100 Things To Do Outside Your Comfort Zone

Face fear. Embrace risk. Your life, on your terms.

By Kendra

When was the last time you did something for the first time?

In 2013, my friend Ally and I committed to doing something new, something outside of our comfort zone or something that scared us everyday. (You can read more about that experience here).

The amount of response we got from this challenge was overwhelming. The number one thing we heard was, “I want to do that too but where should I start?” Ally and I put together this list to pass along to every person who asks us that. Most of these examples we thought of, but we also borrowed a few from the great brain of Google, and an awesome project similar to ours I stumbled on recently called the 52/52 project.

Bookmark this list, share it, tweet it, print it out and put it somewhere you’ll see it often.

I can tell you from a year of fear that crossing off items on this list will change your life, challenge you, and crank your awesome knob to 11.

Some are easy, some are obvious. Some are free, some require a few dollars. I wanted this list to be comprehensive with at least a few activities that anyone at any age, budget or location could partake in.

And please feel free to share with me any feedback from your experience via social networks or email (all my info is on the contact page). I would love to hear from you.

Have fun 
– Kendra & Ally

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The risks of breaking out of your comfort zone isn’t nearly as bad as the risks of staying in it your whole life.

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+ Take a new way home from work.

+ Have a midnight picnic.

+ Buy sidewalk chalk and leave positive messages in high traffic areas or your neighborhood.

+ Starbucks drive thru – pay for the coffee in the car behind you.

+ Approach someone who intimidates you and compliment them.

+ Slow dance on a rooftop (or somewhere epic).

+ Drive around, crank your favorite songs and have a dance off at stoplights to make strangers laugh.

+ Have a marshmallow eating contest with your best friend.

+ Go play Bingo. Get serious about it and talk some mad bingo smack.

+ Hug a stranger.

+ Go for a police ride along.

+ Rent a tandem bike with a friend.

+ Go to lunch by yourself.

+ Have a difficult conversation face to face instead of email/text/phone.

+ Buy coloring books, your favorite ice-cream, and invite the funniest person you know over.

+ Try a new coffee place in town or go somewhere new every time you go out to eat.

+ Take a new fitness class you’ve always wanted to try. Laugh at yourself when you suck.

+ Call your Mother just to tell her how much you love her.

+ Send someone flowers for no reason.

+ Go to a restaurant, order and eat dessert first.

+ Ask for a raise.

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If it scares you, it might be a good thing to try. – Seth Godin

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+ Write 5 thank you cards to your best friends and tell them why they mean so much to you. Send them old school via snail mail. #madfriendkarma

+ Have a dance off in front of your mirror.

+ Pull an all nighter when a fun opportunity arises instead of going home.

+ Go to a public pillow fight, or organize one with your friends.

+ Go to a thrift store with a $20 budget, dress your friend/significant other hilariously, and then go out to lunch in your new spunky outfits.

+ Hunt down a hilarious photo op.

+ Grab a pair of headphones and friend. Have a headphones dance off. Most ridiculous moves win.

+ Drive naked. *not responsible for any consequences or great stories that arise out of this 

+ Jump into a lake with your clothes on.

+ Lead your friend/significant other to a beautiful place blindfolded, bring picnic supplies.

+ Buy a bottle of bubbles, lay in the grass with a friend and blow bubbles while talking about your favorite childhood memories.

+ Lay on the 50 yard line of a football field at night and stargaze.

+ Go for a drive. When you get to an intersection, take turns deciding which way to go. GPS your way back home.

+ Go somewhere you shouldn’t be.

+ Night hike under the stars. Don’t forget the coco 

+ Go to your favorite book store, and leave notes in your favorites books for future readers.

+ Have an indoor camping night. Build a fort out of blankets and furniture. Cook s’mores in the microwave. Turn out all the lights in the house and only navigate with flashlights.

+ Dress to the nines. Go to a dealership, pretend to be married and drive swanky vehicles.

