Makes Sense with Dr. JC Doornick
Episode 147 – Why You Can’t Finish What You Start: Chris Bailey on the Willpower Myth
Released: February 24, 2026
Guest: Chris Bailey, author & productivity researcher
Host: Dr. JC Doornick ("The Dragon")
Brief Overview
In this episode, Dr. JC welcomes back renowned productivity thinker Chris Bailey to discuss his latest book, Intentional. Together, they dive into the real reasons people struggle with follow-through—shifting focus from hacks and willpower to the deeper science and practice of intentional living. The conversation explores why busyness tricks us into feeling productive, why traditional productivity approaches often fail, the true source of procrastination, and practical strategies to align ambition with action.
Key Discussion Points & Insights
The Real Science Behind Procrastination
[07:17–11:32]
- Emotional Regulation, Not Laziness: Chris Bailey frames procrastination as an emotional regulation problem, not a lack of willpower.
- Aversion vs. Desire Equation:
“How motivated we are to complete a task is a function of our desire to do the thing, minus the amount of aversion that we have to doing it.” (Chris Bailey, 07:46)
- Triggers for Procrastination: Boredom, frustration, unpleasantness, unstructured tasks, distance in time, and lack of meaning.
- Intentionality Is "Webby": Motivation emerges from a web of interconnected factors—desire, aversion, values, meaning.
The Busyness Trap & Why Productivity Systems Fail
[11:32–14:26]
- Busy ≠ Productive: Modern productivity is no longer about output or hours, but about the difference made.
- Massive To-Do Lists Increase Cognitive Load: “One of the biggest traps… is we look at how busy we are as a proxy measure for how productive we are.” (Chris Bailey, 13:29)
- Knowledge Work & AI: Evolving from knowledge work to what Bailey calls "guidance work," where leverage and intentionality matter more.
Intentionality vs. Efficiency
[15:40–18:38]
- Self-Reflective Capacity:
“If you never tap into your self-reflective capacity, your productivity is going to be toast. You’re just going to work on what’s latest and loudest.” (Chris Bailey, 15:56)
- Walks & Wandering for Insight: True productivity (including business breakthroughs) often comes from reflective moments, e.g., walks or showers.
Creativity & Letting Go for Breakthroughs
[19:09–22:23]
- Host shares story of MacGyver creator Lee Zlotoff: best ideas came during showers, not at the whiteboard.
- Chris notes that self-reflection is a deep wellspring for intentions and creativity, with mind-wandering being scientifically shown to connect us to goals and future thinking.
AI, Agency, and Outsourcing Intention
[22:52–26:31]
- Don’t Outsource Intentions: While AI can perform knowledge work, humans must provide the intentional direction:
"The ultimate thinking is what to think about in the first place...that’s all about intentionality.” (Chris Bailey, 23:32)
- The ‘Intention Stack’: Values → Priorities → Goals → Plans → Daily Intentions.
“A to-do list is really just a place where we store our intentions. It’s a list of stored intentions.” (Chris Bailey, 25:08)
Gratitude and the Present
[28:16–30:05]
- Dr. JC challenges where gratitude fits in. Chris describes gratitude as a shortcut to abundance—a trait that can be developed, helping us see options and opportunities and enhancing meaning and intentionality.
The Nature & Myth of Goals
[30:40–34:29]
- Goals Are Predictions, Not Absolutes:
“A goal is a prediction of where we believe our current and our planned actions will take us... but we then become attached to that prediction.” (Chris Bailey, 30:55)
- Recommendation: Hold goals loosely, iterate and edit them regularly; don’t let expectations set you up for disappointment.
The 'Intention Stack'—From Values to Daily Actions
[35:40–40:15]
- Visualize stacking intentions in a funnel:
- Values (what matters most) → Priorities → Goals → Plans → Daily Actions
- 12 Human Values (examples: pleasure, security, tradition, benevolence)
- Aligning Goals with Values fuels true motivation.
- Example: If you value pleasure, make workouts pleasurable instead of a means to an end you don’t care about.
Motivation vs. Willpower
[43:02–44:28]
- Alignment between values and intentions makes discipline "second nature."
“When we have that alignment, you really do need less willpower.” (Chris Bailey, 43:02)
The Power and Pitfalls of Aversion
[45:49–49:26]
- Aversion isn’t always self-sabotage—it can also be a healthy signal.
