Life Jenerally Podcast

Jen Squared is back with round two of Am I the Asshole? — and this time we brought backup! Jen's fiancé Cory joins us to judge five wild Reddit stories: a $20K wedding dress with "no budget," a secret bachelorette exposed on social media, a husband who refuses to poop downstairs, siblings who hired cleaners to catch their spite-cleaning mom, and a dad dating his late wife's ex-best friend. Verdicts get heated, b...

On this week's episode, Jen Squared sits down with Holly, a trans woman and longtime friend of Jen Tran's, for an honest and heartfelt conversation about identity, transition, and what it means to live as your true self. Holly shares her journey from quietly carrying a secret she thought she'd take to her grave, to coming out publicly in 2020 and building a life rooted in joy. Along the way, the besties dig into why "...

Jen Squared is joined by OG bestie and cousin Amy Horiuchi to talk all things Billy Idol! The trio reacts to the Hulu documentary Billy Idol Should Be Dead, digging into his wild survival stories, punk roots, and why his music still hits hard decades later. Plus — first Billy Idol memories, karaoke catastrophes, musical theatre tangents, and your weekly health meter check-in!

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Life Jenerally welcomes a special guest — Jen's fiancé Cory Wilkerson — to talk about something we're all feeling: burnout. With over half of employees reporting burnout, Cory shares what he's learning in his leadership course about how great leaders get to know their teams, play to their strengths, and help prevent burnout before it hits. Plus, the Jens catch up on dog grooming, wedding planning, and a ho...

This week, Jen Squared sits down with Elliot Solomon, sibling of a brother on the autism spectrum. From IEPs and meltdowns to Pokémon saves and ADUs — it's an honest, warm conversation about family, neurodivergence, and love. New episodes every Friday on Life Jenerally.

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Jen Squared is back with another book club episode! This week we're diving into Brave New World by Aldous Huxley — a dystopian classic written in 1932 that feels eerily relevant today. We break down the book's themes of government control, caste systems, the soma drug, banned books, and the tragic story of John the Savage. We also explore real-world parallels to modern society including women's health rights, fa...

On this week's episode of Jen Squared, networking doesn't have to feel fake — and Jamison is here to prove it. With over 8 years in HR and recruiting, he shares how genuine connection (not a polished pitch) is what actually opens doors. The Jens also get personal about burnout, the job market, and why your network matters most when things get hard.

FYI: We are  taking a two week hiatus to work on some upcoming episodes a...

What happens to a marriage when caregiving becomes your whole life? Jen Squared sits down with Mariah Cuddy, who raised her daughter Lexi — born with rare Aicardi syndrome — through two decades of medical crises, sleepless nights, and caregiver burnout, all while fighting to keep her marriage intact. This is a raw, heartfelt, and ultimately hopeful conversation about love, resilience, and what it really me...

Jen Squared are joined by returning guest Eric Criswell for an in-person deep dive into Netflix's documentary Reality Check: Inside America's Next Top Model. Together, they unpack what made ANTM a cultural phenomenon — and why it took nearly two decades for the world to fully reckon with how problematic it was.

Trigger warning: This episode discusses sexual assault, eating disorders, racism, and a...

This week’s episode Jen goes solo and brings two guests to talk. Three designers. Three layoffs. Zero warning — and no choice but to figure it out. Kirsten Fanker and David Ciccocioppo pull back the curtain on what life after corporate actually looks like — the freedom, the fear, the Friday morning Zoom that changed everything.

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Jen Squared is back with a fun one! This week, we're diving into the world of Reddit's "Am I the A$$hole?" — because nothing says Friday like a little judgment and a lot of tea. We tackle two juicy dilemmas: a woman who inherits her late ex-husband's 401(k) (and his girlfriend has feelings about it), and a friendship that ends with a literal invoice. We're giving verdicts, sharing opinions, and reminding you &md...

Jen Squared takes a deep dive into the Hulu documentary Lilith Fair: Building a Mystery, celebrating Sarah McLachlan's groundbreaking all-women music festival and the iconic artists who made the nineties a defining era for female musicians. Tune in for a nostalgic, heartfelt conversation that'll have you dusting off your old playlists and asking yourself — what would Sarah McLachlan do?

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