Sean Conway Completed the Most Insane Endurance Challenge

42 year old endurance Masters Athlete Sean Conway joined Rich Roll on his podcast to share lessons learned after crushing an unbelievable feat of voluntary human performance: 105 Ironmans in 105 days.

By Rich Roll,

There’s nothing I love more than tales of ordinary people accomplishing extraordinary things.

But nobody who achieves the extraordinary is ordinary, and while upon first glimpse this real-life Forrest Gump may present as an everyman, he is anything but.

Not only did Sean Conway dare to best one of the world’s most impressive endurance records, he downright decimated it—and somehow made it all look ‘easy’.

In 2021, the Iron Cowboy James Lawrence completed 101 iron-distance triathlons in 101 consecutive days, a record I both witnessed and couldn’t fathom being broken in my lifetime. And yet not too long after, Sean Conway, a dad of two young kids from a small town in Wales by way of Zimbabwe, proceeded to complete 105 consecutive iron-distance triathlons, claims he could have kept going, and believes he could have done 200.

In case you don’t quite grasp the enormity of this feat: Sean swam 2.4 miles, then proceeded to ride 112 miles on his bike, then ran a full marathon—26.2 miles, repeating this routine every day without missing a single day, for 105 days in a row.

Moreover, Sean didn’t even begin his endurance career until age 30, a career in which he has quietly eclipsed more records than most realize.

In our conversation, we unpack Sean’s extraordinary accomplishments, his ‘terrier mindset’, the ‘ten pillars of endurance’, why he doesn’t celebrate small wins, his unique lens on failure, and his reasoning for never, ever having a backup plan.

We also explore Sean’s impressive resume of world-record-setting feats of endurance, which include:

  • climbing up Mount Kilimanjaro in a penguin suit.
  • swimming the length of Great Britain in 135 days, when the furthest he had swum before this challenge was three miles.
  • setting a world record for cycling unsupported across Europe, completing the 4000-mile route in 24 days.
  • completing the Ultimate British Triathlon following a run from John O’Groats to Land’s End without undergoing any kind of training in advance.
  • completing a self-supported 4000+ mile, continuous ultra triathlon that circumnavigated the entire coast of mainland Britain, and
  • setting the world record for the longest triathlon in the world, crushing 4,200 miles in 85 days.

You can watch this amazing podcast on YouTube. As always, the audio version streams wild and free on Apple Podcasts and Spotify.

Sean is quirky, totally authentic, and chock-full of ludicrous stories lifted from a life that prioritizes adventure over security.

My hope is that his example inspires you to transcend self-imposed limitations and craft a challenge that is meaningful to you.

Because we’re all capable of transforming our lives from ordinary to extraordinary.

For more information on Rich Roll and his highly acclaimed podcast, visit