Getting Comfortable With The Uncomfortable: 7 Simple Challenges to Try Today

A comfort challenge is the act of performing an uncomfortable task for the sole purpose of getting more comfortable with the uncomfortable. Comfort challenges are one of the best ways to stretch your comfort zone and live life the way you've always dreamed of living it.

I first learned the incredible benefits of comfort challenges in 2013 from Tim Ferriss, in his book, The Four Hour Workweek. One particular quote from Tim has stuck with me ever since:

“A person's success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.” -Tim Ferriss

According to Tim's metric, I was destined for a pretty underwhelming and unsuccessful life. Like most people, I had spent the majority of my life in comfort, surrounding myself with familiarity.

Since reading The Four Hour Workweek, I've made it a priority to intentionally put myself in uncomfortable situations. I started simple, by taking cold showers, telling uncomfortable jokes to strangers, and speaking in public. Eventually, I moved up to performing at open mic nights, laying down in public spaces while loudly singing the pop song of my choice, and approaching girls on the street to ask for their numbers. My grand finale was laying down in a crowded Starbucks to sing Rihanna's Love The Way You Lie. Comfort challenges allow me to see life through a new lens; they've shown me that the only person truly in charge of my life is myself.

If you want to one day get the courage to quit your job, travel the world, ask your dream partner out on a date, or simply live life more on the edge, practice comfort challenges. Here are seven simple comfort challenges, in ascending order of difficulty, that you can perform today.

1. Maintain Eye Contact

The next time you are in public, pick a stranger, and lock eyes with him or her. The initial response when your eyes meet will be to look away. This time, however, resist it. Maintain eye contact until he or she breaks it first. In the beginning, this will feel incredibly awkward and uncomfortable, but that’s the point!

2. Take a Cold Shower

Before doing anything else in the morning, jump right into a shower with the water set at the coldest possible temperature. The benefits of doing this are tremendous, and you’ll start your day feeling like a superhuman. Cold showers are great for your skin, hair, lungs, and brain. They can even help you shed a few pounds – your body uses a lot of energy to help keep you warm. For more on the benefits of taking cold showers, check out our post, The Mind-Blowing Benefits of Cold Showers.

3. Ask For a 10% Discount

The next time you pay for a coffee, ice cream, or tea, ask the cashier for a 10% discount off your purchase. Don’t give a reason, just ask. Although this seems easy, I've found that most people experience a lot of anxiety when they actually go out and attempt this task. Just remember, anxiety in this case is a good thing. It means that you are releasing some tension and expanding your comfort zone. The worst case scenario in doing this is that the cashier will say no and you’ll continue on with your day. The best case is that you get a 10% discount just for asking! If the cashier asks you why, just say: “No reason, I just felt like asking.”

4. Tell a Corny Joke to a Stranger

Pick a stranger on the street, go up to him, and tell him a short, corny joke. My favorite is this:

You: “Hey, what did the pony say when he had a sore throat?”
Stranger: "Uhh, what?“
You: "Sorry, I’m a little hoarse.”
Stranger laughs and gives you a high five.

It’s incredible to see the reaction on people's faces when you tell this little joke. This one comfort challenge can brighten someone else’s day.

Another good one I've used is to draw a line on a sheet of paper and give it to a girl on the street. When she asks what its for, say "oh, that's my pick-up line." It's incredibly awkward, but give it a try. Again, you're trying to put yourself in uncomfortable situations here; the goal isn't to pick up the girl.

5. Lay Down In Public

Once you get more comfortable with the easier challenges, give this one a try. Go to a crowded area, like a farmers market, and lay down on the floor for 10 seconds. Don’t say anything, and don’t make a big deal out of it. Just lay down for 10 seconds, get back up, and continue on with your day!

6. Ask a Stranger for His or Her Number

This one takes a lot of guts and is one of the hardest ones for me to do. I used to go to the mall three times a week for the sole purpose of approaching girls and asking for their numbers. Go up to a random girl on the street, or in a mall, and ask for her number. If you feel the urge to say something before asking, use this: “Hey, I saw you from across the room and thought you were really cute. I have to go meet my friends, but before I do, can I have your number?”

If you’re a girl, do this to a guy.

7. Sing a Song in Public

This one adds onto the previous challenge (#5) of laying down in public. The idea is to lay down in a crowded area, and sing a song for at least 10 seconds. The first time I did this was in a crowded Starbucks, and it was one of the hardest things I've ever done in my life. The feeling afterwards, however, was insane. In the moments after, I felt unstoppable, like I was on top of the world.

Wrap Up

If you are constantly battling social anxiety, try one of the comfort challenges listed above, and notice how the world opens up to you. Comfort challenges can provide an entirely new perspective on life. They’ve shown me that the only person truly in charge of my life is myself. Use comfort challenges to free yourself from the constraints of your mind, and to prove to yourself that you can have anything you want in life, if you are willing to go after it.

P.S. For a full recount of my first experience laying down in Starbucks and singing a song, check out this post: I Sat On The Floor of Starbucks And Sang a Song. Here's Why...