TDC 079: The Tension Between Resistance & Productive Procrastination: How to Know When It's Time to Ship

TDC 079: The Tension Between Resistance & Productive Procrastination: How to Know When It's Time to Ship

When productive procrastination crosses the line into destructive resistance—and the simple test to know when you must finally ship.

Episode Summary

In this episode of The Digital Contrarian, host Ryan Levesque dives into the critical tension between productive procrastination and destructive resistance.
You'll learn how to distinguish between creative incubation and fear-based avoidance, discover why original thinkers are "quick to start but slow to finish," and uncover a simple litmus test for knowing when your creative window is closing.

Question of the Day 🗣️

What's the one project you've been "productively procrastinating" on—and if you're honest with yourself, has it crossed the line into resistance?

Key Take-aways

• Productive procrastination is idea incubation, not laziness—it's where creative magic happens
• Original thinkers feel doubt but keep it pointed at the idea, not themselves
• There's a thin line where incubation quietly turns into avoidance and resistance
• Creative windows don't stay open forever—market conditions change and energy wanes
• Simple test: Is your procrastination producing new insight or just new excuses?

Timestamped Outline ⏱️

00:00 – Introduction: The tension between resistance & productive procrastination
00:27 – My biggest unfinished project: The Return to Real book
01:00 – Why I've been procrastinating (my string of excuses)
02:31 – At some point you just need to ship the damn thing
03:19 – James Clear: "Writing a book is not good enough is good enough"
03:48 – The power of productive procrastination
04:28 – Adam Grant's core argument: Idea incubation
05:20 – The truth about creative work and windows
06:15 – How do you know when it's time to ship?
07:27 – When resistance rears its ugly head
08:15 – The simple litmus test: Insight vs. excuses
08:56 – Three rules of thumb for when to ship
09:52 – Pressfield's rally cry: The more scared, the more sure
10:07 – Your pep talk: Get your butt in gear and ship
10:34 – Holiday wishes & winter solstice message
11:02 – January 8th Town Hall event announcement

Links & Resources 🔗

Issue 060 of The Digital Contrarian – "Inside a Room with 40+ Million-Copy Bestselling Authors" → https://ryanlevesque.net/inside-a-room-with-40-million-copy-bestselling-authors/

Issue 027 of The Digital Contrarian – "Building Your Strategic Content Ecosystem" → https://ryanlevesque.net/strategic-content-ecosystem/

Join the Return to Real Book Waitlist → https://ryanlevesque.net/return-to-real-book/

Apply for Return to Real Agency (February 2026 Cohort) → https://www.ryanlevesque.net/apply

Connect & CTA 🎯

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Credits
Host: Ryan Levesque
© 2026 RL & Associates LLC. All rights reserved.