Imagine you’re flat broke (maybe some of you don’t have to imagine that).
Somehow you manage to get your hands on $10,000. You’d be elated.
Now imagine that you manage to get your hands on $100,000. But, through a series of unfortunate events, you lose $80,000, leaving you with $20,000.
Would you rather have the $10,000 or the $20,000?
In reality, you’d probably be better off mentally by choosing the route that leads to that $10,000. This is due to loss aversion. You’re way more sensitive to losses than you are to gains.
If you’ve been broke all your life, you’d just get used to it. But if you were once rich and find yourself in the poor house, it would damn near break you.
This is part of the reason people fail to aim high. The fall is way bigger from the top.
“I was losing about a million dollars a week.”
Eventually, he cashed out, selling the company for $15,000,000. This is an amount of money that can set you up for life as long as you’re not a total idiot about the process.
Enter James and his idiot mistakes. He’d made his money amidst the dot com boom. Figuring he was a smart guy because he’d just made so much money, he decided to make some bets on the future and invested in a bunch of internet companies.
The vast majority of companies that boomed during the dot com bubble fell to essentially nothing. There were several times he could’ve exited the game and still have some coin, but he doubled and tripled down on his losers.
“At the end of it all, I had $153 left in my bank account.”
He started Googling ways to kill himself in a way that would allow his children to be able to collect on the insurance money. He lost his home and his marriage crumbled. Worse than having nothing, he had everything and lost it all.
I’ll get to his eventual rebound and the lessons you can learn about success from it, but let’s talk about some of the psychological factors at play when you’re trying to maintain your position at the top.
Doctors are famously known for being horrible investors. They think their intelligence applies to everything when it only applies to that specific domain. They make miscalculated bets based on arrogance.
The minute you start believing you have the ‘golden’ your downfall awaits you. It’s important to always maintain a beginner’s mind no matter how successful you are.
Most people who fall from grace either genuinely believe they have that magic touch, or they’re trying to convince themselves that they’re really smart enough to have earned success in this first place.
This leads to the next downfall that can happen to you when you succeed.
Some people fear success because they don’t believe they deserve it in the first place. This happens for many reasons. One, society slowly conditions you into believing you should feel guilty about being successful.
You don’t go for what you want because if you got it, your lack of worthiness would cause you to unravel. This is the root of self-sabotage. Some part of you doesn’t believe good things are supposed to happen to you, so when they do, you want to screw them up so you can get back to baseline.
Living below your potential isn’t fun, but it helps you stay consistent with your identity. If I could sum up the major problem most people have with self-improvement it’s the need to cling to their existing identity no matter how much it costs them.
You’d think breaking through a certain threshold — financially, status-wise, accomplishments — would alleviate some of the pressure. Wrong, it exacerbates it. You have more responsibility and people to live up to — fans, employees, customers.
You don’t rid yourself of problems, you just get an entirely different set of problems. They’re high-quality problems, e.g., figuring out how to scale your company vs worrying about where your next meal comes from, but in many ways, they can be just as stressful as low-quality problems.
People seek the middle ground for refuge. If you’re super poor, it sucks. But if you’re super-rich, you soon find out just how hard it is to stay rich. If your career never takes off, you’re sad, but if you create classic work, you’re afraid of making a major flop.
All of these points speak to the root of your fear. You want to win, badly, I know you do, but you might not want everything that comes with it. You have to figure out the price of what it takes to win and just decide whether or not you’re willing to pay it.
And, honestly, you should take some time to think about that question in both directions. Most gurus will tell you that you need to achieve world domination at all costs. I’m trying to make you aware of the true costs. Don’t expect an easy ride after you get on top.
Decide whether or not you’re really the type of person who can take on that much weight. For some of you, the answer might just be no and you might be better off just staying in your lane.
We all come with different levels of ambition and shit sandwiches we’re willing to eat. Find your sweet spot. I’m one of the rare people who will tell you that we’re wired differently. One size fits all solutions don’t work. I don’t know who you are at your core. Only you do. Use that knowledge.
