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How to Win Big


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Over the years, I've started a few businesses. I've tried different hobbies. I've taken many risks. Many of them I started as an experiment. I call this experiment getting a Master's Degree in Life. It's my philosophy of how everyone should spend their late teens and twenties.


In a nutshell, it's this:


  • Try as many things as possible.


  • Don't expect a concrete outcome.


  • Be mindful of what works and doesn't work.


  • Play the long game, which inevitably means you'll lose the first few battles but win the war of life while everyone else you know struggles.


Why do I suggest doing this?


It's because I want you to win big. And I want to share with you some key lessons I learned that will help you accomplish your goals.


Warning: This post is going to be a bit long so if you're short on time, I recommend coming back later. Otherwise, I hope you get a lot out of this email.


My philosophy is that you win big in life by trying a bunch of stuff and learning from your mistakes. Life is about experimenting. Life is a game. And any good experiment requires you to step outside of your comfort zone, challenge yourself, take a few steps back every mile you advance, and reassess the progress you've made.


What most people do is they try to shortcut their way to the top. Taking an elevator makes sense. But oftentimes, climbing the mountain teaches you infinitely more about yourself and the world around you, and makes you a more competitive individual.


99% of people lack a master's degree in life. Everyone wants fast success. And in pursuit of it, they only get the crumbs of success. The crumbs of success is the doctor who studied throughout his 20s and 30s to get a 6-figure job. He believed being a doctor was a shortcut to success. But this is because he didn't know what success truly looked like. How could he? His prescription was given to him by everyone else in the 99%. While he ends up graduating in his late 30s and making a bit of bread, he lacks substance in every other way. He's not charming. He lacks people skills. He only has status around his employees, his patients, and (maybe) in his practice. He'll struggle to date his dream woman. She doesn't exist. The version of her he dreamed about faded away 10 years ago when she was 25. Now she's 35 and far less appealing.


The doctor also lacks budgeting skills. He went from earning nearly nothing to earning a lot. Good for him, right? Not so much. When money is a chore to acquire, you value it more. When you gain and lose money frequently, you truly understand how money operates. When you take the elevator to the top of the mountain, you sacrifice the ability to dodge boulders. You don't build grip strength. You lack stamina. You're a lesser man. What good is it to see the peak of the mountain when you cheated yourself out of the journey?


But surely, his health must be superb, right? He is a doctor after all. But what if I told you that learning how to take care of your own health and taking care of the health of others is not the same? It's like a personal trainer that's not built like Adonis. He understands what his books have taught him. He knows the science of fitness. But he lacks nuance. He doesn't understand that mental fortitude and discipline are a massive contributor to fitness. The books don't cover that lesson. But getting a master's degree in life has a different curriculum. You learn to take more risks and get more rewards. You learn that a book can't give insights into everyone. It can't account for every scenario. It can't give you all the answers, but rather it fools you into believing it can.


The doctor who took the shortcut to success simply cheated himself. He focused on one path and in exchange, he's made his ability to improve his health, wealth, and relationships nearly impossible. Not completely impossible. But nearly impossible. And the true difficulty lies in the fact that he's conditioned himself into a new way of thinking. A new way of behaving. Such is the nature of humans. First, we shape our habits. Then our habits shape us. Medical school shaped his habits. Not pursuing a Master's Degree in life shaped his habits. And undoing these poor habits will be difficult. How easily would you be able to break over 10 years of bad habits?


I'm not picking on doctors by the way. You can substitute that career for nearly any career that requires extensive schooling. I only bring this up because it's a path many people take. It's the path that hurts most people.


The key to winning big is to take massive risks and try many things. When I was about 20 years old, I took a bit of risk. As a college student that had an engineering scholarship, I sacrificed it. Deep down, I knew I needed a Master's Degree in life. I opted out of taking the elevator. In exchange, I looked at the top of the mountain, took a deep breath, and trudged up the mountain. Hand to crag. Foot to rock. I'm still climbing. And it's only during the climb that I learned the secret--The Peak is the worst part. The contemplation of climbing is the second best part. The climb itself is ecstasy.


