How Your Relationship With Money Secretly Sabotages You and How to Fix It

Daniel Jeffries
The Startup
Published in
18 min readJul 23, 2018

Money.

Few words have the power to spark such intense love and loathing as that magical word.

Money, light of my life, fire of my loins. My sin, my soul.

Mon-ey: the tip of the tongue tripping off your palate as your lips part in an orgasmic O to whisper that sweet, sweet sound.

It’s a dark and delicious word that’s woven into everything we want and everything we hate, sometimes at the same time. We wish we could do without it and yet everyone secretly craves it, imagining it’ll solve all their problems.

Greed is good.

As a society, we fall in and out of love with the hypnotic power of all-mighty money.

In the 1970’s Disco made us want “more, more, more.” In the 80’s movies like Wall Street told us “Greed is good” and as a culture we celebrated the gaudy display of wealth at every turn, from fast cars, to fast women, to the glittering glimmer of gold on the necks of the fabulously rich and famous. Big hair, leather pants and electric lights marked the music of the time, as rockers and pop stars lived the glamorous life. Even alternative bands like the Pet Shop Boys sang “Let’s make lots of money.” They meant it ironically but few people took it that way at the time.

And yet our love of money alternates with waves of fear and loathing.

In the 90’s a backlash against the culture of flash cash took root, personified with grunge rock. Nirvana, with their checkered shirts and ripped jeans, made the leather pants and laser lights of big hair bands seem profoundly uncool. The crash of the dot coms and the economy made hating the rich a way of life once more.

And it’s never really left us.

The 2008 housing crisis accelerated the hate as not so clever algorithms and predatory banking smashed the world.

It continues to this very moment, a rising backlash against money and the power of those who wield it. “Elites” has turned into the watchword of our age.

Everywhere politicians and reformers rail against them with seething rage, even if they’re secretly elites themselves. We attribute everything wrong with society to the powerful and their insatiable greed. If only we could root them out and put simple, salt of the Earth people in power all would be right with the world.

But is it really true?

Or are the rich just another convenient scapegoat in a long line of scapegoats?

Like so many things, the truth is somewhere in between.

Money is a powerful force unlike any other. It’s more powerful than the wind and the rain and the storms that shatter the sky on a late summer day. It effects everything around us. It’s neither good nor evil but at times it can be both, separating us from each other or uniting us as one.

So what makes money work for us or against us?

Simple.

Our relationship to money is everything.

A bad relationship is like a bad marriage. It destroys everything around it.

A good relationship is like a fiery early morning sunset. It lights up our whole life and makes it easier to do everything we ever wanted to do.

But so many of our relationships to money are terribly broken. We’re locked in a vicious cycle of love and hate.

It’s up to us to break the cycle and make money work for us in a positive way.

But how?

Start over.

We have to rekindle our romance with money.

We have to go back to the moment we first met and begin again.

Just as new crops can’t grow unless we clear the field, a new relationship with money can’t blossom unless we clear out all the past misconceptions holding us back.

If you want to make more money or start a business or get good at trading stocks and cryptocurrency then come take a walk with me and we’ll clear the field together so you’re ready to begin again in a golden land of opportunity and adventure.

The Dark Side of Money

Money changes based on two things:

  • Our experience with it.
  • How we see it.

Let’s start with experience and how it shapes us for good or bad.

First the bad.

It’s often our bad experiences that destroys our ability to make money.

Money, it’s a hit
Don’t give me that do-goody-good bullshit
I’m in the high-fidelity first class traveling set
And I think I need a Lear jet

When I was a young man I went to work for a computer consultant in New York City who had some of the richest clients in the world, including the late Teddy Forstmann of Forstmann Little, a powerhouse private equity firm that’s now gone with the wind. Forstmann owned Gulfstream Air (the private jet company), Yankee Candle and Topps Trading cards. He commanded a personal fortune of over $1.6 billion.

To give you a sense of just how powerful the man was, it came out that he’d beguiled the ravishing princess Diana before her untimely death and that the princess was considering running off with him.

But that’s just the tip of the iceberg.

I once had to reconstruct an Excel doc that got corrupted for the firm. The staff told me they needed it to invite people to their exclusive annual party. By some miracle of IT black magic we managed to get the document rebuilt after days of trying, only to find that it had the personal phone numbers of every major celebrity and CEO in the country.

