Comfort Zone Challenges You’ll Be Glad You Tried

Here's a hodgepodge of challenges that your comfort zone definitely does not want you to read, but that are good for it in the long run.


By definition, comfort zone challenges aren’t “easy.” But just because they’re uncomfortable doesn’t mean they have to be dreadful or even unpleasant. I find that if you take on the right challenges with the right mindset—and, ideally, around the right people—they can be exciting and enjoyable.

I find it helps to keep things in perspective.

The goal of pushing yourself to do comfort challenges isn’t to brag about how hardcore you are, right? At least that’s not the main objective. The point is to do memorable things that improve our lives.

So I look for adventurous comfort zone challenges that expand my capabilities in the right way, score me fulfilling anti-regrets, and leave me wanting more.

Here’s a positively uncomfortable collection of ideas.

Organize A Gratitude Visit

Here’s how Eric Barker summarizes this challenge on his blog.:

  1. Schedule a time to get together with someone who has been good to you.
  2. Write a letter of gratitude to them in advance.
  3. Meet with them and read it out loud.

It’s that simple — and oh-so-powerful. People often cry. And they never forget it. Studies show the happiness boost you get from this can last up to three months. Now that’s some ROI. And the bonus is you get to make someone special very happy as well.

Go Silent for a Day

Take inspiration from this quote in Kate Murphy’s book, You’re Not Listening, from a lady who had to go six weeks without speaking after throat surgery:

“If you can bear to do it for just twenty-four hours, you will learn to be a better listener. You will learn the unimportance of our words and the importance of other people’s words.”

Talk to a Stranger on the Bus

Our brains are wired for survival and procreation, not fulfillment, and society is interested in itself, not you. So we often don’t know what’s good for us.

For example, if you had to take the subway to work, do you think your ride would be more pleasant if you kept to yourself, maybe reading a good book or listening to a good podcast, or if you talked to the stranger beside you?

The overwhelming majority of us prefer the former. But psychologists Nicholas Epley and Juliana Schroeder led a study that shows the opposite is true. Here’s an excerpt from the excellent book, The Good Life:

Before the ride, people overwhelmingly predicted that talking to someone they didn’t know would be a bad experience, and that keeping to themselves would be much better. They were forecasting what would make them happy, and what would make them miserable. The actual experience, however, was the opposite of what they expected.

So, for a satisfying comfort zone challenge, quit believing what your brain tells you and talk to a stranger.

The Coffee Challenge

Entrepreneur Noah Kagan is famous for this one. Here’s how he summarizes it in a blog post of 7 Challenges To Help You Start A Business:

All you’ve gotta do is walk into a coffee shop (or tea shop, or just next time you buy anything) and ask for 10% off your purchase.

And then just wait for a reaction.

Lie Down In Public for 30 Seconds

YouTube video

Honestly, I’m not a fan of this challenge because it can cause discomfort to innocent bystanders.

But maybe I’m in the minority. It seems so, based on the millions of views this video gets and the fact that Till Gross built a [now defunct] “Comfort Zone Crusher” community and app off of its success.

Empty Pocket Walk

Go for a walk with no devices on you aside from that annoying brain of yours. Ideally, do it in nature. Even as I write this, it seems too easy. But I tend to find excuses not to. Whenever I force myself, it never ceases to delight me.

PS: No, hiding your phone in your bag or in the pocket of your poodle’s cute little sweater doesn’t cut it. You need the physical distance from your devices for the challenge to count.

Read an Unusual Book

If you’re not a reader, any book will do.

Otherwise, find a book with good reviews that is most unlike what you normally read and about a subject that means nothing to you.

Your best bet is to go to a bookstore and ask someone who works there to surprise you. All the better if doing so makes you uncomfortable.

If you live in Antarctica, here are two random books I enjoyed way more than I thought I would:

Listen to Everything by a Musician You Dislike

Here’s the pitch from Mike Sowden’s “Everything Is Amazing” newsletter.

Music is a compounding educational experience, and sometimes, what sounds Utterly God-Awful is really a reflection of your ignorance of what it’s trying to achieve inside your ears.

So, by this admittedly controversial way of thinking, if you force yourself to listen to music you hate, it is quite possible that you will come to appreciate it in a new way. This will help teach you that nothing in life is 100% bad.

PS: I did something similar for a food I really disliked, black licorice. Here’s that story, if you’re interested.


Cold exposure is so hot right now in the self-help-o-sphere that I felt lukewarm about including it here. But it works. And it’s quick. So it belongs.

Choose your form of frigidness: an under-dressed winter walk, a shower, a plunge, or a stare from your mother-in-law.


Another suggestion that’s surely been shoved down your throat many times by now. But if you haven’t tried fasting for more than 24 hours, you’re in for a treat. My first-ever 3-day fast completely changed my relationship with food. (That post is also the most popular thing I’ve ever written.)

