The issue is, we’ve all got 10,000 year old brains. And 10,000 years ago, you were only going to know maybe 200 people over the course of you whole life. If you failed, got embarrassed or got rejected, people might gossip over it for…well, for who knows how long? Maybe forever.

So there is this fear of failure or rejection. And what we do to avoid that fear is tell ourselves stories, stories that we would have told “everyone” else 10,000 years ago. “Oh, that wasn’t really my best.” “Oh, I didn’t really care that much.” “Oh, that wasn’t really what I wanted.”

The final step is then we just never really go after what we truly want 100%, because by not really committing there is a built in excuse. We fantasize instead of doing because fantasy is the only place where we can completely avoid rejection or failure (that’s what procrastination is, by the way.)

We tell ourselves all these stories: “Oh, the timing isn’t right.” “I missed my chance.” “I just don’t feel like doing it today.” “Things could have been different if only…” “Oh, it’s too late to respond now.”

No sense in responding now.jpg
When you feel like it’s too late to respond now…

These stories allow our egos to avoid failure or embarrassment by avoiding ever really trying. But it adds up. And when I look back at how I used to live, what amazes me is that I used to spend most of my life pursuing what I didn’t really care about. Why? So that if I failed I could honestly say, “Well, I didn’t care that much, so it’s no big deal.” Who was I trying to convince?


Here’s a story about a young man in high school who is about to decide which girl to ask to the prom. One girl he is in love with. The other girl he merely likes. Which girl does he ask? He probably asks the girl he merely likes, because if she says no, it won’t hurt as much. That, in a nut-shell, is self-sabotage. And it’s time for you to stop giving into it.

Go after what you REALLY want. This is one of the most important, principles of effective personal finance. It might even be the most important principle in personal finance. If you can tell you are “spending on stupid”, then you are almost certainly self-sabotaging. And that self-sabotage of spending on fantasies won’t end until you start to go after what’s really, truly, deeply important to you.

And it’s different for everybody! It’s easier to just buy your kids something than it is to really try to spend time with them. And the really deep issue is that it’s easier to buy yourself something than it is to look for the love, acceptance, status or accomplishments that you really desire. So when you realize that you desperately need to exercise more, you buy a gym membership (which most people never use), or an exercise machine (the same), or maybe just a really nice outfit to work out in.

It's not the outfit holding you back.
Folks, it’s not the outfit holding you back.

Remember the high school boy and his prom date? If he is self-sabotaging, not only will he avoid asking the girl. He will be angry with whoever really did ask her out. That’s envy, but he probably won’t admit to himself that he’s envious. That would sting even more. Instead he’ll come up with all sorts of reasons to hate that guy. (“Oh look, what a hipster.” “Oh gosh, look at that shallow jock.” “Wow, what a nerd.”)

Or. More likely. He’ll find reasons to hate her.

Envy is the most insidious emotion.

We always know when we’re angry, when we’re happy, when we’re grieving. But envy? We’ve got all kinds of ways to pretend we’re not envious. Everything from self-righteous rationalizations to “sour grapes” excuses about how we don’t really want to become that sort of person anyway, when we look at whoever it is that is out there really doing what we want to do.

It’s so much easier, when you’re envious of other people, to try to buy things to “keep up” with them, than it is to actually keep up. And your brain is going to come up with all sorts of ways to tell you that you aren’t experiencing envy, because 10,000 years ago your place in the tribe was critical. Your social standing could determine whether you got a mate at all, and it definitely determined how much help you would get raising your children. Status was a matter of life or death. So you needed to have that status, which meant competing with others…but of course, you didn’t want to be too obvious about it. That could back-fire. Thus, envy. It’s an old and deep emotion.

Here is a widely reported truth about the human condition. Most people are happier making 80,000 dollars per year if everyone else around them is making 70,000, than they are making 90,000 dollars per year if everyone else is making 100,000. Numerous studies have shown that, controlling for all other factors, people are deeply unhappy if they live in a neighborhood where their neighbors make more money than they do. (Are you still sure you want to live in the most expensive house you can afford?)

No matter how beautiful, successful or extraordinary you are, there’s always some reason to envy.

But here is a less widely-reported truth. People who make 70,000 dollars in a year are vastly less likely to care what anyone else is making if last year they made 65,000 dollars. That feeling of forward progress is what stops envy in its tracks.

Go after what you REALLY want.

Envy, self-sabotage, procrastination and all these 10,000 year-old fears all have something very important in common. They keep us in the realm of fantasy–the only place where we can make genuine failure impossible. Now ask yourself. How much of your spending seemed like it would produce wonderful results when you were just sort of thinking about it, fantasizing about it? And what were the results in real life? Fantasy, properly used, is a method of relaxation and/or creativity. It is not necessarily a great guide for day-to-day action. Day-to-day action should be aimed at getting results.

Now, if only we were better at predicting those results…

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