Life Jenerally Podcast

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." ☕ Support the show: buymeacoffee.com/lifejenerally 📩 Email us: [email protected] 📸 Instagram: @life.jenerally 👥 Facebook: Life Generally 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, 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. Want to support the show? Buy us a coffee! ☕ https://buymeacoffee.com/lifejenerally You can find us: 📷 Instagram: @life.jenerally 💻Facebook (Search Life Jenerally): https://www.facebook.com/profile.php?id=61576465589219 📧 Email : [email protected]

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.   Want to support the show? Buy us a coffee! ☕ https://buymeacoffee.com/lifejenerally You can find us: 📷 Instagram @life.jenerally 💻Facebook (Search Life Jenerally) https://www.facebook.com/profile.php?id=61576465589219 📧 Email [email protected]

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!   Want to support the show? Buy us a coffee! ☕ https://buymeacoffee.com/lifejenerally You can find us: 📷 Instagram @life.jenerally 💻Facebook (Search Life Jenerally) https://www.facebook.com/profile.php?id=61576465589219 📧 Email [email protected]

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. Want to support the show? Buy us a coffee! ☕ https://buymeacoffee.com/lifejenerally You can find us: 📷 Instagram @life.jenerally 💻Facebook (Search Life Jenerally) https://www.facebook.com/profile.php?id=61576465589219 📧 Email [email protected]

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.   Want to support the show? Buy us a coffee! ☕ https://buymeacoffee.com/lifejenerally You can find us: 📷 Instagram @life.jenerally 💻Facebook (Search Life Jenerally) https://www.facebook.com/profile.php?id=61576465589219 📧 Email [email protected]

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.   Want to support the show? Buy us a coffee! ☕ https://buymeacoffee.com/lifejenerally You can find us: 📷 Instagram @life.jenerally 💻Facebook (Search: Life Jenerally) https://www.facebook.com/profile.php?id=61576465589219 📧 Email [email protected]

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 https://www.linkedin.com/in/jamisonbennett/ —— Where you can find Life Jenerally and/or support us? ☕️ Support Life Jenerally https://buymeacoffee.com/lifejenerally   📷 Instagram @life.jenerally 💻Facebook https://www.facebook.com/profile.php?id=61576465589219 📧 Email [email protected]

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=   Instagram https://www.instagram.com/wearebravetogether/   ———   ☕️ Support Life Jenerally https://buymeacoffee.com/lifejenerally   📷 Instagram @life.jenerally   💻Facebook https://www.facebook.com/profile.php?id=61576465589219   📧 Email [email protected]  

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.   ☕️ Support Life Jenerally https://buymeacoffee.com/lifejenerally   📷 Instagram @life.jenerally   📧 Email [email protected]

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. Where you find Kirsten Fanker or David Ciccocioppo Kirsten Fanker - Website: https://www.orangeowldesign.com/ or LinkedIn: https://www.linkedin.com/in/kirstenf/ David Ciccocioppo: https://www.linkedin.com/in/david-w-ciccocioppo/ ☕️ Support Life Jenerally: https://buymeacoffee.com/lifejenerally 📷 Instagram: @life.jenerally 📧 Email: [email protected]

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 — don't be an asshole. Grab your cold medicine and tune in. 🎙️   Follow us on Instagram: life.jenerally or email us at [email protected]  Support us:  https://buymeacoffee.com/lifejenerally

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? Follow us on Instagram: life.jenerally or email us at [email protected] Support us: https://buymeacoffee.com/lifejenerally

Jen Squared sits down with 30-year recruiting veteran Gretchen Benes to unpack the truth behind the labels we give ourselves — from inflated LinkedIn titles to the awkward jump from "lady friend" to "girlfriend." Tune in to Life Jenerally and decide for yourself: is it time to label it? Follow us on Instagram: life.jenerally or email us at [email protected]​

Jen Squared host a book club! Book review discussion of Fahrenheit 451, examining its themes of censorship, passive media consumption, and the loss of critical thinking in society. Come and join them on this interesting discussion. Follow us on Instagram: life.jenerally or email us at [email protected].

Jen Squared ring in the new year by reflecting on the highs, challenges, and lessons from the past year, sharing candid thoughts on health, career changes, finances, and personal growth. They then shift to setting intentions for the year ahead, focusing on self-compassion, meaningful goals, and practical steps to move life forward.

Jen Squared sit down with Reality TV insider Eric Criswell to unpack what’s actually real behind the scenes—from casting and story shaping to the economics of the industry. They also explore how AI could transform entertainment, then wrap with a fun genre game and personal check-ins.

In this episode, Jen Squared unpacks the highs and lows of social gatherings — from family tension and work parties to gossip, etiquette, and reading the room. They explore boundaries, burnout, layoffs, and how life transitions show up during the holidays.

In this episode, they break down the difference between pivots and transitions—sharp turns versus gradual change. They share personal stories on divorce, career shifts, aging, health, and mindset in your 40s. Honest, reflective, and relatable conversations about adapting, growing, and moving forward.

In this episode of Life Jenerally, JenSquared talks about what you stop caring about in your 40s—from perfection and people-pleasing to trends and unnecessary stress—and what actually deserves your energy instead.

Adult friendships hit different—and not always in a good way. In this episode, JenSquared dive into why making friends gets harder with age, how community shapes our lives, and what it really takes to build meaningful connections. Honest, thoughtful, and relatable, this episode is a reminder that you don’t have to do life alone.

We are Jen Squared and this is our first podcast. Let's meet!    1xO8mw2V7NTIGr9VwUmd