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My Dream Career Failed — It Became the Best Thing That Happened | Tyler Chisholm
Description
Tyler Chisolm is an entrepreneur, CEO, author, and podcast host who believes curiosity is one of the most powerful tools a person can develop. He is the co-founder and CEO of Clear Motive Marketing Group and the author of Curious as Hell: Leading and Growing with Curiosity.
Through business leadership and over 600 podcast conversations, he has built a reputation for helping people think differently, ask better questions, and grow through uncertainty and change.
In this practical and inspiring conversation, Tyler shares:
• Growing up in a rural farming community that taught grit and self-reliance
• Why entrepreneurship was in his DNA even before he had the language for it
• The bold move at 26 across Canada to chase a commercial pilot dream
• How that dream career completely failed — and why it was still a success
• Finding opportunity in a new city with no network and no plan B
• Building a business and falling in love with marketing and brand
• Why curiosity is the tool that helps you navigate uncertainty
If you’re in your 20s feeling pressure to have the “right” path figured out, or facing a setback that feels like failure, this episode reframes what success and growth actually look like.
Timestamps below ⬇️
#TylerChisolm #CuriousAsHell #Entrepreneurship #Curiosity #ConversationsWithSekani
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Chapters
0:00 - Intro & Welcome Tyler Chisolm
1:40 - Rural Upbringing & Lessons in Grit and Self-Reliance
8:15 - Entrepreneurship Was Everywhere (Even If No One Called It That)
15:30 - The 26-Year-Old Leap: Moving Across Canada for a Pilot Dream
23:10 - When the Dream Career Completely Failed
31:45 - Choosing to Stay and Figure It Out in a New City
40:20 - From Fitness to Marketing: Finding the Real Path
48:50 - Reframing Failure as the Foundation for Success
57:15 - Why Curiosity Is the Ultimate Tool for Growth