Things like that abounded when I worked there. I once saw the price for the wine alone on a single trip of the personal jet and it cost $40,000, a princely sum in the early 90s. Teddy had so much money that he had a full time rabbit catcher on staff at his estate and a gourmet chef in the office to cook for seven people every day.

And that was just one of the people my consultant counted as his clients.

I remember a small hedge fund run by five people who had an office stocked with more antiques and Persian rugs than most museums. Another company’s CEO had pictures of him with Bill Clinton and supreme court justices on the walls, all of them arm and arm. The personal assistants at these companies made hundreds of thousands of dollars a year to guard these precious secrets.

It seemed like a dream job.

It was a nightmare.

I hated every second of it. These were some of the most wretched people on the planet.

I remember someone asking me to fix Teddy’s laptop. I was in his massive office, surrounded by his trophies and plaques, the kind of things rich folks get for doing nothing as various organizations try to woo them and their money. It was clear to me that he had probably never used the machine in his life. It was barely out of the box and not even completely installed right. As I was working on it, his personal secretary came running in screaming:

“You have to go now! He’s coming! He’s coming!”

At first I looked at her like she had two heads. What the hell was she talking about? Why did I have to leave?

Then I understood. I was the help and the help were never to be seen.

I was nothing but a tiny insect in the way.

Now that Teddy is gone he’s often seen as one of the good guys. And why not? Despite everything I just said, in many ways he was a good man and people are more than one thing in life.

He fiercely criticized the nasty practice of raising obscene sums with junk bonds and raiding corporations with leveraged buy outs in the 80’s. He came from the corporate raider era but railed against hostile take overs and financing them with toxic debt.

But I never saw that side of him. I saw only his darker streak.

His former personal assistant told me stories about how he would play vicious games with his staff. She said he once hid his passport and went all the way to the airport before screaming at her for “forgetting it” and making her go back to get it while he waited.

I could tell more stories but I won’t. Quite simply, these were the rich people you fear, the mythical 1% of the 1%, everything you imagine in your darkest conspiracy theories and more.

And that experience poisoned my ideas about money for a decade.

It taught me one thing:

To get rich you to had be cruel and ruthless.

I thought the only way to make a fortune was to take it from everyone. I believed the famous Balzac quote at the beginning of the Godfather “Behind every great fortune is a crime.” Sociopaths and psychopaths thrived at the top, brutally grinding down the little people in front of them with no regard for anyone but themselves.

And I wanted nothing to do with it.

In my unconscious I thought of money as filthy, dark and evil. It was all blood money to me. So when I had opportunities to grow my own stack I always managed to get in my own way.

That’s because everyone gets exactly what they ask for in life.

Even if we don’t know what we’re asking for.

And most of us don’t know what we’re asking for at all.

I certainly didn’t. In hindsight, it’s pretty clear I was asking not to make money because I didn’t want to be one of those vicious people. Hindsight, as they say, is 20/20.

What I wanted was to be a good man and an artist and that meant staying as far away from money as possible.

Our limited experience programs our unconscious quickly and effectively. And our unconscious programming quietly directs our every move, keeping us from a richer and fuller life. We’re totally and completely blind to the machinery of our inner mind, pulled along by invisible strings that we can’t see or feel.

It made me self sabotage all my efforts at making real wealth. I always did good and then found some way to pull back and short circuit the process.

But then I realized something essential:

It was my fault all along.

There was nobody to blame but myself.

It was my own beliefs about money that held me back.

My sample size was too small. I didn’t have enough experience and I’d let that limited experience shape everything I thought about the world.

It was never really about those horrible people after all. It was about who I was and who I needed to become.

Master Yourself, Master Your Money

But who did I need to become?

Was there a different way to make money?

I didn’t know but I was determined to find out. I wanted to find a way to get rich in a way that stayed true to my own beliefs and my own nature. For a long time I didn’t know the answer.

Then something changed everything.

And it started with a promise.

A promise to myself.

For years I wanted to be a writer but I could never really commit to it. That’s how it is for everyone. First comes commitment and then comes mastery of your craft. Without that commitment you will never make the time necessary to achieve mastery.

Steven Pressfield, author of the Legend of Bagger Vance, talks about the journey of the artist in The War of Art. For years Pressfield did everything he could not to write. He procrastinated, made excuses, blamed others, blamed society, blamed his life and job and circumstances.

