Skip The Shortcut. Take The Long Way Instead.

Summary

The Daily Stoic
Episode: Skip The Shortcut. Take The Long Way Instead.
Air Date: May 27, 2026
Host: Ryan Holiday

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Episode Overview

This episode of The Daily Stoic explores the Stoic perspective on shortcuts—technological or otherwise—in the pursuit of wisdom, happiness, and success. Drawing from the teachings of Epictetus, Marcus Aurelius, and Seneca, Ryan Holiday challenges the allure of easy paths, focusing particularly on the rise of artificial intelligence as the latest promise of bypassing genuine effort. The recurring message: wisdom and fulfillment can’t be outsourced or hacked—they must be earned through deliberate, difficult work.

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Key Discussion Points & Insights

1. Stoic View on Shortcuts and Technology (00:51)

• Holiday introduces a story from Epictetus, where a student asks for instructions, but Epictetus counters:

  "It would be better to say... ‘Make my mind adaptable to any circumstances.’"

• Modern society is saturated with promises of “shortcuts” everywhere: get-rich-quick schemes, social media, productivity hacks, and now, artificial intelligence.

• Artificial intelligence is positioned as the “ultimate shortcut”, promising to:

  • Write emails and essays
  • Create art
  • Think and plan for us

• Holiday warns that:

  "AI promises to do the intellectual heavy lifting while we reap the rewards, suggesting we can bypass the learning process altogether." (01:45)

2. Relevance of Stoic Principles Today (02:05)

• Marcus Aurelius is highlighted as a model:

  "Despite being Emperor of Rome, [he] still made time every day to write in his journal, examining his thoughts and actions. He understood that wisdom required ongoing effort, not once, but continually throughout his life."

• There’s an emphasis on the non-transferability of wisdom:

  "There's no app, no hack, no shortcut that could replace the necessary inner work."

• In contemporary contexts, the Stoics would likely caution about seductive technologies—not because technology itself is bad, but because of the false promise that struggle can be avoided.

3. The Value of Effort and the “Long Way” (02:45)

• The struggle itself is often where the deepest growth happens:

  "The Stoics would remind us that the struggle itself, the very difficulty we try to avoid, is often where the most learning value is created. It's often the very work we're trying to avoid. Where wisdom lies." (03:05)

• Wisdom, according to Holiday (channeling Seneca):

  "Wisdom cannot be outsourced. It cannot be hacked and it can definitely not be automated. It has to be earned. The slow way, the hard way, the right way."

• Direct quote of Seneca:

  '"No man is wise without toil."' (03:23)

• Bottom line:

  "Don't take the shortcut, take the long way. That's what's going to get you what you want and ultimately get you where you want to go." (03:30)

4. The Virtue Series (03:38)

• Holiday references his own work as an example of “the long way”:

  "You can check out Wisdom Takes Work, by the way, which was a lot of work. It was the culmination of six plus years of writing, many more years of research and thinking before that."

• Mentions his larger Virtue Series:

  • Courage Is Calling
  • Discipline Is Destiny
  • Right Thing Right Now
  • Wisdom Takes Work

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Notable Quotes & Memorable Moments

• Epictetus on adaptability:

  "Make my mind adaptable to any circumstances." (01:15)

• On artificial intelligence:

  "AI promises to do the intellectual heavy lifting while we reap the rewards, suggesting we can bypass the learning process altogether." (01:45)

• On the necessity of work:

  "Wisdom cannot be outsourced. It cannot be hacked and it can definitely not be automated. It has to be earned. The slow way, the hard way, the right way." (03:10)

• Seneca’s timeless reminder:

  '"No man is wise without toil."' (03:23)

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Important Segment Timestamps

• 00:51 – Stoics on shortcuts; Epictetus student exchange introduction
• 01:45 – AI as the “ultimate shortcut”
• 02:05 – Marcus Aurelius and the daily practice of self-examination
• 03:05 – The value of struggle; where wisdom is found
• 03:23 – Seneca’s quote; wisdom requires toil
• 03:38 – Holiday references his Virtue series and the effort behind it

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Tone and Language

Ryan Holiday’s delivery is thoughtful, direct, and motivational—characteristic of The Daily Stoic’s pragmatic but hopeful approach. He invokes ancient Stoic wisdom with a modern sensibility, urging listeners to value genuine effort over quick fixes.

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Summary

Ryan Holiday’s central message this episode is clear: despite enticing technological advances and modern productivity hacks, there is no substitute for the hard, personal effort required to gain wisdom and live a virtuous life. “Don’t take the shortcut, take the long way. That’s what’s going to get you what you want and ultimately get you where you want to go.” The struggle is not only unavoidable—it is necessary and deeply valuable.

Transcript

[A]

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[B]

I'm here on a job site with Tim, who owns his own electrical contracting business.

[A]

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[B]

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[B]

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[A]

Shockingly low, huh?

[B]

Just a little bit of electrician humor. Do you get it?

[A]

I got it.

[B]

You know, it feels like we have a real connection. All right, I'll stop, get a commercial

[A]

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[B]

much you could save.

[A]

It feels good to Geico.