Jessie & Cynthia
The Reboot Diaries
The Reboot Diaries is all about navigating life’s relaunches with honesty and humor. We share our own stories and lessons learned to remind you that you’re not alone, there’s nothing “wrong” with you, and that every transition can be reframed as part of the journey. Approachable, authentic, and a little funny, it’s support for anyone hitting reset.
Author
Jessie & Cynthia
Category
Podcast website
Latest episode
Jun 17, 2026
Where to listen?
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Episodes
Life on the Road (and Occasionally on Fire) with Fi and Rob (part 1) 10.12.2025 44:45
Send us Fan Mail Two years, countless miles, and one RV fire later, Rob and Fi join The Reboot Diaries to share the real costs, surprises, and perspective shifts that come with rebooting life on the road. Pat 1 of a special 2-part episode! Follow along Fi and Rob's various adventures through there links: Meet with Fi to get advice if you’re thinking about hitting the road and want advice. Sch...
Breaking Up With Social Media (It’s Not Me, It’s You) 03.12.2025 1:00:56
Send us Fan Mail Summary: A conversation about breaking old digital habits, this episode explores what shifts in your life, mood, and identity when you log off, unfollow, and reboot your online world, with a few playful detours into the quirks of our scrolling selves. Support the show
Unemployment, But Make It Art 20.11.2025 50:16
Send us Fan Mail Jessie welcomes special guest Jarod to discuss navigating a layoff, turning uncertainty into creativity, and what happens when you come home and tell your wife you were laid off and are now making a music album. Support the show
Release, Reboot, Repeat 12.11.2025 54:30
Send us Fan Mail Sometimes growth looks less like adding and more like subtracting. In this episode, we talk about the art of letting go of the beliefs, patterns, and possessions that weigh us down, and the freedom (and occasional chaos) that comes after you finally drop the baggage. Support the show
The Shifting Shape of Friendship 05.11.2025 50:22
Send us Fan Mail In this episode of The Reboot Diaries , we talk about how friendships shift and change over the years, what makes that tough, and why it can also be exactly what we need. Support the show
Holding Yourself Accountable 29.10.2025 1:00:09
Send us Fan Mail In this episode of The Reboot Diaries , we tackle the art (and agony) of holding ourselves accountable, from meeting creative deadlines to forcing ourselves through dreaded to-dos, and the tricks, bribes, and laughs that help us get it done. Support the show
Old School Disability: Before Access Was Cool 22.10.2025 1:12:41
Send us Fan Mail In this episode, Jessie shares what it was like growing up with a disability before the ADA — a mix of funny, eye-opening, and “wait, that was legal?” moments from back in the day. Support the show
Therapy: Is This Seat Taken? 15.10.2025 1:00:37
Send us Fan Mail This conversation explores therapy and mental health with honesty and curiosity, focusing on what role therapy may or may not take to truly care for your mind. Support the show
The Clear Cane Chronicles: Behind the Pages 08.10.2025 49:29
Send us Fan Mail In this episode of The Reboot Diaries , Jessie asks Cynthia about her recent Amazon best-seller, The Clear Cane Chronicles. We talk disability, person-centered care, and why sometimes the best way to tackle serious topics is with a lot of laughter. Support the show
Homeward Bound (Again) 01.10.2025 55:40
Send us Fan Mail We unpack the realities of moving back home, from the funny adjustments to the unexpected lessons about identity, independence, and starting fresh. Support the show
Leaps, Bounds, and Occasional Faceplants 24.09.2025 52:13
Send us Fan Mail Cynthia and Jessie trade stories about the career (and other) risks we’ve taken—the wins, the wipeouts, and the laughs in between. Support the show
Champagne Dreams, Tap Water Budget 16.09.2025 47:21
Send us Fan Mail In this episode, we get real about the awkward, frustrating, and sometimes funny process of cutting back after a layoff. From canceling subscriptions and discovering the joys (and limits) of Aldi and Costco, to resisting “treat yourself” habits, we talk about what it actually feels like to transition into spending less while trying to keep your peace of mind—and your snacks. Suppo...
Life After Layoffs 09.09.2025 50:43
Send us Fan Mail In our very first episode of The Reboot Diaries , we dive into why we started this podcast and the big life changes that got us here: layoffs, moves, career pivots, and all the messy in-betweens. We share laughs, lessons, and a reminder that none of us are figuring this out alone. Support the show
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