Dannelle Whiteside and Tamara Gauldin
Against My Better Judgment
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
Podcast website
Latest episode
Jul 7, 2026
Where to listen?
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Episodes
Episode 20: How I learned to Drive in the Rain 16.12.2025 30:40
This episode of Against My Better Judgment takes you on a soggy road trip with Dannelle and her grandmother. Spoiler: Grandma’s calm warnings didn’t stand a chance against Dannelle’s lead foot (a family heirloom courtesy of her mother). Between hydroplaning lessons and hilarious hindsight, she shares how ignoring wisdom can make for the best stories—and the worst driving habits.
Episode 19: How I learned Fight or Flight 09.12.2025 37:24
This episode of Against My Better Judgment dives into Tamara’s real-life “fight or flight” moments—those times when the universe basically yelled, choose now! From awkward encounters to high-stakes decisions, she reveals how she discovered she’s not one to run but to stand her ground. Expect candid stories, a few laughs at her expense, and proof that sometimes fighting back means more than throwin...
Episode 18: How I learned that God is real. 02.12.2025 35:16
This episode of Against My Better Judgment finds Dannelle sharing the uncanny, sometimes hilarious, often tender moments that convinced her there’s more in life than coincidence. From improbable rescues to tiny everyday signs that felt like winks from the universe, she tells candid stories about faith, and the miracles that made her a believer. It’s moving, sometimes funny, and perfect for listene...
Episode 17: How I learned the importance of strategy. 25.11.2025 29:38
This episode of Against My Better Judgment tracks Tamara’s early experiments with strategy that later built her career—think seeing now-moves for tomorrow’s invests and a plan or two coupled with actions that changed everything. She walks through youthful gambits that look charmingly audacious in hindsight, the frameworks she still swears by, and the funny missteps that taught her to plan and pivo...
Episode 16: How I learned work-life integration. 18.11.2025 35:08
This episode of Against My Better Judgment follows Dannelle as she confesses how she stopped chasing the mythical “perfect balance” and started building a life where work and home play nice. Expect stories about the time she turned a work event into a family night of football, and the small rituals that keep her present for both her family and home life. If you like practical tips served with wit...
Episode 15: How I learned that being broke isn't for me 11.11.2025 37:34
This episode of Against My Better Judgment serves hard-earned financial clarity with a side of office drama. In "How I learned..." Tamara explains how she learned that being broke is not for her — the mindset shifts, saving habits, and big risks that propelled real change. In "We'll be the Judge..." Tamara and Dannelle tackle a listener’s dilemma about a co-worker who is self-appointed as the PTO...
Episode 14: How I learned to live without a loved one. 04.11.2025 30:58
This episode of Against My Better Judgment blends the quietly brave with the absurdly petty. In "How I learned..." Dannelle shares how she learned to live without her father as a young adult — she guides us through grief, growth, and the small, stubborn ways life moves forward after loss. In "We'll be the Judge..." Tamara and Dannelle prosecute a hilariously petty case: your friend the Wi‑Fi thief...
Episode 13: How I Learned to Fit In 28.10.2025 38:27
Co-hosts Dannelle Whiteside and Tamara Gauldin launch Season 2 with two fresh segments; "How I learned..." with Tamara’s story about fitting in: the missteps, the compromises, the unexpected friends, and the single moment she realized she didn’t have to change. Then in "We'll be the Judge..." they rule on a listener’s Halloween etiquette query — costume boundaries, candy politics, and whether to k...
Episode 12: That time when I learned fat was not a feeling 14.10.2025 33:01
In this powerful and deeply personal episode of "Against My Better Judgment," Tamara recounts her struggle with the pervasive feeling of "being fat" and how it led to battling an eating disorder. Through her honest and courageous storytelling, Tamara shares the emotional and psychological challenges she faced, the journey towards self-acceptance, and the important realization that fat is not a fee...
Episode 11: That time when my Grandma left me instructions. 07.10.2025 33:28
In this touching and reflective episode of "Against My Better Judgment," Dannelle shares the moment she discovered she was the executor of her grandmother's estate. Through her heartfelt narrative, Dannelle recounts the emotions and responsibilities that came with this revelation, as well as the valuable lessons she learned along the way. Tune in to hear her story and gain insights into the import...
