The Adults Outside the Classroom
Some of the most powerful learning experiences in a young person's life happen outside school — led by parents, mentors, coaches, and community members who care.
What teachers can't do — and you can
Teachers do essential work. Every day they show up for classrooms full of young people with different needs, different backgrounds, and different starting points. They do this under institutional constraints, with limited time, and without the luxury of designing each experience specifically for each student.
But the adults in a young person's life — parents, mentors, coaches, family friends — have something teachers often don't: time, context, and a personal relationship.
You can design experiences that connect directly to who this specific young person is, what they care about, and where they're headed. You can choose the timing. You can make it a family experience. You can be in the room when the learning happens and stay in the relationship long after.
That's not a small thing. Some of the most formative moments in a person's life came from an adult outside of school who took the time to design an experience, ask a good question, or tell a story that stuck.
"What do you actually care about?" is different from "What do you want to study?"
You don't need a curriculum or a lesson plan. You need a good moment and a good question.
You know this young person. You can help them see how their experiences connect to who they're becoming.
Your story — the real one, from your own high school years — is your most powerful teaching tool.
Reflection → Story → Vision
This is a simple framework for a retreat, a weekend afternoon, or a long car ride. Three steps. One unforgettable conversation.
Reflect on what shaped you
Start here. Before the stories, before the vision — make room for reflection. Ask the young person questions that go deeper than the obvious answers.
- What experiences in your life so far have meant the most to you?
- What challenges have you taken on that surprised you?
- What did you figure out about yourself — that you didn't know before?
- What did you create, build, or do that you're still proud of?
Give them time to really think. Not just the obvious answers — the ones that come after a long pause. Those are the ones that matter.
Tell the story
Ask the young person to tell one of those stories in full — not a summary, but the actual story. What was the challenge? What did they do? What happened? What surprised them?
Then — and this is the most important part — the adults in the room do the same.
When a 45-year-old tells a story from their high school years — a real one, with stakes and uncertainty and an outcome that wasn't guaranteed — it shows a teenager something important: those experiences don't disappear. They compound. They become who you are. The adult in the room isn't a finished product — they're a longer version of the same story the teenager is in the middle of.
Create a vision
Now, use what emerged in the first two steps. What do the patterns in these stories suggest about who this person is becoming? What themes kept showing up?
Ask: What do you want to be doing in five years — not the job title, but the kind of work, the kind of impact, the kind of day?
Don't look for one right answer. Prototype three possible futures. Sketch them out — literally, if possible. Which one feels most alive? Which one would make the best story to tell someday? Which one is most consistent with what they just shared about themselves?
The goal isn't a plan. It's a conversation that changes how the young person sees themselves — and what they're capable of.
When the school project becomes a family experience
Some of the most memorable learning experiences are family projects — where a parent, sibling, or family friend gets involved in something a student is doing. Not to take it over, but to be genuinely curious alongside them.
Darin's daughter's wax museum became exactly that. She picked Julia Child. What followed was a family experience: hunting for a French cookbook on eBay, finding pearl necklaces at a thrift store, practicing lines at dinner, watching YouTube videos of Julia Child's show, and helping shape a script that made her daughter feel like she truly understood who this person was.
The school project became a family memory. It became a story they'll tell for years. And the learning — for the seven-year-old who stood in character for a room of strangers — was total.
Look for opportunities to do this with the young people in your life. When they bring home a project that has any spark of real engagement, lean in. Ask questions. Find the cookbook. Get involved.
"The school project became a family memory. And the learning — for the seven-year-old who stood in character for a room of strangers — was total."
Your story is your most powerful tool
For years, Darin was a keynote speaker at WILS — Wisconsin Leadership Seminars — a leadership conference for high school students from across the state. Hundreds of young people in a room, trying to figure out who they were and where they were going.
The most powerful moments in those rooms weren't the frameworks or the models or the advice. They were the stories. A specific story, told honestly — about a moment of failure, or fear, or an unexpected turn — that landed with a room full of teenagers in a way that information never could.
If you ever have the chance to speak to a room of high school students — as a mentor, a guest speaker, a panelist, a coach — remember this: your story is your most powerful tool. Not your advice. Not your credentials. Your story.
Tell the one that was hard. Tell the one where you didn't know what would happen. Tell the one that shaped you. That's the one they'll remember.
Lead with the story, not the lesson
Let the story do the work. The insight will land on its own.
Tell one you didn't know would end well
Uncertainty is what makes stories land. Success stories without stakes teach nothing.
Be the person, not the expert
They don't need your expertise. They need to see that someone like them figured something out.
Connect it to their moment
After the story, ask: "What's the version of this that's true for you right now?"
Resources for the young person in your life
The projects on this site are designed to go public — and many of them work best when a parent or mentor is involved. Browse the project library, or connect the student in your life to resources designed specifically for them.