IWillTeachYouToBeRich - The (hidden) hypocrisy of wanting more

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Hi Reader,

Here’s a thought experiment: If you had a magic pill that would let you live the life of your dreams, what would your life look like?

Let’s get really specific.

  • When you woke up, what would your schedule be? What time would you wake up? What would your house look like? (Remember, this is a magic pill. Your life can be whatever you want — get creative!)

  • What would you do for work? What would you do after work? How would you get home? Would you even have to go to the office?

  • How much money would you make? What would you do MORE of and what would you do LESS of? What would you do with that money as the ultimate extravagance?

When I asked people on Twitter what THEIR Magic Pill Life would be, I got some amazing responses:

But here’s what’s really fascinating: I also got a ton of “REASONABLE” responses. These are the kind of responses that sound logical…but made me scratch my head.

For example…

Why just ONE vacation?

Or…

Hmmm…

If you could have anything in this world, THAT is what you would do??

Write a book on millennials? Dude, you could do that in 6 months. What else? THIS IS A MAGIC PILL!!!

2 things I learned:

  1. 100% of people described a life of MORE. More options, more freedom, and more luxury. The ability to wake up when you want, do the work you want to do, and earn tons of money for it. Awesome.

  2. Lots of people were conservative with their dreams — way too conservative. Remember, this is called the Magic Pill test. You can have literally anything you want! Yet so many answers were about having more time for hobbies or going on an extra week of vacation. I mean, those are cool. But that’s it?

Why do we struggle with this question? Why do we feel guilty about what we really want? Why are we hypocrites about wanting more?

Think about it: In the Magic Pill Test, you can have anything you want, instantly. IT’S A MAGIC PILL, PEOPLE. Why is it still so hard to say what we really want?

I know why, because I used to feel this way...

I grew up in a family of 6. My parents were immigrants who moved here from India. We ate out maybe once a month, and only with a coupon.

There were lots of places in our hometown that we would walk past, knowing we would never, ever go inside. For example, we knew we’d never walk inside a fancy Michelin star restaurant or luxury hotel, much less have the chance to experience them.

As I got older, I started hearing whispers about those luxury experiences and the people who indulged in them. You read magazines with $500 sweaters, you see TV ads for a Lexus, and you think, “Who buys this stuff?”

But there was always an edge to the luxury ads I saw. The media presents these things as aspirational — but the minute you actually buy one of them, it seems society turns against you. You start feeling the hypocrisy: “A Mercedes is the finest automobile out there.” “Ugh, he drives a Mercedes? What a show-off.”

That’s when I started hearing another kind of message.

First, it was “save 10%.” Then, cut back on coffee. Then it became a moral crusade — and it wasn’t simply about saving.

  • “How dare you eat out twice a week!”
  • “Buying a brand-name yogurt at Whole Foods? RIDICULOUS! I save $0.09 on generics every month!”
  • “$100 for a pair of jeans? ARE YOU KIDDING ME?”

Turns out there’s an entire group of people who genuinely believe that wanting more is a moral weakness. And they spend their lives telling you all the things you shouldn’t want.

I’m on the front porch of my luxury house, looking over the hundreds of beautiful plants in the front garden, my belly is comfortably full from a breakfast of espresso with frothed organic milk, almonds, mangoes, and avocados. Aren’t I Mr. Fancypants? No, actually I am not. This stuff isn’t anything to brag about. Although I am enjoying it at the moment, it is actually an indulgence of a weakness, and I had better watch myself, lest I start to depend on this sort of pampering all the time.” (source)

I played along for a while. For example, one of my very first products was called Scrooge Strategy. And I was adamant about the fact that bottled water was for idiots.

But I never stopped being curious about this other world — the world of more, not less. Who were these people who spent $50 on brunch without blinking? Why did they spend so much on a meal when they could get double the food for 1/2 the price down the street? I wanted to know what happened at the places I could never go to.

My old lens: The goal of eating is to make you full. That’s it.

Slowly, I learned there are other reasons people pay for these things.

There are actually lots of lenses to view the world through besides price.

