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Until the Challenge section gets finished, below are a few resources on the subject.
The Town of Challenge Metaphor

Image | What it Represents |
---|---|
Entry by Bike | Representing a more choice-based entry in the ‘town of challenge.’ We decide we want to learn, grow, or face some personal milestone, and so we go there. |
The Forest | The often-gradual entry we make into the town of challenge. Frequently we stumble, slowly, into challenging situations. Such is life. |
The Gym | Exercise your challenge muscles, so they’re strong/capable when you need them. |
The Museum | Inspiration – Quotes, Videos, Songs, Books, Movies, etc. |
First Aid | Ouch, I’m experiencing some challenge! But, I don’t need a hospital. |
Therapy | My challenge is long-term, yet not in need of hospital-like treatment anymore. I could use some help working/being with my challenge(s). |
The Background: mountains/storms/boat | Challenge over a lifetime: perceptions of challenge can shift from difficult mountains, occasional storms and rough seas, to smooth waters, even with challenges on the boat. |
The Playground | Weeeee, let’s play with the ideas and experiences of challenge! |
The School | Learn about the science/nature of challenge as a concept. |
The Community Garden | Communal tending of our challenges/pain/sorrows. |
The Hospital | Oh no! My challenge is serious, and no simple and moderate level of help is going to be enough! It’s acute, and big, now! |
The Bike and the Crashing Airplane | How people get to the Town of Challenge: some seek it as a journey (bike), and some arrive unwillingly (plane crashing). |
Utilities Station and Pipes | On top of the mental/personal aspects of challenge, there are the structural elements that support or hinder one’s experience, built into every situation. These are the circumstantial elements that can create more or less challenge. |
Books
The Obstacle Is the Way by Ryan Holiday
A look through history at how some of the most successful people in history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—have applied stoicism to overcome difficult or even impossible situations.
What Doesn’t Kill You
A tour de force by a swath of authors on stories of exceptional challenges, across many spectra, and how people overcame them.
When Things Fall Apart by Pema Chodron
How can we live our lives when everything seems to fall apart—when we are continually overcome by fear, anxiety, and pain? The answer, Pema Chödrön suggests, might be just the opposite of what you expect.
Videos
Resilience from The School of Life
The route to greater resilience is to explore how well we would cope if so much of what we think we need were to be taken away from us. We would, almost certainly, manage far better than we think in our timid moments.
How the worst moments in our lives make us who we are
Writer Andrew Solomon has spent his career telling stories of the hardships of others. Now he turns inward, bringing us into a childhood of struggle, while also spinning tales of the courageous people he’s met in the years since. In a moving, heartfelt and at times downright funny talk, Solomon gives a powerful call to action to forge meaning from our biggest struggles.
What Do You Do With a Problem
Sometimes there is such clear and simple wisdom hidden in children’s books.
Here are some of the best sections to explore from around the site:
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- Communicate Skillfully - Listening, Compassionate Communication, Intentional Speech, Clean Communication
- Commune with Reality - Curiosity, Awe, Presence
- Show Up Wholeheartedly - Vulnerability, Social Comparison & Imposter Syndrome, Forgiveness, Self-Love, Self-Care
- Find the Right Work for You - The Bliss Map
- Get in the Mood to Think About Life - Earth in Context, Me In Time, Luck & Circumstance, Short Videos from around the web