A 6-month one-on-one program that gives your son something no school can: a genuine sense of who he is and where he's going.
Who this is for
He's not in crisis. He's not failing. He's just drifting — his whole identity tied up in his social life, no real sense of what he's building toward.
The transformation
A personal passion or practice he's found and built on his own terms.
He makes decisions from the inside out — not from fear of what others think.
Not social confidence — the kind that comes from knowing who you are.
A written plan for who he wants to be — and how to keep building it.
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About Oscar
Oscar is 18 years old. He went to Caulfield Grammar, achieved a 90.45 ATAR, and coaches both cricket and Aussie rules. He knows what it feels like to be a teenage boy who is drifting.
Year 10. New school. No direction. He spent that year trying to fit in until he found something that was his. The transformation wasn't dramatic — it was quiet, private, and built one afternoon at a time. Running. Reading. Spending real time alone. Going from skipping school to becoming someone his whole friend group turns to for guidance.
In Year 11, he ran a semester-long mentorship with a Year 9 student through a formal school program. At the end of it, the student's parents reached out to tell him how much of a difference it had made. That outcome is what led him here.
The Program
Each phase builds on the last. By the end, he has the tools to keep doing this work on his own.
Sessions 1–3
Getting honest. Mapping who he is now and the environment shaping him.
Sessions 4–6
Finding something that's his. Exploring passions and building a real practice.
Sessions 7–9
Unpacking values, the approval trap, and where real confidence comes from.
Sessions 10–12
Relationships, reflection, and a forward plan that outlasts the program.
How it works
Send a message — a brief note about your son and what you've noticed. We'll arrange a short call to see if there's a fit.
Both you and your son fill out a short questionnaire separately. This gives Oscar the clearest possible picture before Session 1.
Fortnightly 60-minute sessions, online or in person. Structured but conversational — your son drives where it goes.
You receive a brief update after Session 6 and at program close — so you can see the change, not just hear about it.
What people say
"We watched our son come back to himself over the course of these six months. He found something he cares about, and the confidence that came from that was something no school could have given him."
"Oscar has a rare ability to connect with young men at exactly the right level — not as an authority, but as someone who's genuinely walked the same path and come out the other side."
"After one semester with Oscar, we saw a young man who walked taller, had things he was excited about, and didn't need the approval of everyone around him to feel good about himself."
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Investment
AUD · Full 6-month program
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Payment plan
Monthly · Total $3,500
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Send a short message and we'll arrange a free 20-minute call to see if there's a fit.