researched it and worked on it, have you found that there are, you know, what. What are the things that universally create a wealthy life for people that aren't necessarily specific or individual, but are just the pillars of a great life?
It's really four things. Time People, purpose and health. Money is an enabler to those things in a lot of ways, but it is very rarely an end in and of itself. I derived those four from thousands of conversations across all different people, from different walks of life, different experience sets, talking to young people, asking them what hopes they had for the future, what was their ideal day at 80, what life did they want to build? And then asking people at the end of their life, 90 and 100 year olds, what advice would they give to their younger selves? What would they go back and change about the way that they had walked through their journey? And those four themes keep coming up over and over and over again. Time, people, purpose, and health. We want to feel this degree of time freedom. We want to be surrounded by people that we care about, that care about us. We want to feel a sense of purpose, this sensation of knowing what we are meant to do on a daily basis. And we want to feel healthy of mind and body. And again, money is an enabler to many of those things. We can't be naive and say money doesn't matter, right? Like, I will never tell anyone that money doesn't matter, that you should go off and live in the mountains, you know, drinking warm broth, give up your worldly possessions. If you want to go do that, by all means, I won't be joining you. I actually like money. I like having, having things, being able to take care of people around me. But to think that you can just focus on the one battle, if you will, of making money and that it will ultimately just solve all of these other things that is the path to this rich yet miserable existence that is all too common in the modern era.
What do you think is the most underrated form of wealth?
Time. Wealth is the one that very few people think about to their own detriment. Time wealth is this recognition that time is your most precious asset. Time is the one thing that you cannot get any more of. I often go and ask young people, would you trade lives with Warren Buffett? He's worth $130 billion. He has access to absolutely anyone in the world. He reads and learns for a living. He free flies around on a Boeing business jet. He can basically stay anywhere and do whatever he wants. But you wouldn't trade lives with him because he's 95 years old. There's no way you would agree to trade the amount of time that he has left for all of that money. And he would give anything to be in your shoes to have the amount of time that you have left. He would give up every single dollar that he has. So you recognize with a simple question that your time has quite literally incalculable value. And on a daily basis, how much of that time are we really wasting sitting on our phones, comparing our lives to other people, stressing about the past, anxiety about the future, fundamentally disregarding this one most precious thing that we really have? You are a time billionaire. You have billions of seconds left in your life, but you aren't relating to yourself that way. You aren't treating your time with that degree of reverence and respect that we really should.
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What do you say to people who you know? Because relationships are a crucial source of wealth, and for many people, in their mind at least, the pinnacle of relationships is their life partner or the desire for a life partner. And so many people struggle to find that and feel like, God, it's this area of my life that's so out of my control. Unlike making money where, you know, I might be able to, it feels like I can have more influence over that if I want to work harder, work more hours, pick up the phone more, sell more, you know, I can to some extent exert immediate influence over that area. Whereas people in their love lives feel like, you know, I can try all I like, but I still require another person to sign up to a life with me. And a lot of people feel like every person I meet, you know, even if there's initial attraction, it fades, it fizzles, it never relate results in a relationship. It doesn't ultimately go anywhere. And so there's this kind of real inner turmoil that exists because there's this thing I want more than anything that I feel like is continuously said to me is one of the most important forms of wealth there is, and I can't seem to find it. What do you say to people when there's. There's that problem in their life of I just can't access that wealth?
There's two things I would say here. First off, there's this common turn of phrase that people say, who you choose to partner with in life is the single most important choice that you will ever make. It's a little bit of a fallacy because it is not about a single choice. Love is about a choice that you make every single day. A relationship is a choice that you make every single day. To show up and give your best effort towards this thing. It is work, it is effort on a daily basis over 10, 15, 20, 30, 40, 50 years that you were with this person. To think that you are going to make a decision and it is either a right or a wrong decision places so much weight on that one moment in time when in reality, a good marriage is not based on that one decision. It's based on how you showed up over the tens of thousands of decisions that followed it. Recognizing that fact reassumes agency over it. You are not tied to that one decision you made. You are in control of the decision you make today, the way that you show up in the world today, that is something that I have definitively changed my mind on. That for me personally and in our relationship, my wife and I has been transformative, is to say you are always in control of the decision and the choices that you make right now. And you are not tied to whatever you did in the past. In that way, you didn't make the wrong decision or the right decision. You need to show up in the right way today, and that is what you're in control of. You are at the wheel there. The second thing is to recognize a fundamental flaw of this sort of social media age we live in, which is this obsession and this focus on falling in love rather than growing in love. Falling in love is very, very easy. Growing in love is very hard. Falling in love is what you see on social media. It's the glamorous pictures, the Instagram honeymoon, the vacations, all of these perfect, manicured, filtered moments. Growing in love is what you don't see on social media. It is the hard conversations, it's the challenging moments, it's the struggle that you go through. And we know scientifically that growing in love is where you really create that connection. Shared struggle releases oxytocin, this chemical that creates feelings of love and connection. But when you live in a culture that glamorizes the falling, what you have is people that very quickly opt to press the eject button on these relationships. The second it no longer feels like the falling phase, the second those, like butterflies maybe start to diminish, you have a thousand options on your phone. So you just say, well, it's so easy to press the eject button. I'm just going to go do that. When in fact, all of the great things in relationships are built through enduring just a little bit of what that struggle looks like. That is true for all areas of life. The best things in life are on the other side of something that you don't necessarily want to do. So not being afraid to lean into that growing phase, some of that pain, some of that struggle that may come to just see what's on the other side of it, see another card turn, if you will. So much good can come from that.
