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  • Rob Olsen

Why Didn’t I Think of That?

Updated: Nov 21, 2019



At age 43, my wife asked me a question that I should have asked myself at

age 23. It changed everything!


When I was 23, I was just finishing college, after attending 5 years. I had invested

a lot of my time and money while earning my teaching degree and taking the traditional safe route to my career. Like many people who took the traditional journey of seeking a career, I continued to set professional goals, achieve them, and check them off. I never once considered one of the most important questions that I could have ever been asked. (This is where the story about my wife asking me one of the most life changing questions comes in.)


The BIG Question

About 6 years ago, my wife returned from a company event that she was

so excited about. She couldn’t wait to tell me all about it and wished I

would’ve attended with her to share in the same experience she did. After hearing all

about the event, the speakers she listened to, and the great people she met,

she asked me the question that changed my thinking and my life forever.

What was the question she asked? She asked me, “What is your dream?” It

seems like such a simple question, but I would have to admit, I just sat there

with a blank look on my face and I had absolutely no response for her. This is the very

question I should have asked myself at the age of 23 or maybe even 13, but

neither myself or anyone else had ever asked me that question and frankly, I

had never even considered all of my possibilities (dreams) before applying,

being accepted, and attending a 4-year university. Have you ever been blind-

sided with a question like that?


From that point on, I began to think differently, I looked at the world differently,

I talked to people differently, and quite frankly I started to look at myself and

my career, at the time, differently. During this time of reflection and a shift in my

perspective, there were times when I got down on myself for not ever thinking

this way sooner. There were times I felt frustrated while at the same time I felt fortunate to have been given the opportunity to think differently. I felt envious of people who didn’t worry about Monday and no longer experienced that sinking feeling in their stomach when Sunday evenings rolled around. Have you ever felt that way?


We all know it is important to take time to reflect, so as I reflected on the

past few years and the process I went through to get where I am today, I was

able to identify 4 steps I took to explore my dreams and to start my

journey to fulfilling those dreams. In this post, I want to just focus on the 1st

step of the process I call 4 Steps to Fulfilling Your Dreams. In future posts, I

will uncover and dig deeper on the remaining steps listed below.


Step 1 – Ask yourself the question(s)

No one asked me the tough questions like,

  • What are your dreams?

  • What is your passion?

  • What is something you can see yourself doing the rest of your life?

  • Was I allowed to try something that was non-traditional or go into a career field that I didn’t know anything about? I feared what I didn’t know!


4 Steps to Fulfilling Your Dreams

Step 1 – Ask yourself the question(s)

Step 2 – Give yourself space to explore

Step 3 – Experiment with your ideas

Step 4 – Take massive action


In the comments below, share “Why might it be important to think about our

dreams . . . no matter what age we are?”



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