Canada Has a Risk Problem

*Recorded at StartWell - Toronto's best place for company meetings, events and professional content capture: https://startwell.co/

Canada has no shortage of talent - but according to AJ Tibando, we have a mindset problem.

As CEO of Shift Canada, AJ is leading a national effort to reshape how young people think about risk, failure, and entrepreneurship. Starting with students as early as grade five, Shift’s programs challenge one of the most deeply ingrained barriers in Canadian culture: the fear of getting it wrong.

In this conversation, AJ breaks down why traditional education systems often unintentionally discourage experimentation. When students are rewarded for being right instead of trying, they learn to avoid risk altogether. That mindset doesn’t just stay in the classroom - it follows them into careers, limiting innovation at a national level.

Shift Canada is tackling this head-on by normalizing failure as part of the learning process. By creating “permission structures” where students can try, fail, and try again without judgment, they unlock creativity, confidence, and real problem-solving ability.

But this isn’t just about education - it’s about economic competitiveness. AJ connects the dots between cultural attitudes toward risk and Canada’s ability to produce founders, builders, and bold thinkers.

This episode is a sharp reminder that innovation doesn’t start in boardrooms - it starts much earlier. And if Canada wants to compete globally, it needs to rethink how it prepares the next generation.

CHAPTERS: 00:00 What Shift Canada Does 01:15 Teaching Risk in Schools 03:10 Why Students Fear Failure 05:20 The Problem With Traditional Education 07:45 Creating Permission to Try 10:30 How Mindset Shapes Innovation 13:20 Canada’s Risk Culture Problem 16:00 Why Early Education Matters 18:40 Building Future Entrepreneurs 21:30 What Needs to Change