I suppose that the challenge some people have is feeling like, I value relationships in precisely the way that you just talked about. I really value being a teammate with someone growing together, putting in that effort. I value real relationships and showing up every day. But I feel like I am in a culture where so many other people don't value that. I value that kind of wealth and I'm willing to invest in it. But I keep being met with other people who don't seem to. They are addicted to novelty. They don't want a real relationship, they just want to hook up. They're on dating sites, it seems just to, you know, indulge at the buffet and not to actually have a meaningful connection. So what do you say to people who are like, I, I value that kind of wealth that you just shared, but I'm struggling to find other people in today's society who value that kind of wealth.
Your environment creates your reality. And it is definitively true that there are places and environments where people are going to sort of naturally fall into these different camps. Like I have personally found that dating for my friends that live in New York and LA is much, much harder to find people that really want to create meaningful connections and invest in long term relationships versus the, like, the novelty and the, you know, the sexiness of these cities. And to some extent I get it. And what I feel for is the people that are looking for those deep meaningful bonds and what they're surrounded by and the environment they're in are the opposite. It's people that aren't looking for that thing. And so they're getting constantly this like head fake of I meet someone, I feel that connection with them. I think this could be something and the other person just wants sex, right? Like, I mean, don't need to beat around the bush, right? Like if you are someone that views sex as the deepest connection you can have with another person's heart or soul and the other person views it as like a hobby, that's an issue, right? Like you're never going to get past that. That is a fundamental issue. And I think there are certain places and environments where that is the culture that people are being indoctrinated into and buying into. I believe that we are in control of our environments, whether physically, via geography or emotionally, spiritually, and the people that we allow into our energy in some way, no matter where you are, you can find communities of people that are more aligned with you. I personally think that a lot of it comes from the rooms that you choose to place yourself in. If you become very deliberate about thinking about what are the values of the people that are likely to be in this room that I'm going to place myself into. You start to find value aligned rooms, right? Like if I am really into health, I really care about taking care of myself physically, mentally, emotionally. Spending time in farmer's Markets, there's probably a place where I'm going to find other people that have that similar shared set of values. I probably shouldn't be at the club at midnight on a Friday night if I'm trying to find those people. And so thinking a little bit about mapping your values and then being very clear about what are places where I'm likely to find other people with those values, that exercise actually can inform a lot about how to place yourself into higher likelihood environments of finding that type of person.
If someone is living in LA or New York and they sort of conclude, okay, I. Sahil's right. I am struggling to meet people who are on my wavelength here in terms of wanting a relationship. Everyone wants the, you know, better deal here, or they're just not serious, or they're just focused on their careers. How do you. And maybe as a result of that, they're thinking I should, should I move? Is, is that what Sahil's suggesting? Should I go somewhere else? Should I uproot my life in that way? And for people who do something like that, then of course there's all sorts of tensions that arise. Maybe my family is in this city and it would mean moving further from my family. Maybe it means moving to a city where there's less going on and that feels less exciting to me culturally. You know, maybe this is a city that I'm in love with, but I just feel like it doesn't love me back in my love life. How do you see the tension between different kinds of wealth and when we want to feed one kind, the, the sacrifices that we sometimes have to make to another kind that might decrease our quality of life in an area to try to get more in, in the area that is top of mind right now.
Even thinking about what those trade offs look like, you are better off than 90% of people because the vast majority of people only make decisions on the basis of this, of one type of wealth that we know, which is money. You like, you get a job offer in some other city, it's a lot more than you're making here. You're like, boom, getting on the plane, moving to that place. And you haven't thought about, hey, but all my friends are here, all of my relationships, my family is here. I'm able to be outside 300 days out of the year in California. That has a huge impact on my mental and physical health. You don't weigh those things. So even thinking about that is a plus and a positive. There are always going to be trade offs. You are always going to encounter these decisions where one thing is going up, another thing's going down. These sort of dimmer switches of your life, if you will. The recognition that your life has seasons and what you prioritize or focus on during any one season can and will change is deeply empowering. There's this idea of, that I talk about in the book, of the surfer mentality that when a surfer gets up on a wave, they embrace the present moment. They enjoy this wave with the awareness that the wave is eventually going to end and maybe even crash down on top of them because they know that there are always more waves coming. The exact same thing applies to your life. You can just enjoy the present wave. You don't need to stress about past waves that you may have read ridden that may have gone well or not well. You don't need to worry about future waves. You can just enjoy the present wave that you are on. Make these trade offs the best of your ability, knowing that there are always more waves coming in the future.
