Dannelle Whiteside and Tamara Gauldin

Against My Better Judgment

Comedy EN ↓ 45 episodes

Against My Better Judgment is where two friends—Dannelle Whiteside and Tamara Gauldin—get real about life and the lessons we learn the hard way. With a mix of humor, heart, and honesty, each episode dives into personal stories and the moments we knew better… but did it anyway.

Author

Dannelle Whiteside and Tamara Gauldin

Category

Comedy

Latest episode

Jul 7, 2026

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Episodes

Episode 45: Just Because I don’t have children doesn't mean I don’t know child rearing 07.07.2026

This episode of Against My Better Judgment blends lived experience with a sprinkle of “please stop underestimating me.” In “Just Because I Don’t Have Children Doesn’t Mean I Don’t Know Child Rearing,” Tamara explores the wisdom gained from community, caregiving, observation, and the many ways adults show up for kids beyond parenthood. She reflects on expertise that isn’t tied to biology, the assum...

Episode 44: Just Because I’m busy doesn't mean that I don’t have time time 30.06.2026

This episode of Against My Better Judgment blends time management truth with a sprinkle of “I prioritize what matters.” In “Just Because I’m Busy Doesn’t Mean I Don’t Have Time,” Dannelle unpacks the assumptions people make about full schedules, shifting capacities, and the difference between being unavailable and being intentional. She reflects on how she allocates energy, honors commitments, and...

Episode 43: Just Because I’m nice doesn't mean that I’m a people-pleaser or weak 23.06.2026

This episode of Against My Better Judgment blends kindness with a sprinkle of “don’t get it twisted.” In “Just Because I’m Nice Doesn’t Mean I’m a People-Pleaser or Weak,” Tamara explores the difference between compassion and compliance, softness and surrender. She reflects on the strength behind gentleness, the boundaries behind generosity, and the power of choosing kindness without letting it be...

Episode 42: Just Because I’m extroverted, doesn't mean that I’m not an introvert 16.06.2026

This episode of Against My Better Judgment blends personality nuance with a sprinkle of “I love people, but also please leave me alone.” In “Just Because I’m Extroverted Doesn’t Mean I’m Not an Introvert,” Dannelle unpacks the tension of being energized by connection yet deeply protective of solitude. She reflects on identity beyond labels, the myths of social ease, and the quiet truth that humans...

Episode 41: Just Because I’m laughing doesn't mean that I’m happy 09.06.2026

This episode of Against My Better Judgment blends emotional honesty with a sprinkle of "I'm fine ... but am I?" humor. In "Just Because I'm Laughing Doesn't Mean I'm Happy," Tamara explores the complicated art of masking - the smile that covers stress, the jokes that soften truth, and the moments when laughter becomes a shield. She reflects on what it means to be seen, supported, and understood be...

Episode 40: Just Because I’m a Boss doesn’t mean I’m a B@#$! 02.06.2026

This episode of Against My Better Judgment blends leadership clarity with a sprinkle of “please don’t confuse boundaries with attitude.” In “Just Because I’m a Boss Doesn’t Mean I’m a B@#$!,” Dannelle unpacks the double standards, tone policing, and quiet calculations that come with being a woman in charge. She reflects on authority without apology, confidence without caricature, and the freedom t...

Episode 39: Just Because I can do a lot does not mean that I can do Everything 19.05.2026

This episode of Against My Better Judgment blends self-awareness with a sprinkle of “I am not your superhero, actually” humor. In “Just Because I Can Do A Lot Does Not Mean I Can Do Everything,” Dannelle reflects on the seasons when competence became a trap and capability turned into an unspoken expectation. She unpacks the quiet burnout, and how asking for HELP is necessary. Expect honesty, gentl...

Episode 38: Just Because I’m spiritual does not mean I’m Religious 12.05.2026

This episode of Against My Better Judgment blends introspection with a sprinkle of “please don’t put me in your box” humor. In “Just Because I’m Spiritual Does Not Mean I’m Religious,” Tamara explores the difference between personal connection and institutional expectation — the rituals that ground her, the questions that shaped her, and the freedom she’s found in defining faith on her own terms....

Episode 37: How We Do Partnership (featuring our first-ever special guest) 21.04.2026

This episode of Against My Better Judgment blends collaboration with a sprinkle of “we’re really doing this together” delight. In “How We Do Partnership,” Dannelle and Tamara welcome the podcast’s first special guest to explore what it takes to build, maintain, and honor a true partnership — whether romantic, professional, or the beautifully complicated in-between. They dig into communication, com...

Episode 36: How We Do Sportsmanship 14.04.2026

This episode of Against My Better Judgment blends competitive spirit with a sprinkle of “I’m trying to be a good person but also… I like to win” energy. In “How We Do Sportsmanship,” Tamara breaks down the art of playing fair, losing gracefully, and celebrating without being insufferable. She shares the lessons learned from childhood games, and the unspoken rules that govern everything from board...

Episode 35: How We Do Citizenship 07.04.2026

This episode of Against My Better Judgment mixes civic responsibility with a dash of “why is adulthood like this” reality. In “How We Do Citizenship,” Dannelle unpacks what it means to show up for your community — from the everyday choices that quietly shape the world around us to the big moments that demand courage, clarity, and a little bit of common sense. She reflects on belonging, accountabil...

