3 Lessons I Learned from Chasing My Dream

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A compass doesn't give directions. It only shows where your true both is located.

A compass doesn’t give directions. It only shows where your true north is.

After many years of working for someone else I decided I wanted to start my own business. I want to be an entrepreneur. There! I said it out loud. After traveling down that path for the past few years trying to hone in on what exactly I wanted to do, I’ve discovered a few things that might help you decide if you should venture down this path.

1. You will question everything you know.
At some point during this journey, you are going to question everything you think you know. It happens to me daily, sometimes hourly. You may think you understand your strengths, but you will question them. Some days you will question if you actually have any strengths. I don’t remember a time where I have ever felt as dumb as I have felt while I was chasing this elusive dream of mine. I’m spending time and money talking to much smarter people than myself only to feel like I’m getting nowhere.

2. You will be told you’re crazy.
Not just by total strangers, but by your family and friends. Well-meaning friends and family won’t understand what you are trying to do, especially if your dream involves non-traditional work, i.e. going to an office or place of work, working a set amount of hours and spending more time with your co-workers than your family. You will get more grief if you tell them you want to be an “er”, Blogger, Podcaster, writer, etc. This blows people’s minds, “How can you make a living at that?” “You need to be realistic!” Keep in mind these people want the best for you. Many times if they see you are serious and committed they will back off. Sometimes they won’t.

3. You will come face to face with your greatest fears.
Fear will overcome you. Tell you you aren’t good enough, smart enough or savvy enough to be successful. Fear creeps up on you and slides in unnoticed into your psyche and taunts you from different angles. It may be a whisper in the quiet while you try to build. It may be a shout from a door being slammed in your face setting you back in the process. Either way, Fear will come and find you, sit next to you and cast doubt on everything.

Despite all this fear and questioning, Here’s why you should try to start something anyways.


None of us want to look back and wonder why we didn’t start something. Seth Godin says, “Go make a ruckus.” I don’t want to ever regret not doing something I felt led to do.


If you have even a little inkling to start your own business or project do it! Regret is a powerful emotion that can haunt you. Wayne Gretzky said “You miss 100% of the shots you don’t take.” If your dream is to have your own food truck or start an Alpaca farm why not start now? Someone needs to read your short story. Write it!

Fear is special since it get a place on both parts of the list. Remember when you were a kid and you were scared there was a monster in your closet? I do. That extra dark place in a dark room where you were absolutely sure something horrible was waiting to get you. It wasn’t cute like Sulley from Monster’s Inc. either. You pulled the covers up over your head to be safe, but you didn’t move. With a little experience and courage, you eventually got up, walked over and proved to yourself it was only a shadow playing tricks with your overactive imagination. How great did you feel when you finally conquered the monster in the closet?

You owe it to your loved ones to be the best version of yourself you can be. That will most likely happen when you are happy with your life. Part of being happy is facing fear and powering past potential regret. Being content knowing you are doing what you are supposed to be doing makes you more fun to be around.


Tell Me…

What your dreams are in the comments.


  1 comment for “3 Lessons I Learned from Chasing My Dream

  1. October 16, 2015 at 9:42 am

    Way to own your dreams and you nailed it on the head. When you decide to do something different that othershe don’t understand they will not be sure how to support or be on board. Sometimes we just need to push past regrets punch fear in the nose and move on. Look forward to hearing more of your story. Dream chasing is scary ..

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