To what extent do you think someone should prioritize wealth today versus wealth in the future? Because this, there's certain things that we sacrifice today going well, I'll, you know, I'll, I'll later on I'm going to have a much better time as a result of this. And I, I don't know, I forget the author's name. Who wrote Die with Zero?
Bill Perkins.
Bill Perkins. And this is a, you know, for those of you out there who haven't read this book, there's an interesting book called Die with Zero which is all about how people keep too much money. And actually the ideal scenario is that you die with zero money because you've already given away what you wanted to give away and you've spent everything that you could have spent on ways that actually made your life better instead of taking it with you to a place you can't take it with you to. But of course the opposite of die with zero is die with a lot. And that's. People do that because they're constantly, you know, there's this feeling of holding onto this delayed gratification later on. How do you view experiencing wealth today versus, you know, having a life that feels a bit more miserable today because it's going to be better in the future. And that's not just in terms of money or spending, is in terms of time. You know, I'm giving up all this time right now to build a life because one day I'm going to suddenly have all this time and enjoy it. How do you see this?
I personally believe that there is nothing more rewarding than the hard earned win in life. I think that the greatest joy and greatest fulfillment and satisfaction we experience as human beings is that sensation of meaningful struggle that leads to this feeling of the hard earned win. Like, I really pushed and worked hard on this thing and I earned this result. That is delayed gratification in a nutshell. And so when we talk about, oh, but I'm enduring misery today, I would actually argue that that feeling of the struggle, assuming it is a struggle that you find meaningful, that you have chosen this struggle, is really the pathway to experiencing fulfillment and joy as a person. Instant gratification will not make you happy, right? Like the instant gratification is, is the thing that leads to most misery in life. It is, you know, the choosing to eat ice cream in every single moment. Metaphorical ice cream or literal ice cream. You know, whether that's in your relationships and just dating millions of people, having, you know, all sorts of flings, or whether it's in your work, you're just chasing the shiny object constantly that's grabbing your attention. You know, if it's in the food you eat and the choices that you make physically that will lead to a life of misery. Because for one thing, you won't enjoy those things nearly as much when you get them all the time, right? Like, the impermanence of these things is what makes them uniquely beautiful. A sunset is not going to be nearly as beautiful if it is a permanent sunset outside. It's impermanence. The fact that it is only there for a few minutes is what makes it so unique. Life is the same way. Life's impermanence is what makes it so special. That's why I think we've lost the plot a bit when we talk about living forever. I don't want to live forever. What motivation would I have on a daily basis to make the most of this time that I have with these people that I love? These moments would be less beautiful in this. I think it was in the Odyssey or maybe in the Iliad, Homer writes that you will never be lovelier than you are now. You will never be more beautiful. The very impermanence of these moments is what makes them so special and so wrestling with that tension to say, I am going to try to be present and embrace these present moments because my younger self prayed for these things that I now have and my older self would give anything to be back in doing this. Wrestling with the tension between that mentality and investing for this future, enduring that Meaningful struggle, those things that you find that is the tension of life, and that is where the magic happens, that flow, that sensation.
It's tricky because, you know, there are those among us, and I count myself in this group who. Who struggle to know exactly when is the right time to. To let things go or to have more balance in life, or because it's you. You know, you get conditioned from an early age, maybe by parents, maybe by environment, maybe by the need to survive to, you know, run in a certain direction. And it's very hard to rewire ourselves to go, well, maybe Rome isn't burning anymore. You know, maybe I don't need to work this hard now. Or maybe I do. I'm not sure. I feel like I. You know, I get anxious anytime I'm not working this hard. And you know that those tensions arise for people at a nervous system level. So reorienting ourselves towards a different kind of wealth is something our nervous system has to get comfortable with as much as anything. Because it's one thing to say, I'm just going to start valuing this other kind of wealth now. So I don't know. What's an example. Someone who's a Taipei person who works all the time, who says, I really need to start investing more in my friendships because I've taken for granted my friendships, and as a result, I'm less close to everyone in my life. Maybe I don't have many friends, maybe I have no real friends. And on the brief. The occasions where I do actually have a really rewarding evening with someone and it feels fulfilling, I leave and I feel, like, filled up again. And I feel like, oh, my God, I need to do that more.
But.
But what asserts itself the next day is that wiring of I need to get back to work. And for a lot of people is really, even though they may say they want more friends or say they want deeper friendships, or say they want a relationship or a better relationship, actually, the. The. The deep shift that's required for them to start investing in something different is. Is utterly terrifying. How do you guide people through that process of actually putting their money where their mouth is in ways that scares the hell out of them?