“‘It’s worse to have had it and lost it than to have never have had it at all’ is the worst mental model I’ve ever heard There’s a certain swagger, an aura you just can’t lose if you’ve hit the peaks temporarily. Nothing more powerful than being able to call upon past experience.” Brute de Force
For a while, he just wallowed in his own misery. Crying on the floor alone every night and waking up to the bottle. Once everything had set in and he knew that if he wasn’t going to kill himself, he’d have to carry on with life, James asked himself a simple question:
“What things was I doing well on the way up? And what were the things I was doing wrong on the way down?”
So he went back to what worked. He came up with the idea for his first company through his now-famous practice of writing down 10 ideas per day. So, he started coming up with ideas every day.
He used his daily practices:
This practice can be useful if you experience a tough fall. It’s one I’ve adopted into my own life.
Eventually, this lead to him starting a blog, writing books, and creating an entirely new business based on the content he wouldn’t have been able to create had he not failed. His rags to riches back to rags story led back to riches.
Never try to fail on purpose. If you can win and maintain it, do that. Just understand that there are hidden gems you can discover from climbing the mountain you once fell from.
From the peak of my net worth, I’m down about $100,000. It didn’t drop all the way to zero, but it dropped enough for me to have many sleepless nights. In fact, right now, everything in my life is down from all-time highs. My income dropped, my views dropped, email list growth slowed down, didn’t write a book in 2021 like I’d down every year previous.
I’ve thought about what would happen if it all went to shit. Well, I’d still be alive. I’d still have people that loved and cared about me. Most importantly, I’d still have the knowledge and skills I gained over the past seven years. They can’t be taken away from me and I can always rely on them to build back up, even if it would suck.
Lots of people who lose big, or lose it all, come to the same realization. Not much in their life had actually changed except for things like numbers on a screen, a blow to their status, or a hit to their ego. Maybe you lose some toys, some adoration, some [xxxxx], but is it really all that bad? You’re still you, the same person who had enough talent to pull it off in the first place. Once you remember that, you’re golden.
Everyone loves the story arc of the heroes’ journey. The protagonist starts out lowly and unassuming. They receive their ‘call to adventure’ and finally break out of their complacency and mediocrity. They encounter some obstacles along the way and eventually return home the victor.
The most critical part of the journey, what makes the story good, is that catastrophic event that happens right before victory where it seems all hope is lost. Even though you know the Avengers will save the world, eventually, the story is better if Thanos snaps his fingers first.
As much as we’re afraid of loss, part of us identifies with overcoming it. We all want to be more courageous, but the moments where you’re most afraid require the most courage. Part of you wants that crushing blow, but another part of you doesn’t think you’ll be able to overcome it.
There’s not much else you can do but have faith. You can’t truly know how you’ll handle the highs and lows before you go through them. There just has to be that part of you that says it’ll be okay either way. Where does that come from, though? How can you get that feeling?
It all comes down to this. If you don’t trust yourself, then what’s the point of all of this? What are you doing with your life? You’re with yourself all the time. You know yourself better than anyone. And you know what to do.
Everyone knows how to run their lives. They know what they should and shouldn’t. They know what they want and what they pretend they want. We all have a gut and an intuition that tells us exactly how to live, but many of us don’t trust it.
We’re always looking for answers to questions we already know the answer to and seeking out signs that are right in front of our noses. All self-help writing does is remind you of the things you already know to be true and trust yourself to execute on them.
As far as the highs and lows go, do the best you can to stay mentally prepared for what may come. You can’t control wins and losses, totally, but you can always control how prepared you are, how sharp your mind is, how many skills and talents you can stack to be able to deal with anything.
Go through enough highs and lows and you realize the ultimate truth.
It’s all a game.
You get one spin on this rock.
Emotions are just physiological responses. If you were really present you’d just fully feel them and let them pass instead of running from them.
When you’re happy be happy. When you’re sad be sad. But still, understand you have a life to live.
How much life do we waste running away from the game instead of just playing it?
What’s really better? Losing? Or never entering the arena at all?
The cold hard truth about it all is that most of us are so afraid of our own emotions that we’d literally rather die than face them.
If you never face those emotions head-on, you’re already dead because you’re not in the game.
Why are you here?
Or just exist?