70 - Leveling Up in Real Life: Kevin Anderson on Gamifying Personal Growth Through Journaling

Kevin Anderson has journaled every day since 2020, and he thinks of the habit as a real-life video game. In this inspiring conversation, Kevin shares how journaling helps him track emotions, celebrate wins, and evolve through life’s challenges. He opens up about printing his entries into a growing bookshelf of colorful Day One books, the joy of documenting the things that make him laugh, and how his practice helps him zoom out to see the full arc of his personal growth over time. Whether through naming his journal volumes or reflecting on legacy, Kevin’s approach to keeping a journal is playful, powerful, and triumphant. We close the episode with a first for the podcast—a live “On This Day” journal reading. Visit dayoneapp.com/podcast/episode-70-kevin-anderson for more on this episode. 

C.J. Chilvers has journaled every night since 2010, treating the practice as a form of quiet reflection—part habit, part meditation. In this episode, C.J. shares how a simple routine became a sustaining creative force in his life, why giving himself permission to complain was an early breakthrough, and how journaling helps him clear his head at the end of each day. We also talk about the value of keeping things unstructured and where he sees journaling evolving next. Visit dayoneapp.com/podcast/episode-69-cj-chilvers for more on this episode.   

What if anxiety isn’t something we need to get rid of, but something we can learn to thrive with? In this episode, Dr. David Rosmarin—associate professor at Harvard Medical School, program director at McLean Hospital, and author of Thriving with Anxiety—offers a hopeful and practical reframe of how we understand and respond to anxiety. Dr. Rosmarin shares his four-step approach for dealing with anxiety, and how journaling can support each stage. From naming what you’re afraid of to learning how to release what’s outside your control, this conversation is a compassionate and practical look at working with anxiety, not against it. Visit dayoneapp.com/podcast/episode-68-dr-david-rosmarin for resources mentioned in this episode.  Note: This episode discusses strategies for working with everyday anxiety, and is intended for general reflection and support. If anxiety is interfering with your daily life, we encourage you to seek help from a licensed mental health professional. 

Entrepreneur and adventurer Dale Majors has kept a daily journal for more than 4,000 consecutive days (that's nearly 11 years!) using Day One. In this episode, he shares how a simple streak turned into a life-changing habit—one that brings clarity, presence, and intention to everything from running a business to raising six kids. Dale opens up about the prompts that guide his mornings, why he journals while walking, and how embracing consistency over perfection has helped him build a journaling practice that lasts. Visit dayoneapp.com/podcast/episode-67-dale-majors for a list of prompts shared in this episode, including links to use them in your Day One journal.

In this episode, ICF certified coach Kelly Gallagher joins the podcast for a thoughtful conversation about how coaching and journaling complement one another to deepen self-awareness and accelerate growth. We explore the layered nature of personal insight, how reflection between coaching sessions amplifies progress, and why journaling can serve as both mirror and guide. Kelly shares the value of asking better questions, how coaching uncovers old narratives, and why writing things down helps change take root. You’ll also hear practical journaling prompts and reflections on using writing as a tool for both personal and professional clarity. Visit dayoneapp.com/podcast/episode-66-kelly-gallagher for a list of prompts shared in this episode, including links to use them in your Day One journal.

Wellness expert Dr. Hava Rose joins the podcast for a candid and insightful conversation about journaling as a tool for emotional processing, pattern recognition, and inner healing. She reflects on how journaling became a lifeline in her teen years and how it continues to support her through grief and seasons of personal transformation. Together, we explore the importance of emotional vocabulary, the influence of unconscious programming, and how the simple act of writing can create space for clarity, boundaries, and growth. You’ll also discover practical journaling tips, creative journaling prompts, and Hava’s approach to building a wellbeing practice rooted in connection—and in the power of pause. Get more links from this episode: dayoneapp.com/podcast/episode-65-dr-hava-rose

Licensed therapist and avid journaler Annie Tormos joins the podcast to explore how journaling can move from a passive habit to an active practice for growth, healing, and self-discovery. In this episode, Annie shares how journaling has supported her personally and professionally—and how Day One’s new Go Deeper feature helped her uncover meaningful insight in just one session. She reflects on the difference between simply recapping your day and writing with intention, and how prompts can create moments of clarity we didn’t know we were ready for. Annie also opens up about her own journaling rituals, her journey through grief, and why she now considers her journal a consistent and non-judgmental companion. Listen in for thoughtful reflections, practical encouragement, and a journaling challenge to help you go deeper this week. Sign up to try Go Deeper, Day One's new AI-powered journaling prompts: dayoneapp.com/labs Learn more about Go Deeper: dayoneapp.com/labs/go-deeper/ Get more links from this episode: dayoneapp.com/podcast/episode-64-annie-tormos  

In this episode, we sit down with Day One founder Paul Mayne to walk through the newly redesigned navigation—now live in version 2025.6 for iOS. (To see the full walkthrough, watch the episode on YouTube.) Paul shares the thinking behind the update, a full demo of the new journal picker and tab layout, and a look at the redesigned “More” tab with refreshed features like On This Day, Daily Prompts, and Streaks.  We also reveal what’s coming next—including a more guided journaling experience—and share highlights from other recent platform updates, like the launch of Day One for Windows, Shared Journals for Mac, and a cleaner template gallery on Android. Stick around for this episode’s journaling challenge—it's inspired by a simple question we recently asked strangers on the street. Links to all the news featured in this episode: dayoneapp.com/podcast/episode-63-nav-update

Want to make journaling even easier? Josh Kincaid, a longtime Day One user, shares how iOS Shortcuts have transformed his journaling routine. From saving daily newspaper front pages to logging moods with colors, this episode explores creative ways to streamline journal entries. The discussion covers making journaling more consistent, the impact of looking back on past entries, and how small automations can enhance a daily writing habit. Links to Josh’s iOS shortcuts and resources are available at:  dayoneapp.com/podcast/episode-62-josh-kincaid Sign up to be the first to try new Day One features at: dayoneapp.com/labs

Mindfulness teacher and coach Katie Seaman joins Kristen Webb Wright on the podcast to explore how journaling can help us tune into the present moment with greater awareness, curiosity, and self-compassion. In this episode, Katie shares how journaling and mindfulness work together to bring clarity and deepen self-understanding. She discusses the importance of noticing both our external and internal worlds, tracking patterns over time, and using journaling as a tool for self-trust and resilience. She also opens up about her personal journaling practice, from creative sketching to seasonal reflections, and how she incorporates mindfulness into her daily writing.  Listen in for inspiration, practical techniques, and a simple journaling challenge to help you cultivate more presence in your daily life. Learn more about Katie's work: simplypresent.co.uk Visit dayoneapp.com/podcast/episode-61-katie-seaman for more info on this episode.