The traditional wisdom around these areas of life has been that they exist on these on off switches, that in your hypothetical example, if you are right now a person who is really focused on your career, on financial wealth, that switch has been turned on, and all these other areas of your life have effectively been off. You've said, too bad. Family and friends, that was flitched off too bad. Health switched off, Mental health switched off. And what you're asserting right now is that you're trying to make a shift and so this area is just going to get flipped on. That mentality of these on off switches is inherently self limiting because it is a belief that these things are either on or off and that there's no in between. State the truth is that all of these areas of life exist on these dimmer switches. And you don't need to go from 0 to 100, from, from off to on. What you need to do is just turn it up a tiny, tiny bit. Meaning if I'm going to try to start investing in these different areas of life, the first thing I can do with relationships is just remind myself to send a text to one friend to just let them know that I'm thinking about them. It doesn't have to be like, oh, I'm spending hours with these friends every single week. I'm doing three dinners a week, I'm doing a million things. Just the one tiny action is infinitely better than doing nothing. You know, the recognition here in all of these areas of life is that anything above zero compounds. Anything above zero compounds. But ambitious people don't think that way. Ambitious people constantly allow optimal to get in the way of beneficial. So they think in that on off switch mindset, they think that, 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 to go out with this person, so I'm not even going to send them the text. When the truth is that the text is infinitely better than nothing. Anything above zero compounds. So for anyone that is sort of trying to make this transition, the thing to think about is what is the dimmer switch on low version of this area of life. If I've never worked out, I'm not going to go to all of a sudden working out for two hours a day. I'm not all of a sudden going to be Brian Johnson or Andrew Huberman. That's not the goal. They're on level 100. I just need to be on level one to get started. And level one could be sending the text. It could be a 15 minute walk every day, whatever that area of life is. What is the tiny thing that I can do today that leaves me slightly better off tomorrow?
What do you say to people who think of that and it can't they all that comes to mind for them when they even think that way is I'm so late and I'M so behind and this area, this pile in my life is so small that I. I feel like it's hopeless, or I feel like I'm everyone else, you know, in my love life, I've focused on, let's say, my work and my this, my that I am nowhere in my love life and all of my friends are married or, you know, I've already left it too late to build financial wealth because I'm now in my 40s or 50s. And the compounding that can occur for people that builds wealth over time, it already is too late for me to experience that real compounding effect that takes place over a lifetime of building wealth. What do you say to people who feel like when they think of going and doing that, turning that dimmer switch on, Because I love that analogy. That they feel like it's just too little, too late for me and it's a lost cause because everyone else is already so far ahead and I'm so far behind.
Every single time I thought I was too late, it was still early. Over and over again in my own life, there were times when I was like, I'm too late to start writing on Twitter, right? Like, oh, Twitter's been out for 15 years. I can't go build a platform there. It was still early. Every single time in any of these areas of life that you start thinking that recognize that it is based on this false comparison that you were making to other people around you. Any timelines that you have in your mind on which you are supposed to do something are based on these comparisons that are completely arbitrary. Like, we have these ideas in our mind that we have to make Forbes 30 under 30, or Forbes whatever, whatever the new list is, whatever these things are. Ray Kroc started McDonald's at 53, right? Like, these people that you admire. Morris Chang, the founder of, you know, probably the most geopolitically important company in the world, founded it in his 50s. Like, these people that have built these extraordinary empires, things in these different areas of life got started way later than you would ever advise someone to get started on these things. And so while we glamorize the people that just, like, knew exactly what they were supposed to be doing from age 18 and just, you know, hit the compound button and it worked out great. I mean, Warren Buffett didn't make his first billion dollars until after age 50. He's worth $130 billion today. How did that happen? Compounding small things become big things.
Who do you look up to now compared to who you may have looked up to five or 10 years ago.
This is an interesting question because the people you admire do dictate a lot of your actions in life. I look, I used to celebrate and admire the people that we read books about. You know, these success stories. Entrepreneurs, investors, these people that have made a whole lot of money. And my entire life changed when I realized that I would never want to trade lives with the people that I was reading books about. We celebrate these success stories of people who have made hundreds of millions, maybe billions of dollars. And we ignore the fact that they have three ex wives and four kids that don't talk to them. And we tell those people that they won the game. And for my own life, a big shift happened when I recognized that that was not a game that I cared to win. I wouldn't say that I have anyone today that I look to and say, like, oh, I want that life. There are people in different domains that I really admire for the way that they're pursuing things. My role model in my life is my father. He's my best friend and someone that I feel has maybe accidentally hit on a lot of these things that I talk about and that I feel like I've come to learn in the way that he's lived. You know, his decision to choose love with my mom, when it made absolutely no sense. You know, my. My dad comes from a white family from the Bronx, New York. My mother was born and raised in India. And when my dad wanted to marry my mom, his father told him that he had to choose between his family and her. He was not okay with it. And my dad walked out the door and never saw his family again. Oh, my God.
How old was he at the time?
He was, let's see, 25.
Wow.
