Curiosity & Adventure Spiral

The Daring in a Jar Challenge

Dare to get off the couch!My Comfortable Life

Puffy recliner. Fleecy blanket. Steamy tea. Binge television. Glowing fireplace. I ache for cozy, lazy moments when my mind and body can sink into a fog of “relaxation.” I crave time to do nothing but feel snuggly.

Furniture, clothing, shoes, food, climate–when given a choice I lean toward luxurious, convenient contentment. Ahhh… soothing, so delightful. 

When I am most comfortable I feel deliciously numb. The pace of my life slows. Time becomes irrelevant. Just soft, warm, comfy “now-ness” reigns. On vacation or after times of big stress this is a blessing, but too much comfort during the rest of the year can slow down change, can blanket my other needs, can suffocate my life’s fizzle.

“The ultimate measure of a man is not where he stands in moments of comfort and convenience, but where he stands at times of challenge and controversy.” Martin Luther King, Jr.

Comfort is rest, not experience. I don’t want to be defined by comfort. I want my dash to be dazzling, engaged, and purposeful.

And while I’m thinking about comfort…

Comfort is something we look forward to rather than look back on. We don’t post many selfies of coziness and hazy relaxing on social media. We are wired for action, not streaming television. Our love of entertainment isn’t what makes us human, it’s our ability to think, feel, and do.

Our heroes don’t say: “Be the sleep that you wish to see in this world.” We are inspired by experience.

We can take some time for comfort every day, but it’s equally important to make time for daring. Live with intention.

Daring and Double Daring

Kids get it. I dare you to do a handstand. I double dare you to do a handstand and a somersault. Kids challenge themselves and each other just for fun. When did I stop daring myself and daring my friends?

I need more daring in my life so I created “Daring in a Jar” as a way to push myself off the couch, out of the house, away from my screens, and into engaged living.

I gathered some scissors, coloured paper, and an empty jar. I cut the paper into small pieces and started writing down (one item per piece) all the things I wanted to do but was too scared or lazy or distracted to get to. On orange paper I wrote 50 action items that ranged in difficulty from “wash the car” to “plan a road trip” to “cook an authentic Italian meal.” On red paper I wrote 15 major life goals that ranged from “pay off credit card” to “write a novel.”

Each month I will pull a handful of slips, 4 orange and 1 red. The idea is to do one action item (orange) a week and one learning focus (red) a month. If a slip has bad timing (for example, it may be difficult to go skiing in July) I can put it back in the jar. My goal is to complete all 50 orange slips and learn about at least 12 red slip items by August 2016.

In mid-July I pulled four orange:

  • Personally wash the car (and I mean really wash it inside and out without a car wash)
  • Keep a gratitude journal for a week
  • Ask someone for help (and choose something that makes me squirm)
  • Get a massage (amazing!)

And I pulled one red:

  • Be a good friend (so for a month I will reflect on and research how to be a good friend, examine my relationships to see how I can be more generous, think about what I need from my friends to feel fulfilled, and then try some new strategies out on my friends!)

“The best time to plant a tree was 20 years ago. The second best time is now.” Chinese Proverb

Daring in a JarCreate Your Own Daring

I shared my “Daring in a Jar” with some friends. We decided it would be fun to get together and help each other fill our jars with dares, just to be sure no one is too hard or too soft on themselves. Someone else mentioned it would be a fun project to take on as a family. Plan a Daring Party or have a Daring Dinner.

Whether you play alone or with others, dare yourself. Live your dares out loud. Tell people what you are doing. Share your fears. Embrace vulnerability. Laugh when you’re surprised. Celebrate every mountain.

…Let’s get off the couch and step away from the electronics!

“I dare you…”



  • Pat Skene

    This is such a great idea Jess! It makes us think about our lives, what we want to do and what we want to change. It’s like anything else, if you don’t make a plan, it’s not going to happen. For years now, my husband and I make sure we have one adventure a month. It’s kind of like a date, but with a bit of pizzazz. Something we wouldn’t ordinarily do, if we didn’t make the effort. It doesn’t have to be big, just something out of our routine and different. And after 38 years together, we still love exploring new things, even though we are now both physically limited in what we can do. Not very daring, but it works. Great post!

    • Jessica Outram

      Thanks! I’m very excited about this. What a great tradition you have! It’s so important to have pizzazz. How do you decide which adventure to choose each month? Sounds like some monthly daring to me!

  • Pamela Vanderburg

    What and amazing fun idea! Thinking I may do this long distance with my high school girlfriends. We are planning a reunion next summer and this is a fantastic beginning!

    • Jessica Outram

      Thanks, Pamela. I bet it would be great fun to do it long distance with friends. Fun thing to share and talk about too! You can bring everyone a jar with some blank sheets cut-up inside to help them get started!

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