Leap Challenge Day 1: The Importance of Dreaming
One of the most frustrating things for me growing up was the mixed messaging I received about dreams. My teachers and guidance counselors would tell me they wanted me to follow my dreams—but they never looked favorably on all the daydreaming I did.
I think we face those same mixed messages as adults. The world of grown-ups plays lip service to the idea of dreams, but always errs on the side of being “practical”. Maybe it’s the weight of all the broken dreams we’ve accumulated. Maybe it’s the perception that as we grow older our opportunities seem to shrink exponentially.
Whatever the reason for it, our lack of dreaming is killing us. Dreams are what move us and keep us moving. They direct us and give us hope. When we stop dreaming, we lose something that makes us essentially human—we cease living and start settling.
So, your task for today is to dream.
Leap Task #1: Write down 50 dreams in your Leap Journal (a physical notebook or document on your computer where you’ll record and store all your Leap Challenge outputs). Not what you dreamt last night, I want you to right down your wildest—and not so wildest—aims, goals, and aspirations.
I understand 50 may seem daunting to some—and downright impossible to others. So I’ve provided some tips below to help you out. If they help, great. If you don’t want to use them, no problem. Just write down 50 of your dreams by the end of the day. These are just some ideas to prime the pump:
- Write these “dream categories” down in your Leap Journal: Educational, Physical, Relational, Spiritual, Financial, Professional, Material, Family, Adventure, Community. There are 10 categories, so you only have to come up with 5 dreams in each and you’ll have your 50. Don’t like those categories? think up your own.
- Answer these questions: If someone showed up and gave you all the money you ever wanted, what would you do? When you were a child, what did you want to be when you grew up? What kind of legacy do want to leave when you’re gone?
- What are you passionate about? What are you really good at? What does the world need? Find the intersection of those three things and I guarantee you’ll find some big dreams.
Was it easy or hard to come up with 50? What did the list (or the exercise) reveal to you about yourself?

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