CHAPTERS
- 0:00 – 3:40
Why some goals feel effortless while others die in the “graveyard of forgotten goals”
Chris Bailey explains the personal puzzle that drove his book: despite being “productive,” he still had goals that consistently fell away. He frames goal follow-through as a web of factors—especially procrastination (aversion) and values (motivation)—that determine whether a goal feels meaningful or like a chore.
- •Most people have a “graveyard” of abandoned goals
- •Goal attainment is influenced by multiple interacting factors, not willpower alone
- •Procrastination and values are central forces behind follow-through
- •Meaninglessness often signals misalignment with what truly motivates you
- 3:40 – 7:05
The science of values: 12 core human motivations that shape what you pursue
Bailey pushes back on the cliché version of values-work by pointing to established academic research (notably Shalom Schwartz). He outlines a set of fundamental values and emphasizes that each person has a unique mix, which strongly influences what feels motivating.
- •Values research is robust and cross-cultural (Schwartz’s framework)
- •People differ in their “top” values (e.g., self-direction, pleasure, security)
- •Some values are low for many (e.g., power), but still matter for some
- •Your strongest values predict what you’ll naturally follow through on
- 7:05 – 10:55
Goals vs values—and the ‘intention stack’ that connects daily actions to identity
Goals aren’t the same as values, but Bailey argues they’re both forms of intention operating at different time horizons. He introduces the “intention stack,” showing how to-do items, plans, goals, priorities, and values can align to make effort feel easier and more coherent.
- •Values are intentions about who you intend to be; goals are intentions about what you intend to do
- •Intentions exist at multiple layers: present intentions → plans → goals → priorities → values
- •Alignment across layers creates a powerful motivational tailwind
- •Misalignment creates friction and makes goals feel forced
- 10:55 – 14:29
How to align goals with what matters (and why ‘face’ goals often backfire)
Using fitness as an example, Bailey shows how the same behavior can be driven by different values. Goals built around social approval (“face”) can be fragile if you don’t truly value that, while goals tied to security, accomplishment, or longevity can feel intrinsically meaningful.
- •The same outcome (getting fit) can express different values depending on the person
- •Many people set goals around ‘face’/appearance that don’t match their true motivations
- •Value-aligned goals feel more effortless and less procrastination-prone
- •Even gender patterns show different value links to fitness motivations
- 14:29 – 18:29
Why intentions slip: treating goals as predictions (not promises) and rewriting them often
Bailey reframes goals as predictions about where current and planned actions will lead—not fixed commitments. When we treat predictions as expectations, we create disappointment; the solution is to hold goals more loosely, revise them, and sometimes drop them.
- •Goals are ‘predictions in disguise,’ and humans predict poorly
- •Predictions become expectations, which become disappointment
- •New Year’s resolution failure is partly an expectations problem
- •Editing and dropping goals can improve long-term follow-through
- 18:29 – 20:35
Default vs deliberate intentions: autopilot, awakening moments, and self-reflective capacity
The conversation distinguishes between automatic, habit-driven ‘default intentions’ and consciously chosen ‘deliberate intentions.’ Bailey describes the “snap out of autopilot” moments where self-reflection returns and you can deliberately steer your day.
- •Default intentions are largely habits and automatic reactions to context
- •Deliberate intentions arise when you pause and ask what you really want
- •Self-reflective capacity enables intentional course-correction
- •Frequent ‘awakening moments’ increase agency and follow-through
- 20:35 – 28:24
Where default intentions come from: social contagion, biology, and the power of mental wandering
Bailey lists the sources of intentions, from social environment and pleasure/pain drives to bodily needs. He also highlights that mind-wandering—especially in the gaps between activities—can generate better intentions, learning loops, and future-oriented planning.
- •Default intentions are shaped by social contagion and environment
- •Biology and basic drives also generate automatic intentions
- •Learning creates new response patterns for future situations
- •Mind-wandering (often future-focused) can produce valuable intentions
- 28:24 – 32:53
Why ‘SMART goals’ may be holding you back (and where the idea actually came from)
Bailey argues SMART goals are culturally popular but not strongly supported by the evidence people assume exists. He critiques the “realistic” component as potentially limiting, notes redundancy in the acronym, and explains its origins in management writing rather than rigorous academic work.
