“Many of our fears are tissue-paper-thin, and a single courageous step would carry us clear through them.”
 – Brendan Francis Behan, Irish writer

There’s a concept that best-selling author, entrepreneur, and my personal hero Tim Ferriss introduces in his book The 4-Hour Workweek called Comfort Challenges.

A Comfort Challenge is a physical or mental challenge intended to take you out of your comfort zone to face innate human fears. Fears like rejection, criticism, failure, or just plain feeling like an idiot.

I tend to refer to this trip through Europe as one big Comfort Challenge. Whether I’m awkwardly mumbling words in a foreign language, blatantly sticking out in a rural Polish village, or asking strangers to be part of a film project, I’ve been more uncomfortable than not. Even writing for this blog and opening up to you (and the rest of the world) with my thoughts and experiences is something that still makes me self-conscious and uncomfortable every week.

But I’m learning to find comfort in the uncomfortable. And I’m convinced more every day that challenging our comfort level and facing fears head-on are the key to success, reaching our biggest dreams and deepest desires, and leveling-up as an individual.

I’d like to share a recent comfort challenge I put myself through involving a date with a Serbian girl, hundreds of strangers in Belgrade, and the cold, hard ground.

A Really Uncomfortable Date

A couple weeks ago, I met a Serbian girl briefly one night at a bar. As she was leaving, I asked for her number so we could meet up sometime for a drink.

A few days later, we made plans to meet at 8:00pm in Belgrade’s Republic Square. After eventually finding each other, we start walking down the long pedestrian drag in central Belgrade.

Immediately, she tells me I’m not allowed to make fun of her bad English. This is funny to me because 1) her English is actually pretty good and 2) I’ve been fumbling my way through a handful of European languages like an idiot since June.

But she’s self-conscious that her English isn’t perfect. As we talk more, I understand what she means. She’ll sometimes use the wrong words, say words in the wrong order, or pronounce words slightly off, like saying “want” when she means to say “won’t”, as in:

“I want speak English if you laugh at me!”

In other words, the exact things that make foreign girls so frickin’ adorable when they talk.

Knowing how she feels, I instantly try and put her at ease. I tell her I don’t care how she sounds and I’ll help her learn. It’s impossible to learn unless you stop being afraid of failing and risk looking like a fool.

Belgrade’s Republic Square

At one point in mid-conversation, she trips over the sidewalk a bit, but quickly catches herself.

“Oh my God, if I fall I will be so embarrassed!” she says.

“Well, if you fall, I’ll fall on the ground with you so we can both be embarrassed.” I offered.

“Really? You’d do that?”

“Yep. Actually, let’s just get it over with and sit on the ground together right now.”

“Are you serious?!” she asks with a half-smile and sense of intrigue, wondering if I’d actually do it.

Without thinking, I grab her hand and pull her down to the ground with me so we’re both sitting in the middle of this busy pedestrian walk at night. Hundreds of people walking by confused or amused.

She’s laughing and looking around her. “I can’t believe we’re doing this! What if someone sees me!”

“Who cares? What will they do?” I challenge.

“People think I’m a serious person. They would never think I would do this.”

After sitting and talking for ten minutes on the ground, we stand back up. We walk further down the drag as I tell her about comfort challenges and facing fears. She asks about other comfort challenges we could do.

“How about laying down flat on the ground? It’d be similar, but more challenging than just sitting.” I suggest.

Again, she’s intrigued. “Really?! Should we do it?”

“Sure, why not?”

Again, without thinking, I grab her hand and move us toward the ground again. We crouch down hesitantly at first, but then hastily position ourselves side-by-side on the the cold stone. As we look upward to the black sky, I strain to see the faint stars competing with the lights of cafes and storefronts.

The cold, stone pedestrian walk in Belgrade, Serbia

Our eyes bounce around this new horizontal world —  the sky, the lights, the people, and each other. But we each quickly realize comfort isn’t found in the sky or the strangers or the lights. It’s found in each other and our shared uneasiness. Something magical has happened — we’ve transcended the typical uncomfortableness of staring into a stranger’s eyes.

And now we’re looking at each other, laughing uncontrollably. People walking by wonder if we’re okay. Several people stop and in Serbian, ask things like: Are you ok? Do you need anything? Do you need money? Maybe a blanket or a pillow? Do you want some milk?

Some people actually laugh with us. We stay on the ground for about ten minutes. In a weird way, we’re at home on the ground now. We talk about how scary it is to think about laying on the ground, but how that fear instantly fades into a dissipating uneasiness the moment you do it.

As soon as we get up, it’s obvious we’ve bonded through the minor suffering of a comfort challenge. And although we’ve only known each other for less than an hour, we’ve become as comfortable as close friends.

Eventually we decide to be civil and dip into a cafe for some tea. After a few hours in the cafe, it turns out I didn’t scare her too much and we made plans to see each other again.

The Fear-Facing Formula

The act of facing a fear or being uncomfortable is simple, but it’s not easy. In the situation above, I would’ve hardly been brave enough to lay down in the middle of Belgrade by myself. But because certain factors were in play, it happened.

Fortunately, when we have trouble convincing ourselves to face fears, I believe this formula will help:

Successfully Facing Fears = Accountability + Support + Deadline + Reward

After I told my date we would lay on the ground, I couldn’t back away without looking like a pansy.

Support. Misery loves company. And if we consider being uncomfortable a form of misery, then we’re more likely to do something if we have the support of friends or a sexy Serbian.

Deadline. The window of opportunity to lay on the ground presented itself immediately. If we made plans to lay on the ground the next day, it probably wouldn’t have happened. A short, firm deadline ensured it happened.

Reward. Having the two of us lay on the ground would produce one of two outcomes: I quickly scare this girl away, or draw her closer. The potential reward made it worth it.

And Now…A Physical Challenge!

I’d like to try an experiment. If the above situation intrigued you at all and you want to challenge your own comfort level, I hope you’ll join me in playing a game.

I’m launching a Comfort Challenge Contest. Using the formula above, here are the rules:

1. Accountability: Send me an email by Sunday, November 18 and tell me you’re in. I’ll hold you to it.

2. Support: To everyone playing, I’ll send a list of comfort challenges to pick from (but open to your ideas as well). AND…I’ll do the same comfort challenge as you (assuming I can do it from wherever I am).

3. Deadline: We both have 1 week to execute the comfort challenge. By Sunday, November 25 you’ll send me a summary of how you executed the comfort challenge, along with your thoughts. I’ll compile the list of completed comfort challenges.

4. Reward: The top three most uncomfortable or boldest acts (voted on by people on this email list) will get a free copy of Tim Ferriss’s new book The 4-Hour Chef, trailer below:

(Although I wish I was, I’m not affiliated with Tim for this promotion. I just think he puts out great stuff and want to support him.)

I hope you’ll join me in this challenge. Let’s become better together! Are you in?

UPDATE: To read about the bold acts by fellow readers, check out The Comfort Challenge-Challenge: Stories from the Trenches.


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