On this week's episode, Jen Squared sits down with Diana Sugihara, who left her 14-year corporate career to become the full-time caregiver for her aging parents. Diana shares why she chose a "soft transition" instead of waiting for a crisis, the physical and financial realities nobody warns you about, and how stepping back from work reshaped her identity, her marriage, and her relationship with her parents. A real, funny, and honest conversation about caregiving, timing, and letting go of "A+ work" for "good enough."

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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, boundaries get preached, and somehow it always comes back to bathrooms.

Plus: wedding dress updates, job hunt real talk, burnout meters, and big news for anyone with PCOS.

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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 "just Google it" can be harmful, what terms like pansexual and nonbinary actually mean, the safety realities trans women navigate every day, and how to show up for the trans people in your life. Funny, raw, and full of love — this one's for everybody.

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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 honeymoon trip to Tennessee that includes Dollywood and a five-star hotel inside a Bass Pro Shop.

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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, fast fashion, and the suppression of independent thought. Heads up — this episode covers adult and heavy subject matter including sexuality and suicide. Listen with that in mind. New episodes every Friday on Life Jenerally.

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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 and take a short break. We will be back on Friday the 15th of May! Help us spread the word of Life Jenerally by subscribing, and share with your friends and family. That will be greatly appreciated!

To find Jamison

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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 means to be built to last.

Additional Information:

We are brave together

https://www.wearebravetogether.org/

Becoming Brave Together Book

https://www.amazon.com/Becoming-Brave-Together-Extraordinary-Caregiving/dp/B0CY8PP1K4?qid=&sr=

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https://www.instagram.com/wearebravetogether/

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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 alcohol use.

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