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Chasing Trail

I once read that I should write something worth reading, or I should do something worth writing about

Newsletter · By Caleb Olson · English · Paid tier available · Official site

Indexed issues, last 90 days
3
Latest publication
Sep 16, 2026
Audience
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Earliest in this view
Jul 28, 2026

Latest issues

  1. Issue · Sep 16, 2026

    People I’d Love to Beat (opens the original)

    Excerpt · Positive tone

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    Each year, usually after UTMB, I start dreaming up future plans and thinking about where next year’s races might take me. This time, rather than prioritizing cool destinations or specific series or qualifiers, I have another idea.I’ve spent plenty of time thinking about races I’d like to someday win, but very little thinking about people I’d like to someday beat. It feels weird to talk about beating people, winning and losing. Is a 2nd place finisher a loser? Kind of, but also it’s still great.

  2. Issue · Aug 28, 2026

    UTMB Dreams (opens the original)

    Excerpt · Neutral tone

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    Dear Diary,It’s the final week of December 2025. Wrapping up Week 4 with my new coaches, Brett and Brad. They’ve been great so far and I’m really excited to be working with them. We have an interesting 4 week block cycle going right now where Week 1 is just general easy base volume, Week 2 is focused on downhill and beating up the quads, Week 3 targets uphill specificity and strength, and Week 4 is packed with 5 higher intensity workouts in a row.During yesterday’s 30x20s on/40s off my left hams

  3. Issue · Jul 28, 2026

    Speedgoat 50k (opens the original)

    Excerpt · Neutral tone

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    In 2021, Speedgoat 50k was one of the longest, toughest races I’d done in my life up to that point. I went into it tapered and excited. My first 100k, CCC, was going to be a month later and I thought Speedgoat would be the perfect test before the race. My time was 5:52, I got 9th, and it was awesome. CCC that year also went well for where I was at the time, so it was confirmed that Speedgoat is, indeed, good prep.<a class="image-link image2 is-viewable-img" href="https://substackcdn.com/image/fe

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