To this day, I never met my dad's parents. He has three siblings I've never met.
So he fell out of contact with his siblings as well.
Yeah, entirely. Wow. And the ripple effect of that decision, which I am sure brought him an enormous amount of grief, brought my mother an enormous amount of grief to feel like she was the catalyst for breaking up this family. The ripple effect of that decision has been enormous. In the way that my dad has pursued life with my sister and I, in the way that he has shown up to support us as a father, as a mentor, as a role model, and most importantly, just this idea that love really has no bounds, that these relationships, the people that you create your life with, that is the real power and the real wealth on this journey.
For me, something really important that that story brings up is that we sometimes have to let go of one way, that we may feel wealthy right now in order to have more of it in another way. And our relationships are really a profound example of that. Because a lot of the relationships, you know, we can have a very toxic friendship that because we're constantly monopolized by that toxic friendship, we don't have any space for other friends in our life. We're not. We can't invite in any new energy because this person's just all consuming in what they demand of us. Or we're. Our mental health is constantly suffering because of that relationship. In a way that means we really don't have any bandwidth emotionally and psychologically for new people in our life. Or we can't even recognize a good thing when we see it because we've just got the shutters on with this person. Of course, the same happens romantically and it can happen with family, it can happen with anyone. But it's a real kind of. In some ways, it's a leap of faith that if I let go of this, what feels like wealth over here and that's going to create space, that something new is going to come in.
Yeah. And that your love doesn't have to make sense to anyone else. I always remember that being instilled by my parents that like these things that you ascribe value to in life, whether it's love and relationships or in some other domain, they don't have to make sense to anyone else but you. It is perfectly reasonable to live a life that looks confusing to others, to choose the things that you value and place value on and to act accordingly. And you don't need to opt into the things that everyone else tells you should matter. It's also a reminder that some of the most beautiful things in life dance on this razor's edge. My grandmother, my mom's mother, before she passed away, said, never fear sadness as it tends to sit right next to love. And I reflected on that for years. That some of the most beautiful things in life do dance on this razor's edge. And you cannot have the good without exposing yourself to the bad. So if you're going to fear sadness and try to avoid it in all ways, you will never reap the benefits of true, deep, raw, vulnerable love. And I think that my parents and their story and the things that they went through to get to where they are, you know, they're 42 years married, 43 years this month married, and really role models of what a deep, loving relationship looks like. They're A case study in that you have to lean into the sadness if you're going to be exposed to the depths of love.
Yeah.
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Back to the interview. What is something that for you in living by the principles of your book and really designing a life that's wealthy in accordance to your values and your principles, has there been anything along the way that you've had to let go of or spend less time doing or, you know, shift energy away from that's just been really, really painful or difficult in putting your money where your mouth is in really living by this set of principles?
Yeah, I mean, I walked away from eight figures of money when I left the job and path that I was on to go down this path. I mean, I was working in the world of finance at a private equity fund. I was on a path to make an enormous amount of money with a high degree of certainty and a lot of safety and security to it. And I left that path to go down this new one that I was carving that has no certainty and no security. And oddly enough, I think I will end up making more doing the things I'm doing now because I care about them and they really mean something to me. But in the short term, a whole lot of trade offs associated with that to say I'm gonna lean into these things that I really feel deeply and see what comes of it. And you know, that's again, it's a struggle when you start living and choosing things that are very different from the people around you. The biggest struggle with that, frankly, was not even the financial Because I don't really care about fancy things all that much. The biggest struggle was the people. Because when you start living differently, when you start changing, when you start growing in a different direction, you no longer fit into the environment that you previously existed in. And that manifests as this enormous expanse of loneliness where the people that you used to consider your people, you almost no longer speak the same language. And they may belittle you or say things, make the little comments, whatever it might be. Your growth exposes a sort of insecurity in them, you know, a road not taken, I think, for many of them. And that was really challenging because there were a lot of people in my life that I really thought were real friends. And my change in the path I walked down exposed that it was nothing more than a surface level transactional connection. And I had never experienced that in my life before. And that was painful to recognize that most of your friends aren't really your friends. They're just along for the ride when it's fun, convenient, valuable, and they'll be gone when it's none of those things. The beauty that came from it was in recognizing that your real friends are the ones who are there for you when you have nothing to offer in return, when you've made these crazy decisions, when you've walked down this very different path, when things aren't working out. And to find those people and to identify them through this change and to recognize that you find those people by being that to someone else. There is an enormous beauty that has come from that in my own journey.
Can you talk more about that? Because a lot of people feel like they want to invite relationships and people into their life that are different from the ones they've had before. Maybe they have had friends or family where they feel like the. The. The friendships weren't reciprocal, where they gave a lot more than they got, or where they realized in some cases too late that that person absolutely wasn't there for them when the shit hit the fan. And they want to invite either real friendships into their life, or they want to invite real romantic relationships into their life with people that feel dependable and trustworthy and will actually be there for them. But maybe along the way, they've lost some trust in themselves. They're like, well, if I could misread all of those relationships, if I could think they were something they're not, then I don't even trust myself anymore, let alone other people. How can people, you know, move on from those chapters and then go back into the world of friendships and relationships and genuinely find something different and really know it when they see it and trust themselves that when they see it and they think they have it, that that really is it, given that they made a mistake already in the past of thinking it was it when it wasn't.
