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If you're ambitious, you've heard a thousand tips on how to live a happier, better life. Forget all of them. I grew up in a blue collar family, and today I know lots of different billionaires. I've met thousands of successful founders, and I've hired hundreds of people. And across all of those lives, I've spotted patterns in the people who are most happy. But instead of giving you another list on how to live well, I'm going to invert it. Here are five guaranteed ways to live a miserable life. Do the opposite. You might actually live a good one. I feel like I can rule the world. I know I could be what I, I want to. I put my all in it. Like no days off. Step number one, don't have a best friend. If you want to be miserable, tons and tons of acquaintances will do just fine. One of my favorite philosophers to read about is Aristotle, and he broke friendships into three different types. The first is utility, and these are friends where you get something out of them. For example, money favors connections. Basically, once the usefulness ends, so does the friendship. This is sort of like coworkers. The second is pleasure. And these are friends that exist just for fun. You get together, you party, you have a good time, and then once that ends, you're done. It's basically like when you are three years old and you play with another friend. Once the play date is over, the friendship is over. And finally, virtue. These are the rarest and most valuable. These are people who you admire and they admire you back and they make each other feel better and you stick with them no matter what. In modern terms, they're your best friends. If you want to have a great life, focus on that last category. The good news, according to Aristotle, is that you only need one to three best friends. I've got three. It's Jack, Ramon and Neville. Have you ever seen that movie the Town where Ben Affleck, he goes into his buddy's room and he says, I need your help. We're going to hurt someone and I can't tell you what it is and you can never ask about it. And then the guy responds with, sounds good. Whose car are we going to take? That's Ramon. I've got one of those friends. A grown man calling another grown man his best friends and me telling them I love him. Make fun of me all you want, but knowing that these guys have my back and have my best interest in mind, it makes me sleep like a baby. Now I want to show you a study that proves my point. So for the last 85 years, Harvard has been running this study, which is now the longest study of adult life ever done. And they tracked hundreds of people from youth all the way to old age. The Atlantic. They put together a 15,000 word article all about this study. It's a wonderful article, but I'm going to save you the time and tell you exactly what the results were. After decades of data, the number one predictor of long term health and happiness. It was not money, it wasn't fame, it wasn't power, it wasn't even exercise. It was the quality of close relationships. They found that what protects you is having a few people, even just one, one person who you can count on through thick or thin. In other words, a BFF baby. Step number two for living a miserable life, don't decide. Spend tons of time planning and thinking and very little time doing. Miserable people are indecisive. And if you want to join them, don't commit to anything. Stay in research mode forever. Careers where you live, who you want to date, just keep on shopping. Let me tell you a story about Dan Gilbert. Dan Gilbert is a psychologist. Who's the goat on studying happiness? He's got this amazing book called Stumbling on Happiness. So my favorite part from his book is an experiment where he went to a college campus and he selected two groups of students. Now, both groups, he let them come and select a piece of artwork that they could hang in their dorm room. Except here's the difference. Group one, they were allowed to come in a week later and swap out their art if they were unhappy with their original pick. Group two was locked in. Whatever they picked, they had to keep. Now here's the results. Group one, the group that was allowed to change out their art if they were unhappy with it, they were less and less happy with the art that they picked over time because they kept wondering, did they choose wrong? Group two, the ones that had to be locked into the ones that they originally picked, they actually got happier when they measured them over time or over the trailing hit handful of months. They convince themselves that they love the piece of art that they picked. And the takeaway is once we're locked into a decision, the brain makes peace with the decision. It literally manufactures happiness. Happy people take more action while other miserable people wait for the right decision. Let's say it takes someone six months to make a business plan and the same amount of time that that person is planning. You could have started six months prior to and run hundreds of experiments and in that time figured out what does and doesn't Work. Now, if you're like a lot of people and you are in this indecisive bucket, I've got good news for you. Nearly all decisions are reversible. Now, let me tell you a quick story. When I was about 21 years old, I left school, I left college a little bit early, and I moved from Tennessee to San Francisco because I wanted to get into startups. And I was incredibly afraid. I didn't want to fail, but also I didn't want to be homeless. And I didn't have a lot of money, but I saved up around $2,000, which at the time was more than enough money to buy a plane ticket home back to my hometown of St. Louis. And I remember calling my mom and I said, if this doesn't work, am I allowed to move back home for six or 12 months? Is that okay? And she said, yes. And in my head, I just thought then the worst case scenario is taken care of and anything that I achieve above that, I'm happy. So I shouldn't doubt this decision because the worst case, the downside, it's protected against, I'm okay. And I accept that. Now, how do you make different decisions reversible? Well, I think if you were to sit down and figure out what can I do to test or try something, you can figure out a lot of ways that you could do that. So, for example, when I was deciding which neighborhood or which city I wanted to live in, it was pretty easy to just go and rent an Airbnb in different neighborhoods a week at a time. And although this did at the time cost a lot of money, it was significantly cheaper than just going and buying a home or renting an apartment and regretting that decision and having to be stuck with the long term consequences. So most decisions are reversible. And it's your job to figure out how do you tiptoe and try before you buy, which is true in a lot of different situations. Now, in order, though, to make this all work, most decisions which we're going to talk about later need to be time bound. So if you're deciding where are you going to live, where are you going to work, who you want to marry, I think it's a lot easier in life to say, I, I have six months to decide this, and at the end of this six months or at the end of this month, I am making a decision no matter what, because more often than not making a decision and acting will lead you to be a lot happier than spending months and months just thinking, now, if you guys Want a really embarrassing story. When I was younger, and it involves moving to San Francisco still from. From Tennessee, I read this book by Dale Carnegie. It was called how to Stop Worrying and Start Start Living. And he had this amazing quote. It was, inaction breeds doubt and fear. So get out and get busy now. That was sort of my live laugh, love moment. And so we'll put a Screenshot on, on YouTube, but I've got a tattoo on my feet that says act now. Cheesy, kind of lame. Of course it is, but very effective. Step number three on how to be miserable. Don't set goals, and certainly do not track progress. A book that changed my life was Titan, which is the biography of John Rockefeller. John Rockefeller, he was a tycoon in the early 1900s, and he was the richest man to ever live. He was two times richer than Elon Musk is today. Now, one of my favorite stories from the book is When John was 16 years old, he said, I want to be rich. And according to John, his first step in becoming rich was tracking all of his expenses and his salary. And he had a book called Ledger A where he wrote down every expense and wrote down every bit of income. I stole that idea from him. And when I was around 23, 24 years old, I wanted to try to save up to $50,000. And so in order to do that, I had to reduce my monthly expenses to $2,000. And when I did that, I spent about six months tracking every single cent. Every time I spent anything, any dollar, any cent, I wrote it down manually. And just doing that, just doing that tracking thing, it became so much easier to reduce my expenses to 2000 and to track them. So I'll give you another example. If you want to lose weight, starting today, if you track all of your calories and weigh yourself every single day, if you only do those two things, you will 100% start to lose weight. But if you really want to improve, you have to pair tracking with goals. So many people come to Sean and I to ask for business advice, and the first thing that I say to them when they're asking a question is I go, wait, hang on. Just really quick. Where do you want to be in 5 and 10 years? Do you want to sell your company? Do you want to make it huge with tons of employees? Do you just want a little lifestyle business? Do you want to make $500,000 a year? Do you want to make $2 million a year? Do you want to sell the company? Make $100 million? Imagine going to a trainer and being like, hey, make me fit. It'd be impossible. The trainer needs to know, do you want to have all this muscle like Arnold Schwarzenegger? Do you want to be lean? Do you want to be able to run a fast 5k? Do you want to get great at swimming or cycling? Because you have to have a goal in mind in order to determine where you want to go and what actions you're going to take on a daily basis. Now, when it comes to goal setting, I don't think people really do it well. Our real goal is smart, which stands for specific, measurable, achievable, relevant, and time bound. Let me give you an example. When I was younger, about 23 years old, I had a goal to make $20 million liquid by the age of 30. That meant I had six, seven years to build a business that could get to around 15 million in revenue, which I could then sell for around $30 million and walk away with 20 million bucks after tax. And that's where the idea for the Hustle came from, the newsletter business that I started. And I broke this down