Free Outside

Yassine Diboun comes on to talk about imposter syndrome, ultra running, positivity, sobriety, community, and why none of us actually feel as confident as we pretend to.

Yassine has been in the ultra running world for nearly 20 years, from the old-school blog era and handwritten race applications to modern 200 milers and social media comparison culture. We talk about how the sport has changed, why we still get nervous at races, and how you can be incredibly accomplished at one thing while still feeling like a beginner at another.

We also dive into Yassine’s “good wolf vs bad wolf” mindset, how he practices positivity without pretending life is perfect, and why community might actually be the most important part of trail running.

Along the way we cover:

The early days of ultra running
Cocodona 250 and Mammoth 200
Heat training and race anxiety
Hallucinations and sleep deprivation
Why comparison steals joy
Sobriety and endurance sports
Kids, trail running, and staying playful
Why hard things should still be fun
The mental side of ultra running

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#Trailrunning #Runningnews #Outdoors #Outdooradventure

Allison Mercer and I recap the chaos of Cocodona 250. From a tracker glitch that placed Jeff in Africa in 1969, to GI issues, hallucinations, Mingus basketball, sleepless nights, and a fifth straight top 10 finish, this year’s race felt bigger, faster, and stranger than ever. They also dive into the intensity of the competition, the growth of the sport, the power of crew and pacers, and the heavier moments that reminded everyone just how serious these events can be.

Cocodona 250 starts in two days, so I’m talking through the plan, the nerves, the training block, and why this race still matters so much to me. This episode is also the two-year anniversary of the Free Outside Podcast, which launched during Cocodona because I was too nervous to watch whether anyone listened.

I get into the pressure after the Appalachian Trail FKT, a clunky but meaningful Cocodona build, working with a nutritionist and mental performance coach, and the three values I’m carrying into the race: presence, community, and trust. Or, fittingly, PCT.

Presence: be here now.
Community: let people help.
Trust: trust yourself.

This is my Cocodona 250 race plan, but also a reminder that hard things are better when they are rooted in joy, connection, and a reason that actually means something.

Support our Sponsors:
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Subscribe to Substack: http://freeoutside.substack.com

Support this content on patreon: HTTP://patreon.com/freeoutside

Buy my book "Free Outside" on Amazon: https://amzn.to/39LpoSF

Email me to buy a signed copy of my book, "Free Outside" at [email protected]

Watch the movie about setting the record on the Colorado Trail: https://tubitv.com/movies/100019916/free-outside

Website: www.Freeoutside.com
Instagram: thefreeoutside
facebook: www.facebook.com/freeoutside

#Trailrunning #Runningnews #Outdoors #Outdooradventure

Cocodona 250 is here, and right after recording this, I’m heading out the door to go run it.

So naturally, the best thing to do before a 250-mile race is sit down and try to predict everything that’s about to happen.

In this episode of the Free Outside Podcast, I’m joined by Tara Dower and Allison Mercer to break down the Cocodona 250 field, storylines, and everything we think might happen… knowing full well that none of it will go according to plan.

We talk about:

Why the women’s field might be the most exciting part of the race
Dark horses, favorites, and who could surprise everyone
How 200+ mile races actually play out (hint: not how you think)
Influencers vs contenders and why Cocodona is its own world
Live stream chaos, race coverage, and being way too exposed mid-race
Falling… a lot of falling
And why we do all of this in the first place

This is part preview, part comedy, and part reminder that these races are supposed to be fun, even when they feel overwhelming.

If you’re watching Cocodona this year, this will get you ready.
If you’re running it… good luck.

Support our Sponsors:
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Janji (code: Freeoutside): https://snp.link/a0bfb726
CS Coffee: CSinstant.coffee
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Subscribe to Substack: http://freeoutside.substack.com

Support this content on patreon: HTTP://patreon.com/freeoutside

Buy my book "Free Outside" on Amazon: https://amzn.to/39LpoSF

Email me to buy a signed copy of my book, "Free Outside" at [email protected]

Watch the movie about setting the record on the Colorado Trail: https://tubitv.com/movies/100019916/free-outside

Website: www.Freeoutside.com
Instagram: thefreeoutside
facebook: www.facebook.com/freeoutside

#Trailrunning #Runningnews #Outdoors #Outdooradventure

What if ultrarunning wasn’t about suffering… but about having more fun?
Andrea Moore has run 200s, 300s, and more races than most people would ever consider—and somehow, she makes all of it look like a moving party.

We talk about:

Why the back of the pack might be having the most fun
The real “secret” to 200-mile races
Snacks, bush naps, and the weird moments that actually matter
DNFs, dark moments, and why they don’t define you
Why no one remembers results—but they remember stories

If you’re heading into Cocodona 250 or just curious about ultras, this is a different way to think about it.

Less pressure. More curiosity. More fun.

Support our Sponsors:
Sawyer: https://sawyerdirect.net/
Janji (code: Freeoutside): https://snp.link/a0bfb726
CS Coffee: CSinstant.coffee
Garage Grown Gear: https://snp.link/db1ba8ab

Subscribe to Substack: http://freeoutside.substack.com

Support this content on patreon: HTTP://patreon.com/freeoutside

Buy my book "Free Outside" on Amazon: https://amzn.to/39LpoSF

Email me to buy a signed copy of my book, "Free Outside" at [email protected]

Watch the movie about setting the record on the Colorado Trail: https://tubitv.com/movies/100019916/free-outside

Website: www.Freeoutside.com
Instagram: thefreeoutside
facebook: www.facebook.com/freeoutside

#Trailrunning #Runningnews #Outdoors #Outdooradventure