Don’t Wait To Try It

Summary

The Daily Stoic Podcast – “Don’t Wait To Try It”
Host: Ryan Holiday | Date: July 8, 2026

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Episode Overview

In this episode, Ryan Holiday explores the Stoic imperative to act—encouraging listeners to stop procrastinating and start trying the things they've long considered but delayed. Drawing inspiration from Stoic thinkers like Seneca, he discusses the pitfalls of waiting for the "right" time and introduces two key Stoic concepts—Memento Mori and Premeditatio Malorum—as practical tools to overcome hesitation and take meaningful action.

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Key Discussion Points & Insights

1. Personal Anecdote: Embracing Action Through Experience

• Ryan shares his family’s travels for his current Daily Stoic tour, recounting their journey from Seattle to San Francisco, with stops and stays at different Airbnbs.
  • [00:00] “I started in Seattle. My family and I drove all the way down. Now I'm in San Francisco.”
• He reveals how, earlier in his writing career, listing his house on Airbnb helped make the leap from a marketing job to writing feasible by covering the mortgage.
  • [00:23] “That's how we helped cover the mortgage. That's how I was able to make the transition from a marketing person to a writer.”

2. The Stoic Problem: Delaying Action

• The central theme: People often daydream about new experiences, relationships, or ventures but delay taking the first step.
  • [01:10] “You've thought about living somewhere else... testing the job market... asking someone out... taking lessons. But what do we do? Well, like a fool, as Seneca says, we put it off. We delay starting.”
• Common rationalizations include waiting for more information, for things to settle, or for greater comfort—yet these rarely materialize as actual starting points.

3. Stoic Mantras for Action

• Memento Mori (Remember Death):
  • Life is finite—action should not be endlessly postponed.
  • [01:31] “Life is short. You don't know how long you have, you don't know that you have later.”
• Premeditatio Malorum (Picturing the Worst-Case):
  • By rationally considering what could go wrong, fears often shrink, and one discovers they’re more capable than imagined.
  • [01:41] “What's the worst case scenario? Actually think through the worst case scenario. If you try this thing and you'll find that it's probably not so bad... you'll be able to handle whatever it is.”

4. The Only Path is Action

• Waiting and hesitation are empty practices.
  • [02:06] “We learn nothing new by putting things off to another day. It's in acting that we discover whether the thing was right for us or not. Waiting teaches nothing. Hesitation teaches nothing. The only way to know is to start.”
• Discomfort is inherent to growth and transformation—philosophical tools are means to move past discomfort, not avoid it.
  • [02:30] “The path to becoming a better, more resilient person isn't usually comfortable.”

5. Making Philosophy Practical

• Ryan emphasizes his own daily reminders—carrying a Memento Mori coin or ring as tangible cues to stop waiting and summon urgency.
  • [03:06] “It's a reminder to stop waiting.”
  • [03:07] “Every time I touch it, I feel that little bit of urgency.”
• Premeditatio Malorum gives courage at decisive moments, reframing fear and nudging action, even (and especially) in the face of risk.
  • [03:15] “The idea is to face the worst case scenario. You realize you can handle it, and then you move forward anyway.”

6. From Thinking to Embodying Stoicism

• Physical Stoic tokens (medallions, rings) serve as bridges between abstract philosophy and real-life practice, encouraging thousands worldwide to translate theory into genuine action.
  • [03:34] “They turn hesitation into action, philosophy into practice... At times when they need to remember that philosophy requires action. And that is how you move from thinking about stoicism to embodying it.”

