103 Best Comfort Zone Challenges In (2021)

8 min read

Behold my incredible list of 103 comfort zone challenges.

A comfort zone challenge is a great way to show yourself that nothing bad happens when you get out of your shell.

In my role as a certified life coach, I have worked with hundreds of people who have benefitted from diving into a comfort zone challenge. 

That’s why I’m excited to present this massive list of ways to step outside your comfort zone. 

Let’s dive right into it.

Why Is It Hard To Leave Your Comfort Zone?  

Your brain’s main goal is self-preservation. It just wants to keep you alive and comfortable, ideally while saving energy. It doesn’t care about anything else nearly as much. That explains why you’ll find it such a challenge to stab yourself in the eye. 

It’s also a reasonable explanation of why trying new things scares us. We have no reference of what will happen when we try something new, so our brain has no idea if it’s safe. Could it be a risk to your physical health? Could someone try and hurt you? The brain doesn’t know, so it sends your physical body into panic mode, also known as ‘fight or flight’ mode.

Notice how these sensations fade once we have gained mental references of completing a challenge. Once we’ve done something the first time, it’s not such a challenge to push ourselves to try it again.   

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But why is it such a struggle to try and leave our comfort zone socially? 

One of the most common ideas about this is that humans are historically tribal creatures. Back in caveman times, if we did anything to alienate ourselves from the tribe, we’d be outcast and that would mean certain death.

Supposedly, thousands of years in the future, the human DNA still makes us fear being socially outcast.

A simpler explanation is that social embarassment is uncomfortable, and our brain would prefer that we stay comfortable every hour of every day. 

Comfort Zone Challenges
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How Do You Challenge Your Comfort Zone? 

There are many ways to challenge your comfort zone. Here are some ideas that I have found to be effective. 

  • Find your ‘why’. When you have a strong enough ‘why’, you’ll find a how. Your ‘why’ could be that you’re sick and tired of being so shy and awkward around people. Whatever it is, write down in your phone and read it when you feel like giving up.  
  • Do your toughest challenges in the morning. Willpower is a finite resource that depletes throughout the day. So, you’re best off performing your toughest challenges in the morning. Wake up early if you have to. 
  • Get support from your friends. When your buddies are cheering you on, it feels less like you’re going to annoy the human ‘tribe’ by leaving your comfort zone. In fact, you’ll annoy your peers by not completing the challenge. Talk about a mental switcheroo!    
  • Dive in quickly. You can outthink your brain by diving into a comfort zone challenge without hesitation. Try counting backwards from five and doing the damn thing before you get to zero.
  • Build momentum. As mentioned above, leaving your comfort zone and escaping the inertia of your personal daily routine becomes easier the more you do it. So, why not create a 30 day challenge where you complete at least one task from the list below every day?         

How To Step Outside Your Comfort Zone: 103 Ideas

I did my best to put these comfort zone challenges in order of difficulty, although I’m sure everyone will have their own opinions as far as what challenges are harder.

Warm-Up Comfort Zone Exercises

In all likelihood, a lot of people drawn to this article are likely to be shy, introverted and socially uncomfortable anxiety sufferers. To these people, I recommend the following challenges to warm up. 

  1. Share this blog post with a buddy and ask if they want to spend the day helping you do as many of these challenges as possible.     
  2. Take a different route to work.
  3. Turn off your phone and treat yourself to a 24-hour digital detox. 
  4. Meditate for 20 minutes.
  5. Cook yourself a new foreign cuisine you’ve never had the courage to try. 
  6. Have lunch in public by yourself. See a movie by yourself. Or something else you’d usually feel too awkward to do alone 
  7. Commit to making eye contact with everyone you pass for a whole day. Make sure they break it first. 
  8. Go to a cafe and pay for someone else’s coffee.
  9. Dance to your favourite song in front of the mirror. 
  10. Stare at yourself in the mirror and talk for one minute straight about how awesome you are. 
  11. Take an ice cold shower! 
  12. Write all your thoughts and feelings in a journal. Don’t hold back. 
  13. Write down 50 things you love about yourself.
  14. Share something creative you made with your social media followers.
  15. Ask 10 people for directions.
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Trying New Things Comfort Zone Exercises

Trying something new is a big part of leaving our comfort zones. Indeed, many people fear taking even a small break from their day-to-day routine. The embarrassment of being a beginner is too much to take, which is a shame. After all, the only way you’ll ever find a new hobby or passion is to try a new one! 

  1. Sign up for local cooking classes.
  2. Take a dance lesson.
  3. Go camping, even if it’s only in your back garden.
  4. Go ziplining.
  5. Ride a bucking bull.
  6. Ask your significant other to take you on a surprise date. Have them lead you there with a blindfold. 
  7. Take an improv class
  8. Join a Toastmasters group to conquer your public speaking fears
  9. Go to a bar, and ask the server to make you a surprise cocktail.
  10. Take a day trip to that place you always wanted to go, but never made time for. 
  11. Travel alone somewhere.
  12. Sign up for a new fitness class (boxercise, bikram yoga, spin, Zumba etc) 

Intermediate Comfort Zone Exercises

Now you’re warmed up and you’ve taken a few steps outside of your comfort zone, try these challenges on for size.  