+ Walk around the city all night and find a place to eat breakfast at dawn.

+ Go to a restaurant, convince the cook to create something completely new for you.

+ Rent a movie you’ve never seen before. Mute it and improvise the dialogue.

+ Take a class you’ve always wanted to take.

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Don’t be afraid of your fears. They’re not there to scare you. They’re there to let you know that something is worth it. ― C. JoyBell C.

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+ Make a new recipe you’ve never tried before.

+ Email 5 of your closest friends, and ask them this. (Then return the favor)

•  If you had to deliver my eulogy and sum up what you would remember about me most in a few sentences, what would they be?
• What is your favorite memory of us?
• What advice do you think I need to know about life?

+ Get a Craniosacral massage. (That’s a head massage if you weren’t aware… I had to Google it too…thanks Ally!) 

+ Say no to something you don’t like to do but often do out of guilt.

+ Wake up early. Go for a walk at sunrise and cook yourself a huge breakfast. Just because.

+ Ask someone on a date who you think is out of your league.

+ Ride a bucking bull.

+ Two words: Naked Twister.

+ Buy a pack of sticky notes. Start anonymously leaving compliments around for friends, coworkers, lovers or strangers. (one of my favs!)

+ Eat a bug.

+ Go watch improv (or, if you’re a real badass, sign up for a class… most of the places offer the first for free)

+ Journal 20 Amazing Things You Bring To The World.

+ Fellas :: Grow a mustache, shave it hilariously & let it last for a day. Ladies :: paint your nails an outrageous color you wouldn’t be caught dead wearing. Keep it on for a day.

+ Eat somewhere out of your budget.

+ Attend a costume party, and go all out.

+ Date someone totally outside of your comfort zone.

+ Go zip lining.

+ Hire a photographer, and get head shots… just because.

+ Unplug from email, social media and your phone for 24 hrs.

+ Sing karaoke.

+ Make a fool of yourself on a dance floor in public.

+ Go all out on a bubble bath. Candles, music, and a dangerous amount of bubbles.

+ Take a day trip to somewhere you’ve always wanted to go.

+ Crash a wedding.

+ Make a free hugs sign, stand in a high traffic place and dish out some lovin’

+ Buy lunch for a homeless person, or better yet, take them out to lunch and hear their story.

+ Go spelunking. (Exploring caves)

+ Dining in the dark. Go somewhere that hosts an event or create your own for yourself/friends.

+ Go experience a gun range.

+ Train for a physical event.

+ Raise money for a charity.

+ Ditch your head and follow your heart for a decision.

+ Apply for jobs that intimidate you.

+ Stand up for yourself.

+ Ask for constructive criticism at work.

+ Try a new food (like a new fruit, or seaweed!)

+ Be vulnerable.

+ Invite a co-worker you don’t know well to lunch and get to know them better.

+ Be extra honest or playful with your partner in an intimate setting.

+ Do something spontaneous.

+ Act like a kid for a day – finger painting, coloring books, or going to the zoo.

+ Set up a tent and camp in your backyard.

+ Play hooky from work or school. Spend it doing something FUN or for yourself.

+ Dress up for no good reason, or wear something you normally wouldn’t.

+ Travel alone.

+ Ask someone on a date (brownie points if you’re a gal who does this)

+ Call an old friend it’s long overdue with // reconnect with someone from your past.

+ Give an HONEST opinion instead of a canned safe one.

+ Strike up a conversation with a stranger.

+ Spend a whole day answering the question, “How are you today?” with the response, “Outstanding! How are you?” (It’s more uncomfortable than you think).

+ Attend a Meetup group.

+ Go to a local shelter and walk the dogs

+ Bake some cookies for the old folks home.

+ Go for a ride on a motorcycle.

+ Pick your boyfriend up from the airport wearing a long jacket with nothing underneath 

+ Give online dating a chance.

+ When ordering a drink at a restaurant, tell the waiter to surprise you.

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