Chris Bailey Talks About Intentionality, Values, and Finishing What You Start

In this episode of A Productive Conversation, I sit down once again with author and researcher Chris Bailey to explore what it really means to live—and work—intentionally. This conversation centers on his latest book, Intentional: How to Finish What You Start, and the decade of curiosity that led him there.
We dig into why goals often fail us, how culture shapes our relationship with productivity, and why values—not habits, hacks, or willpower—sit at the core of meaningful progress. This isn’t a surface-level productivity chat. It’s a thoughtful examination of why we do what we do, and how to align our days with who we actually are.

Six Discussion Points

• Why values—not goals—are the true drivers of intentional action
• The “intention stack” and how daily actions connect to lifelong direction
• Why SMART goals aren’t as smart as we’ve been led to believe
• Cultural differences in how productivity and calm are valued
• Night owls, morning routines, and the danger of “sepia-toned” goals
• The role of reflection in escaping default behavior and finishing what matters

Three Connection Points

1. Buy the book
2. Check out Chris's website
3. Listen to Chris's first appearance the podcast (from October 2014!)

This episode is a reminder that productivity isn’t about doing more—it’s about doing what fits. If you’ve ever felt friction between your goals and your values, or wondered why “good habits” still leave you unsatisfied, this conversation will give you plenty to reflect on—and return to.