What if everything you’ve been taught about success was wrong?
Sean Conway, 7x world-record-holding endurance athlete, spent his twenties building what looked like a “successful” photography business — earning money, working with major brands, and living the comfortable life he thought he wanted.
He followed the blueprint for what we’ve all been taught success should look like — stability, money, and status — but behind closed doors, he was miserable.
Trapped by routine and expectation, he realised that the version of “success” he had built his life around wasn’t his own — it was what he’d been taught to want.
So, in a moment of total honesty, he sold his company for €1, packed his bike, and set out to cycle around the world — not to escape life, but to understand what it really means to live.
That decision changed everything.
Over the next decade, Sean became one of the most accomplished endurance athletes in the world.
He swam the entire length of Britain, ran from one end of the country to the other, cycled across Europe in record time, and became the first person ever to complete 105 Ironman-distance triathlons in 105 days.
Sean’s journey isn’t only about breaking records.
It’s about breaking the illusion that success is something you can buy, rather than something you can become.
In this powerful and revealing conversation, he shares:
- What it was like growing up among elephants and adventure — and how an extraordinary childhood in the wild sparked his hunger to live life differently.
- How his love for photography took him from Zimbabwe to London at just 20 years old — with only £100 and a dream to create something bigger.
- The grind, loneliness, and lessons of building a business from nothing — and the moment he realised that success without purpose means nothing.
- Why he sold his company for £1 and walked away from everything — choosing freedom, authenticity, and meaning over comfort and control.
- The transformative journey of cycling around the world — and what it taught him about simplicity, pain, and the quiet happiness found in struggle.
Follow Sean:
📸 Instagram- https://www.instagram.com/seanconwayadventure/
🎥 YouTube – @SeanConwayEndurance
🌐 Website – https://www.seanconway.com
💼 LinkedIn – https://www.linkedin.com/in/sean-conway-2486b563/
Follow The Host, Theodor Ekstrand:
📸 Instagram – https://www.instagram.com/theodorekstrand
🎥 YouTube – @theodor_ekstrand
🎵 TikTok – https://www.tiktok.com/@theodor_ekstrand
💼 LinkedIn – https://www.linkedin.com/in/theodor-ekstrand/
Podcast Host: Theodor Ekstrand
Thumbnail partly created with AI.
Images are illustrative and do not depict real events.