  1. Do a childish activity, something your inner child would love. Bonus points if it’s in public! 
  2. Tell someone your deepest darkest secret.
  3. Dress in your best outfit, go to a car dealership, and ask to test-drive the most expensive vehicle. 
  4. Walk around with a big sign revealing your favourite food. ‘I Love Burgers’, for example. 
  5. Go to a restaurant and order the biggest dessert only. 
  6. Ask your boss for a raise.
  7. Meditate in public.
  8. Practice bioenergetic exercises.
  9. Make a bucket list and share it online.
  10. Create a list of five things you would do if you weren’t afraid. Share it online.
  11. Buy post-it notes and start leaving random compliments for strangers. 
  12. Go to a restaurant and convince the staff to create something completely new for you.  
  13. Play a kinky game at home with your partner. Something to keep the relationship fresh 😉  
  14. Walk down the street and compliment the first 10 people you see.  
  15. Try the Singing With Strangers challenge. Find a stranger and ask them to sing with you on video. 
  16. Jump into a lake with your clothes on.
  17. Belt out your favourite song at karaoke.
  18. Buy an amazing outfit you’d normally think is too sexy for someone like you. 
  19. Hop on a social media live stream and talk about your passion for at least five minutes
  20. Ask someone for constructive criticism. 
  21. When you’re at a restaurant or a cafe, ask for something you don’t see on the menu.
  22. Make a social media post about your biggest insecurity. 
  23. Hire a professional photographer and arrange to have your photo taken in public.  
  24. Apply for a job that intimidates you.

Social Comfort Zone Exercises

A lot of people engage in comfort zone challenges so they can learn to be more socially free. These challenges will help you achieve that goal. 

  1. Say ‘good morning’ to everyone you pass on your way to work. Bonus points if it’s not the morning. 
  2. Give someone a spontaneous and creative gift without their input.
  3. Send someone a handwritten thank you letter in the mail. 
  4. Reach out to an old friend you haven’t spoken to for years. 
  5. Go to the library, ask the librarian what their favorite book is and rent it out.
  6. Volunteer for a day.
  7. Send five ‘Thank You’ cards to your best friends and hand-deliver it to them. 
  8. Invite a co-worker you don’t know well to lunch with you.
  9. When someone asks how you are, respond with, ‘Absolutely Positively Fantastic!’ Notice how it brightens their day. 
  10. Stand in public with a sign saying ‘Free Hugs’. Try and get at least five hugs. 
  11. Phone someone and apologise for something you did to hurt them in the past. 
  12. Phone your parents just to tell them how much you love them.
  13. Try and high five everyone as you leave a conversation. Don’t let them leave you hanging!
  14. Ask a stranger if you can tell them a joke. Then, tell it. 
  15. Ask that same stranger for their favourite joke.
  16. Next time you take public transport, ask if you can drive.
  17. Next time you’re at a supermarket, buy the cashier a chocolate bar.
  18. Give someone a bunch of flowers.
  19. Play the 36 Questions To Fall In Love with someone.
  20. Go for a walk in the park and commit to asking everyone you pass how their day is going.
  21. Call someone who hurt you in the past, and tell them exactly how they made you feel. 
  22. Arrange a public pillow fight with your personal friendship group. How about guys vs girls?! Bring spare pillows so passers-by can get involved.
  23. Create a social media post telling 20 of your distant contacts what you admire about them. 
  24. Bake some cookies and bring them to the old people’s home. 
  25. Ask someone ‘out of your league’ on a date.  
  26. Date someone who is normally your type. Give them a chance. 
  27. Ask people to donate to your favorite charity. 
  28. Call five of your closest companions and ask what their favorite memory of you is. Return the favor afterwards. 
  29. Arrange a silent disco in public with your friends. 
  30. When you’re at a restaurant or a cafe, ask the person behind what they recommend. 
  31. Buy breakfast for a homeless person. Better yet, take them out to eat breakfast together. Listen to their story.
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Embarrassing Comfort Zone Exercises

Comfort zone challenges can help us get over fear of embarrassment. This list of challenges might seem horrific ways to make a fool of yourself. But, in most cases, you’ll learn that people really don’t care what strangers are doing with their life. At most, they’ll stare at you for a couple of seconds. 

  1. Paint your nails an outrageous color. 
  2. Dance in public to your favourite song. Shake your body like never before!
  3. Go to a cafe and ask for someone to buy you a coffee! 
  4. Dance the waltz with a friend in public. 
  5. Ask a stranger to dance with you in public.  
  6. Drive around with the windows down, blasting Disney music at full volume.
  7. Step outside and talk to a lamppost for three minutes. Share your opinion on something. 
  8. Visit a thrift store with a companion. Buy each other an outrageous outfit to wear for the rest of the day. 
  9. Take an unflattering selfie and upload it as your social media profile photo for 24 hours. 
  10. Stare at someone through a restaurant window and watch them eat their food for one minute.  
  11. Buy a bottle of bubbles. Have your buddy blow them while you chase and pop them. 
  12. Grow an awful mustache. Keep it for at least a day.  
  13. Remember the terrible fancy dress outfit you wore to that costume party last time? Wear it all day. 
  14. Ask people for directions to the nearest sexual health clinic. 

Expert Comfort Zone Exercises

Perhaps you already consider yourself as a fearless social being. A master of personal development who never gets socially uncomfortable. Nothing scares you and you’re willing to try anything. Don’t worry, I have some comfort zone challenges that will surely push you to your limits too. 

  1. Busk in public. 
  2. Ask for a discount on everything you buy in a day. Maybe you can even get something for free. 
  3. Channel your inner ‘Yes Man’, by saying ‘yes’ to everything for a day.
  4. Spend a day making decisions based on the toss of a coin. 
  5. Lie on the sidewalk and stare at the sky for one minute.
  6. Go outside with one red paperclip and try to trade your way up to a free lunch.  
  7. Go to a bar or nightclub by yourself and try to make friends.  
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Any Questions About These Comfort Zone Exercises? 

I hope you enjoyed this article. Out of all the posts I’ve written, this was one of the most fun. 

If you’d like to ask a question, add more fun ideas to step outside of your comfort zone or mention anything related to escaping your comfort zone, feel free to leave a comment below. 

It’s always great to hear from people who read my blog posts. 

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