Introduction

On April 20, 2006, when my son was roughly six months old, I realized that we didn’t have enough money to pay our bills. It was shocking and incredibly painful. Although I had come to some valuable realizations already, the fact that we didn’t have enough money to make ends meet, and we had tens of thousands of dollars in credit card debt, student loan debt, car loans, and a bunch of financed furniture and equipment in our home, meant that something had to change. Now.

I buried myself in personal finance books, coupling them with the philosophy and economics books I had already been reading. Over the next few months, I started to take some radical steps to fix our financial state.

More importantly, I began to realize that this entire experience was one that other people were struggling with. How can a person balance all the aspects of modern life on a limited income? How can we find personal and professional happiness in an increasingly complex world where real wages for most of us haven’t changed in decades?

So, in October 2006, I started TheSimpleDollar.com on my own with no fanfare to share these experiences. Within two months, I had 100,000 visitors. Today, The Simple Dollar has nearly a million visitors a month and tens of thousands more who receive articles by email.

Along the way, I’ve had conversations with thousands of people who were struggling with questions like these in their own lives. I’ve heard countless stories of people digging through the challenging connections between their money, their happiness, their daily choices, and their mission in life.

I began to live my life as a laboratory for these ideas in many ways, and I shared these experiences with my readers. I tried countless methods of reducing my spending. I quit my job and devoted myself to writing full time, a truly scary endeavor. I bought a home, and then wondered if it was the right move after all. I had a second child.

And along the way, I learned some surprising lessons about our modern lives. Many of the rules that we use to live our lives are broken. They were written down many years ago to describe a way of living that no longer exists. Our grandparents couldn’t imagine the ability to share information via the Internet, the power of communication from nearly anywhere via cell phone, the ability to sell one’s ideas and products anywhere—and buy them from anywhere—thanks to globalization. Those are the realities of life today, and they’re rewriting more than just the rules of how we make friends and do business.

The most valuable investment today is not in the form of a dollar, but in the form of a relationship. All the income we need can come from a large set of healthy relationships.

Debt is a prison of our own choosing, and we’re enticed to enter that prison by the availability of a variety and quality of goods unimaginable fifty years ago.

Life is far more unpredictable than most of us think, and it gets more unpredictable all the time—and almost all planning ignores that key fact.

Saving for your child’s undergraduate education is almost useless because the value of a bachelor’s degree—and the methods we are using to get there—are changing radically.

Being a reliable employee is a path to the unemployment line—we’ve entered a new era where an employee-employer relationship is an exchange of a new kind of value.

Overspecialization is a dangerous trap. The route to the top relies on a Swiss army knife of transferable skills, regardless of your career path.

The American dream of a nice home of your own is just one card in a rigged game of three-card monte—and you have to pay a desperate price to play. Instead, there’s a much smarter way to find a place to live.

If these ideas intrigue you, keep reading. I’ll touch upon these ideas and many others—and share in detail how they work in my own life and in the lives of many other people—as we talk about change.

I’m going to start, though, with an area that hits home to far too many people and keeps them from even thinking about moving on and fulfilling their dreams.

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