Learn About Wisdom

Here you’ll find everything you need to go deeper on your Wisdom journey. Learn about Wisdom teaching and Wisdom Schools. Explore online courses and book study groups, and browse through a treasure chest of books, video, and audio resources.

Go Deeper On Your Wisdom Journey


An essential reading list for serious wisdom students including books by Cynthia and others.

Online Courses

Browse our growing archive of online courses by Cynthia and soon-to-be-others in the Wisdom School community.


Browse our growing archive of teaching talks and audio files by Cynthia and others in the Wisdom School Community.

Video and Podcasts

Watch and listen to our growing collection of videos and podcasts by Cynthia and others in the Wisdom community.

Wisdom isn’t knowing more …
It’s knowing with more of you.

Come to Wisdom School

Wisdom Schools are our signature integral learning experience here at Wisdom Waypoints and a unique opportunity to put all the pieces together. Stimulating teaching, sparkling conversation, contemplative prayer, and conscious practical work, all anchored in the ancient Benedictine rhythm of ora et labora, “pray and work.”  On-the-ground Wisdom schools typically last just under a week and are offered in various locales around the world. Online Wisdom schools are offered several times a year, right here on this website. Here’s your chance to integrate theory and practice and make some new best friends in the process!  

Go on a Retreat

Retreats are a more traditional Christian format, featuring silence, contemplative worship, and spacious unscheduled time for personal prayer and reflection. You can leave your work gloves at home (although you may want to being your yoga mat, since most retreats offer daily opportunities for gentle embodiment practice.) Wisdom Waypoints retreats come in two flavors: immersion retreats, where the focus is on deepening spiritual practice, and teaching retreats, where the focus is on exploring a spiritual text or topic in a quiet, contemplative way. 

Wisdom to Ponder

“If you seek Wisdom in the first place, you will find that Wisdom is joyous. If you seek the joy of Wisdom in the first place, you will fall prey to illusions.”  

~ Valentin Tomberg, Meditations on the Tarot

Join a Book Circle

Wisdom Waypoints has launched a two-year, four-book Foundational Wisdom Practice Book Circle Series that includes: The Wisdom Way of Knowing, Mystical Hope, The Wisdom Jesus, and Centering Prayer and Inner Awakening. These Wisdom books engage learners in the foundational teaching of our Wisdom lineage.

Ask Cynthia

Ever had a question you wanted to ask Cynthia? Here’s your chance.

Here’s one question Cynthia answered from one of her Wisdom Schools: “What does inner awakening look or feel like from the inside? Can it be seen from the outside?”

Work in Progress

Civics for Wisdom Students

In response to the ongoing political turmoil in the United States and around the world, Wisdom Waypoints launched a major initiative in fall 2020 to bring a Wisdom perspective to the impasse. Drawing on our own Wisdom network of seasoned lawyers, policy makers, and educators, we are in the process of developing a whole new curriculum for teaching and skillful action. Stay tuned! 

Wisdom for Kids

Kids take to wisdom like ducklings take to water because it fits their learning style: embodied, practical, creative, open-ended. Work is underway to collect a series of Wisdom resources (chants, activities, teachings) that are authentic and kid-appropriate. You are welcome to join this work.

Search Wisdom Resources

Search our growing archive of curated Wisdom Resources by any search phrase, category, type, tag, author, series or source.