Leap Challenge Day 1: The Importance of Dreaming

LeadershipOne 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?

14 thoughts on “Leap Challenge Day 1: The Importance of Dreaming”

  1. I found it easier than I expected to come up with 50 (51 actually) dreams I have. It was somewhat refreshing as well. This may be because I’ve spent the last year developing a comprehensive Life Plan, so much of this is fresh in my mind continually.

    What did it reveal? I have audaciously big dreams! But I also have some dreams that are small, and surprisingly so. Yet they are extremely important to me.


    1. I ended up with 51 on my list as well, Jeff—although I wasn’t sure I was going to get there!

      I haven’t done this exercise in years—and not since getting married and having 3 kids. It was interesting how those life events have changed me (and my dreams).

      I too noted some very small—but extremely important—dreams. Thanks for sharing.

  2. The first 30 or so were fairly easy since I’ve already started a Lifetime Bucket List. The last 20 were hard, but I got creative knowing I can change the list. I learned that I have very few material needs and that my focus is certainly focusing more on the eternal.

    1. I had a similar experience. I ran up 25 without blinking an eye, then had to squeeze pretty hard for the next 25.

      Reviewing my list it looks like the first half was full of stuff that was near the surface, while the second half drew me deeper into more “eternal” dreams as well.

      Thanks Kari!

  3. This was very difficult. I learned what I already knew – I am a realist and tend to tie dreams to what I think I can achieve. So I stalled at 19 dreams. Struggled to 29. And then let fly with all kinds of things I may never achieve, but would certainly love to. That may be a breakthrough… on day one! :)

    1. I so loved your comment, Julie, thank you so much for sharing!

      Funny thing is, I’m not a realist at all and I found this surprisingly difficult this time around. As I mentioned earlier I haven’t done this exercise since getting married and having kids. It was interesting how things shifted.

  4. Hi everyone—

    Sorry for my delay in responding today, I’m still getting used to the new self-hosted blog (I didn’t get emails alerting me to comments and apparently I had to approve a few of them).

    Anyway, I’ll try to be more responsive in the future. Thanks for the participation today!

  5. I’m behind and just catching up here on this leap challenge.  Just started reading it yesterday.  So, I’m making my 50 list.  Was good to have categories to think through.  Does it matter if some of those categories have fewer things in them and some others are overflowing past 5?

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