You can never move forward in life until you forgive yourself for the struggles and the mistakes that you made in the past. You will never move forward if you are continuing to cling to this idea that you made some mistake that is a testament to your character or your intelligence as a human being today. Recognizing and embracing that these periods of loneliness are a cost of entry for the change and the growth that you asked for. Necessary, that natural, you have to pay that tax to get the life that you want. On the other side, I have always found as personally empowering because it means that you can lean into the solitude that that period creates. It creates the space to think about what you truly care about finding in your new people, in the new environment. It means that you can think about the values that you want to put out into the world and how those are going to be a magnet to attract those type of people into your life. That space that it creates, that the loneliness creates, is a blessing in your journey. I think that appreciating that and leaning into that, not shying away and hiding from it, is really where most people will find the real benefit.
When you talk about putting your values into the world, what does that look like in practice? Because some people might go, I thought I was putting my values into the world. Clearly I wasn't, or I was attracting the wrong thing. How do people know they're putting their values into the world? And what does that like in day to day interactions with new people? What does that look like?
I think that there's a couple things here. First off, ask yourself this question. If a third party were to observe me for a week, what would they say my priorities and my values are? The recognition here is that there are really two types of priorities and values. There are the priorities and values we say we have, and then there are the priorities and values our actions show we have. And oftentimes there's a big gap between the two. I know, I've been there. When you start taking action to close that gap, your life improves. But you cannot close that gap until you recognize that it exists in the first place. So sit down for 30 minutes and journal on that question. Really think about it. What would that third party say? Your actions, your priorities, your value? What would they say those things really are and then think about how you can slowly start to close that gap in your life. I think that part of it comes from the environments that you place yourself into. What we talked about earlier. Are you placing yourself in environments where your values that you ascribe to, that you feel you hold close, are able to shine through? If I am really family oriented, if I really care about health, I cannot be spending my time in environments where that is not going to be able to shine, where it is not going to amplify that set of values. I can't. If I'm really into, you know, fun and experiences and a little bit of like, craziness and youthfulness, like, that's great, that's fine. If that's your set of values, you can find environments that will really make that shine. And I think that where people feel a lot of tension in life and where we feel this like almost internal nervous system level discord in our own life is when we are in environments that do not match and sort of do not amplify the natural frequency that our, that our values have. So really thinking carefully about that, you place yourself into environments that allow you to shine that sort of naturally amplify that frequency and attract other people to it.
I keep coming back to this, this thought that it. One of the hardest things about all of this is that we have over our lives, consciously or unconsciously set up patterns, habits, ways of being that make us feel safe. And that those, those become our addictions. And it's really hard to break free of those things, even if we say that we're going to value something else. Someone may say they want love, but they may default to a sarcasm constantly that makes them feel safe because that's an early tool they developed to be able to control conversations. And so that habit of being overly sarcastic all the time pushes people away and makes it really hard for anyone to experience true connection and sincerity with them. And they'll go away and say, I just really, I can't meet anyone. I really want to meet someone. And it's so hard and it's just. But they can't give up that weapon that they have, that has in many ways been a survival tool. And it's helped them for so long to feel like they're in control or they've got some kind of significance or power. Maybe there was a time in their life where they did not feel safe to, to be sincere. But that time is over. But the, the weapon remains their favorite weapon or the one they rely on the most. And saying, I'M going to value this kind of wealth. I really want connection. I really want to be loved. I really want to be close to someone. And then dropping that thing that is your safety that you've used for so long is one of the hardest things people will ever have to do.
I, I, you're absolutely right. You know, it's, it's sort of a derivative of this idea of the Icarus Paradox. You know, like the story of Icarus creates these wings out of wax to fly off this island and it's initially very successful and it's incredible. He's going to get away, but then he flies too close to the sun and the wings melt and he falls to his death. And the idea broadly applied, is that the thing that makes you successful at the outset may actually be the thing that kills you. You get this pride and pridefulness in the, in the answer that you had and it's no longer the right answer for the rest of your life. These things that provided safety and maybe helped us in a lot of ways can hurt us later on if they hold us back. I really believe that the answers that you seek in life are found in the questions that you avoid. These questions that we avoid asking ourselves because it's uncomfortable, it's painful to do so Often that is where you really find the gold and the magic in life is when you are willing to sit down and confront yourself on these things. Ask yourself these questions that require you to tear away at your ego a little bit, to tear away at what you assumed, what you knew for sure that just wasn't so. To paraphrase Mark Twain, there is a lot of good that comes from being willing to do that, to hold yourself to the fire a little bit in life.
