A Productive Conversation

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 PointsWhy values—not goals—are the true drivers of intentional actionThe “intention stack” and how daily actions connect to lifelong directionWhy SMART goals aren’t as smart as we’ve been led to believeCultural differences in how productivity and calm are valuedNight owls, morning routines, and the danger of “sepia-toned” goalsThe role of reflection in escaping default behavior and finishing what mattersThree Connection PointsBuy the bookCheck out Chris's websiteListen 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.

A VERY SPECIAL EPISODE: The 12 Tips of TimeCrafting

This is a reflective, solo episode where I share twelve essential TimeCrafting tips—not as rules or resolutions, but as orienting ideas you can return to whenever your days feel scattered or misaligned. Think of this as a pause at the edge of the calendar year, and an invitation to relate to time differently. These tips are meant to be lived with, not completed. You don’t need all twelve. One idea is often enough to begin again. Whether you’re closing out a year or simply noticing that your relationship with time feels off, this episode offers a grounded way to reset without pressure.These twelve tips aren’t meant to be applied all at once—or perfectly. They’re ideas to return to when you notice drift, friction, or fatigue creeping in. Progress doesn’t require dramatic restarts. It asks for awareness, honesty, and the willingness to come back. Wherever you are in your year—or your life—I hope this episode helps you take a gentle step toward what matters.You don’t have to absorb all of this at once—just stay with it, and let one idea meet you where you are.During the episode, I mention both The 12 Days of TimeCrafting (which is a limited time offering) and my membership community. If you become a member, you'll have access to The 12 Days of TimeCrafting beyond its limited-time release period... and so much more. You can learn more about this community here.

Productivity A to Z with Erik Fisher: Volume 2 (Part 1)

In December 2024, Erik Fisher and I sit down to explore the alphabet of productivity — a tradition that started as a one-off idea and has now become an annual ritual. This year, we dove back in to see how our thinking has shifted, sharpened, or completely transformed. Turns out, a lot can change in a year… especially when life, work, and expectations rearrange themselves without asking permission.In this special episode of A Productive Conversation, Erik joins me to unpack the first half of our A-to-Z list – the second part is featured on Eriks' podcast, Beyond the to-Do List. It’s a rich mix of practice, philosophy, and the very human realities that shape how we show up to our work. If you’re craving a more grounded, nuanced approach to productivity, this conversation is an invitation to rethink your rhythms.Exploring productivity through the alphabet isn’t about clever wordplay — it’s about noticing how our relationship with work evolves year after year. Erik and I always walk away from these conversations reminded that productivity isn’t fixed; it’s lived. And in that spirit, we’ll pick up with N to Z on his show next. I hope you’ll join us there.

Faisal Hoque Talks About Humanity, AI, and What Comes Next

This time on A Productive Conversation, I sit down with someone who has spent decades at the intersection of technology, leadership, and what it means to remain truly human. Faisal Hoque isn’t just writing about AI from afar—he has lived inside this world for more than thirty years. From founding multiple companies to advising global organizations and government agencies, he brings a rare blend of deep technical expertise and grounded philosophical clarity.In this conversation, we get into his newest book, Transcend: Unlocking Humanity in the Age of AI, and explore the place where innovation meets conscience. We talk about fear and fascination, the frameworks that help us navigate uncertainty, and the practical ways AI is already reshaping how we think, work, and relate. It’s a wide-ranging, honest exchange about what we stand to gain—and what we can’t afford to lose.Six Discussion PointsWhy the rise of generative AI is only the beginning—and why thinking still mattersHow fear and fascination operate as “twin cousins” in our relationship with emerging technologyUsing the OPEN and CARE frameworks as complementary guides for opportunity and riskWhat organizations often overlook when AI governance becomes purely operationalThe philosophical crossroads ahead: outsourcing cognition vs. elevating human capacityHow empathy, devotion, and even love should shape the way we design and interact with technologyThree Connection PointsTranscend: Unlocking Humanity in the Age of AIFaisal’s websiteFaisal’s writing at Psychology TodayGetting to speak with Faisal reinforced something I’ve been thinking about for a long time: technology can extend what we do, but only we can determine who we become. AI may accelerate our output, sharpen our insights, and open new doors—but it can’t choose our purpose. That part remains ours. This conversation left me more convinced than ever that if we want a future worth inhabiting, we have to bring our humanity to the center of it.

PM Talks S2E12: Legacy

This episode marks the final PM Talks conversation of the 2025 calendar year, and it’s a fitting one: Patrick and I explore legacy — not as something we engineer, but as something that unfolds in the stories others tell about us. As always, this episode is part of our monthly PM Talks series, and it might be the most reflective note we’ve ended on so far.We talk about time, presence, family, uncertainty, and the way small choices echo long after we’re gone. This one weaves philosophy into the everyday in a way that feels real, grounding, and honestly necessary as we close out the year.Six Discussion PointsWhy time feels like it’s accelerating as we age, and how presence slows the smaller slices of our daysThe balance between certainty and agency — and how we navigate what we do and don’t controlWhy trying to “control” your legacy is ultimately a losing battleHow stories — both true and inferred — shape the legacies we inherit and the ones we leaveThe importance of documenting your own story so others don’t have to invent one laterHow everyday tasks, decisions, and moments of presence quietly become the stories others use to remember usThree Connection PointsPatrick’s workThe Productivity DietOur episode on uncertaintyLegacy isn’t a monument — it’s a story, shaped by moments we’re often too busy to notice. This conversation reminded me that what endures isn’t the grand plan, but the small choices, the presence we bring, and the stories people choose to carry forward. Thanks for being with us through another year of PM Talks. There’s a lot more ahead in the next season.