  • Experience: For a 100X better time, reserve a VIP Tour at Disney World. Yes, it’s more expensive, but it’s the difference between standing in line for 90+ minutes for each ride and skipping the line entirely. And you’ll see the park in a way 99% of visitors never will.
  • Status: Status matters. A Rolex watch or Loro Piana sweater is functionally the same as something 1/100th the cost, but it signifies certain things about who’s wearing it. Don’t laugh — most people scoff at status (which is ironic since every one of us factors in status to other parts of our lives: the college we attend, the neighborhood we live in, the job we take).
  • Convenience: Have a lot on your plate? A personal assistant can handle all the details. You don’t have to worry about the logistics of everyday life. Or how about never having to shop for groceries again? Pay a little more and get it delivered straight to your door.
  • Better results: Why pay for a trainer or tutor when you could get the same information for free? Because with a good trainer or tutor, all you have to do is show up. I don’t want to figure out the best training plan on my own. I don’t have the time. I just want the results.
  • Affordability: A $5,000 ticket for front row tickets at a concert might seem like a lot. But if the person earns $500,000/year, that $5,000 could be equivalent to someone else’s nosebleed tickets.
  • Certainty: Getting a tailored, customized piece of clothing and knowing that it will fit perfectly as soon as you receive it.
  • Sometimes you just want it! “Why do you want it?” “Because I want it.”

This was incredibly liberating. It helped explain so much of the world that I couldn’t understand when I was playing the single lens of “price is everything.”

It’s like you’ve got 7 lenses on the table and you just keep picking up the same one every time. Price, price, price. What about using the other ones?

When I was 22, I didn’t understand why you’d ever pay $100 for a shirt. But as I got older, it clicked. There were other lenses to view the world through.

I USED TO THINK: Ordering private cars or even taxis was stupid. Why get a car when you can just take the bus or subway?
NOW: I have my personal assistant order me a private car to drive me around whenever I’m in a new city. 

I USED TO THINK: Who cares about buying “nice” clothes? LOL, what a waste of money. I would never pay $300 for a sweater, I can get the same thing for $20 at TJ Maxx. P.S. They should like me for who I am!
NOW: I realize your clothes send a signal about who you are. There are also differences in quality. And honestly, I just like a nice cashmere sweater. Ain’t nothin wrong with that.

I USED TO THINK: Why would anyone pay $20 for a salad? That’s like 2 bites of food. I’d still be hungry after that meal!
NOW: I realize being full is one reason to eat food — but there’s also the texture, taste, the ambiance of the place where you eat. Food can be an experience, not just calories.

I’m also glad that I challenged the messages I received while growing up. If I’d still believed that “wanting less” is virtuous, I would have been missing out on an entire layer of society — one I wanted to understand.

Look, sometimes price really is the only lens that matters. If I’m buying paper clips, you think I care about the service?

But in so many parts of life, price is not the only reason to get something. Or even the primary reason.

The difference is, now I know why I’m making any decision — I no longer just act on autopilot.

Plus, do you really want to follow the same knee-jerk beliefs you formed when you were in your teens? How many of you used to pirate music (“LOL who would ever pay for music??”) until one day, you realized you’d rather just pay for a Spotify subscription?

It’s like a 4th grader saying boys/girls have cooties. You think you’re going to believe that forever? Maybe they have cooties now…but in a few years, they won’t.

Go through the Magic Pill Test. What would your life look like if you could take a magic pill and do anything?

If your answer is “exactly what I’m doing now,” awesome — keep doing it!

But if you have a gnawing desire — something you’d want to try, even once — like splurging on your family for an amazing vacation or buying a Tesla Model 3 because you want it — my suggestion is:

Don’t deny it. Embrace it.

If you want more, let me show you how.

Yes! It takes hard work.

Yes, it’s easier to convince yourself you don’t actually want more.

Yes, it’s easy to listen to people around tell you, “You should be happy!” (Listen, I’m happy — but I’m not satisfied. I want to push myself to see what I can achieve. I want more, not less.)

But most of all, I’m going after more because that’s what I want. I don’t care if that’s weird.

This was an important lesson for me. I hope it will be for you, too.

And I’m curious: After reading this, is there one example of what MORE means to you… that you don’t usually share because it sounds “crazy” or “unrealistic”?

Reply to this email. Let me know.

Thanks for reading,

P.S. Want to learn more about all the different lenses you can view the world through besides price? Check out my Advanced Personal Finance product, which goes in-depth on this topic.

P.P.S. Got another email about "wanting more" for you tomorrow. Watch your inbox.


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