What would be from all of the work you've done across these different kinds of wealth and the writings that you've done, what is the most universal? Like you have someone in front of you and you just want to impart on them, like these are truths. This is not, this is the non subjective part. If I were to hand you a survival manual for getting more out of life or enjoying life more in spite of yourself or your previous patterns, what would some of those truths be from then? All the people you've spoken to take.
At least one hour a month completely by yourself, to zoom out and just be with your own thoughts. Very few of us create the space in our lives to even ask these questions in the first place, to think about where we are, where we're headed. Do we need to course correct what are the challenges that I'm facing? What are my dreams? What do I want my life to even look like? What is the life that I'm even building forward toward? What is the money for? We find ourselves running these races, climbing all these mountains, going after these goals. And we very rarely ask that question, what is the money for in the first place? We make our happiness conditional on these achievements, on these things. We say, I'll be happy when I get this. I'll be happy when I get that, whatever the thing is. And there's this beautiful line in this movie, cool Runnings. It's kind of this, like, silly Disney movie. Jamaican bobsled team John Candy says to one of the players, a gold medal is a wonderful thing, but if you're not enough without it, you're never going to be enough with it. I would get that line tattooed on my brain if I could. So often in life, everyone falls victim to this. We convince ourselves that we are going to be enough when we get something. Bonus, title, promotion, relationship, health, whatever that thing is. And the truth is that if you're not enough without it, you're never going to be enough with it.
Okay, so one hour a month asking bigger questions, standing back from your life. What would be another truth?
Relationships are the single greatest investment that you can make. I think scientifically now we have an abundance of evidence to point to the fact that investments in relationships pay the most significant dividends in your health and happiness.
And what do you. Have you stumbled across any habits that you think really reliably help build relationships? Because a lot of people and. And I kind of want to differentiate here between relationships where it's like the plane is already in the air because you're already good friends with that person or you already have that partner or that family member, but also the person who maybe is living in a city right now or anywhere and feels like I'm lonely and I don't have many people in my life. I don't have, you know, a community. I don't feel like I have good friendships to decide to invest more in. That kind of don't exist in my life right now. I don't feel like I have people I can rely on, depend on. Maybe they're not close to their family, they don't have a partner. What does investing in relationships look like for that person who feels like they're almost starting from the beginning, at whatever age?
I think the simplest version of a habit that can build relationships is when you think something nice about someone, let them know Right then. And for people that you know and you already have the plane off the ground, this is, you know, you think about them, you send them a text, you give them a phone call. Super simple. It doesn't need to be catching up. It's just like, hey, I was thinking about you saw this picture of us from a few years ago. This is great. Continues to build and compound that relationship and that connection with new people. I personally, like I walk through my life, I'm never bashful about just saying something nice to someone. Like see someone you know in line at the coffee shop, hey, I like your shirt. And if the person reacts in a weird way to it, that's fine. We probably weren't going to be friends in the first place. But I don't ever feel bad about telling someone something that I appreciated about them. I have personally found that a lot of good and some incredible relationships have come from just saying the thing that you thought nice about someone in the moment not being afraid to kind of like just lean into what you're experiencing on a daily basis. The other habit personally that I have found really valuable is never be afraid to send the double text. Relationships, romantic maybe is a little bit different in this regard. But with friendships, there are a million times where people text me once and I was just swamped when it came through and I missed it. If that person was then afraid to be the one to send another text, to follow up or to ping on another thing, a second thing, and they were waiting saying like, oh, no, I don't want to be needy. I don't want to send the thing. We might never develop a relationship. I am never afraid to be the one to sort of follow up on something. If I really like want to lean into a relationship and I think the person is interesting and I think I can provide value and we have some sort of connection, I have no issue.
How. Where does that come from? Because a lot of people either their ego gets in the way in a, in a kind of arrogant sense of I shouldn't have to and how dare they not text me back, I'm not going to send them another. Other people, their ego gets in the way and very fragile sense of a very sensitive way of. I, you know, I feel really rejected and that makes me sad and you know, I, I feel pathetic for reaching out again and that, you know, that just doesn't feel like, you know, I feel like I'm going to be seen for being so needy and that's how I feel. Anyway, I don't want to be seen for it and how, how are you built or what have you learned that has allowed you to not overthink those moments?
I think part of it is that I believe that I can be a great friend and valuable to people. I just, I believe that about myself. I have a sort of earned and built confidence in myself that I know that I can contribute something to these relationships.
So how can people who haven't developed that confidence because their experience. What I hear when you say that is I've had some very positive reference points for having been a valuable friend, for people wanting to have me around for being a valuable person. But there's an awful lot of people in this life who have experienced disproportionate rejection. And what it has taught them is I'm worthless and I really don't have a lot of value in someone's life. And so when they don't get the text back, there isn't that inner confidence already built on those reference points that says, I know when you really get to know me, you're going to realize how valuable I am in your life? All they see is a confirmation of the worthlessness they've always felt compounded by rejection after rejection. What would you say to that person?
