Challenges to Take Your Life in Extraordinary Directions

A thought-provoking collection of challenges to shake up your status quo and take your life in extraordinary directions.


My goal with The Zag is to help you enjoy an extraordinary life by enthusiastically and persistently challenging your status quo.

Every ten(-ish) days, I share a new challenge in my “Consider This” newsletter.

But why wait?

Here’s a slew of complacency-crushing challenges.


  • 🏆 Top 10 most impactful in my life.
  • 👍 Strongly recommend.
  • ✍️ Story from my life.
  • 🥧 Easy as pie.
  • 🧠 Potential mindset shifter. 
  • 📖 Includes lessons from an excellent book. 
  • ♻︎ Habit challenge.


Before jumping into any challenge, consider these frameworks for taking on your status quo. They help you pick the right challenges and achieve the results you want. 

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Extraordinary Physical Health

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Extraordinary Relationships

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Extraordinary Adventures

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Extraordinary Learning

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Extraordinary Career & Finances

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Extraordinary Productivity

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Extraordinary Sense of Self

Take The Advent-ure Calendar Challenge

Like an advent calendar, except you get a surprise little challenge every weekday to jolt you out of complacency.

20 challenges. $20.

Fill your next month with adventure:

About the author

👋 I'm Chris. Everything you read on is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

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The Zag shares my adventures off of the boring beaten paths of life and ideas for finding your own unfollowable path.