Ch.1 Toolkit – The Chase – The Overachiever’s Dilemma Book

CH 1: The Chase


Why in the age of abundance, where most professionals experience more prosperity than at any other time in human history, are so many unsatisfied with their accomplishments? As an overachiever, at each stage of your life you’ve created ambitious goals and worked hard to achieve them. This chapter asks you to reflect on your life’s accomplishments and evaluate your satisfaction levels.


As an overachiever, at each stage in your life you set ambitious goals and worked hard to achieve them. This first exercise is designed to help you examine how you’ve enjoyed your efforts over the years.

Click here to download The Shift pdf.

First, fill out each column utilizing the following as a guideline:

  • Success – Reflect back on your life from middle school until today. During each period list an achievement that at the time you were absolutely certain would make you feel extremely successful.
    • For example:
      • Middle School – Make the football team
      • High School – Get accepted to Harvard
      • 22 – 30 Years – Earn $100,000+
      • 30 – 40 Years – Make partner
      • 40-50 Years – Buy a lake house
      • 50 + Years – Become CEO
  • Enjoyment – Next, take a guess at how long you remember actually enjoying the achievement before you recognized it wasn’t enough and needed to accomplish something else to truly feel successful. Was it a day, a week, a month?

Finally, list up to three goals you are striving to achieve today that you believe are the key to delivering your happiness and satisfaction.

Once this is complete, look back at this exercise and ask yourself the following question: “What am I actually working so hard to achieve?”

TED Talk

What Makes a Good Life? Lessons from the longest study on happiness


Creating your Own Definition: This will provide you with some questions near the middle of the page to help guide you in forming your own definition of success

9 Different Ways to Define Success: If you are struggling to find your own definition of success, here is a quick read to help. It consists of nine very “successful” people explaining how they see success.


CH 1  |  CH 2  |  CH 3  |  CH 4  |  CH 5  |  CH 6

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