The Homeless Millionaire: How Making Money Is Only Half the Battle

Warning: this article gets a little more intense than my usual ones. I do this only so you may understand me clearly.

Imagine if people were completely honest with each other. How would they communicate differently?

To give an example, let me tell a hypothetical story.

Two young, first-time parents in the maternity ward witness the birth of their baby. They are ecstatic, but also nervous for a hundred reasons. The doctor walks up to them, clipboard in hand, and says:

“Everything is fine. You’re going to have a healthy young boy/girl. Congratulations.”

But if he were truly honest, I believe the doctor would say something like this:

“We’ve found no glaring health issues right now. Your child will probably be fine for the first 10 or so years of their life. Then, as they hit puberty, their desires will start to grate against the expectations of the modern civilized world. He/she will probably go to college, on your insistence, because you were told it’s the only chance they have to get a good job. As compensation, you will let them pick a degree they want, even though it will not prove practical in the real world. Then, once out, they will be wholly unprepared for the job market and expectations of adulthood.

But life will sand them down over time. They will get a dull, boring, barely tolerable office job where they stare at a computer screen and hunch their back 8 hours a day. After several decades of this, they will return here to get their questions answered about new, growing health problems. Exhaustion, social anxiety, back pain, eye strain, obesity, dependence on substances like alcohol, unusually frequent colds and other minor illnesses. But they will not go easier on themselves or change their lifestyle. They will not risk quitting this ladder of jobs they have been climbing. They have slowly, painstakingly worked their way into higher positions in their workplace, saving their money, spending it only during emergencies.

For what, you ask? Wealthy retirement. Their suffering is all in the name of finally having a million dollars. Because once someone has a million dollars, they’re set for life and can retire in luxury.

Eventually, somewhere around age 50 or 60, your child will finally be an official millionaire, with seven figures in the bank. And they will be at their most miserable, least healthy, and least socially connected and satisfied in the history of their life.

Immediately, after retiring semi-early and faced with a panicked sense of “I need to spend this money, or else it’s worth nothing,” they spend their million dollars.

They spend it on my care, to finally address their health problems via the fastest, most expensive means. They spend it on companionship, going through expensive seminars to learn how to attract other people, or cosmetic surgery to patch up perceived flaws in their appearance, or paying escorts for their time, or spending money conspicuously in bars and clubs to draw attention. They spend it on vacations to places they wanted to see, with no experience in how to travel wisely and make the most of every dollar. Most of all, they spend it on things. Huge TVs with video games and sound systems. A large house. A sports car. Fine art to impress houseguests. If your child is kindhearted, they may also give some of it to charitable causes.

They spend and spend, because they already spent most of their time on this planet, so now it’s time to spend money instead. And before they know it, they are not a millionaire anymore. In fact, they are rapidly on the path to being broke. And so, beaten, dazed, and disillusioned beyond repair, they return to the job they so proudly retired from and get back to work for another 10 to 15 years, until finally they retire permanently in semi-comfortable living, convinced that while they may not be healthy, or happy, or satisfied that their dreams and aspirations came true, they are at least wise to the ways of the world, through their suffering. And it is this wisdom through pain that they will carry, like a badge of honor, to their grave.

But until then, your child is currently healthy. So congratulations.”

Okay, Cleo, What’s This About?

I know that was a bit of a haymaker. But I wanted to make a potent illustration of what I’m talking about:

Being a millionaire means nothing. It is the most empty goal any person could chase.

I know this may be confusing, coming from a person who is teaching you to make money online and live in luxury. I’m certainly not against you making millions of dollars. But my point is that chasing a million dollars for its own sake is the worst thing you can possibly do in a career.

Have one million (or even several million) dollars in the bank does not protect you from the pain of:

  • Health problems
  • Social issues
  • Limited life experience
  • Not following your dreams
  • Feeling like something is missing.

And what’s the biggest cause of all these things? Our current work environment.

I want people to make money online, start side hustles, and get online businesses running for them today so that they can quit their unfulfilling day jobs as soon as possible. If you stay in an unfulfilling, damaging environment, what is the point of how much money it makes?

