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Cara Lai, MA

Cara Lai spent most of her life trying to figure out how to be happy—or at least avoid total misery—which ultimately led to her spending the majority of her adulthood meditating. She’s explored the wild beauty of the human experience through many adventures in consciousness, including long retreats, chronic illness, and the profound experiences of childbirth and motherhood.

Cara once worked as an artist, wilderness guide, social worker and psychotherapist, but traded it in for an all-out mindfulness rampage. She’s a working mom whose teaching is relatable, authentic, funny, sometimes crass, and accessible for many people. She teaches teens and adults at Spirit Rock, Insight Meditation Society, and Ten Percent Happier—ultimately hoping to get woke enough to bend spoons with her mind in front of large audiences. And to help everyone get totally free.

Upcoming Programs by Cara Lai, MA

An Undefended Heart: A Big Heart City Retreat (390R26) - On Land

Also Vinny Ferraro and Matthew Brensilver, PhD

December 6 - 11, 2026

Registration opens at 9:00am (Pacific Time) on October 7, 2025, and closes at 11:59pm (Pacific Time) on December 5, 2026. A waiting list will be created if the retreat fills early. Interested in Commuting to the retreat? - learn more below. In need of a scholarship? - see "Scholarship offerings" information below. Description This retreat […]

An Undefended Heart: A Big Heart City Retreat (390A26) - Self-Paced@Home/Online

Also Vinny Ferraro and Matthew Brensilver, PhD

December 6 - 11, 2026

Join Waitlist for On-Land Retreat Registration closes at 3:00pm (Pacific Time) on December 6, 2026. A waiting list will be created if the program fills early. Recordings* will be available for this program. We’re offering this retreat in two formats over the same dates. 1. On-land Residential Retreat: Learn more here - SOLD OUT 2. […]

Young Adult Insight Meditation Retreat (236R27) - On Land

Also Matthew Brensilver, PhD, Vinny Ferraro, Hakim Tafari and Fernmarie Rodriguez

June 14 - 18, 2027

Registration opens at 9:00am (Pacific Time) on July 15, 2026, and closes at 11:59pm (Pacific Time) on June 13, 2027. A waiting list will be created if the retreat fills early. Applying for a residential scholarship? - see our Financial Support FAQ's. Interested in Commuting to the retreat? - learn more below. Designed for young […]

The Family Retreat - Application 2027 (248R27)

Also Diana Winston, Ofosu Jones-Quartey and Ajahn Nyaniko

July 28 - August 1, 2027

Applications open at 9:00am (Pacific Time) on January 20, 2027, and close at 11:59pm (Pacific Time) on March 23, 2027. All applications received after this date will be wait listed. Admission for this retreat is by application and a lottery-style selection in order to maintain a diverse community of practitioners - see Selection Details below […]

Finding Freedom through Insight Meditation (252R27) - On Land

Also Brian Lesage and Matthew Brensilver, PhD

August 27 - September 1, 2027

Registration opens at 9:00am (Pacific Time) on September 2, 2026, and closes at 11:59pm (Pacific Time) on August 26, 2027. A waiting list will be created if the retreat fills early. Applying for a residential scholarship? - see our Financial Support FAQs. Interested in Commuting to the retreat? - learn more below. Description Insight Meditation […]

An Undefended Heart (286R27) - On Land

Also Vinny Ferraro and Matthew Brensilver, PhD

December 1 - 6, 2027

Registration opens at 9:00am (Pacific Time) on September 2, 2026, and closes at 11:59pm (Pacific Time) on November 30, 2027. A waiting list will be created if the retreat fills early. Applying for a residential scholarship? - see our Financial Support FAQs. Interested in Commuting to the retreat? - learn more below. Description This retreat […]

Liberation through Deep Rest (290R27) - On Land

Also Yong Oh and Matthew Brensilver, PhD

December 13 - 17, 2027

Registration opens at 9:00am (Pacific Time) on September 2, 2026, and closes at 11:59pm (Pacific Time) on December 12, 2027. A waiting list will be created if the retreat fills early. Applying for a residential scholarship? - see our Financial Support FAQs. Interested in Commuting to the retreat? - learn more below. Description The Buddha […]