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In 2003, my wife and I purchased a brand new townhome with all the trimmings. It was about 1250 square feet. I made six figures that year as an animal artist and soon we decided that our home was too small. In 2004 I jumped back into the business world and we built a brand-new home (a little more than twice the size). In 2006 we wanted something more, so we sold that home and bought an even nicer one in Alpine. It was one of the smaller houses in the area at just under 5000 square feet. It also appraised at well over half a million dollars. My monthly mortgage payment was $3800. I was 26 years old.

I more or less skipped college. For some reason, from a young age making money was easy for me. I found accomplishment almost everywhere I applied myself. I didn’t need college to make a good living.

My wife and I went on fantastic trips to different parts of the world. We had money to spend on all sorts of things. Gadgets. Décor. Furniture. Clothes. Cars.

And in the middle of it all, I became extremely entitled. I believed that the world owed me something because… well… I was awesome. What I didn’t know was that when you become entitled and you think you’re awesome, you always end up losing more than you’d ever imagine.


Believe me when I tell you that I lost a lot.

I wish I could go back in time, take that younger Dan Pearce by the shoulders, shake the hell out of him, and scream a few things to him about it all.

“Don’t worry about money now,” I’d tell him. “You’ll have your entire life to worry about money.”

He’d look at me like I was crazy. But that wouldn’t stop me.

“You will forever regret not going to school, no matter how successful you become. You’ve gotta believe me because right now you can’t see it.” I’m sure he’d snort at that. After all, he knew that he would never regret it. Not when he was making the kind of money he was. School was just a waste of time for him. “Please listen to me,” I’d continue. “School isn’t just about money. It’s about opportunity, options, and advantages in the future.”

At this point he’d probably tell me to get lost. The young Dan Pearce didn’t care much for anyone telling him he could do things better. After all. He was… awesome.

But how often do you get to go back in time and try to tell yourself important things? Not very often, so I’d keep going.

“Don’t become house poor. In two years you’re going to want to build something bigger. And in another two years you’ll buy a house that’s so expensive it will destroy many fragile parts of you and your marriage.”

Hopefully at this point I’ve grabbed his attention.

“Dan, you’re going to get divorced. Not just once, but twice.”

“That’s impossible,” he’d tell me. “I’m too successful for that.”

I’d put my hand on his shoulder. “Not only is it going to happen, it’s going to happen by the time you’re thirty if you don’t change some things right now.”

Hopefully he’d humble himself enough to ask me what those things were.


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Dan Pearce is an American born writer, photographer, and artist. His books include "The All-Important, Well-Fed, Giant White Man" and "The Real Dad Rules." He is best known for his blog (and supporting Facebook page) "Single Dad Laughing," with 2 million followers as of 2018.