Why Tim Ferriss Wants You to Lie Down on the Sidewalk

Three Types of Comfort Challenges and How They’ll Change You for the Better

You’re lying down on the floor of a Starbucks. You can feel the hard floor. It’s a little bit sticky. You don’t move. People start to stare, thinking, “What is he doing?” You close your eyes, take a deep breath and hold the pose for 20 seconds. Then you get up and order a cup of coffee.

Why would you ever do this?

Tim Ferriss, the bestselling author and entrepreneur, recommends trying what he calls “Comfort Zone Challenges” for a number of different reasons. They can help you build confidence and also convince you that what might seem impossible at first is actually fully achievable.

But there’s an even stronger benefit.

Every wildly successful person has to take risks. Before Elon Musk was the startup hero we know him as today, he had to ask investors for funding to build rockets. People thought he was crazy.

If you want to do something truly innovative or exciting, you’ll get dragged down if you need outside validation along the way. Instead, it’s better to cultivate a mindset of just trying something, feeling optimistic and not worrying so much about how it looks to others.

Still, many of us are not going to walk outside right now and just lie down on the sidewalk. That’s OK. You can benefit from these exercises even if you try something just slightly outside your comfort zone.

Here are three different types of comfort challenges and how you can get started:

Interacting with Strangers

The four guys in Yes Theory make a living out of their uncomfortable interactions with strangers. On their popular YouTube channel, they’ve asked people on the street to get matching tattoos, asked billionaires if they could camp in their backyards and asked strangers if they’ll go on a blind date.

It makes me cringe just thinking about it!

Their YouTube channel has over 1.9 million subscribers. Most of the episodes end with the hosts feeling elated and surrounded by new friends. They talk excitedly about how they just had to push themselves and move the bar of what they thought was possible.

This is what the advanced level of a comfort challenge looks like. But before you start walking the streets and asking people for phone numbers, let’s start small. Think about your comfort level approaching strangers and then find a challenge just beyond that.

Level one: Random acts of connecting:

  • Tell someone on the subway that you like their shoes
  • Ask the delivery guy if he’s had a long day
  • Message someone you have a friend in common with and introduce yourself
  • At work, while your lunch heats up in the break room, chat with a new coworker instead of looking at your phone and sending memes

If any of this is slightly uncomfortable but makes you feel better afterwards, you are on the right track.

Trying Something New

Remember that MTV show “Made”? That was the best show. Average high school kids would start off awkward or uncoordinated and get “made” into something like a Latin Dancer, a Soccer Star or a Ladies Man. Almost every episode involves throwing up during a workout, getting a classic makeover and all the tears.

Ashly Perez, a very hilarious BuzzFeed contributor recently did a “Made”-style video called “I Learned How to Dance in 30 Days.” We see her practice body-rolling, buy heels for the first time ever, and perform for her coworkers. It’s all very endearing and inspirational.

It’s exciting to try something new when it goes against how we might see ourselves. For Ashly, she was fighting against the thought, “I’m the type of girl who is smart, but not beautiful or sexy.”

Pick a challenge that goes directly against how you see yourself. You’ll broaden the scope of what you think is possible.

One of the stories I tell about myself: “I’m a terrible driver.” Mostly because it’s true. The last time my friends let me drive, I got into a (minor) accident within 7 minutes. So I challenged myself to drive upstate. Three hours later, when I didn’t kill either myself or other people, I felt invincible.

Challenges to surprise yourself:

  • “I’m unathletic” — Try adventure sports like rock climbing, trapeze, or parkour
  • “I’m awkward” — Try dance classes like hip hop or tango or a sport like gymnastics
  • “I’m not funny” — Try improv or a comedy sketch writing class

Doing Something Alone

Why is it so hard to do something you enjoy by yourself? You might love brunch at a restaurant near your apartment but just the thought of going by yourself, sitting alone, and everyone watching you … is enough to make you stay at home.

Kate McCulley’s blog, Adventurous Kate, centers around traveling the world by yourself. She has tons of stories and general travel advice, but also focuses on tips for traveling solo, especially as a female.

One of my favorite tips of hers is something simple. When you’re out at a restaurant, hanging out by the pool or sitting in a lounge all alone, starting to feel awkward: order a glass of champagne. Why, you might ask? “Who is the kind of woman who goes and orders a glass of champagne for herself,” she writes, “on her own, assuming it’s not a wedding or New Year’s? A confident woman. A chic woman. A woman who enjoys the finer things in life.”

That’s the whole point of doing something alone. It’s not about pretending your girlfriend is on her way. It’s about taking something that makes you nervous, flipping it around and drawing newfound confidence from it.

Some things to try completely solo:

  • Volunteering
  • Seeing a movie
  • Eating out
  • Going to a party / event

What are 3 challenges you’d like to try in each category: Interacting with Strangers, Trying Something New, and Doing Something Alone?

Share this article with a friend and ask them to take on a challenge with you!