Exercising Our Teens' Self-Reflection Muscles
How do we help our adolescents go deeper?
Beginning in June, I’ll start one of my favorite phases of the college planning process with my junior year clients: helping them with brainstorming and drafting their college essays. It’s often the thing that students fear the most, focused as they are on picking the “right” topic.
I have all kinds of practical tips and strategies for crafting a student-centered and compelling essay that doesn’t sound crowd-sourced and written by a group of 50-somethings, but that’s not the point of this newsletter. (Although, if you know of a student looking for essay support, they can check out my essay package in the consulting services I outline on my website.)
What students think is the hardest challenge, picking a topic, isn’t actually what shows up to be the issue. Where I find students struggling the most is with the self-reflection required to tell their most authentic story.
The first phase of my process with them is spent mining their lives for details about their values, interests, personal qualities, and skills. We talk about life experiences, large and small, and the communities that matter to them. We can usually identify these things with some accuracy, and then when I start asking the next questions, “What changed for you there? What do you think propels this interest? How do you relate to that community and how does it impact you? Why do you think that particular experience had such an effect? Why is this such a deep value for you?” they struggle to articulate their answers.
I don’t blame them. Most school assignments up until this point don’t ask students for this kind of deep dive, unless perhaps they’ve been in a creative writing class. And because a college essay feels like another class assignment, students approach it with a similar lens to a basic English class essay, but with the added pressure of the high stakes for college admission and some misconceptions of what they should write about. No wonder they freeze a little.
What I love about coaching students through this process is that with a little patience and some guidance, they start to understand how to ask the deeper questions of themselves and find a way to articulate their insights. I love helping them see the through lines in their lives, the people who have impacted them, why they hold the values they do, and what that means about their personal qualities and who they are becoming, so that they can share that with their readers. I feel so privileged to have students tell me their stories and, as the Quakers put it, let their lives speak.
But this self-reflection shouldn’t be something that only shows up in the college application season. Ideally, we’re engaging our kids at earlier ages and stages as they grow their capacities for abstract thinking, others-focused attention, and connecting the dots between diverse ideas. This is generally a good practice that helps our teens understand themselves and the world around them just a little bit better.
How do we do this? I’ve found it happens best with neutral, casual conversational invitations. Dr. Lisa Damour puts it this way: “All teenagers have two sides: a mature, broadminded side, and an immature, impulsive side. The side you speak to is usually the side that shows up to the conversation.”
You definitely don’t want to corner a surly teen and ask a bunch of scattershot questions about the meaning of life after you’ve blasted them for slamming their door.
A better way is to just be aware of when you can take an observation they make, an encounter they have, or even a news item, and solicit their input from a place of curiosity to know how they think. Then ask the next questions without an interrogative edge. “I’m curious how you see that,” “Tell me more about what you observed,” “I’d love your thoughts on this thing that I read,” “What would you advise me to do about this? Why?”
Our teens are way more thoughtful than we give them credit for, but they do need help to sift, frame, and understand themselves and their experiences. The more they can be encouraged to articulate these things out loud, the more self-knowledge they can build through that process and strengthen their communication and connections to others.
Our teens actually do like talking with their trusted adults—when we also show up to the conversation with our mature and broadminded side. There is a special magic that happens when your teen riffs and then goes deeper, and you can go along with them, stretching their capacity just a little bit more with thoughtful curiosity.