Then one day he was so sick of driving a cab and not writing that he went home, dug out his typewriter from under a pile of crap and he wrote. After that he did the dishes in pure bliss and from that day forward he knew he was a writer.

It took him ten more years before he sold his first book.

Most people think he became a writer when he sold that book but it’s not true. It started that fateful day a decade earlier when he committed to the process of getting good.

And getting good takes time.

It takes many years of pounding away at the keyboard every single day, week after week, month after month, year after year. There are no shortcuts. It’s just dedication and time.

This is true of everything.

Whether you want to get good at building houses, trading cryptocurrency, starting a business empire, becoming a doctor, or anything else that requires skill and dedication, it starts with a sacred bond made with yourself.

This is no easy task.

We don’t select a deep, life-long commitment the way we select soup over salad. We have to suffer so much that we have no choice but to give in and focus our lives to something greater.

I spent years dabbling with writing but never really committing to it. I wrote some short stories, dashed off a few bad novels and screenplays but I wasn’t really getting much better. I tried to sell the books and when they didn’t sell I mostly gave up or wrote whenever I felt like it.

Then one day I knew I’d tried every possible way to avoid doing what I loved and I’d had enough. My soul had grown sick. Deep inside I was dying, every day a damp, drizzly December in my soul.

That’s when I knew I wanted to do one thing and one thing alone: write.

I dedicated myself to writing every day and I promised myself I would not stop unless I died. From that moment forward I knew I would do whatever was necessary to get good at slinging words around a page.

There is no substitute for mastering your craft.

It took another ten years before people started reading this blog and my books in big numbers.

I like to say it only took me twenty years to become an overnight success.

Maybe you’re wondering how committing to writing has anything to do with money?

Good question.

When we find something that we’re truly passionate about, that we really love, and we finally take the plunge, everything changes.

We radiate a new kind of energy to the world. We attract new kinds of people because we’re coming from a place of power and authenticity. And other people can feel it. They see it in you and your words and your actions. It’s like taking your light out from under a basket and putting it on a mountaintop so it shines for all the world to see.

It’s terrifying and wonderful at the same time. It means you can crash and burn because putting yourself on the line is a major risk. But as Hemingway said “Our only value as human beings is the risks we’re willing to take.”

And when we take those risks we suddenly meet people we never expected to meet. And that’s where the rich and powerful come back into the picture, as well as my relationship with money.

Because of my work I’ve met people all over the world, from all walks of life, rich and poor and everything in between. I’ve met authors and venture capitalists and artists, the homeless and the super rich, the powerful and the not so powerful. I’ve traveled and stood on the streets of the greatest cities in the world watching the sunset and wondering just how I got here after all this time?

And that’s when I realized there was a second path to money, one very different from the first.

While the weakest and most insidious rich people tread the path of violence and hate, another group of very special people tread the path of light, a healthy path, a path of openness and abundance. These are people who don’t see the world as a zero sum game and everyone else as their plaything.

And like many others these folks saw my light on the mountaintop and they wanted to connect with it.

So what is it people really see in me now?

What they sense is my ability to create value for other people.

Writing, relationships, entrepreneurship, teaching and so many other aspects of life are about so much more than ourselves.

Writing isn’t just about me and what I want to say. It’s a partnership between me and you, the reader.

If I just write whatever I feel like then nobody will read it. Yet it’s more than that too. If I write only what you want to read, with no regard for my true self, then what’s the point? I’d be a slave to the page and we’d have a parasitic relationship.

A true relationship is built on trust, trust that’s earned or lost over time.

It’s a give and take. We create value for each other.

It’s both selfish and selfless.

And that’s the way it is with money too.

Once I learned how to give freely of myself I began to attract the kind of people who do the same in their own life.

An amazing lady I met through my writing and through cryptocurrency projects just had her birthday party. She invited us to the south of France, rented a massive chateau for all of us to party and hired a two star Michelin chef to serve us dinner. It was as incredible as you might imagine, the rolling green of wine fields stretched out under an endless blue sky as fantastic old cottages and castles stood shining in the fields, memories from a time gone by.

And while that might sound like just the same kind of gaudy display of money I once saw working as a nobody IT guy in New York City, it’s not.

It was something totally different because this was a different kind of woman. She cares more about other people than herself. She once collapsed from fatigue after cooking for everyone for three hours straight just because she wanted them all to enjoy an amazing meal.