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Memorable Quotes

• “Waiting teaches nothing. The only way to know is to start.” – Ryan Holiday [02:14]
• “Every time I touch [the Memento Mori ring], I feel that little bit of urgency.” – Ryan Holiday [03:07]
• “The idea is to face the worst case scenario. You realize you can handle it, and then you move forward anyway.” – Ryan Holiday [03:15]

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Notable Moments & Timestamps

• [00:00] Personal story of using Airbnb to facilitate lifestyle change
• [01:10] Discussion of the psychology behind procrastinating on new experiences
• [01:31] Introduction of Memento Mori as a rallying cry to act
• [01:41] Explanation of Premeditatio Malorum to rationalize and diminish fear
• [02:06] Declaration against waiting as a path to knowledge or improvement
• [03:06–03:15] How physical reminders ground philosophical principles in everyday life

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Final Takeaway

Ryan’s core message: Don’t wait to try what you’ve been considering. Use Stoic tools—Memento Mori and Premeditatio Malorum—to break the cycle of delay and move from philosophical contemplation to tangible practice. Action, not endless deliberation, is both the path to learning and fulfillment.

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Transcript

[A]

I'm on the road for these daily Stoic talks I'm doing. I started in Seattle. My family and I drove all the way down. Now I'm in San Francisco.

[B]

We're in Sacramento tomorrow.

[A]

I've actually been booking houses on Airbnb all along the way. We stayed in this awesome one in Mendocino. Last night, we stayed in a lovely one on the ocean in Bremerton, Washington. It's been awesome. And that's usually how we stay as a family. When we're traveling, we book houses or apartments on Airbnb. But what a lot of people don't know is that when I first started as a writer, I used to list my house on Airbnb, my first house, this little house in East Austin. We would book it out when we were out of town, which is what Airbnb is so great at. And then when we moved out to the country, I would write at it during the week and book it out on the weekends. And that's how we helped cover the mortgage. That's how I was able to make the transition from a marketing person to a writer. Wherever you live, but especially if you live in a city that's hosting a bunch of events this summer or you're traveling, you should think about listing your house or apartment or condo as on Airbnb. It might be worth more than you think. And you can find out how [e-mail]

[B]

host welcome to the Daily Stoic podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world. Don't wait to try it. You've thought about living somewhere else. You thought about testing the job market. You thought about asking someone out. You thought about taking lessons. But what do we do? Well, like a fool, as Seneca says, we put it off. We delay starting. We say we'll do it later. We say we'll do it when we have more information, when things settle down, when we're more comfortable and secure. There are two stoic exercises, both built around Latin expressions that can serve as mantras. The first, memento mori, right? Remember, death. Life is short. You don't know how long you have, you don't know that you have later. And the second is premeditatio malorum. What's the worst case scenario? Actually think through the worst case scenario. If you try this thing and you'll find that it's probably not so bad, it's not as scary as you think, and you'll be able to handle whatever it is you run through these exercises. And then you stop fooling yourself. You do it. You do it with your eyes open. Maybe you don't get the job. Maybe they say no to the date. Maybe you find out you don't actually enjoy playing the piano. So what? We learn nothing new by putting things off to another day. It's in acting that we discover whether the thing was right for us or not. Waiting teaches nothing. Hesitation teaches nothing. The only way to know is to start. And while these concepts can be uncomfortable to confront, the path to becoming a better, more resilient person isn't usually comfortable. That's what Memento Morian Premeditatio Malorum is about. It's supposed to be tools that transform how you practice stoicism. Every single day I carry the Memento Mori coin in my pocket. Or maybe if you've ever seen me do a podcast or talk, I usually am wearing a Memento Mori ring. I'm fiddling with it.

[A]

It's a reminder to stop waiting.

[B]

Every time I touch it, I feel that little bit of urgency. And the Premeditatio Malorum idea is what gives you courage when fear holds you back. The idea is to hold it, to face the worst case scenario. You realize you can handle it, and then you move forward anyway. These medallions, which we've sold here for Daily Stoke for many years now, they take the abstract and they make it real. They turn hesitation into action, philosophy into practice. Thousands of people all over the world carry them daily and they touch them before making big decisions. Difficult moments at times when they need to remember that philosophy requires action. And that is how you move from thinking about stoicism to embodying it. You can grab both of [e-mail].