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.
Episodes
35 episodes
Between Predictability and Possibility
In this episode of Reboot Diaries, we explore the constant pull between stability and freedom, and what happens when the life that keeps us secure starts competing with the life that makes us feel alive.
Healthy-ish on a Budget
What happens when taking care of your health becomes a financial calculation? This episode explores the trade-offs, stress, and creative workarounds that come with navigating life without employer-sponsored health insurance.
Main Character Energy… or Main Character Pressure?
In this episode, we unpack the subtle (and sometimes exhausting) pressure to be “interesting,” and question whether we’re actually living our lives or quietly curating them for an audience.
Who Are You Without the Applause?
In this episode, we unpack the subtle ways validation shapes our decisions, relationships, and sense of self. We explore what it means to build real self-trust and how life shifts when you stop waiting for permission to be who you already ar...
Productivity: Why Cynthia Won't Take a Vacation
Cynthia and Jessie unpack the difference between being busy and actually feeling fulfilled, and question why productivity so often feels tied to our worth.
How Much Should People Change for Each Other?
This episode explores the tension between being accepted as you are and being asked to grow within a relationship. It digs into when change is a sign of love and investment, and when it starts to feel like losing yourself.
Being the ‘Strong One’
Cynthia and Jessie talk about the invisible weight of 'being strong' and how that role can quietly shape relationships, identity, and emotional well-being...whether we intend it to or not.
Rebooting in the Age of AI
A conversation about whether artificial intelligence is truly improving our lives, or simply reshaping how we work, think, and reinvent ourselves.
Boundaries Are the New Bubble Bath
A layered discussion about whether self-care is about comfort, courage, or something much bigger.
Comparison Is a Thief… But Also Data?
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.
Is This Responsible… or Just What We Were Told?
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 ...
Entrepreneur: A Title or a Trigger?
A conversation about why the word “entrepreneur” feels empowering to some, intimidating to others, and deeply tied to identity.
Ego vs. Pride: A Cage Match No One Asked For
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.
Checking In on Our 2026 Selves
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 e...
Love Is Real, Valentine’s Day Is Optional
An honest conversation about Valentine’s Day, life transitions, and the joy of not caring that much anymore.
Going All-in on the Reboot: Writing on the Road (an Interview with Liz Fraser)
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 whi...
Older, Bolder, Still Forgetting Why We Walked Into the Room
We dig into the myths and realities of aging, including the parts no one warned us about and the parts we wish they had.
Positivity, But Make It Honest
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 pre...
The Introvert vs. The Network
Two very different comfort levels unpack how networking can be both a drain and a powerful catalyst.
The Soft-Launch of Our 2026 Selves
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.
Tis the Season (for Mild Panic)
A festive exploration of how to survive the holidays without throwing tinsel at anyone.
Life on the Road (and Occasionally on Fire) with Rob and Fi (part 2)
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 F...
Life on the Road (and Occasionally on Fire) with Fi and Rob (part 1)
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 F...
Breaking Up With Social Media (It’s Not Me, It’s You)
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 scrolli...