As many of you know, I suffer from some pretty serious mental illnesses. For instance, the other day I was attacked by bats in my house. There were no bats. This is a normal experience for me, and I function fine as long as I stay centered and don’t emotionally react too much.

Speaking of emotional reactions, in order to survive I’ve had to confront, analyze and understand my darkest, strangest and least admirable emotions. It has been difficult, often soul-crushing. And one of the things I’ve noticed is that “winning” and “losing” seems to matter a great deal, even with the most trivial things.

Playing video games is a great example. My father noticed this about me when I was a child, that I would get unbelievably aggravated if I failed to do well at a video game in the arcade. I just thought it was because I was young. But now, sometimes, while playing games on my phone, I notice that if I do poorly I literally start crying. It doesn’t happen often, but it does happen.

That’s how much of an emotional response is provoked by winning and losing.

At some point in my life, I decided to be ruthlessly honest with myself about my reactions to things that are really important. And I noticed some really awful truths about myself. Even when I do things that are clearly wrong, or are clearly mistakes, as long as I come out the “winner” in the interaction, it doesn’t bother me much.

In other words, even when I treat people badly, I don’t feel badly as long as I seem to win the personal conflict. Furthermore, I don’t remain angry with people unless I “lose” the personal conflict, even when they are outright abusive towards me.

At one time I tried to figure out how to change this aspect of myself. I asked myself, “how do I stop caring so much about winning and losing?” Then one day I realized that that was a terrible question. I will always be petty.

Here is a good question.

How can I change my emotional definition of winning?

I started asking this question after I learned that, when getting out of debt, it’s often best to pay off your smallest debts first. Why? Then you have a small victory to celebrate. And in celebrating that victory, you make further victories more likely.

I wondered if I could apply that concept to more of my life. I started celebrating all kinds of small victories if they moved me closer to being the sort of person I really want to be.

Any time I do any work on Spend Smart Live Rich, I celebrate. Any time I connect with someone who is sick, isolated, in jail, or just unhappy, I celebrate. Any time I act ethically in the face of temptation or peer pressure, I celebrate. Any time I do something healthy, like exercise, I celebrate.

You get the idea.

And when I say celebrate, I mean that, at least in my mind, I celebrate like people do in Vegas when they hit a jackpot. I celebrate like people do when the home team wins the super-bowl. Hey, in public, I can’t go too crazy, but I go crazy in my head. And in private? I go all-out.

Those constant celebrations eventually changed how I emotionally defined winning. And that changed the story I tell about myself, and thus, my identity. So now, when I do the right thing, when I defeat procrastination, I actually feel like a winner. And these personal battles happen far more often than interpersonal conflicts.

A recovering addict that I know posts on Facebook every little victory over her addiction. Every time the number of days that she’s been clean reaches any sort of a milestone, she posts about it and celebrates it. And she expects that her friends will too. Follow her example. What’s happening is that she is emotionally re-defining what it means to win.

So if you want to do a better job of saving money, then literally cheer yourself on every single time that you increase the level of your savings account. Want to get out of debt? Cheer yourself every single time the balance goes down.

Want to really get a hold of your finances? Go after what you really want. And pat yourself on the back every single time you take a defined step towards your real goals, no matter how small that step is.

The problem I had on the past is that I had emotionally defined winning as either big successes in the far off future that I could not control, or as dominance of other people.

But people who get dominated resent it. They want revenge. They aren’t going to help me get a promotion, or come over to advise me on how to fix my house so that I don’t waste 2,000 dollars on a contractor who doesn’t know what he’s doing. (Which one of my friends recently did, saving me tons of time and money.) Dominance may get me a temporary high, but it never moved me a single inch closer to financial independence.

And focusing on things I have no control over will, eventually, lead to misery. Even if, for a while, I make extraordinary progress towards my big far off goals, some day my luck’s going to run out. And when that happens, if my focus has been on things I cannot control, I will crash like a junkie coming down from a high.

This is to say nothing of the fact that “big successes” are so far in the future that I won’t get an emotional payoff soon enough to really change my identity anyway!

So the good news here is that you can use your pettiest impulses to achieve extraordinary goals. If you can successfully define winning as taking small steps to achieve the impossible, you will eventually start to feel compelled to do what’s necessary in much the same way that you are compelled by your Facebook addiction to check your notifications every 10 minutes.

You will find that you can’t help but do the right thing, just like I am standing here at my computer writing. I was going to quit but I can’t let it go. It is like an addiction, and that is wonderful. Yes, seriously, you can get addicted to doing the right thing.

Your emotions don’t always have your best interests in heart, in large part because many of them are still living in the world as it existed 10,000 years ago. But no matter how outdated, petty or small your emotions might seem, they can be harnessed to push you to overcome any obstacle.

The whole key is to celebrate small victories along the way. It’s those little day-to-day celebrations that will change your actual identity. The “big stuff”, the grand commitments, the high-flown speeches, they won’t really change you. They merely inspire you, and that’s not enough. Because inspiration is just another fleeting emotion that doesn’t stick around.


  1. We all make decisions with our emotions.
  2. Those emotions are often incredibly petty.
  3. The pettiness can usually be defined as “winning” and “losing”, in the crudest senses of those words.
  4. When you celebrate small victories on your path to change, you are changing what winning and losing means.
  5. Changing your emotional definition of winning and losing changes your unconscious choices and gets you addicted to a positive path of change.

(There is now a part 2 to this post. Check it out!)