“From Wine Culture to Wake-Up Call: Jenn’s Realignment”

🎧 In this episode of The Tragedy Academy Podcast, Jay speaks with Jenn Bouler — known on Instagram as “Jenn with two Ns” — about the unseen layers of addiction, the masks we wear to fit in, and what happens when you finally take yours off. 🎙️
✨ Jenn’s story isn’t marked by trauma or chaos, making it resonate even deeper. A happy childhood. A solid career. A beautiful son. And yet, beneath the surface, alcohol crept in not to numb the pain… but to mute the pressure of perfection. In this episode, she shares what it means to hit a “high bottom,” how the wine-mom culture glamorizes escape, and what finally drove her to reclaim her identity from behind the bottle.
With candor, heart, and Jay’s signature mix of humor and insight, this conversation dives deep into the cultural constructs of “normal” drinking, the shame that lingers behind the scenes, and the power of showing up for yourself, one sober day at a time. From grocery store wine planning to white-chip meetings, Jenn’s path reminds us: the real you is always worth meeting.
🔑 Key Takeaways:
🐾 [00:03:22] “Becky” — Jenn’s drinking alter ego — gave her temporary escape, but not real freedom
🍷 [00:16:58] Planning for weekend drinking is a red flag we normalize in middle-class culture
💔 [00:28:38] Friends and family lovingly noticed before she did: “You’re drinking more every time I visit.”
👩‍👦 [00:30:03] Her son, just five at the time, became her biggest reason for change
💡 [00:35:04] “I came for my son. I stayed for me.” — How a support meeting changed her entire frame
👤 Guest Bio:
Jenn Bouler is a Tampa-based mom, sales rep, indoor cycling instructor, and founder of Jen Walks Dogs, a business built on joy and connection. Eight years sober as of 2025, she shares her journey of recovery and self-discovery with refreshing honesty. A Midwest native with a big heart and a contagious smile, Jenn lives her life with passion, presence, and a deep desire to help others feel less alone.
📣 CTA for Guest:
Want to follow Jenn’s journey? Connect with her on:
Instagram:
 • @jenn_bouler
 • @jenn_b_spin (Indoor Cycling)
 • @jenn_walks_dogs (Dog Walking)
Whether on a bike, a sidewalk, or holding space in her community, Jenn radiates truth and transformation. Follow her for daily reminders that growth can be graceful, and joy is always worth chasing. 🐶💛🚴‍♀️
🌀 Conclusion: This episode isn’t just about sobriety but sovereignty. About taking back your life, one intentional breath at a time. Thank you, Jenn, for being a lighthouse.
🎧 Tune in next week for another honest, heart-opening episode of The Tragedy Academy Podcast.
Be cool and keep learning. 🌿🕊️
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