Do you want to do a monthly challenge but need some extra:

  • Motivation?
  • Structure?
  • Accountability?
  • Company?
  • Fun?

Then join me for a Month of Discomfort!

Month of discomfort calendar

You’ll get:

💻 Access to a private online group of fellow challengers

👨‍✈️ A dedicated team leader (me)

🔧 An “Anti-Failure Plan” structure to follow

🤝 An assigned accountability buddy

💡 Prompts, ideas, and inspiration throughout the month

🍾 A successful month challenge, guaranteed!

💵 All for only $30.

The Next One’s Soon

Get on the waiting list:

— Accountability —

Discomfort Loves Company

The Month of Discomfort turns up the peer pressure:

  • A private online group where everyone commits to their plan and shares their progress.
  • A leader to make sure you and everyone else is on track.
  • An assigned accountability buddy to keep each other

— Fun —

“Challenging” isn’t a synonym for unpleasant.

I’ll help you sprinkle your monthly challenge with little tweaks to make it more fun and less monotonous and boring.

And to keep things spicy, I’ll post regular prompts, ideas, and motivations on the community platform.

Chris headshot

— Leadership —

Call me Captain Discomfort.

Hey! I’m Chris.

I’ll be leading your Month of Discomfort and helping you succeed with prompts, pushes, and support.

And I’ll be participating in my own monthly challenge, too.

Challenge community screenshot

— Company —

Be part of our Circle.

The Month of Discomfort uses a private community platform called Circle for all announcements and group interaction.

It’s designed to facilitate and encourage interaction among us Discomfort-ers.

The only thing I dislike about it is the lack of mobile usability.

— Structure —

An “Anti-Failure Plan” will live up to its name.

The “Anti-Failure Plan” is a template based on my research on how to succeed at any 30-day challenge.

It’s optional, takes only about an hour to fill out, and not only increases your chances of succeeding at your 30-day challenge, but also makes it more impactful and memorable.

$30 to Participate

The best deal this side of buy-one-get-one free Dairy Queen Blizzards on your birthday.

And if you disagree…

100% Money-Back Guarantee

If at any point before, during, or after the month, you feel the Month of Discomfort isn’t doing it for you, let me know and I’ll give you a full refund with zero questions asked.

What Are You Waiting For?

If you can’t wait to join the next Month of Discomfort, leave your email to be the first to know.


Is the refund policy truly 100%, no questions asked, any time?


If at any point you feel like you’re not getting your money’s worth or need to drop out, all you have to do is email me saying, “Chris, I’m out. Can you please refund me?”

I’d appreciate it if you could help me learn and improve by elaborating on your reasons for requesting the refund. But if you rather not, I understand. I’ll refund you ASAP without asking questions.

Can you help me think of a monthly challenge?


First, look for inspiration within this list of crazy and creative monthly challenges.

Also think of different types of challenge you could do:

  • A project. E.g., publish your first YouTube video, declutter and clean your home, or teach yourself to knit.
  • A daily challenge. E.g., 30 straight days of yoga, trying something new every day, or performing an act of kindness every day.
  • A new skill. E.g., Learning to take better-looking photos with your phone or becoming an expert sourdough baker.
  • A theme. E.g., “In-Person November,” “Try New Things November,” “A Month of Discomfort.”

And if you’re still unsure, email me at

Do I need to do something every day of the month?

Not necessarily.

You decide what you need to do to make the month memorable and impactful.

For some 30-day challenges, e.g., no sugar/alcohol/podcasts, you’re probably best off making sure to do it every day. But for other challenges or projects, as long as you’re making continuous progress throughout the month, you may not need to.

How does the accountability buddy thing work?

When you sign up for a Month of Discomfort, I will ask you what level of interaction you want with your accountability buddy.

Based on your response, I will then pair you off with someone with a similar desired interaction level at the beginning of the month.

Every week, I will send you a reminder to check up on each other and discussion prompts to guide your interaction.

How much time should I expect to commit?
  • 2 to 3+ hours of preparation. To prepare for your month to remember, you’ll be asked to fine-tune your month challenge, fill out an anti-failure plan, prepare a physical calendar, and get acquainted with your accountability partner.
  • 30+ minutes per week of group participation. This includes interacting with the group and sharing your progress.
  • However much time your challenge takes. It could take zero extra time, as would be the case if you challenge yourself to read books instead of watch TV. Or it could take a lot of time if you target to do half-a-million steps in a month or write a thank you letter to 30 people in 30 days.

Still have questions? Email me at

Let’s get uncomfortable together.

Sign up to get notified of the next cohort.