into small chunks that made it very approachable, and I felt very achievable. And so my goal for the first year of my newsletter business was to grow the subscriber base by 3% and every single week. Because I knew that if I did that and I had the audience, advertisers would then come. And so every week, it was just a question of, did I grow subscribers by 3% or not? What am I gonna do on Monday, Tuesday, Wednesday, Thursday, Friday? I'm gonna do anything that it takes to grow that subscriber base by 3%. That forced me to focus, and it meant no side hustles, no different business ideas, and just meant work on that one thing for 60 hours. And by the way, it worked. I ended up selling. I was 31, not 30. But the goal, in my opinion, it doesn't really matter if you hit it. It just matters that you have the goal and you break it down into chunks that you can act on every single day. And then that goal is specific and time bound, because having a place, a destination to go to, it makes life so much easier. Because distractions are incredibly loud and miserable people. They listen to those distractions, and goals help you keep on track. Now, the last thing about goals, here's how I think of goals. I track my fitness quarterly. I track my spending monthly. I track the things that I'm learning every month. I track my income annually, my net worth every five years, and my company. I Try to look at it over the decade. The reason I chose those intervals is because achieving anything great, it takes a lot longer than you think. And also I need a little bit of dopamine hits. And so having a dopamine hit every month where I could look at my spending, you know, am I doing good or am I doing bad? That helps me keep going, that gives me progress. Fitness goals, you can see progress typically on a fitness related thing every three months. And tracking it that way, it gives me motivation to keep on going. But it also allows me enough time to achieve something pretty interesting. Now I want to tell you guys a story. My wife and I, we do something very nerdy. So every single month on our calendar we have one actually this Tuesday at 8:30pm we have a meeting, or we call it our monthly recap meeting. And it started earlier, like nine years ago, when we were just getting our careers going and we were only about a year and a half into dating and we had combined finances where we would do a recap on our income and our expenses. And we basically would ask ourselves back then the same questions that we ask ourselves today, which is, are we happy with how we are spending money? Is there any experiences or services that we want to acquire to make our lives better? I'll give you an example. When we were younger, it was like, hey, you know, I'm spending a lot of time cleaning the house. $150 is all we would have to spend in order to have a cleaner. And that could save me many, many, many hours. Let's try that this month and see if that makes us any happier. And those are basically the same conversations that we have now. And maybe some of the numbers might be a little bit bigger, but honestly, they're really not. The majority of decisions that we make during those monthly meetings are pretty small. And it's kind of fun to see what changes our happiness the month after. All right, a few episodes ago, I talked about something and I got thousands of messages asking me to go deeper into explain and that's what I'm about to do. So I told you guys how I use ChatGPT as a life coach or a thought partner. And what I did was I uploaded all types of amazing information. So I uploaded my personal finances, my net worth, my goals, different books that I like, issues going on in my personal life and businesses. I uploaded so much information and so the output is that I have this GPT that I can ask questions that I'm having issues with in my life, like how should I respond to this email. What's the right decision? Knowing that you know, my goals for the future, things like that. And so I worked with HubSpot to put together a step by step process, showing the audience, showing you the software that I used to make this, the information that I had chatgpt ask me all this stuff, so it's super easy for you to use. And like I said, I use this like 10 or 20 times a day. It's literally changed my life. And so if you want that, it's free, there's a link below, just click it, enter your email, and we will send you everything you need to know. To set this up in just about 20 minutes and I'll show you how I use it again 10 to 20 times a day. All right, so check it out. The link is below in the description. Back to the episode. Step number four for being miserable. Switching from thing to thing every quarter or every year. Mastery and compounding, it's for suckers. Starting from scratch will be a lot easier. This is actually the number one most common miserable traits I see amongst ambitious people who have a ton of promise. They don't stick to things for long enough to see the eventual payoff. And I've thought about this a lot and I think the reason why you or anyone else tends to switch from thing to thing is because anything worth doing, it basically requires you to pay a known cost today for an unknown payoff in the future. And it's that uncertainty, plus a lack of discipline that makes people switch from thing to thing. Because the pain of focus, it shows up daily in time, in energy and in money. But