And this was a different kind of party too.

It wasn’t all getting drunk and dancing, although there was certainly a bit of that too. It was about the amazing conversations I had with almost everyone there, people who were attracted to her light and her kindness.

People worked and played and shared.

All of them had their own businesses, did charity work all across the world and not just weekend charity work but the kind of work that takes time and commitment. They helped people in areas hit hard by disasters, political and natural, and areas crippled by the worst poverty.

They all wanted to change the world for the better.

And they were doing it, not just talking about it or wishing for it or waiting for it to happen.

You see, there are really two paths to money:

  • The path of selfishness.
  • The path of creating value for others.

Only the second path is worth it.

When you meet folks from the second path you realize they care deeply about people and they want you to be successful too, not just themselves.

If you’ve never met rich folks in your life you may have a stereotype of them in mind that’s driven by fear, but direct experience is the only true teacher in life. If we never meet anyone from a different walk of life it’s easy to demonize them.

I understand the impulse, believe me.

My experience as a young man showed me only one side of the spectrum. And if that’s all you ever see it’s hard to transcend it.

I don’t pretend that every person in power is good and filled with a charitable heart and a passion for making the world a better place. That would just be naive.

But it’s equally naive to paint everyone with the same broad brush and assume everyone with power is a parasite who eats the poor for breakfast.

When we paint everyone with a broad brush we’re lying to ourselves. We’re willfully blind, trapped by the fallacy of composition. There are good and bad people in all walks of life. The rich are no different.

But if you refuse to see it, if you lump everyone with money into the same boat than you’ll never make money yourself. You’ll see it as filthy and disgusting, just as I did, and you’ll secretly sabotage yourself at every step.

That kind of thinking doesn’t just hurt others, it hurts you and your ability to ask for and get what you want in life.

Money does not make us good or evil. It’s a catalyst. It simple accelerates who we already are before we have it.

If we’re cold blooded bastards before we made our first million it’s pretty much guaranteed we’ll be that after it too. Cut throat people leave destruction in their wake. This is not something to emulate but something to despise.

But the second path to wealth is very different. The true way to make money is to make something that everyone wants and needs. You want to build something that drives communities and passion. When you do that you raise the tide for everyone and it only makes you richer in the process. There’s something for you and something for everyone else.

Balance is best in all things.

How we see the world, makes the world.

Wrong thinking, wrong outcome. Right thinking, right outcome.

Of course, it would have been wonderful to meet these kinds of people earlier in life but I wasn’t so lucky. It doesn’t matter though. In many ways I simply wasn’t ready. I hadn’t learned to create my own value and to give freely of my ideas and time. And I don’t worry about it much any more anyway.

I’m right where I need to be. Everything happens at precisely the time it’s meant to. Right now I’m just thankful that I’ve met those kind of people at this point in my life.

It’s completely changed my view of how to work with money.

Money is now part of my normal flow.

You don’t make money by taking it from everyone. You make it by helping other people get rich themselves.

That’s my goal for every single one of my readers.

If I can get all of you to take a step back and take a look at money the right way then I know you’ll find exactly what I found.

Money becomes so much easier to make when you know how to work with it, how to flow with it, how to ride the river and stop resisting it. You will naturally create value for other people and ask for nothing in return. I’m not super rich and I probably never will be but I get exactly what I need, when I need it.

You can too. Wealth is relative. How much do you really need to live the life of your dreams? Probably a lot more than you’re asking for now and a whole heck of a lot less than what you imagine would make you feel rich.

Most people don’t need millions to do the things they love and not feel like their cell phone will get shut off next week.

Know what you really need and ask for it.

And when you tap into the flow of money, you won’t have to worry about where you next check is coming from because it will come back to you from somewhere even though you never asked. It may come from the same source or a different source but it doesn’t matter, it will come, as sure as karma.

Money is energy. It pools and flows and changes. You align with it. You don’t force it. You go with it.

And once you know how to work with it, it’s the most powerful tool on the planet other than your own indomitable will and the strength of your heart and mind.

There are two paths to money.

And I, I took the one less traveled by.

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A bit about me: I’m an author, engineer and serial entrepreneur. During the last two decades, I’ve covered a broad range of tech from Linux to virtualization and containers.

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Daniel Jeffries
The Startup

I am an author, futurist, systems architect, and thinker.