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Technology and Trust: On Building the Relationship

“I’m a big believer in boredom…. All the [technology] stuff is wonderful, but having nothing to do can be wonderful, too.” Thought-provoking words from the man whose company produces one of the most powerful tools for distracting ourselves from any feelings of boredom. Not only Steve Jobs, but seventeenth-century French philosopher Blaise Pascal, too, understood the dangers of perpetual entertainment, the inability to sit alone in a room by oneself. 

Given the current cultural moment, a particular arena in which children—and, indeed, parents too—need to grow in self-mastery is that of screens and technology. This week on HeightsCast, we feature a talk given by Colin Gleason, head of lower school. First given at last Saturday’s Parenting Conference, this talk addresses how parents can foster the interior dispositions their sons will need to use technology well, and not to be used by it. He encourages parents to train their young sons in other arenas in order to prepare for healthy use of technology. Moreover, he speaks to the need for parents to model the virtues they’d like to see, and accompany their boys in a close and intimate relationship once they begin their digital journey.

Colin underscores that trust is not merely a result of but rather a means to achieving peace. If parents want their children to grow in virtue, they need to first trust that they can do so; for an intimate and personal relationship provides the proper culture for the growth of virtue. While external guardrails can be helpful and are at times necessary, in the end, virtue will be the best defense against evil and the strongest guarantee of the good.


  • 3:30 A common sense convention 
  • 6:30 Fostering internal guides
  • 9:20 Trust 
  • 10:25 Training
    • 11:45 Let him be hungry 
    • 15:35 Let him be bored 
    • 19:30 Let him stay outside 
  • 23:15 Modeling
    • 24:05 Detachment 
    • 25:15 Manners
  • 26:00 Establishing an intimate and personal relationship
    • 26:39 Freedom
    • 32:45 Ownership
    • 33:50 Learning from mistakes 
    • 34:20 Encouragement
    • 37:50 Trust  

Missed the conference but don’t want to miss out on the content? Check out the Freedom and Technology Collection

About the Guest

Colin Gleason

Head of Lower School, The Heights School

Colin Gleason serves as Head of the Lower School at The Heights, where he graduated in 1999. After college, he returned to his alma mater where he has taught a variety of classes: 3rd Grade Homeroom; Natural History; Chess; Storytelling; and currently, Moral Theology in the Upper School. He served four years as the Director of Admissions before taking on his current position as Head of the Lower School in 2010, overseeing his beloved Valley where he began as a student. Colin has also served as the Head Varsity Soccer Coach since 2010, and has been named Coach of the Year by the Washington Catholic Athletic Conference and All Met Coach of the Year by the Washington Post. During the summer, Colin directs The Heights Soccer Camp and The Dangerous Camp for Boys. He holds a Bachelor of Arts in Classics from Washington and Lee University and a Master of Liberal Arts from Johns Hopkins University. He and his wife, Nicole, and their five children live in Kensington.

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