Every single person in the world has something of value to add to others. Any experiences of worthlessness and rejection that you have had in your life are much more a byproduct of the other person on that interactions insecurity than it was of anything about you. I have had negative interactions with people precipitated by me at a time in my life when I was deeply insecure about my own life and my own journey. I have created some of those negative interactions and it was always a result of something going on in my life. Some insecurity or pain or struggle or trauma I was experiencing. It was very rarely the way that the other person approached the interaction or the fact that I thought they couldn't contribute something. Their insecurity is exposed in that situation. So any feelings of worthlessness need to be cast aside to recognize that you just haven't found the right person yet.
Just to. Because I, I want to steel man this argument for people if they're like, yes, but my experience is so kind of overwhelmingly negative from people. You know, if you take someone's love life, for example, and a grant that you said, you know, maybe double texting doesn't, that doesn't hold quite as well in that context as others. But it's actually the idea I think does hold that the More we believe in our value and the more we believe we have something real to offer that the less we're measuring every little moment of whether someone does or doesn't text us or how long their text is or whatever. We're not measuring so often because we're just. There's almost a. There's a deeper security in us that we're going to. We're going to influence the situation for that person who's like, yeah, but I truly am rejected way more than other people are. I don't look like other people. You know, I don't. I'm not objectively attractive. Maybe I feel objectively unattractive physically. I don't represent people's normal type or a culturally accepted attractive type of person. There's things about me that are eccentric or different or, you know, I think my experience has taught me are quite unattractive to people. And so they just have this overwhelming amount of evidence that says you're really not for most people. And so far my experience is I'm not for anybody. How can someone from that place of insecurity and lack of self worth begin again with almost us? Like a. More an attitude of, yes, but something could happen if I brought a different energy.
I think that there's a piece of it that is deconstructing a little bit in your own mind. What is it that comes across in some of these initial interactions that is causing another person to react in the way that they're reacting? Is there a way that I'm approaching the interaction that I maybe need to change? There's sort of a little bit of introspection that comes with it. And then there is a faith that if I have addressed those things, if I am just maybe not for everyone, there's nothing wrong with that. There's nothing wrong with being someone that isn't for everyone. I actually, personally, I end up liking people who are a little quirky, weird or different a lot more in the long run. And that might be the case that that person has experienced a lot of rejection. I like people that ask quirky questions, that have kind of quirky interests, that are into different or weird things, that are living kind of differently because it's more interesting than the status quo. You're not going to be for everyone and you're going to get and feel experience a whole lot of rejection along the way. But having a fear of even putting yourself into the wave, like to back to that surfer analogy saying like, I'm not even going to put myself into the water, you can't catch any wave sitting on the shore. And so there is a fear that needs to be conquered there to say that if I just continue to sit on the shore, I'm never going to catch any waves.
Yeah, and I think that there's a. I think it's important to recognize we may not, we may never catch as many waves as the, the more athletic surfers, but there's still some experience of living to be had by being out on the water.
It's also not about how many waves you catch in life. It might just be about catching that one magical wave that is so meaningful to you. I, I mean, I had, I was reflecting on this after my 10 year high school reunion that like, I went to this 10 year high school reunion and all the kids that were kind of like popular in high school had like split off. None of them were friends with each other anymore. It was all like these surface level connections, myself included. And the kind of like quirky, nerdy kids that I would have made fun of in high school were all still like super close. They were also kind and interesting. They had like, continued to be their own quirky, weird selves in that they were not insecure about that at the time. They got made fun of for it, but they had just kind of leaned into those things, embraced themselves and they weren't trying to be someone that they weren't. And I was talking to my wife about it later that it made me sad because I recognized that, like, these things that I viewed through my high school, juvenile, immature lens as being so weird and different. Like, why is this person so quirky and odd? It was actually something really beautiful about them as a human. That took me a long time to figure out. I mean, when you're a kid, your mental model for the world is, how do I fit in? I just need to fit into some box. Just please put me in this box and let it, let it fit in. And as an adult, you get paid for being different. Your greatest success in life comes from being weird. I mean, the people that we admire, all these amazing success stories, some of the weirdest people in history. Right? Elon Musk is not a normal human being, nor would he say that he is. He had that SNL skit where he said that, like, I'm sending people to Mars, I'm doing all these things. What did you expect me to be a normal cool guy too? Like, it's not, it doesn't, it doesn't work. And so we also just need to learn to lean into and embrace these things that make us unique and different. These pattern interrupts, if you will, about who we are.
Amazing. Well, so Hill, your book is called the Five Types of Wealth. Where can people get it? I assume everywhere. I know it's been selling like crazy.
Yeah. On Amazon, anywhere books are sold. Local bookstores always appreciated.
Amazing. I really appreciate your time, man. It's been a pleasure talking with you and I hope we can do it again.
Felt like a real treat for me, so thank you.
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