Steve Sammons
  • marketing
  • leadership
  • technology
    • SEO
Steve Sammons
  • marketing
  • leadership
  • technology
    • SEO

Why I Put a Stoic Next to Caleb

The Obstacle Is the Way

I wrote a post about Caleb asking for the mountain — “Give Me the Hard One.”

“The Obstacle Is the Way” by Ryan Holiday is the closest thing I know to a secular twin of that post.

The whole book runs on the exact move Caleb makes. Its epigraph is Marcus Aurelius — “What stands in the way becomes the way.” Holiday’s argument is that the obstacle isn’t the detour. It’s the path. That’s Caleb pointing at the fortified hill country and saying, give me this one. He doesn’t tolerate the hard land. He asks for it.

It tracks my post almost line for line.

Holiday’s first discipline is perception — the idea that an event means whatever you decide it will mean. Strength or weakness, your call. That’s the “Same data. Different conclusion.” beat. Ten scouts and Caleb saw identical giants. The only variable was internal.

The book is also a rebuke of comfort. Holiday’s premise is that we’ve grown soft, that we now carry more obstacles inside us than out. That’s my BIG IDEA nearly word-for-word. We negotiate for easier paths. Softer landings-

And it’s short. Story-driven — Grant, Edison, Lincoln. The kind of book you read in an afternoon and hand to someone.

Now the part I want to own.

This is a secular book. Stoic, not Christian. I didn’t include it in spite of that. I included it because of that.

When the same truth shows up in a tradition with no shared scripture, no shared vocabulary, no agreement on God — and still lands in the same place — that’s worth noticing. Two books climbing the same hill from the same trail tell you nothing. Two books reaching the same summit from opposite trailheads tell you the summit is real.

So I put it here on purpose. Next to Caleb. A companion read, not a substitute.

If you want the explicitly spiritual version, that’s Viktor Frankl’s “Man’s Search for Meaning” — the last human freedom is to choose your spirit in any circumstance. Which is just another name for Caleb’s “different spirit.” Holiday leans on Frankl in his final pages. So the two shake hands.

Same mountain. Different paths up.

Recent Posts
  • Give Me the Hard One
  • When Following Beats Leading
  • When Death Isn’t the Hard Part
  • When Skill Isn’t Enough
steve-sammons
Steve shares insights and strategies for business transformation, brand development, and sustainable growth—always rooted in faith-based principles and a commitment to purposeful leadership across diverse industries.
Receive Updates

We don’t spam!
Read our privacy policy for more info.

Check your inbox or spam folder to confirm your subscription.

Steve Sammons
  • Facebook
  • Twitter
  • LinkedIn
Copyright 2025

Input your search keywords and press Enter.