Betting on Yourself

A one-day retreat exploring what it means to bet on yourself and how it can take shape in your life.

10.00 AM to 3.30 PM

Roof Garden

Roof Garden

Topic

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

If part of you feels curious, come deepen that curiosity with us.

What you'll leave with

A clearer sense of what's actually holding you back and what betting on yourself could look like in your own life.

A renewed feeling of agency, without the pressure to have it all figured out.

A few simple, practical ways to move forward from wherever you are right now.

Led By

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.

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.

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

10:00 AM
Doors open

10:00 - 10:30 AM
Check-In and Refreshments

10:30 - 10:45 AM
Welcome from your hosts

10:45 - 11:45 AM
The Myth of the All-In Bet with Clement Chu
A session grounded in lived experience that redefines what it means to bet on yourself, challenging conventional paths and sparking new ways of thinking.

11:45 - 12:30 PM
Lunch by Chef Jen

12:30 - 2:00 PM
The Psychology of Betting on Yourself with Lindsay Prajza
An exploration of the psychology behind self-trust, uncovering the beliefs, patterns, and internal barriers that shape our choices, and how to overcome them.

2:00 - 2:15 PM
Break

2:15 - 3:45 PM
It's How You Play the Game with Shinjini Sur
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.

3:45 - 4:00 PM
Goodbyes

Venue

Date

Time

10.00 AM to 3.30 PM

Location

1 Roof Garden Lane, Toronto

Tickets

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