317 — The Goal You Keep Setting and Not Following Through On? Here's What's Actually Wrong With Bestselling Author Chris Bailey

May 19, 2026

Pick up a copy of ⁠The Mental Strength Playbook⁠.

Do you ever set a goal you genuinely cared about — get healthier, write the book, finally save money — and two weeks later you can’t make yourself take any action? Even when you have motivation and a good plan, sometimes, the action doesn’t happen.

Closing the gap between what you intend to do and what you actually do has far less to do with trying harder than you’d expect, and far more to do with a smarter approach.

My guest today is Chris Bailey, a productivity expert and the bestselling author of Intentional. He draws on years of research — and conversations with Buddhist monks — to explain what actually moves us from intention to action, and why forcing yourself is the least effective tool you have.

Some of the things we discuss are:

The reason your goal keeps turning into disappointment and the one word Chris uses to describe what a goal actually is
The simple subtraction problem happening in your brain every time you choose the couch over the goal
How to conduct an “aversion audit”
The five things that make a task feel impossible to start and why naming them is half the battle
Why the early-rising, tea-drinking version of you in your head is sabotaging you and what the research says about whether 5am people are actually more successful
The 12 values and how to instantly tell if a goal is even yours
What it means when you can’t connect a goal to anything you value — and the uncomfortable truth about whose goal it might be
Why guilt isn’t the enemy and what it’s actually trying to tell you
My three favorite strategies that will help you start to get more intentional today

Key Takeaways:

Understanding Goals: Goals should be seen as predictions rather than fixed endpoints. This flexible mindset will help you reach your goals.
Aversion Audit: Identify aversive elements in tasks—such as boredom or lack of structure—that hinder goal progress, and find ways to overcome these obstacles.
Intrinsic Motivation: Align goals with your core values for sustainable motivation.
Reflection and Maintenance: Regularly reflecting on and celebrating small milestones will help you stay enthusiastic about your next goal.

Notable Quotes:

"A goal is really just a prediction about where your current and future actions will take you."

"The road to hell is paved with good intentions, but what's the gap there? It's rarely willpower."

"If something's a priority for you, you've probably done it already."

"Intentions come from so many different sources, it's about finding that self-awareness in intention."

Timestamp Summary

0:00 — Why a desire, plan, and motivation aren’t enough

3:17 — The single goal 40–45% of the world is chasing at any given moment

7:41 — The two kinds of intentions running your life—and the one you never actually chose

13:29 — The donut-vs-kale equation that explains every goal you've quit by day five

17:40 — Why treating your goal as a "destination" traps you in a disappointment loop

23:15 — The 12 values behind every action you'll ever take (validated across 80+ countries)

29:27 — Chris's "sepia-tone" 5am fantasy—and the research that finally killed it

35:03 — What guilt is actually trying to tell you about your half-finished projects

45:47 — The one piece of advice in Chris's own book that he admits he can't follow

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