the reward doesn't come for months or sometimes years. And that uncertainty, it's very painful and it makes people quit. But if you're ambitious, you need to know that the path to winning, this is how it feels. You lose sleep, you second guess yourself and you wonder if you're wasting years of your life. You put in hours and you burn so much energy and the scoreboard still basically says zero. And it says that sometimes for years. But this is the price that people pay if they want to win. And the worst part is that no one is going to be able to tell you if the thing that you're doing is actually going to work. The only way forward is to keep paying that cost while the end payout is still unknown. I want to tell you a quick story. Last week I was with the founder of eight Sleep. It's this guy named Mateo. Eight Sleep is a company that makes these really smart mattresses that does hundreds of millions in revenue, and it's worth billions of dollars. The entire talk that he did it was about how his company failed and nearly died five different times, the most recent one being, like, a couple years ago. Now, imagine if you switch projects after failure. Number two, switching just because something is hard and uncertain. That's a trap. The times I've grown most in life are the times when I felt like I wanted to quit most or I wanted to go and start something new. We've had a guy in this podcast named Palmer Luckey, who's a billionaire. He invented the Oculus, and he has another company worth tens of billions of dollars. He has this amazing quote. At some point in business and in life and in romance, you have to commit to a path. A lot of my peers, they keep all of their options open, so they end up jumping from thing to thing. If you don't commit, you're going to fail. You have to say, this is the path that I'm on, for better or worse, and I'm going to double down on it. My last company, the Hustle, the year we sold, I was 31 years old, and we were going to do about $18 million in revenue. I frankly didn't have a lot of peers. I didn't know a lot of people who were ambitious like me. And this meant that I was making decisions that could cost me maybe five, ten, even more millions of dollars worth of money. I was making them all by myself. This all changed, however, when I got a group of peers. And that's, by the way, how this podcast sort of started. Sean was in my group, and we met every month. It sort of became a personal board of directors, and it, frankly, changed my life. And that's why I started my company. Hampton joinhampton.com the entire idea is that we make core groups just like this, just like the. That I had of other entrepreneurs who have been there, done that. And we give you guys a time and a place to sit down and have these very honest, confidential conversations where you can share business ideas. You could talk about hiring. You could talk about all these decisions that you typically have to make all by yourself. The biggest risk, in my opinion, is not failing. You're going to be fine. Your business is probably going to work. It's that in 10 years, you look back and you think, damn, I blew it. I blew this opportunity because I was making decisions by myself. I was making decisions out of fear, and I did not grow. I did not maximize the opportunity. I'm telling you, it can save you 10 years of headache and of heartache, and you can make better decisions so much faster. And the best part is that with Hampton, these core groups that we make, we make them in real life in your city. We're in Atlanta, Austin, Boston, Chicago, Dallas, Denver, London, LA, Miami, NY, SF, Toronto, and Vancouver. And so if you're running an Internet company that does at least $3 million a year in revenue, or you've raised at least $3 million in funding, or you've sold the company for at least $10 million, go to join Hampton.com this is my company, Sam from MFM. I review every single person who applies. So again, join Hampton.com Step number five is going to make a lot of you guys angry. I know the comments on YouTube are going to be full. I know a lot of people are going to tweet at me. You're going to be pissed off. But step number five is to don't buy index funds and instead invest all of your money picking individual stocks. The reason I have a thing about finances on here is because a lot of you listening to mfm, you're here because you want to make money. You're here because you want to get rich. I think there's basically only four ways to get really rich. One is to get lucky by marrying someone, winning the lottery, or joining a rocket ship startup. Two is to get into sales. Those guys make unlimited amounts of money. Three is starting a small business, which this podcast a lot about. And four, which is probably the most practical and straightforward way is to have a good salary, live below your means, and invest all of your extra money into index funds. But if you're listening to mfm, you like action. You like doing stuff. That was the whole point of the first couple steps of how not to be miserable was about acting. But when it comes to getting rich, one of the best ways to get rich is to have patience and not actually do a ton of acting. If you invested only $6,000 a year into the S&P 500, by retirement, you'd have over $1 million. Now, most of you listening, you make over six figures. And so you can probably actually get there a lot faster. But here's