Sacrificing my scholarship and taking the climb was tremendously difficult. I had no support. Actually, I had the opposite. I was insanely broke. I was insanely unhealthy and overweight. And I was insanely lacking in confidence. My curriculum led me to start a business called College Conqueror. My goal wasn't to get rich. It was to be helpful. It was to be useful. I'd reach out to big creators to try and guest post on their websites. Not much luck. I'd eventually get back into college while running College Conqueror. But at this point, my new curriculum taught me that my old curriculum was inferior. It was an elevator. And it wasn't a reliable one. I still wanted to climb. I eventually found creators that would allow me to guest post. I built up a small following. I made a little bit of money from my unintentional business by allowing other businesses to place ads on my website. My traffic was decent--a few hundred visitors a day. Not great. But when you're new to the online monetization world, the few bucks you'd see deposited in your account might as well have been thousands of dollars.


I made $20-30 every few days here and there. Nothing special. But it was the first time I earned money outside of working a typical job. It was an experience I'd only get from climbing.


You don't get these views from the elevator. My happiness was high. My confidence was growing. And when you're winning, you want to win more. When you're climbing, you have no choice but to keep climbing...or fall. Eventually, you begin to love the climb for the sake of the climb. I began to read voraciously. I consumed whatever book I could get my hands on at the local library. The mountain showed me ways to get in shape even on a terrible diet. The mountain showed me the secrets about money that no class or financial advisor would teach. The mountain showed me how to truly stretch my money even when I was making around $11,000 per year (poverty income). The mountain showed me what to say and how to say certain things to build rapport with people (particularly women).


The elevator has no women. The elevator has no secrets. The elevator is just a boring and predictable elevator. Nothing more and nothing less.


Most people I knew were at the peak of the mountain by the time I was barely climbing. My hands were still unused to the jagged and rough scrapes of the mountain. Sometimes the pain my unconditioned hands felt made me second-guess myself. Should I stop? Should I just go back down the mountain? Should I give up and take the elevator like everyone else? But then I'd look down, see how far I've already climbed. and embraced the journey more. And so I kept climbing.


At this point, my friends were at the peak. They've been there for years. They're bored. They're mentally old and fatigued. Sure, they could take the elevator back down and climb up. Like I did. But what would be the point? They already know what awaits them at the peak. They sadly will never understand that the peak is an illusory goal. But only those who chose to climb could ever understand that.


Each time the elevator reached the peak, I'd hear a ding. Ding. Ding. Ding. I'd been climbing for at least a full year straight at this point. And it seemed like the ding was constant. It echoed in my ear. Day and night all I'd hear is that ding. It began to take its toll. It upset me. And so, I stopped climbing. I found a place on the mountain to rest. And for another year, I debated if continuing was worth it. Every ding was a sign of someone reaching the peak. At the time it seemed like everyone was winning. And it felt like I was losing. I felt like a loser. "When would I hear my ding?", I thought to myself. I eventually saw someone taking the exact same path as me. He was climbing. In the exact same way. On the exact same route. I watched as he climbed out of view. Months felt like seconds. Then, a ding. Not from the elevator. From him.


After giving up on College Conqueror, I eventually discovered someone else had essentially done the exact same business model as me. Although, their model was inferior in its presentation and quality. Nevertheless, I was able to estimate their earnings. They were making bank. My model was making bank. I could've been making bank. But I wasn't. Because I stopped climbing and lost faith in myself. Hearing that ding made me mad. It was different. It wasn't from the elevator, which I knew guaranteed a ding. It was from a climb, which until now, I doubted led to a ding.


But hearing someone else get their bell was all the proof I needed. Now, I knew that if I climbed enough, I'd hear it...eventually.


I continued climbing.


And I continued climbing.


And I became deaf to the dings.


And I became blind to the elevator passing me by.


And this was the secret to winning big.


Before I knew it, I had passed the peak. But how?


The peak is the highest you can go.


I passed the peak of the mountain that had an elevator.


I was winning big. And when you decide to climb the mountain and win big, you learn that the mountain you're on has no peak. It has no elevator. It's an infinite climb. And you have the exclusive ability to go higher than any elevator can go.


Do you understand the secret to winning big?


I hope this lights a fire under your ass.

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