Choosing Failure. Why we make bad decisions and how to make better ones.

In my life, I have made a lot of good decisions. Decisions that I reflect back on, and I feel like a proud father watching his child take their first step. Like when I decided to go to the gym for the first time and embarrass myself doing bicep curls with 5lbs. There are other decisions that I look back on and cringe. Like the time I tried to shoplift 13 Cadbury Creme eggs from Safeway by shoving them up my sleeve.  

How can I be capable of such inspiring decisions and at the same time reach such incredibly foolish conclusions? Unfortunately, there isn’t really a way to become a better decision maker. Many of the outcomes of our decisions are, in many ways, just dumb luck.

 “We are prone to overestimate how much we understand about the world and to underestimate the role of chance in events.”
-Daniel Kahneman

There is a lot of research out there on this (see Thinking, Fast and Slow or The Drunkards Walk). Does this mean that there is no difference between choices? Obviously not. The choice not to steal those creme eggs was obviously much better. The point is that trying to make a better decision is much trickier than we think. I have found the key to maximizing the quality of the decisions I make, is by improving the state from which I make them.

In his New York Times article Why you will marry the wrong person, Alain de Botton aptly noted that,

“We make mistakes, too, because we are so lonely. No one can be in an optimal frame of mind to choose a partner when remaining single feels unbearable. We have to be wholly at peace with the prospect of many years of solitude in order to be appropriately picky; otherwise, we risk loving no longer being single rather more than we love the partner who spared us that fate.”

This is true of relationships, but also true in every other aspect of our life. To be able to make the right choice, we have to be ok with making the wrong choice or sometimes, making no choice at all. Looking back when I made bad decisions, to lie (about failing a class), to cheat (while in an amazing relationship), or to steal (from family); decisions so bad, that still today, I get an upwelling of disgust and self-hatred when I think of them. Each bad decision was made when I was in a bad place. Each time, my life was feeling dark and lonely. Those periods were all transitory, but at the time they felt permanent.

The effects of those decisions, however, were not passing. I will feel their consequences for the rest of my life. If I had been able to just wait, I probably would not have made those mistakes or at least not to the degree that I did. Many people view making better decisions as attempting to bring things into their life, be it ideas, resources, people etc. But sometimes the best decision is doing nothing and giving the bad stuff in your life, time and space to evaporate.

We get into bad relationships because we are unhappy being single and alone. This is the emotional equivalent of going grocery shopping while hungry. You are going to buy a lot of cookies and very little spinach. When you make a decision from a place of negativity, of insufficiency, regardless of your skill and practice, you are choosing failure.

Ok, so I shouldn’t be sad when I am single? But that’s what motivates me to find love!

Being motivated by deficiency will work in the short-term, but in the long-term, it will cause you to make bad decisions. This is why the best investors are often already wealthy, they are willing to lose. If you are gambling and you need to win, you have already lost. To begin to master your ability to make decisions there are a number of key principles that you need to accept and incorporate into your life.

  • Everything is always changing. Your mood, the weather, the economy and how much your girlfriend likes you. They are always in flux. Accept it and move on.
  • Life moves at different speeds. Your emotions can move very fast or very slowly. Ironically, the harder you try to escape an emotion, the longer it lingers. The harder you try to hold onto a feeling, the faster it fades.
  • There is no rush. There is no fire. Take a second. There is never enough time to do everything, but there is always enough time to do what matters.
  • Your immediate reaction is usually wrong. Especially, if shit is going wrong in your life. “Intuition cannot be trusted in the absence of stable regularities in the environment.” Move away from unconscious reactions and towards conscious responses.
  • The answer is to pause. Take a breath, count to ten, subtract 58 from 134, plan your dream vacation, picture your crush sitting on your face. Do whatever you need to do, but always pause. Let the better thoughts catch up with the shitty ones. The bigger the decision, the higher the consequences, the longer the pause should be.

“Anything that is important, that has long term consequences is a candidate for slow thinking.”
-Brian Tracy

I had a friend tell me about when her house almost burned down. Her sister in a panic grabbed some money and jewellery. These items, upon reflection, weren’t that important. Had she been given a week to make a list of 5 things she could save from the fire, I’m sure it would have been vastly different. (Autographed photo of the backstreet boys)

Humans can be trained to think well under pressure, but we will almost always think better when given extra time. So here is a step by step playbook for handling the next important decision you face. Hopefully, you can avoid explaining to your mom why you got arrested for stealing Cadbury creme eggs.

  1. Delay. Delay. Delay. Give every big decision at least a night. It’s Friday night, you’re at the bar and you’re a little tipsy. You see a cute girl is eyeing you up but you know your girlfriend is at home waiting for you. The longer you give yourself to think about that decision the more you are going to realize how quick the pleasure from that back alley hand job will fade and how shitty it is to pack all your gym gear into a cardboard box.
  2. Be honest with yourself. Be honest about why you are making the decisions and what you want from it. By identifying your motivations, you can better understand where you should go. You are not doing shots because it’s your friend’s sister’s aunt’s birthday, it’s probably because the cute barista told you that you look like a sad starfish. And trust me, the Cuervo definitely won’t help your marine scent.
  3. Don’t make decisions during periods of distress. Try to not make a decision when there are bad things going on in your life. I know this is hard because they often go hand in hand but, if at all possible, delay decisions until after a crisis has occurred. Once I had burned myself with coconut oil, and at that exact moment, my girlfriend called to make dinner plans. Let’s just say it wasn’t a positive interaction. Twenty minutes later when the pain subsided, my decision to yell at her for wanting macaroni, did not feel as reasoned.
  4. The outcomes of your decisions can’t make you happier. Accept that while you may make a better decision, making the better decision won’t make you any happier than if you had made the wrong decision. This might sound counterintuitive to the entire purpose of the article, so don’t overthink this, it could lead you down a strange path. It is just a paradox of life that the harder you try to be cool, the less cool you will be. Outcomes are out of your control and if you are unhappy making the decision, regardless of the outcome, it will not make you happy. The decision cannot convert you into something you are not. The more you focus on where you are at the moment of the decision the better, the more you focus on the success of the decision, the worse it will be.
    “Those who seek validation the least in life, are the most likely to get it.”
  5. Decisions are magnifying glasses for the state of your life. Decisions magnify whatever is going on in our life at that time, so if you are making bad decisions in one area, it’s probably a good idea to examine the other areas of your life. We all know if you spent all night putting out a fire because you got stoned and put an electric kettle on the stove-top, you are not going to make good decisions at work.
  6. Separate your identity from your decisions. You are going to make mistakes, that doesn’t make you a mistake. (If your parents didn’t mean to conceive you, that makes you a mistake). Don’t dwell on bad decisions. Try to understand where you went wrong, but don’t obsess. You are never going to be perfect. And your parents probably won’t ever figure out how to use condoms either.
  7. There is nothing wrong with trying to win the game, but never lose yourself in it. Life and everything in it is just a game. And if you take it too seriously, you might end up “2 and a half hours into a game of Monopoly, flipping the board and screaming “FUCK THIS GAME! It’s 4 in the morning grandma, YOU WIN!” Relax. In the words of someone brilliant; care less, live more. Life is a game, and our decisions represent our moves. But win or lose, never forget its still just a game.


Choose wisely.

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