When you gain agency over your time—whether stepping out of a traditional 9-to-5 job or shifting into self-employment—it can feel liberating… and overwhelming. Kerry Hoffman knows this tension well. As someone who helps individuals and teams make sense of what they’re doing and when they’re doing it, she offers a refreshingly practical approach to task management and planning that embraces both the structure and spontaneity life demands.

In this episode of A Productive Conversation, Kerry and I dive into the habits and mindset shifts required to design a system that supports how you want to live—not just how you work. From flipping mattresses to prepping for quarterly reviews, it’s about giving your tasks a home… and giving yourself a break.

Six Discussion Points

Why gaining control over your time can feel disorienting—and how to reclaim clarity through structure
The power of defining homes for different kinds of tasks (calendar, project manager, spreadsheet, etc.)
The liberating magic of mundane reminders (yes, even "flip the mattress")
How building a system frees up bandwidth and unlocks more unplanned time
How reflecting after the experience makes the memory stronger (and more fun)
Why teams need to define what ASAP really means—and who decides what's "possible"

Three Connection Points

Kerry reminded me of something vital in this conversation: structure isn’t about control—it’s about creating space. Space for spontaneity, reflection, even a non-alcoholic beer at the end of the day (which we talk about, too). Her blend of grounded tools and generous mindset makes the work of planning feel like an act of care, not constraint.

Star Trek: The Next Generation w/ Art & Labor

Struggle Session

Introduction

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