The Reboot Diaries

Send us Fan Mail When money, identity, and career goals collide, how do you decide whether to take the first offer or keep searching for something better? Part 2 of our season finale. Support the show

Send us Fan Mail When money, identity, and career goals collide, how do you decide whether to take the first offer or keep searching for something better? Part 1 of our season finale. Support the show

Send us Fan Mail Is there harm in holding onto a fantasy life? How much of our dissatisfaction comes from comparing real life to the imaginary version we thought we’d have by now? Cynthia and Jessie talk about shifting priorities, where satisfaction comes from, and the ups and downs of dreaming big. Support the show

Send us Fan Mail 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. Support the show

Send us Fan Mail 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. Support the show

Send us Fan Mail 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. Support the show

Send us Fan Mail 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 are. Support the show

Send us Fan Mail Cynthia and Jessie unpack the difference between being busy and actually feeling fulfilled, and question why productivity so often feels tied to our worth. Support the show

Send us Fan Mail 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. Support the show

Send us Fan Mail 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. Support the show

Send us Fan Mail A conversation about whether artificial intelligence is truly improving our lives, or simply reshaping how we work, think, and reinvent ourselves. Support the show

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

Send us Fan Mail 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

Send us Fan Mail 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

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

Send us Fan Mail 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

Send us Fan Mail 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

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

Send us Fan Mail 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 tran...

Send us Fan Mail 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

Send us Fan Mail 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

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

Send us Fan Mail 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

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

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 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. Sch...