The human brain likes to pick the easy, comfortable path. Unfortunately, this path often leads to poor outcomes and at best a mediocre life. The paths that provide the most growth are uncomfortable.

With this challenge, our goal is to train our brain out of choosing the easy path. Choosing discomfort will become our new default. We will become comfortable with discomfort.

Practicing discomfort in benign situations will strengthen our tolerance for discomfort. So that when we’re faced with a difficult decision in the future, discomfort is not a barrier to our decisions.

Challenge Examples

  • Lie on a busy sidewalk for 30 seconds.
  • Ask for 10% off your drink at a cafe.
  • Fast for a day.
  • Ask a cute guy or gal on a date.
  • Wear a Trump/Hillary/etc. hat to the wrong event. This is especially uncomfortable if you you don’t agree with the ideology of the hat you’re wearing or tend to stay away from politics.
  • Do standup at an open mic.
  • Take a cold shower.
  • Ask someone you admire professionally out to dinner.
  • Go to a networking event and only ask deep questions, no small talk.


  1. Do (at least) one thing every day for 30 days that challenges your comfort zone.
  2. Don’t tell people you’re doing the challenge in order to relieve the pressure of one of your challenges. For example, if your challenge is to wear an embarrassing shirt, don’t tell people you’re wearing it for the challenge as this relieves most of the discomfort and defeats the purpose. Use your judgement to decide when it’s appropriate to mention the challenge.
  3. If your challenges involves other people, it should be more uncomfortable for you than those around you. You should be in the vulnerable position not the other person.
  4. Do not skip days.
  5. You can break any of the rules to suit your needs. But make sure you’re breaking them for the right reasons. I’d recommend you set rules before you start and stick to them.

Discomfort is nothing to be afraid of. We’re not talking about pain. Just a little discomfort! Make sure you’re gauging your emotional and physical discomfort, picking challenges that will push you just enough. Too much and you may scare yourself from choosing the uncomfortable path again. Too little and you won’t gain anything.


Post your progress using the hashtag #30daysOfDiscomfort

Join the Discord chat group


Want ideas on what to do for your challenge? Check out the following resources: