8 Proven Steps to Winning Life’s Unfair Games

I just finished reading the book Moneyball: The Art of Winning an Unfair Game, and it’s a thought-provoking book. The book talks about how a baseball team with no money, Oakland A’s, could win so many games in the Big League. In a game where the rich teams had 4 times the amount of money available to the poor teams, only the rich teams could afford the best players and therefore won more games. But Oakland A’s was an anomaly; it had little money but won a lot of games. How come?

Here is how they did it: Oakland A’s found inefficiencies in the baseball market and tap into them. That allowed them to hire good players overlooked by other teams. Since the players were overlooked by other teams, they were cheap. And since they were good, they contributed a lot to the team’s performance.

How could they find such inefficiencies? There were two things they did:

  1. They questioned the conventional wisdom
    They took a skeptical look at the conventional wisdom in baseball about what contributed to winning. Through rigorous research done by them and some other parties, they found that the factors that actually contribute to winning is different from what most people think.
  2. They measure things differently
    Since they found different contributing factors to winning, they measured things differently. This is why they found inefficiencies in the market overlooked by other teams.

These give me some ideas to help us win “games”, especially the unfair ones, in life. Most likely you will find such games in your job, but you might also find them in other occassions.

Here are 8 steps to winning life’s unfair games:

1. Know the end result you want

Before anything else, you should know exactly what you want. This requires thought. In Oakland A’s case, their goal was to win as many games as possible, not to retain their stars. This was because they found that the fans would come to games when the team was winning, regardless of whether or not they had their stars with them. They then aligned their strategies with this goal. They often couldn’t afford to retain their stars, but they could find ways to win more games.

2. Ask yourself: what is the conventional wisdom?

Now you should ask yourself what the conventional wisdom says about how to achieve your goal. List them. This is what most people think you should do to achieve your goal, and this is what the majority of people are doing.

3. Question the conventional wisdom

This is not easy, but this is how you can find opportunities. Your best weapon is why. By asking why you may find that:

  • The conventional wisdom is unreasonable
    There is simply no evidence that it works. Most likely it became conventional wisdom because some people said so. In baseball for example, the way people count things can be traced back to a different game: cricket. Because the man who improved the box score in 1859 was familiar with cricket, he brought the ideas to baseball without thinking about whether or not that was the best way to count things in baseball.
  • The conventional wisdom is not the best way to achieve the goal
    The conventional wisdom might contribute something to achieve the goal, but there could be other more significant factors that are overlooked by other people.

4. Find the real contributing factors to achieving your goal

The goal of questioning the conventional wisdom is to find the real contributing factors to achieving your goal. The more different they are from the conventional wisdom, the bigger the opportunities you have. To avoid guessing, it will be better if you can find data to support your ideas. If that’s not possible, at least make sure that you use clear logic.

5. Determine the kind of stats you need

After you find some ideas in step 4, think about the kind of stats you need to test your assumptions and help you do things correctly. For now, don’t think about how to get the stats; you will worry about that later. Just think about the ideal stats you need.

6. Find the measurement tools

The next step is to find the tools you need to give the stats in step 5. Sometimes the tools are available, and sometimes they aren’t. If you can’t find the tools that exactly meet your needs, just find the best possible ones.

7. Measure what you do

The next obvious step is to measure what you do when you apply your ideas. As I said in step 5, measurement is important to make sure that your assumptions are correct and you do things correctly.

8. Adjust yourself accordingly

The measurement gives you the feedback you need to adjust your actions. This way you can do the right things better over time.


Applying these ideas is not easy. It’s far easier to just see what other people do and follow the crowd. But following the crowd is a sure way to be in the majority. If you want to be above the majority, you should see things differently.


  1. Great post! My husband just listened to Money Ball on a road trip and I love how you captured and reapplied Bean’s wisdom. Great concrete steps for how to think outside the box, too.


  2. Hey Donald. I haven’t read Money Ball but it sounds like a great book.

    I’ve always been a big believer on questioning conventional wisdom. When I set up my first personal training studio in Australia 25 years ago everyone told me it could not work. ‘Conventional wisdom’ said that it could never work.

    Twenty five years later as the owner of the largest personal training studio in the Southern Hemisphere I can tell you you must always question conventional wisdom.

    Great Post!


  3. Awesome post! I haven’t read Moneyball, but I love baseball (I’m actually a Red Sox fan), so I’m familiar with the basic concept of it (find players that contribute and cost less). This article seems like a great breakdown of all of that, but what I love most about it is that you applied sports concepts to life in general. Fabulous!

    I really enjoy this blog because 1) The articles are not overwhelmingly long, 2) They are easy to read and skim through, and most importantly 3) They discuss new and original ideas, or put creative spins on common articles.

    Please keep up the great work!

  4. Hi,
    I’m a Bay Area guy, so I have to correct the way you are phrasing the team’s name. It’s the Oakland A’s (not Oakland A). A’s stands for Athletics but in Baseball parlance they are referred to as the Oakland A’s. Sometimes sportscasters will refer to them as the Athletics or The A’s.

    Nice post. Sounds like an interesting book.



  5. Kristen,

    Great concrete steps for how to think outside the box, too.

    Thinking outside the box is what I learn the most from the book. What a coincidence that your husband just listened to Moneyball 🙂

    Yours is an amazing story! It must be very hard to fight against conventional wisdom, but you did it.

    Thanks for the encouragement! I try to apply whatever I read to my life, and with Moneyball, this post is the result. I will do my best to provide better value in future articles.

    I’ve fixed the post. Thanks for correcting me!

  6. I found that questioning the conventional wisdom is a common trait among a lot of successful people I met while touring the country to interview more than 80 highly successful individuals in conjunction with my soon to be released third book.

    For example, there was a doctor in Hawaii who, about 15 years ago, opened up a 24 hour medical care service that catered to the tourist trade. No one else had been doing that. It was a largely ignored part of the market. Needless to say, this doctor wound up making millions when he sold the practice later on.

    Your article was excellent. Keep it up.

    Take care

    Mr Positioning (Stanley F. Bronstein, Atty, CPA, Author and Professional Speaker)

  7. Donald, Moneyball is a good read, and you cut right to the chase about questioning conventional wisdom. I remember when one of the big weekly news mags started running a Conventional Wisdom sidebar early on in the magazine, saying whose fortunes were up or down. All you had to do was track that thing for a short while and it became evident that the CW doesn’t often know what it’s talking about. Conventional wisdom is the result of the herd following the leader and making the flawed assumption that the leader knows where he or she is headed. My gut tells me, and research supports, that wherever you find initiative, you are likely to find an individual stepping away from the crowd, stepping up, stepping forward, and walking towards an improbable possibility until it becomes probable and then inevitable. Only individuals can take the initiative to rely on their own wisdom, make a judgment call, fail forward and keep going, until enough is learned from the no answers to lead to a yes. If they do this persuasively, they can gain the support to make a positive change. Yes, everything is changing, but groups can’t take initiative, they can only follow it. That’s why, when it comes to changing anything for the better, the individual is what make’s the difference.
    Thanks for your interesting blog!

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  9. Stanley,
    It’s wonderful to know that your research confirm the importance of questioning conventional wisdom. Thanks for sharing it.

    There is a lot of wisdom in your comment.

    Conventional wisdom is the result of the herd following the leader and making the flawed assumption that the leader knows where he or she is headed.

    That’s a good analysis of where conventional wisdom comes from. There are indeed a lot people who just follow the leader without questioning whether or not the reader is right. The result is conventional wisdom. Great thoughts!

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