AI Journaling With Sean Dadashi

Sonia sits down with Sean Dadashi, co-founder of Rosebud, an AI-guided journaling app built to deepen self-reflection, emotional awareness, and intentional healing. Together, they explore how journaling can move beyond venting and become a powerful tool for insight — helping you recognize emotional patterns, understand triggers, and reshape the internal narratives that shape sobriety and personal growth. The conversation expands into the evolving role of AI in mental health and self-development. They discuss how guided prompts, voice journaling, emotional tagging, and pattern recognition can make reflection more accessible — especially for those intimidated by a blank page. At the same time, they examine the importance of keeping therapy, community, and real human connection at the center of healing, while using technology as a supportive tool rather than a replacement. Sonia and Sean also walk through specific journaling practices, including Rose-Bud-Thorn reflections, somatic journaling, gratitude work, boundary-setting exercises, and intention setting. They explore how Rosebud can support therapy preparation, unsent letters, difficult conversations, and voice-based emotional processing. Throughout the episode, they highlight how digital journaling can help expand emotional vocabulary, identify recurring behavioral patterns, and deepen therapeutic work between sessions. On a more personal note, Sonia shares her love of pen-to-paper journaling — the colored pens, the bedside rituals — and reflects on what it means to shift from analog habits to digital tools in a way that enhances, rather than replaces, the reflective experience. This is Sisters in Sobriety, the support community that helps women change their relationship with alcohol. Check out our substack for extra tips, tricks and resources. Highlights00:00 — Introduction to Sean Dadashi and the mission behind Rosebud 01:45 — Sean’s early relationship with journaling during family divorce 04:10 — Moving from handwritten journals to digital reflection 06:20 — Recognizing emotional and behavioral patterns over time 08:05 — The “blank page problem” and barriers to starting journaling 09:40 — How the “Go Deeper” function guides layered reflection 11:30 — AI summaries, emotional tagging, and weekly reports 13:05 — Metrics, character tracking, and narrative insights 14:10 — Naming emotions and therapist-informed AI design 15:20 — How Rosebud differs from generic chatbots 16:40 — AI memory and long-term pattern recognition 17:25 — Asking big-picture life questions through journal history 18:50 — Year-end reflection archetypes and narrative mapping 20:10 — AI personas: nurturing vs. direct reflection styles 21:05 — Preventing AI from replacing human connection 22:30 — Platform limits and ethical guardrails 24:00 — Crisis response and safety considerations 28:40 — Using journaling alongside therapy and coaching 31:10 — Preparing for therapy sessions through reflection insights 32:15 — Pen-and-paper vs. digital journaling debate 34:05 — Voice journaling and emotional expression 36:10 — Importing handwritten journals via photo transcription 38:15 — Rose-Bud-Thorn framework and evening reflections 40:20 — Somatic journaling and body-based awareness 41:10 — Letter writing, boundary setting, and hard conversations 43:00 — Facilitating real-life conversations using AI support 44:05 — Intention setting and future-self visualization 45:50 — Creating mantras and symbolic yearly totems 46:40 — Building sustainable daily reflection practices 47:30 — Closing thoughts and episode wrap-up Rosebud https://my.rosebud.app/ SIS Links 💌 Sisters In Sobriety Substack – where the magic (and the mocktail recipes) happen 📬 Sisters In Sobriety Email 📸 Sisters In Sobriety Instagram 🌐 Kathleen’s Website Kathleen does not endorse any products mentioned in this podcast 📸 Kathleen’s Instagram Hosted on Acast. See acast.com/privacy for more information.