the trap that a lot of you guys listening, this happens a lot to young men. This happened to me when I was younger. It's thinking that you are smarter than the market and you're in a rush. Now, let me tell you some facts. So over the last 10 years, 97% of active stock fund managers. So basically, people who pick stocks on A daily basis, they underperformed the index. These are people whose job relies on making money off of stocks. They're Harvard MBAs. They are just these nerds that stare at Bloomberg terminals all day. They've got thousands of employees, they have teams of analysts, and they still can't beat the index funds. And I've done this before, and I get why people do this. So my dumb story is at the bottom of the market. During COVID I sold all of my positions because I thought the market was done. And then it ripped right back up. And I have lost a fortune because of that mistake. And that's when a smart friend told me afterwards, he said something that actually changed my life. It's a very cliche thing, but he said it's not about timing the market, it's about time in the market. Over the past 20 years, if you were to stay in the market, stay invested the whole time, you would have made roughly 10% a year, which is pretty good. That means that your money doubles every seven years. However, if you miss the best 10 days, your returns halved to about 5%. And if you missed the best 20 days, so the best 20 days out of 3,650 days, your gains would be almost exactly zero. Picking those 20 days, picking those right stocks, it's very hard, it's nearly impossible. Very few people do it. And if you're listening to this, you probably aren't in that category, and you probably should not do it if you want to be happy. I sold my company in 2021, and I put almost all of my money into a very basic Vanguard index fund. And over the past five years, it's now worth 71% more. And I've done nothing. Now, we've lived in a great economy and markets have been ripping, but the fact is, is that since the beginning of the stock market, it has grown consistently over a long period of time, between 9 and 10% a year. Now, a lot of people are going to get mad because they like buying stocks. It does feel good. I get it. It feels great. And if you are in that category, you should buy a very few, a very small amount of stocks, and that should be part of your entertainment budget. So if you want to make a lot of money in your sleep and not do a lot of work and have very little stress, invest in index funds. And if you really want to get rich, try and start a business. That can be a risky thing, but picking individual stocks, amongst most everyone I know who does it, it almost always ends poorly. So just buy the index. So if someone's looking over your shoulder right now and they see what you're watching, or they see that you're listening to something and they ask, I want you to tell them I just listened to something that told me the five Simple Steps to Live a Miserable life. Now, if you want to tell them how to have a good life, here's a recap. Step number one, have a best friend. Have someone who you love to death and you know that they have your best interest in mind. Step number two, Decide. Spend more time acting and doing and less time planning. Step number three, Set goals and track progress regularly. Step number four, do not switch from thing to thing every quarter or every year. Mastery and compounding. It works. And step five, get rich. And one straightforward way on doing that is to invest in index funds. Do not go and think that you are a stock picking genius. It's nearly impossible. All right, that's it my friends. Go to YouTube if you're not already there and let me know what you think about this in the comments. I'll talk to you guys soon. I feel like I can rule the world I know I could be what I want to I put my all in it like my days off on a road Less trick travel never looking back. This episode is brought to you by HubSpot Media. They have a cool new podcast that's for AI called the Next Wave. It's by Matt Wolfe and Nathan Lands and they're basically talking about all the new tools that are coming out, how the landscape is changing, what's going on with AI tech. So if you want to be up to date on AI tech, it's a cool podcast you could check out. Listen to the Next Wave wherever you get your podcasts.
Episode: How to live an asymmetric life
Date: October 17, 2025
Host: Hubspot Media (Sam Parr as primary speaker)
In this solo episode of "My First Million," Sam Parr explores the counterintuitive idea of improving your life by understanding what makes a life miserable—and then doing the opposite. Drawing on personal anecdotes, philosophy, and research, Sam shares five “guaranteed” steps to misery as a framework for identifying and embracing the choices that actually lead to happiness, fulfillment, and financial well-being. The episode is fast-paced, actionable, and packed with memorable stories and practical tips for ambitious listeners seeking an asymmetric (high upside, low downside) approach to life and business.
This episode is packed with actionable, time-tested advice delivered in a direct, practical tone familiar to “My First Million” fans. Listeners are challenged to invert five misery-inducing habits and instead embrace relationships, decisiveness, clear goals, consistency, and basic personal finance principles for an asymmetric, abundant life.