My long, strange relationship with money

We moved here when I was five years old

Money and I have always had an odd relationship.

After all, how is it that I, your humble host, have come so far as to wind up writing a blog about my attempt to reach pretirement?

While I’ve had some good luck, some bad luck, learned from a lot of mistakes and was smart enough to make adjustments when needed, the real reason I’m here isn’t really any of those. I had one thing on my side that has been with me through it all: I have always been well-grounded in what life is really about. I never fell in love with money.

We moved to a little family farm when I was five years old, leaving behind a suburban rental house. I guess my parents were excited to be back-to-the-landers, something that was in vogue at the time and seems to come back into fad with every bad economy. Dad worked at the local plant and spent all his free time fixing the shack of a house. One year we had two feet of snow in our kitchen. Mom was a housewife and eventually sold Avon (leaving me in the backseat during sales calls).

My first memory of money of any kind came with the fifty-cent pieces my grandma would tuck into birthday cards. It sure felt like a lot of money! But since there was nothing for me to spend it on, it was irrelevant.

Money began to take on real meaning when the local convenience store put in an Asteroids and a Centipede game. Ah, so the more quarters I find, the more fun I can have! The money hoarding began in earnest. Quarters mysteriously disappeared from my parent’s change jar.

When my parents finally divorced, we went from poor to dirt poor. Mom was trying to make it as a real estate agent, just as things were collapsing. She waited tables at a local diner in the evening to make ends meet. We ate government cheese (not recommended!).

A whole other aspect of money struck me when I took my first official “job” at 14 years old, cleaning the gym at school, including the nasty locker rooms. That’s when I realized that, “THIS SUCKS!”

My mother was relatively savvy with money, but still never reached any level of financial independence. My father always wanted to be rich and so spent himself into deep debt many times trying to keep up with the Jones’s. I’ve lost track of how many times he went bankrupt, but I’m sure it’s at least four.

In my teens, I was probably rebelling against his mindset by deciding chasing dollars wasn’t for me. Naturally I went too far to the other extreme and almost intentionally chose a life of poverty. I was happiest when everything I owned fit in my car. And I was never uncomfortable. I gradually made more money, but the more I made, the more I spent. Fortunately I did learn from some teachers and others and never had any debt.

I always knew I would go to college, but I had no idea how it would be possible. When my dad moved to California, I went along since it was more of an adventure than staying where I had been with my old friends and also college is much cheaper there. Aside from those first few years where I lived with him, I put myself through college with no help from my parents otherwise.

Writing was the only thing I was really good at and enjoyed doing so I chose a career in journalism. It went fine, although advancement was nearly impossible as newspapers were shedding jobs rapidly. So at age 29, it finally hit me that it was a dead-end. I moved into marketing, nearly doubling my salary (from nearly nothing to almost twice that) and finally leaving the poverty line behind.

But then, suddenly I found myself strapped to a roller coaster.

Timing is everything sometimes. Just as I moved into marketing, the dotcom boom went off. I went from one dotcom to another (literally laid off from one on the day that was to be my final interview at another). Well next thing you know, hundreds of thousands in stock options were coming my way. My cube-mates and I would giggle to ourselves as we ended days $50,000 richer than we started them.

As you might guess, I screwed that up, too. Well, maybe screwed up is too strong, I did much better than many and worse than some. It benefited me greatly and I would not be writing here today without that money. However, had I understood then what I know now I would be looking at retirement, not pretirement and I could have reached pretirement without that money (and so can you!). And that’s why I feel I can contribute to the pretirement discussion.

Anyway, when the money started to roll in, I read up on investing and listened to all sorts of experts. My best move, it seemed, was real estate. Now you might assume after reading this section that the next thing to happen was I lost it all. Fortunately, no. I actually did quite well. But I could have done much better. And I committed two mortal sins I didn’t know I was committing at the time: I over-improved my properties and I used principal to do it. But I made money, too.

The great recession cost me hundreds of thousands of theoretical dollars but fortunately I always remained solvent and above water on equity. I was even making nice money from rent when many were being turned out of their homes!

I finally settled down, got married and we bought a larger house with a view of the water. I sold the house I owned before I met my wife and used that money to pay off my half of our house. We also added to our family last year so now I have college funds to think about.

Now I’m a stay-at-home dad and I do consulting to cover my remaining bills. I’m not yet financially independent but I’m close. I’ve learned so much on my journey. I’m looking forward to sharing some of what I’ve learned and a little about my next few steps as well. Hopefully I can avoid too many more big mistakes in the future. After all, I’ve already made enough mistakes for a lifetime.