Max Steps

Wake up early, strap on a pair of comfortable shoes, pack a second pair of socks, recruit a friend, and walk and talk nonstop, all day.

In a recent “urban hike” around Vancouver with my dad and my friend, Dave, I set my all-time record with 56,973 steps. I could have done more (Dave kept going and broke 100,000!), but it was still a challenge that left me wanting more.

Climb a Mountain

Taste test with friends outside in the summer with one of our bucket list items, Mount Currie, behind us
Started from the bottom…
…now we’re here.

Mount Currie looms 2,500 meters or so over my parents’ farm in Pemberton, British Columbia. One day, my brother and our friend set off at 5:30 am to see what the view is like from the top. We returned just after 8 pm to enjoy a well-deserved beer in the hot tub.

Since then, every time I look at the mountain, I reminisce fondly about our adventure.

Go Wild for a Few Days

Spend three or more days where wild animals live, cell reception is gone, and there are no toilets.

It’s less comfortable than wherever you’re reading this now and will rewire your brain with what’s called the “3-day effect.” As I explained in that link telling the story of my own camping experience, the discomfort of the wild is the ultimate form of self-helping:

  • Exercise. Carrying a heavy pack over large distances, “rucking,” is maybe the most natural calorie-burning, muscle-strengthening type of training there is.
  • Stoic lessons. You’re reminded that even with very little, you’ll still be fine. More than fine.
  • Light exposure. When camping, you can’t avoid abiding by neuroscientist Andrew Huberman‘s number one well-being recommendation: get outdoor light exposure first thing in the morning and again during sunset.
  • Sleep. Not only did I sleep well, but I also slept long—up to 10 hours straight! Matthew Walker, author of Why We Sleep, one of the sledgehammer books that changed my thinking, would approve.
  • Social connection. Lots of time to talk with no distraction. Plus, when it’s your group against nature, it fosters a feeling of community—even tribalism. I recommend Tribe, by Sebastian Junger, for more on this.
  • Awe. The power, scale, and beauty of nature have a way of putting you in your place.
  • Cold exposure. Or heat exposure, depending on where you go. In our case, getting in and out of the river had us shivering.
  • Appreciation for the environment. After drinking from the stream for days, it was sad to see it merge with a river that I wouldn’t even want to swim in.
  • Diet. I’m not sure if a diet of dehydrated foods and nuts is ideal, but for many it’s probably better for them than the crap they usually stuff down their throats.)

Learn How to Tie Your Shoes Faster

As insubstantial as it may seem, learning this extra fast shoe-tying technique is one of my favorite personal challenges of the past year.

Here’s the video I learned from:

YouTube video

I did it as part of the “Adventure Calendar” I led in December (more on this below). The video makes it seem easy. Figuring it out and then practicing over and over until it felt natural took quite a while, though. Even now, eight months later, I get a teeny bit giddy every time I tie my shorts or shoes.

It’s fun! Sometimes I try to show off to others. They think it’s stupid. Their loss.

Hold Your Breath

Try it now! I won’t even take a minute.

How long did you go? How do you feel? You still with me?

Another breathtaking comfort zone challenge is CO2 tolerance training, which I learned about when I re-trained myself to nose-breathe:

  • Start with a normal breath out.
  • Pinch your nose and keep your mouth shut.
  • Walk as many paces as you feel comfortable.
  • Unpinch and breath at the point where you can return to steady breathing within two to three breaths. Start easy.
  • Continue walking for one or two minutes while breathing easily through your nose.
  • Repeat for a total of six breath holds, steadily increasing your number of paces each time.

Tape Your Mouth

As with the previous challenge, this exercise helped me re-condition myself to breathe from my nose instead of my mouth.

The first night was tough, uncomfortable, and weird. But, like with any challenge, your body adapts. I continue taping it every night, but now it’s not uncomfortable but comforting—a cue that it’s time to rest up.

30-Day Challenges

Here’s a wild list of ideas to stimulate your creativity in coming up with your own:

Try New Things

Here’s a fun list of things I tried that all left a lasting, positive mark on my life:

A Month of Challenges

Take on the Adventure Calendar Challenge to open up a surprise new comfort zone challenge every weekday for a month (20 in total):

Get Yourself a Custom Comfort Zone Challenge

It’s free.

Here’s how:

  1. Subscribe to my newsletter, “Consider This,” to get an original status quo challenging idea every week. (Easy. And you can unsubscribe right after if you want.)
  1. Respond to the questions in the automatic welcome email. (A bit harder.)
  2. Read the email that I guarantee to write back to you. (Easy breezy.)
  3. Do whatever I challenge you to do in that email or send an email back giving me a good excuse why not. (Hardest.)
About the author

👋 I'm Chris. Everything you read on is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

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The Zag shares my adventures off of the boring beaten paths of life and ideas for finding your own unfollowable path.