Episode 34: How we do Hardship 31.03.2026

This episode of Against My Better Judgment blends resilience with a sprinkle of “life really tried it” humor. In “How We Do Hardship,” Tamara walks through the seasons that stretched her, sharpened her, and reminded her she’s built sturdier than she realized. She shares the coping tools, and quiet inner shifts that helped her navigate the moments that felt heavier than expected — and the surprisin...

Episode 33: How we do Mentorship 24.03.2026

This episode of Against My Better Judgment blends generational wisdom with a dash of mentor‑mentee comedy. In “How We Do Mentorship,” Dannelle unpacks the teachers, elders, and unexpected guides who shaped her path — the lessons that stuck, the ones she had to unlearn, and the joy of pouring into others with intention. She reflects on mentorship as a reciprocal, evolving relationship rooted in hon...

Episode 32: How we do Ownership 17.03.2026

This episode of Against My Better Judgment blends personal accountability with a sprinkle of “I really did that, didn’t I?” humility. In “How We Do Ownership,” Tamara reflects on the moments that forced her to step up — the choices she’s proud of, the ones she’d like to return to sender, and the growth that comes from claiming all of it without flinching. She explores responsibility as a practice,...

Episode 31: How we do Allyship 10.03.2026

This episode of Against My Better Judgment blends intentional growth with a sprinkle of social‑justice‑adjacent culture. In “How We Do Allyship,” Dannelle reflects on what it means to show up — consistently, humbly, and without making it a performance. She shares the missteps, mindset shifts, and meaningful moments that shaped her understanding of Allyship.

Episode 30: How we do Leadership 03.03.2026

This episode of Against My Better Judgment mixes courageous self‑reflection with the kind of workplace absurdity that makes you question who put certain people in charge. In “How We Do Leadership,” Tamara walks through the lessons, stumbles, and surprising strengths that shaped her approach to leading — the clarity, the compassion, and the quiet confidence that shows up even when she’d rather not.

Episode 29: How we do Kinship 24.02.2026

This episode of Against My Better Judgment blends inherited wisdom with the kind of family‑adjacent chaos that keeps group texts spicy. In “How We Do Kinship,” Dannelle unpacks the ties that hold us together — the chosen, the blood‑related, and the ones we claim only on holidays. She explores belonging, boundaries, and the tender work of staying connected even when life pulls in opposite direction...

Episode 28: How we do Discipleship. 17.02.2026

This episode of Against My Better Judgment blends spiritual growth with a sprinkle of church‑adjacent comedy. In “How We Do Discipleship,” Tamara reflects on the mentors, missteps, and meaningful moments that shaped her faith journey — the practices that ground her, the questions that stretch her, and the grace that keeps her steady when life is doing the absolute most.

Episode 27: How We Do Scholarships. 10.02.2026

This episode of Against My Better Judgment serves academic realness with a side of learned curiosity. In “How We Do Scholarship,” Dannelle walks us through her relationship with learning — the curiosity that fuels her, the discipline that saves her, and the academic politics. She unpacks her blueprint to try to stay relevant and informed.

Episode 26: How We Do Friendships. 03.02.2026

This episode of Against My Better Judgment explores the beautiful mess of adult friendships with a side of social‑circle drama. In “How We Do Friendships,” Tamara breaks down the art of choosing your people — the loyalty, the boundaries, and the subtle red flags you pretend you didn’t see. She shares the lessons, the losses, and the laughable moments that shape how we show up for each other.

Episode 25: How I learned Boundaries 20.01.2026

This episode of Against My Better Judgment traces Tamara’s journey into understanding boundaries—where they’re drawn, why they matter, and how they protect both compassion and clarity. Through personal stories that are equal parts funny and eye-opening, she shows how boundaries aren’t walls, but bridges to healthier relationships and self-respect.

Episode 24: How I learned What’s in a name 13.01.2026

This episode of Against My Better Judgment uncovers how Dannelle learned the power behind a name. From moments of misunderstanding to revelations of identity and belonging, she shares how names carry stories, shape connections, and remind us that who we are is often spoken before anything else.

Episode 23: How I learned Compassion 06.01.2026

This episode of Against My Better Judgment explores Tamara’s journey into compassion, shaped by her grandmother’s open kitchen and encounters with people who taught her what generosity really looks like. Through heartfelt, funny, and eye-opening stories, she shows how compassion isn’t just a virtue—it’s a practice that changes how you see the world.

Episode 22: How I learned the Importance of a New Year’s resolution 30.12.2025

This episode of Against My Better Judgment explores how Dannelle came to see New Year’s resolutions not as empty promises, but as powerful tools for reflection and growth. With candid stories and relatable humor, she reveals how setting intentions—even imperfect ones—can shape the year ahead in surprising ways.

Episode 21: How I learned The Meaning of Christmas 23.12.2025

This episode of Against My Better Judgment follows Dannelle’s discovery of Christmas beyond the glitter and gifts. What does Christmas really mean? For Danelle, the answer came not from gifts or glitter, but from a moment of clarity that changed her perspective forever. Join her as she recounts the journey that revealed the heart of the holiday.

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