The Daily Stoic Podcast

BONUS | No One Is Coming to Give You Permission
February 5, 2026
Host: Ryan Holiday
Guest: Brent (Daily Stoic collaborator/producer)

Episode Overview

In this candid, conversational bonus episode, Ryan Holiday and his longtime collaborator Brent discuss the pervasive challenge of starting—particularly starting creative or ambitious projects in the absence of external permission, deadlines, or validation. Framed by the principles of Stoicism, the conversation explores procrastination, imposter syndrome, perfectionism, and the practicalities of moving from intention to action. The episode is both a self-examination and a relatable guide for listeners who, too, are stalled by waiting for "permission" to begin their work.

Key Discussion Points & Insights

The Challenge of Starting Without Permission

• The Allure of External Validation and Deadlines (04:06–08:35)

  • Brent shares his difficulty initiating projects (like writing a book) when there's no contract, commitment, or authority figure setting expectations.
    • "[I struggle] to start things for which there is not like a contract or a like commitment that you would like get in trouble if you didn't meet." (04:01, Ryan)
    • Brent admits to waiting for a "stamp of approval" to begin, tying this to imposter syndrome and external validation.
  • Ryan notes even he can face the same inertia with open-ended projects: "The open-ended nature of like no one is asking for it, no one necessarily wants it... I can always make an excuse." (05:13, Ryan)

• Deadlines, Accountability, and Artificial Pressure (07:12–08:18)

  • Both discuss how artificial deadlines (a publisher, an advertiser, a contract) help break perfectionist loops and spur action.
  • Notable anecdote: Publishers threatening to cancel Brent’s contract finally pushed him to finish his last book.

Imposter Syndrome & Opportunity Cost

• Seeking Permission as a Symptom of Self-Doubt (06:09–06:23; 10:48–11:11)

  • Brent openly identifies feelings of imposter syndrome: "I'm probably looking for like a stamp of approval that like this is worth your time also, like outsourcing that part of it as well." (06:23, Brent)
  • Ryan: "Most of the people who are high achievers also struggle with high amounts of procrastination and excuses and paralyzation and perfectionism." (09:31, Ryan)

• Opportunity Cost and Busyness (04:08–10:44)

  • Brent lays out how a never-ending checklist of urgent tasks crowds out important but non-urgent, self-driven projects (like his book or new podcast).
  • Ryan notes this is often a cover for deeper hesitation: "If the book sold tomorrow, I would find the time to write it in addition to everything else." (10:38, Brent)

The Trap of Perfectionism and Fantasy Planning

• The Myth of Perfect Conditions (35:38–39:33)
  • Both discuss the myth of the "writer’s retreat"—the idea that inspiration or productivity will strike in ideal conditions, at a special place or time.
    • "I hate writing retreats because it's basically an expensive form of procrastination." (35:38, Ryan)
  • Ryan asserts the best place to do the work is "wherever you are, whenever you have time." (38:46, Ryan)

Procrastination: Big vs. Small Tasks

• Differentiating "Good" and "Bad" Procrastination (21:48–22:16, 28:01–29:39)
  • Ryan distinguishes between healthy delay (where procrastination signals a decision is unwise) and unhealthy delay (where resistance is simply fear or avoidance).
  • He shares personal examples—sometimes ignoring an email is just compounding stress, not wisdom.

Facing the Fear of Success (and its Consequences)

• What If It Works Out? (17:25–18:44)
  • Brent voices a unique anxiety: fear that starting and succeeding will bring even more responsibility and less bandwidth.
  • Ryan reframes this as a problem worth having, highlighting his own experience: "You'll cross that bridge the same way you've crossed every one of those bridges... now you have a scaling problem, which you're actually uniquely qualified and practiced at solving." (18:34, Ryan)

Stoic Wisdom Applied

• Seneca’s Maxim on Starting (18:59)

  • "The one thing that all fools have in Common is they're always getting ready to start." (18:59, Ryan quoting Seneca)
  • The trick is getting past the endless "getting ready," and just beginning.

• Epictetus’ Call to Action (41:37)

  • "First say to yourself what you would be. And then do what you have to do." (41:37, Ryan quoting Epictetus)
  • The encouragement to define your goal and take the required action, regardless of external acknowledgement.

Actionable Advice

• Set Manageable, Consistent Routines (16:08–17:21, 24:13)

  • Ryan advises Brent (and listeners) to commit a certain amount of daily or weekly time to the new project, regardless of whether conditions are perfect:
    • "I'm going to give it one hour a day for, you know, for all of 2025 and just see where it is." (16:13, Ryan)
    • Referencing Tim Ferriss’s idea: try things in small, consistent batches ("do six episodes, then evaluate," etc.).

• Lessons from Publishing & Creative Transitions (44:19–45:14)

  • Ryan and Brent reflect on how moving from one genre or success to another often means accepting that the next project may be less commercially successful—but more personally valuable.
    • "The Conspiracy is my worst selling book. It’s one of, if not my favorite book of yours." (44:36, Brent)
    • "Day to day, I'm loving doing it because... I'm learning and growing. So it's success even if I was doing it for... Even if it was a money losing project." (44:59, Ryan)

Notable Quotes & Memorable Moments

• On Permission & Procrastination:

  • "You're just like waiting for some... you're waiting for like the bell to go off to start and that's not probably going to happen... It's all gotta be self-driven."
    — Ryan, 19:12

• On Success & Risk:

  • "Mostly only yours to do. And if there was a magical solution, someone would've figured it out already."
    — Ryan, 39:29

• On Creative Responsibility:

  • "I want the things, you know, I want the podcast to be doing well. I want the book to be under development. It's just something about... the doing."
    — Brent, 43:56

• On Crushing Perfectionism:

  • "Start the clock, right? Like, you should start, like, who you're going to be a year in and two years in and five years in is, like, obviously much better than who you are at the beginning."
    — Ryan, 27:19

Episode Structure / Timestamps for Key Segments

• [04:06] – Conversation begins: The struggle to start without external deadlines
• [06:09] – Imposter syndrome and waiting for validation
• [07:12] – Artificial deadlines and accountability workarounds
• [10:38] – Opportunity cost and the justification trap
• [16:08] – Ryan’s actionable advice: Commit consistent time, even if small
• [18:59] – Seneca’s advice: Stop “getting ready,” just do
• [21:48] – Evaluating procrastination: When to push through, when to reconsider
• [29:39] – Email “bankruptcy” and how small tasks accumulate
• [35:38] – Debunking writing retreats and the myth of perfect conditions
• [39:33] – "The best place to write is wherever you are, whenever you have time"
• [41:37] – Epictetus: “First, say to yourself what you would be...”
• [44:19] – Understanding and redefining creative success

Takeaways for Listeners

• No one is coming to give you permission or the perfect moment to begin—act regardless.
• Perfectionism is often a mask for fear; “good enough” is better than never started.
• Create personal routines and artificial accountability if external pressure is missing.
• The act of doing will clarify both your enjoyment and your capacity for the thing.
• Stoic wisdom: Define your aim, then act decisively—even if no audience (yet) is waiting.
• Opportunities multiply as you act; don't fall for the fantasy of the perfect starting conditions.

For more practical Stoic advice and to join Ryan’s challenges, visit dailystoic.com/challenge.