Timeline

My life at a glance

1990

I was born in Toronto, Canada.

2009

At age 18, I booked a one-way flight across the country to chase my dream of flying helicopters.

2017

I was laid off 8 times in 8 years in aviation and wondered how I would persevere and keep moving forward.

2020

After a decade in the industry, I finally felt I had “made it.” I paid off all my debt and worked only half the year, but something was missing.

2022

I decided to quit my 14-year successful career in aviation and pursue my business full-time, hoping to impact someone else's life.

2023

I spoke at the largest TEDx in Canada, TEDx SFU, to over 1000 live attendees with my talk titled - Life Beyond the Dead Man’s Curve.

Hi, I’m Chris.

I’ve been in and out of the hover for my entire life. Struggling to make forward progress for years at times.

After leading a successful 14-year career in aviation as a Commercial Helicopter Pilot and Aircraft Maintenance Engineer, I flew into business to impact the next generation in their careers and lives.

I became accustomed to navigating turbulent times in high-stress and high-pressure environments in some of the world's remotest places.
‍
I share industry-shaping insights and practical tools to help connect, engage, and overcome adversity in organizations and schools.

A full-time founder of Mentee, 2 x author, keynote/TEDx speaker, and CTI coach.

Today, I’m on a mission to help the next generation impact the world through my Dare to Fly framework by setting the course, starting with yes, taking the controls, and navigating forward.

Dare to Fly is a leadership framework to engage together, persevere forward, and seize each new opportunity.

The only way forward is to fly.

From being broke at 18 and in $55,000 of debt to writing two books and giving a TED talk.

I’ve done everything from heli-skiing at 10,000 feet to bodybuilding competitions to diving with sharks.

Since then, I’ve had some nice wins. And also my fair share of setbacks, failures, and disappointments.

Book Chris

My core beliefs

These principles have helped me create a beautiful life and career.

Serve with Intention.

Having an abundance mindset and serving others with intention has always helped me learn, progress, and be a better human. It helps me feel good about what I’m doing, and others have done the same for me.

The Importance of Today.

Life is short, and nothing is guaranteed. Every day I wake up, I have a new opportunity, whether going for a walk or delivering a message to impact over 1000 people on stage. Each day matters.

Forward Progress.

For nearly two decades, I’ve prioritized my health and fitness, and it’s taught me a lot about life. Progress happens over time. Consistency and discipline are keys to every aspect you want to improve.

Show Up.

After nearly 20 jobs in several industries, showing up has never failed me. Whether going for an interview, contacting a prospect, or making that first sale. You'll be ahead of the curve if you show up and stay true to your word.

Dare to Fly.

As a professional aviator for over 14 years, I learned firsthand the importance of taking flight in your life and career. It’s about moving forward to get you closer to what you want most. Too many people are stuck in the hover - doing the same things, expecting different results.

How Chris
can help

Hover over to learn more

Speaking

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Courses

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Community

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Blog

Read over 200+ articles on work, life, and productivity.

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Coaching

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Meet Chris

14-year aviator, entrepreneur, and career expert Chris Wilson helps you with his 3-step Dare to Fly framework to connect, engage, and navigate what’s next.

Timeline

1990

2009

2017

2020

2022

2023

Dare to Fly is a leadership framework to engage together, persevere forward, and seize each new opportunity.

From being broke at 18 and in $55,000 of debt to writing two books and giving a TED talk.

Chris is on a mission to help the next generation unlock the tools to engage together, navigate adversity, and seize each new opportunity.

My core beliefs

Serve with Intention.

The Importance of Today.

Forward Progress.

Show Up.

Dare to Fly.

How Chris
can help

Speaking

Courses

Community

Blog

Coaching

Meet Chris

14-year aviator, entrepreneur, and career expert Chris Wilson helps you with his 3-step Dare to Fly framework to connect, engage, and navigate what’s next.

Timeline

1990

2009

2017

2020

2022

2023

Dare to Fly is a leadership framework to engage together, persevere forward, and seize each new opportunity.

From being broke at 18 and in $55,000 of debt to writing two books and giving a TED talk.

Chris is on a mission to help the next generation unlock the tools to engage together, navigate adversity, and seize each new opportunity.

My core beliefs

Serve with Intention.

The Importance of Today.

Forward Progress.

Show Up.

Dare to Fly.

How Chriscan help

Speaking

Courses

Community

Blog

Coaching

The Work to Live Newsletter

How Chris
can help