In the 4-Hour Work Week (review here). Tim Ferris was the first to defy the conventional concept of working until a late-life retirement, instead teaching people how to live comfortably and make good money with the power of the internet, making money through small amounts of work, and having the freedom to go on mini-retirements multiple times a year. But the world does not change overnight. Many people still work in harmful, soul-crushing 9-5 day jobs. And if they truly desire to do so, if they have no entrepreneurial spirit and no desire to have lots of money, I can understand that. I may not agree with it, but I can understand.

But if you want to do things in life, if you want to have lots of money to spend how you wish, then sacrificing most of your time being alive, your health, and your happiness to make that much money is throwing out the baby with the bath water. Do not do that to yourself.

What Is the Homeless Millionaire?

The Homeless Millionaire is something I want you to remember, to think about every so often, so that you can take inventory on your career path and steer yourself toward more money and more time to be happy. The Homeless Millionaire is a metaphor. It does not mean that he or she literally has no home and is out on the street.

It’s just that they feel that way, even in a soft, comfortable, king-sized bed in a luxury apartment.

What’s worse, I ask you? To be content in poverty, or miserable in wealth? I say miserable in wealth, because not only are you unhappy, but you are wastefully unhappy. You have things other people want, and yet they achieve nothing good in your hands. It’s like buying an expensive steak dinner, taking one bite, and remembering you have a toothache and throwing it in the garbage.

You must have a happy home within yourself. You must live a life that makes you happy. Remember the Temptations?

“Papa was a rollin’ stone,

Wherever he laid his hat was his home.”

Truly wealthy people, meaning having both literal money and metaphorical wealth in the form of health, friends, achievements, etc. these people are at home in their own skin. They are never stranded, never lost. They are not unhappy in the present to theoretically be happy in the future. They always know what to do and they are always on the way to something better. Nothing is a desperate, dogged struggle for them, because they employ balance and consider the deeper cost to everything they do.

That deeper cost is time.

Value your time. You cannot make any of it back.

Find a sane, healthy way to get to your goals in life. Mach 5 may be fast, but it’s fast because not only is the car’s engine powerful, but because the car is light and unburdened.

Most people who become millionaires do not live the kind of life people imagine millionaires would have. There’s no relaxing on a tropical beach, slung up in a hammock drinking a mai tai. There’s no travelling the world regularly. There’s no networking with famous people. Because they chased a number, and didn’t build a self-sustaining wealthy lifestyle, that million dollars had no platform to stay stable and grow.

What I want for you is to get happy, to get satisfied with where your life is going, as soon as possible. Then, and only then, are you in the right state of mind to learn what I have to share, and to try the things that I suggest.

The Secret to Being Happy Before You Get What You Want

I know, we’re all chasing gratification. How can we be happy if we don’t have what we want yet? It’s something even I struggle with. Everyone always has something they want. Achieve one goal, and another will instantly replace it.

So I’ll tell you a secret. It’s not the fulfillment of goals that leads to happiness. Sure, fulfilling goals is satisfying, but it’s like the icing on the cake.

Real happiness, the proper mindset of an entrepreneur, comes from the sense of mastering one’s life. How do you get that feeling? By making sure that, while on the journey to making more money, you are also pursuing other things and maintaining a balance that lifts up all aspects of your life.

  • If you’re not as fit or healthy as you’d like to be, exercise and find a diet you can commit to without being miserable.
  • If you’re lonely, start dating, or look at ways to get more friends, if that’s all you need. Stay involved with your family.
  • If you don’t feel spiritually fulfilled, take more time for introspection and looking inward.
  • Most of all, if you’re not happy at your job, start looking into ways of reducing your time there. I strongly recommend finding a way to work remotely at least some of the time, proposing it to your boss, and then inching your way into an arrangement where you work from home full time.

Let these other sides of your life grow in tandem with the entrepreneur, money side. That way, you will not just learn to love the process of making money and getting rich, but by the time you realize “I made it, I have more money than I know what to do with,” you are truly in a state to enjoy it to its fullest. Both out of the pristine condition of your life, and from the security of knowing you built your wealth in a way that will never drain away, but keep growing instead.

That’s all I wish for you, and I hope you wish it for yourself as well. 🙂

Refuse unhappiness.



P.S. Feeling overwhelmed? Click here to see the product that got me started making money online.

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