As parents, we want our kids to feel confident. So we encourage them. We tell them we’re proud of them. We remind them that they’re smart, capable, talented, funny, strong, and all the other things we genuinely see in them.
But there’s an uncomfortable truth about confidence: our kids can’t build all of it from what we tell them. At some point, they have to experience their own capability.
On this episode of Parenting Shrink Wrapped, Melissa and I talk with Jasmyne Chandler, a trauma-informed professional life coach for teens, young adults, and parents and the founder of Guided Passages. Her work raises a really interesting question for parents: Are we giving our teens enough opportunities to do hard things?
Confidence Comes From Experience
During our conversation, Jasmyne describes taking groups of teens on backpacking trips into the wilderness. The teens carry their gear, hike into camp, disconnect from their phones, participate in group councils, and, depending on their age, complete solo experiences that give them time to reflect on where they’ve been and who they’re becoming.
These experiences are intentionally challenging because there is something powerful about reaching the other side of something difficult and realizing, I did that. That’s different from Mom or Dad saying, “You can do it.” It’s evidence. And that evidence becomes part of how a teen sees themselves.
Teens Want to Be Taken Seriously
Another part of Jasmyne’s program involves sitting together in what she calls “council.” Everyone gets a chance to speak, everyone else listens, and the teens are asked questions many adults rarely stop to ask them.
What are you ready to leave behind? What do you want to step into? What has been holding you back? What matters to you?
Think about how unusual that can be for a teenager. Their lives are full of adults reminding them about homework, applications, schedules, chores, grades, practices, college, and what they need to do next. How often does someone simply sit down and say, Tell me who you are becoming?
Teenagers frequently tell us that adults don’t understand them or listen to them. Sometimes giving them a voice may be more important than having the perfect response.
The Things Teens Are Carrying
Jasmyne also talks about something much heavier that she sees among teens: self-hatred, comparison, judgment, the opinions of other people, and bullying themselves internally. And yes, social media can amplify all of it.
Melissa points out something we see all the time: many teens would never speak to a friend the way they speak to themselves. Some very successful kids can be especially vulnerable, too. Athletes, high achievers, and kids who seem to have everything together may learn to motivate themselves by being relentlessly critical.
From the outside, that can look like discipline. Inside, the soundtrack may sound very different.
Teenagers Are Supposed to Push Boundaries
There’s another important piece of this conversation. Teens naturally seek novelty, independence, status, and challenge. It’s the nature of adolescence.
The question becomes: Where do they get those experiences?
If we don’t give teens healthy ways to stretch themselves, they may create their own. Sometimes that looks harmless. Sometimes it looks like risky behavior, substances, dangerous stunts, destructive choices, or doing something simply because their friends dared them.
A meaningful challenge gives teenagers another way to say: I’m growing up. I can handle more. I did something difficult. I earned more responsibility.
You Don’t Need a Wilderness Trip
Thankfully, none of this means you need to book your teenager a 10-day backpacking expedition tomorrow. The bigger lesson is much more accessible.
Look for opportunities that allow your teen to stretch. Let them take responsibility for something that actually matters. Let them solve a problem before jumping in. Let them try something they aren’t sure they can do. Give them increasing freedom along with increasing responsibility. Mark important transitions instead of allowing them to quietly pass by. And ask deeper questions.
When they accomplish something difficult, don’t immediately move on to the next thing. Help them see it.
“You were nervous about doing that, and you did it anyway.”
“You figured that out on your own.”
“I noticed how you handled that.”
“You stuck with something that was really uncomfortable.”
That’s not empty praise. That’s helping them recognize their own growth.
Our Teens Need Opportunities to Become
We spend a lot of parenting energy protecting our kids from the hard stuff, and sometimes that’s exactly our job. But sometimes our job is to create a safe enough container for them to experience the hard stuff themselves.
Because eventually we aren’t raising children who need us to solve every problem. We’re raising adults.
And becoming one requires practice.
Listen to my full conversation with Jasmyne Chandler on Parenting Shrink Wrapped wherever you get your podcasts.