Episode 10: That time when the kids came over 30.09.2025 36:20
In this insightful and entertaining episode of "Against My Better Judgment," Tamara shares her experiences and tips on hosting kids in a childless home. From preparing for the adventure to understanding the correct etiquette, Tamara offers practical advice and humorous anecdotes that will help you navigate the challenges and joys of having young guests. Tune in to hear her stories and learn how to...
Episode 9: That time when I had a Surprise Baby! 23.09.2025 36:37
In this episode of Against My Better Judgment, Dannelle gets real about the plot twist that even she didn’t see coming—a surprise third pregnancy when life felt full enough with two boys already. She unpacks the mix of disbelief and excitement. If you've ever found yourself saying, “Well, that wasn’t on the calendar,” this one’s for you.
Episode 8: That time when I joined FB at 45 years old. 16.09.2025 31:35
In this amusing and insightful episode of "Against My Better Judgment," Tamara shares her experience of diving into the world of social media after 45 years of resisting the hype. From joining Facebook to exploring four other platforms, Tamara offers a unique perspective on the challenges and surprises of navigating the digital landscape. Tune in to hear her stories, the lessons she learned, and h...
Episode 7: That time when I had an anxiety attack 09.09.2025 35:26
In this candid and relatable episode of "Against My Better Judgment," Dannelle opens up about her experience with an anxiety attack and how she discovered that coffee and life don't mix. Through her honest and heartfelt storytelling, Dannelle shares the moments leading up to the attack, the symptoms she experienced, and the steps she took to manage her anxiety. Tune in to hear her story and gain v...
Episode 6: That Time When I Almost Got Scammed 02.09.2025 37:15
In this gripping and eye-opening episode of "Against My Better Judgment," Dannelle shares her harrowing experience of narrowly avoiding a scam that involved cash withdrawals and the sheriff's department. Through her detailed account, Dannelle reveals the red flags she noticed and the steps she took to protect herself. Tune in to hear her story and learn valuable tips on how to recognize and avoid...
Episode 5: That time when I discovered a stranger living in my house 26.08.2025 36:48
In this astonishing and intriguing episode of "Against My Better Judgment," Tamara recounts the unbelievable story of how a friend's mistaken identity led to her unknowingly accepting a stranger into her home for months. Through her captivating narrative, Tamara shares the bizarre events that unfolded and the lessons she learned from this extraordinary experience. Tune in to hear her story and dis...
Episode 4: That time when I realized my brother is my mom’s favorite 19.08.2025 32:28
In this heartfelt and humorous episode of "Against My Better Judgment," Dannelle takes us on a journey through various scenarios to when she realized her brother is her mom's favorite child. From childhood memories to recent events, Dannelle shares her experiences and insights, offering a mix of laughter and introspection. Tune in to hear her candid stories and discover how family dynamics can sha...
Episode 3: That Time When We Went on a Mission Trip 12.08.2025 37:02
In this episode, Dannelle and Tamara swap stories about the very different mission trips they each took—moments that stretched their faith, tested their patience, and left them forever changed. From awkward cultural missteps to powerful spiritual lessons, they explore how serving in unfamiliar places shaped their views on purpose and compassion.
Episode 2: That time when I made a crazy choice to upend My life. 05.08.2025 29:51
In this episode of "Against My Better Judgment," Tamara gets real about a pivotal moment when she made a choice draft a resignation letter—leaving behind security and predictability for a future that was anything but certain. Dannelle and Tamara unpack what it takes to follow a nudge that doesn’t make sense on paper, the fear that comes with risking it all, and the surprising ways faith and friend...
Episode 1: That Time When We Started a Podcast 29.07.2025 31:51
Welcome to the very first episode of Against My Better Judgment! In this kickoff, two longtime friends—Dannelle and Tamara—decide to hit record on the conversations they’ve been having for years. They share why they started this podcast, what you can expect each week, and the stories that pushed them to finally take the leap (even if it was, well... against their better judgment). This episode’s s...
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