- Strategy: Aversion journaling—write about why you’re resisting a task to clarify if it’s self-sabotage or a deeper signal to drop/adjust the goal.
How Intentional Adds to Classic Productivity Books
[51:21–54:13]
- Chris positions his work as a more human, inside-out approach—bridging science, spirit, and actionable strategies.
“What I love to do with these books is look at the causes and effects within our mind... and make a bridge from those to the practical, tactical things we need to be doing.” (Chris Bailey, 52:08)
Practical Ritual: The Rule of Three
[56:33–58:43]
-
Daily, weekly, yearly: Each morning, list the three main things you want to have accomplished by day’s end. Repeat for the week and year.
-
Align daily intentions with larger goals and values for sustained follow-through.
“In choosing only three, you choose a lot of other stuff that you don’t prioritize, right? You choose which intentions that you have that day rise above the others.” (Chris Bailey, 56:46)
Notable Quotes & Memorable Moments
-
Procrastination and Motivation:
“Procrastination is not a time management problem or a productivity problem. It’s an emotional regulation problem.” (Chris Bailey, 07:46)
-
On To-Do Lists:
“Busyness is really no different from an active form of laziness when it doesn’t lead us to accomplish anything of importance... we’re just on autopilot.” (Chris Bailey, 13:12)
-
On AI and Agency:
“You’re not only responsible for your own intentions now, you’re responsible for the intentions of machines.” (Chris Bailey, 23:08)
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On Values:
"Values are our true motivational nature." (Chris Bailey, 39:00)
-
On Gratitude:
“Gratitude is quite a beautiful thing, and it’s, you know, this beautiful shortcut to abundance.” (Chris Bailey, 28:53)
-
On Aversion and Journaling:
“Aversion is such a helpful signal...or it could be a sign you need to change your relationship with what you’re doing, which is what overcoming aversion is all about.” (Chris Bailey, 49:14)
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On the Real Secret to Productivity:
“Not all tasks are created equal. For every minute we spend mentoring a new employee, we’ll make many, many more minutes back...” (Chris Bailey, 17:44)
Timestamps of Key Segments
| Timestamp | Segment / Topic | |-----------|-------------------------------------------------------------------| | 07:17 | Why We Procrastinate (Desire–Aversion equation) | | 11:32 | The Busyness Trap and Failure of To-Do Lists | | 15:40 | Why Intentionality Beats Efficiency (Self-Reflective Capacity) | | 18:38 | Creativity, Showers, Walks, and Self-Reflection | | 22:52 | Using AI Without Outsourcing Intentions – The Intention Stack | | 28:16 | The Power of Gratitude in Self-Reflection | | 30:40 | The Myth of Goal Setting – Goals As Predictions | | 35:40 | The Intention Stack—Values–Actions Funnel Explained | | 43:02 | Alignment Makes Willpower Less Necessary | | 45:49 | Aversion—When to Push, When to Drop Goals (Aversion Journaling) | | 51:21 | What Makes Intentional Different from Classic Productivity Books| | 56:33 | The Rule of Three—A Practical Intentionality Ritual |
Final Takeaways
- Intentional living means aligning daily actions with deeper values and priorities—not just chasing hacks, tools, or endless to-do lists.
- Procrastination is rooted in emotion (aversion), not laziness or lack of discipline.
- AI and tech can extend leverage, but only if humans retain ownership of intention.
- "Stacking" intentions (from values down to daily tasks) makes follow-through natural and reduces need for willpower.
- Practical rituals (like the Rule of Three) help bridge ambition and action.
- Gratitude, reflection, and habitually pausing ("hmmm") provide fertile soil for intentional, meaningful productivity.
For Listeners Who Haven’t Tuned In
This episode reframes productivity, challenging the myth that more hacks, tools, or willpower are the answer. Chris Bailey and Dr. JC invite you to ask what you truly want, why you want it, and how your daily behaviors and tools can be guided by values and conscious intention. The conversation mixes practical tactics (e.g., the daily Rule of Three, aversion journaling), big ideas (the Intention Stack, busyness as laziness), and real-world anecdotes. It’s a must-listen for anyone feeling stuck, busy but unfulfilled, or looking for the missing layer behind goal achievement.
Recommended Reading:
- Intentional and Hyperfocus by Chris Bailey
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