You Made It Weird with Pete Holmes

Guest: Steven Pressfield
Date: July 26, 2023

Brief Overview

In this deeply personal and philosophical episode, Pete Holmes sits down with acclaimed author Steven Pressfield ("The War of Art," "Government Cheese") to explore the inner battles of creativity, the forces of resistance, and the nature of fulfillment. The conversation weaves through Pressfield's journey from feeling "feckless" and lost to finding his creative voice, discusses the origins and mechanics of resistance, examines the spiritual aspects of work and purpose, and meditates on the universal desire for meaning. The episode is rich with insights, memorable moments, and a blend of humor and depth.

Key Discussion Points & Insights

1. The Nature of Creativity and Resistance

• Pete shares how Pressfield’s "The War of Art" helped him overcome his own resistance with creative projects.
• Resistance is characterized as an internal, almost externalized force that sabotages our calling and keeps us from doing our work.
• Pressfield shares the origin story of how "resistance" derailed his early creative and personal life, leading him down a path of shame and blue-collar jobs before clawing his way back through writing.
  • “What does it feel like to not create? Isn’t that why you create? Because it feels better than not creating?” – Pete Holmes [13:01]
  • “I forgot even what the question was. We were talking about…what it felt like to not write. Oh. So I felt like a complete loser at that point.” – Steven Pressfield [14:52]
• Discusses how the act of not pursuing one’s calling becomes "cancerous," impacting health, mood, and sense of self.
  • “That unwritten joke goes into a bad channel inside you and becomes…cancer. It must get out. It’s like a living thing.” – Steven Pressfield [27:45]

2. Breaking Out of "Loserdom" and the Importance of Work

• Pressfield highlights the years-long, difficult process of reclaiming his confidence and sense of purpose through writing, even when early works failed commercially.
  • “The way out of it, the way back is…through work, in my opinion. There’s magic involved, but it’s also really just that showing up every day, every day for the goddess.” – Steven Pressfield [42:27]
• Both agree on the importance of not judging daily output by its immediate quality, but by the act of showing up and trying.
  • “Did I put in the time and did I try hard? And if I did, then I pat myself on the back and say, OK, that was a good day.” – Steven Pressfield [31:54]

3. Resistance as an Intelligent Force, Spirituality, and Ego

• The conversation delves into resistance’s almost demonic intelligence, and how it can manifest as distraction, temptation, or even "good" opportunities that are actually traps.
  • “Somehow resistance can produce in the real world a quote-unquote opportunity that is actually the death of her dream.” – Steven Pressfield [48:35]
• Pete and Steven draw parallels between resistance, the ego, spiritual traditions (including the Bhagavad Gita and A Course in Miracles), and the mythic hero’s journey.
  • “We could call that the Christ, I suppose, if that’s the Antichrist. Christ, or life, or oneness, or universe, or flow, or whatever.” – Pete Holmes [39:03]
• They discuss the drive toward wholeness and healing, referencing biblical parables (e.g., the Prodigal Son, Garden of Eden), and the way creativity is a return to divine inheritance.
  • “We have these ideas. You’re talking about the risk of no risk…there’s the risk of not risking.” – Pete Holmes [29:04]

4. Masculinity, Femininity, and the Creative Process

• The discussion addresses how the creative struggle is often painted in masculine terms but is inherently universal—using the archetypes of the warrior and the mother.
  • “In practice, the most warrior-like individual I can think of is a mother. …What is art except bringing forth new life, right?” – Steven Pressfield [64:59]
• The duality of toughness and nurturing as complementary forces needed to face resistance.

5. Practical Wisdom and Lessons for Creatives

• The necessity of embracing discomfort and difficult emotions as signs you’re moving towards purpose ("the law of the cold plunge").
  • “Get your whole body in it, it’s better because you get overwhelmed and your body doesn’t know where to feel pain, so you feel no pain…Get in it the whole way or it’s gonna punish you.” – Pete Holmes [68:41]
• Pressfield’s advice: Believe in the existence of a higher level (the muse, the goddess, the source of inspiration) and position yourself—through daily effort and skill—to be receptive to it.
  • “Life exists on at least two levels…our purpose…is to believe in first, believe in that other level, and then find a way to reach it.” – Steven Pressfield [89:50]
• The importance of following one’s unique calling, even if it’s not celebrated or visible to the world.
  • "Whatever that calling is, it’s unique to you and unique to me. ...It’s like we were born with it, we were born with a seed inside us." – Steven Pressfield [93:02]

Notable Quotes & Memorable Moments

• On creative inertia:
  “If you have a great joke on your mind and you don’t follow on, that’s not a benign action…It becomes cancer.” – Steven Pressfield [27:45]
• On spiritual resistance:
  “It’s so diabolical and so intelligent and so nuanced…It can’t just be some dumb element. It’s Voldemort.” – Steven Pressfield [37:42]
• On "good opportunities" as resistance:
  “Somehow resistance can produce in the real world a quote-unquote opportunity that is actually the death of her dream.” – Steven Pressfield [48:35]
• On masculine and feminine creative forces:
  “Male or female, we have to summon some—no bullshit—strength to face this devil, day after day after day.” – Steven Pressfield [66:28]
• On the role of work in creativity:
  “It’s not cinematic, it’s not glamorous, it’s tedious, it’s boring. It’s digging.” – Steven Pressfield [92:02]
• On finding unique purpose:
  "It’s unique to you and unique to me. ...The movie that your wife is writing is unique to her. Nobody else could do it.” – Steven Pressfield [93:02]

Timestamps for Important Segments

• Discussing anxiety & creative discomfort:
  [07:24]–[10:21]
• Pressfield’s early struggles with writing, shame, & “loserdom”:
  [12:13]–[17:25]
• On mythic structure, Bagger Vance, and the Bhagavad Gita:
  [20:29]–[23:59]
• The nature of resistance ("the devil" vs. "the muse"):
  [35:58]–[40:03]
• The health risks of creative stagnation:
  [27:44]–[29:36]
• The cold plunge & law of embracing discomfort:
  [67:09]–[69:56]
• Societal roles, fulfillment beyond fame:
  [94:36]–[98:47]
• Parting wisdom, calling, returning what you’ve been given:
  [89:15]–[93:49]

Tone & Language

The episode maintains an open, reflective, and occasionally playful tone. Pete blends humor with deep philosophical inquiry, matching Steven’s candid, concise, and wise delivery. Personal anecdotes, mythic references, and spiritual language abound, giving the episode a lively and authentic feel.

Final Takeaway

Steven Pressfield and Pete Holmes offer a profound meditation on the sometimes agonizing, always mysterious process of making art and living a meaningful life. By demystifying resistance, championing patient work, and aspiring toward one's unique purpose, the conversation leaves listeners with practical wisdom and inspiration—whether their “calling” is making art, finding balance, or simply showing up for life’s deeper meaning.