Against My Better Judgment

Dannelle Whiteside and Tamara Gauldin
  • 5.0 (16)
  • Comedy
  • Updated Weekly

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.

  1. 5d ago

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

    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 beyond the punchline

    30 min

  2. Jun 2

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

    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 that comes from leading with intention instead of performance.

    29 min

  3. May 19

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

    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, gentle conviction, and a few laughs at the expense of overachiever culture.

    33 min

  4. May 12

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

    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. She shares the moments that deepened her spirituality without requiring her to subscribe to anyone else’s rulebook. Expect warmth, clarity, and a few knowing laughs about the assumptions people love to make.

    37 min

  5. Apr 21

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

    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, compromise, and quiet agreements that make shared life possible. Expect heartfelt moments, unexpected laughter, and a fresh perspective on what it means to choose someone — and keep choosing them — on purpose.

    44 min

  6. Apr 14

    Episode 36: How We Do Sportsmanship

    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 games to workplace dynamics. Equal parts reflective and hilariously honest, this episode reminds us that character shows up even when the score is tied.

    38 min

  7. Apr 7

    Episode 35: How We Do Citizenship

    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, accountability, and the surprising ways citizenship shows. Expect thoughtful insight, gentle nudges, and a call for accountability.

    38 min

  8. Mar 31

    Episode 34: How we do Hardship

    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 surprising clarity that hardship leaves behind when the dust settles.

    38 min
See All (41)

5
out of 5
16 Ratings

About

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.

Information

  • Creator
    Dannelle Whiteside and Tamara Gauldin
  • Years Active
    2025 - 2026
  • Episodes
    41
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    Against My Better Judgment