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PODCAST

The Reboot Diaries

Jessie & Cynthia

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.

comedy personal journals

All Episodes

61:41

Boundaries Are the New Bubble Bath

The Reboot Diaries ·

2026/03/25

Send us Fan Mail A layered discussion about whether self-care is about comfort, courage, or something much bigger. Support the show

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70:32

Comparison Is a Thief… But Also Data?

The Reboot Diaries ·

2026/03/18

Send a text Comparison can steal our joy. But if we look closely, it might also reveal what we value, what we want, and where we’re ready to grow. Support the show

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64:58

Is This Responsible… or Just What We Were Told?

The Reboot Diaries ·

2026/03/11

Send a text In this episode of Reboot Diaries, we unpack the life rules we inherited, from college degrees to union jobs, and ask whether chasing stability still makes sense in a shifting economy, especially when the pull of self-sufficiency gets stronger. Support the show

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60:41

Entrepreneur: A Title or a Trigger?

The Reboot Diaries ·

2026/03/04

Send a text A conversation about why the word “entrepreneur” feels empowering to some, intimidating to others, and deeply tied to identity. Support the show

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66:41

Ego vs. Pride: A Cage Match No One Asked For

The Reboot Diaries ·

2026/02/25

Send a text We talk ego vs. pride, why one is loud when we’re insecure, the other is steady when we’re grounded, and how both show up when we’re rebooting our lives. Support the show

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53:49

Checking In on Our 2026 Selves

The Reboot Diaries ·

2026/02/18

Send a text In this follow-up to The Soft Launch of Our 2026 Self, we check back in on the goals we set, how they’re actually showing up in real life, and what’s already shifted. Less about resolutions and more about noticing patterns, adjusting expectations, and staying in conversation with the version of ourselves we’re becoming. Support the show

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27:33

Love Is Real, Valentine’s Day Is Optional

The Reboot Diaries ·

2026/02/11

Send a text An honest conversation about Valentine’s Day, life transitions, and the joy of not caring that much anymore. Support the show

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56:41

Going All-in on the Reboot: Writing on the Road (an...

The Reboot Diaries ·

2026/02/04

In this episode, Jessie interviews Liz Fraser, a writer who made a major life shift: choosing uncertainty and living without a permanent home base in order to follow a creative calling. For the past two years, she’s been writing novels while constantly moving, building a life that supports the work instead of squeezing the work into the margins. We talk about highs, lows, and transitioning into this new life. Support the show

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59:22

Older, Bolder, Still Forgetting Why We Walked Into...

The Reboot Diaries ·

2026/01/28

We dig into the myths and realities of aging, including the parts no one warned us about and the parts we wish they had. Support the show

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62:39

Positivity, But Make It Honest

The Reboot Diaries ·

2026/01/20

A conversation about what staying positive actually looks like when life is messy, moods are wobbly, and forced cheer is off the table. We explore honest optimism, small bright spots, and the practical habits that help us keep going without pretending everything is fine. Support the show

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51:26

The Introvert vs. The Network

The Reboot Diaries ·

2026/01/14

Two very different comfort levels unpack how networking can be both a drain and a powerful catalyst. Support the show

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59:35

The Soft-Launch of Our 2026 Selves

The Reboot Diaries ·

2026/01/06

A conversation about beginning the new year with honesty: letting go of outdated goals, choosing what matters now, and designing a year that actually fits your life. Support the show

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55:54

Tis the Season (for Mild Panic)

The Reboot Diaries ·

2025/12/17

A festive exploration of how to survive the holidays without throwing tinsel at anyone. Support the show

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45:55

Life on the Road (and Occasionally on Fire) with Rob...

The Reboot Diaries ·

2025/12/11

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 2 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. Schedule time here: https://tidycal.com/ffkahani/connection Follow them on instagram to hear more about their travels a...

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44:45

Life on the Road (and Occasionally on Fire) with Fi...

The Reboot Diaries ·

2025/12/10

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. Schedule time here: https://tidycal.com/ffkahani/connection Follow them on instagram to hear more about their travels a...

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60:56

Breaking Up With Social Media (It’s Not Me, It’s You)

The Reboot Diaries ·

2025/12/03

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

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50:16

Unemployment, But Make It Art

The Reboot Diaries ·

2025/11/20

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

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54:30

Release, Reboot, Repeat

The Reboot Diaries ·

2025/11/12

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

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50:22

The Shifting Shape of Friendship

The Reboot Diaries ·

2025/11/05

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

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60:09

Holding Yourself Accountable

The Reboot Diaries ·

2025/10/29

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

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27 results

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