Betting on Yourself
Saturday 2 May 2026, Toronto
A one-day retreat exploring what it means to bet on yourself and how it can take shape in your life.
You might already feel it, that quiet pull to do something more, or differently. And at the same time, the hesitation. The questions, the doubt, the instinct to stay where things feel safe or familiar.
This retreat is for that space in between.
“Betting on Yourself” isn’t about having it all figured out. It’s about giving yourself the time and space to step back, see yourself more clearly, and explore what might be possible.
Over the course of the day, you’ll be guided through experiences that gently challenge familiar ways of thinking, surface what may be holding you back, and help you begin to define what betting on yourself could actually look like in your life.
You’ll leave not with pressure or prescriptions, but with perspective, a renewed sense of agency, and a few simple, practical ways to move forward.
If part of you feels curious, come deepen that curiosity with us.
Your Hosts,
Kim and Nabil
Experts
Clement Chu, Community Builder
Clement represents a different way of betting on yourself, becoming a driving force behind community and culture outside of his day job. As a co-founder of Asian Roots Collective, he has helped create platforms that celebrate identity and connection. His path challenges the idea that purpose must come from work, showing instead how impact, creativity, and ambition can be built in parallel.
Lindsay Prajza, Psychotherapist
Lindsay supports clients in navigating doubt, fear, and the pressures of modern life with clarity and compassion. Blending relational psychotherapy, evidence-based strategies, and a neuroscience-informed lens, she helps people build confidence, resilience, and deep self-trust so they can feel more connected to who they’re becoming.
Shinjini Sur, Mindset Shaper & Learning Designer
Shin designs and facilitates play-based learning that inspires collective knowledge sharing and personal epiphanies. Drawing on her expertise guiding high-energy, reflective group experiences, Shin creates spaces where people can explore new perspectives, build trust, and embrace growth with openness.
Programme
Saturday 2 May 2026
1 Roof Garden Lane, Toronto
Doors Open
10:00 AM
Check-In and Refreshments
10:00 - 10:30 AM
Welcome Address
10:30 - 10:45 AM
The Myth of the All-In Bet with Clement Chu
10:45 - 11:45 AM
A session grounded in lived experience that redefines what it means to bet on yourself, challenging conventional paths and sparking new ways of thinking.
Lunch by Chef Jen
11:45 - 12:30 PM
The Psychology of Betting on Yourself with Lindsay Prajza
12:30 - 2:00 PM
An exploration of the psychology behind self-trust, uncovering the beliefs, patterns, and internal barriers that shape our choices, and how to overcome them.
Break
2:00 - 2:15 PM
It's How You Play the Game with Shinjini Sur
2:15 - 3:45 PM
A guided playshop where you translate insight from the day into action, exploring what betting on yourself could feel like in practice and leaving with tools and perspectives to move forward.
Goodbyes
3:45 - 4:00 PM
Chef Jen Nickle
Chef Jen Nickle is a Toronto-based chef known for creating deeply personal, seasonal dining experiences that bring people together.
Her cooking is rooted in care, connection, and the belief that a shared meal can be as meaningful as the work that happens around it.
We’re proud to be working with Chef Jen who’ll be providing a bountiful lunch that will help you pause and connect with one another.