- •SMART goals feel intuitive but lack strong research support as commonly presented
- •‘Realistic’ can lower ambition; challenging goals can produce higher attainment
- •Parts of SMART overlap (measurable vs specific)
- •The framework spread through business culture more than academia
- 32:53 – 35:55
Procrastination explained: desire minus aversion—and the six task triggers
Bailey defines procrastination as an emotional/visceral aversion response more than a logical choice. He introduces the core model: how much you care depends on desire minus aversion, and lists key task features that increase aversion and lead to delay.
- •Procrastination is primarily emotional, not rational
- •Motivation can be modeled as desire − aversion
- •Aversion triggers: boring, frustrating, unpleasant, far away, unstructured, meaningless
- •Many tasks trigger multiple aversion factors at once (e.g., taxes)
- 35:55 – 45:12
The easiest ways to beat procrastination: structure, delegation, rewards, and ‘aversion journaling’
The discussion turns practical: structure is the lowest-hanging fruit, and delegation can eliminate entire blocks of aversive work. Bailey also suggests making tasks more enjoyable with rewards/gamification, blocking distractions, journaling resistance, and shrinking the task until it’s doable.
- •Add structure to reduce resistance; ‘unstructured’ is highly solvable
- •Delegate when possible to bypass aversion entirely
- •Pair aversive tasks with rewards (points, treats, habit stacking)
- •Use blockers (Freedom/Cold Turkey) to remove tempting alternatives
- •Try ‘aversion journaling’ to diagnose resistance and generate a tactical fix
- •Shrink the task duration until starting feels possible
- 45:12 – 54:22
Ugly goals, sepia-tone fantasies, and the ‘socially acceptable cosplay of ambition’
Bailey distinguishes between goals that remain inherently unpleasant even after editing and goals you should drop because they aren’t truly yours. They discuss “sepia tone goals” (idealized lifestyle fantasies like waking at 5:30 a.m.) and how social signaling and guilt can keep misfit goals alive.
- •Some goals stay ‘ugly’ even after reframing—then decide: pursue or drop
- •Use the ‘tangible payoff of having done it’ as a litmus test
- •‘Sepia tone goals’ glamorize change while hiding daily tradeoffs
- •Many goals are social signaling—what you want others to hear
- •Conformity vs self-direction values change how social expectations feel
- 54:22 – 57:35
Building deeper goals: values alignment plus positive social contagion
To make intentions feel deeper, Bailey returns to values and the social environment. Without becoming extreme about cutting people out, he recommends intentionally adding supportive communities—groups, meetups, and shared practice—because connection makes goals feel more meaningful and sustainable.
- •Depth comes from aligning goals with your strongest values
- •Social contagion can be intentionally increased (running groups, communities)
- •You don’t need to purge relationships to be intentional—life is complex
- •Human connection is one of the deepest motivators for persistence
- 57:35 – 1:05:17
Designing intentions that stick: the Rule of Three and stacking time horizons
Bailey presents intentionality as a trainable skill and offers a simple operating system: the Rule of Three. By setting three outcomes for the day and week, you connect daily actions to broader plans and values, improving prioritization and follow-through across the intention stack.
- •Intentionality and follow-through improve with practice like a skill
- •Rule of Three: pick the three things you’ll want done by day’s end
- •Extend the Rule of Three to weekly intentions to guide daily choices
- •Link daily intentions → weekly intentions → plans/goals → values
- 1:05:17 – 1:08:30
The biggest overlooked idea: your values are built from your default intentions
Bailey argues default behaviors aren’t just obstacles—they reveal the underlying motivations that form your values. By observing defaults with curiosity (not only frustration), you can better understand who you are and deliberately layer new intentions on top of what’s already shaped you.
- •Default intentions create a pattern that reflects your underlying values
- •Many defaults are worth understanding and even appreciating, not just fixing
- •Self-observation can reveal the motivation beneath habits (even unhelpful ones)
- •Deliberate intentions can redirect life without rejecting your humanity
- 1:08:30 – 1:09:18
Wrap-up: where to find Chris Bailey and his book ‘Intentional’
Bailey shares where listeners can find his work and the new book, including the audiobook. The conversation closes with final thanks and show sign-off.
- •Book: ‘Intentional: How to Finish What You Start’
- •Audiobook available
- •Website/newsletter: chrisbailey.com
- •Closing remarks and sign-off
