Things Go Sideways

KiKi L'Italien
  • 5.0 (9)
  • Mental Health
  • Weekly

When life, leadership, or the world go sideways, certainty doesn't show up on schedule. Things Go Sideways is a podcast for the middle of it — the part where the plan has cracked, but nothing new has fully formed yet. Each episode is a slow, honest conversation with someone living through change: a career ending, an identity shifting, a sense that what used to work no longer fits. We don't rush to lessons or tidy conclusions. We stay with what's real long enough to notice what's true. Hosted by KiKi L'Italien, Things Go Sideways is not pitching you advice, motivation, or transformation content. This podcast is bringing you orientation. A place to make sense of uncertainty without pretending you already know what comes next. (Because most of the time, we don't — and that's not a failure.) This podcast exists to help people stay present long enough to learn when certainty is gone.

  1. 5d ago

    AI Slop, Sparring Partners, and Betting on Yourself with Corey Brown

    Episode: Corey Brown on AI, His New Book, and His Sideways Story Corey Brown has spent 30 years building things on the web. He led dev teams, built a music discovery platform with Claude Code in a weekend, and just published his first book — The Expert Prompt — about bringing your hard-earned expertise to AI instead of letting AI drive the bus. In this episode, Corey tells the story of quitting his VP role with nothing lined up, betting on himself, and building a coaching practice around the idea that AI fills the gaps — but your expertise drives. We talk about AI slop, sparring-partner prompts, and the AI agents (Wren and Duet) that now run his inbox while he sleeps. When things go sideways, pushing through can stop working before you know what comes next. Corey Brown — founder of No Treble, author of The Expert Prompt, and longtime web developer — joins Things Go Sideways to talk about the moment he knew it was time to walk away from a career he loved, with nothing lined up behind it. Corey shares the story of writing his first book at 58, how a single Python script opened the door to AI, why he treats every LLM like a sparring partner (not a yes-man), and how his AI agent "Wren" now manages his inbox, his calendar, and his to-do list while he sleeps. If you've ever felt that pull — that quiet voice telling you it's time for something different — this conversation is for you. Guest: Corey Brown — Author of The Expert Prompt, AI consultant and coach, founder of No Treble. Find him at coreybrown.me. Host: KiKi L'Italien — Things Go Sideways podcast. Chapters: 00:00 — Introduction  00:16 — Introduction & The Expert Prompt 03:17 — Discovering AI with ChatGPT & Python 07:42 — AI Slop & Human Expertise 12:41 — The Sparring Partner Prompt 20:59 — Betting on Yourself: Quitting Without a Plan 37:51 — AI Agents: Wren & Duet 43:20 — Corey's Closing Advice #ThingsGoSideways #CareerPivot #AI #ExpertPrompt #CoreyBrown #MidlifePivot #CareerChange #ArtificialIntelligence #Podcast #LifeTransitions #AIAgents #QuitYourJob #BettingOnYourself

  2. Oct 25

    I Couldn't Find My Car: Lisa Conway on Menopause, ADHD & Burnout

    One day Lisa Conway drove to a shopping center and had no memory of getting there. She couldn't find her car, and for her it was the moment everything went sideways. Lisa has spent more than 30 years in hair and beauty as a stylist, multi-salon owner, coach, and author of The Naked Salon. She built a business by solving every problem in front of her: write a book, start a podcast, keep going. Underneath, her memory was slipping, menopause was hitting hard, and years of hair color, nails, lashes, and cosmetics had built into what she calls a toxic overload. She didn't stop long enough to notice until her body made her. She talks with KiKi L'Italien about the memory blackouts, putting a chair in front of the oven so she wouldn't forget a cake, and being diagnosed with ADHD in her late 50s. When she walked into the psychiatrist's office, his first question was "What took you so long?" She also talks about the shame that followed, giving up the hair color she was known for, and why she now questions what "success" even means. In this episode: – Growing up with curly hair in a family of nine, and the belief that she only had value if she looked a certain way and produced something – Building a coaching business that grew while she grew unhappy – Menopause, memory loss, and the shopping center moment – Getting an ADHD diagnosis later in life, and how problem-solving hid what was going on underneath – Letting her hair go gray after decades in the beauty industry – People-pleasing, learning to pause, and why "no is a full sentence" – Her 25-hour rule for salon owners who are doing too much – Becoming a "runaway grandma" in Bali and finding a spirituality of her own – Why the failures are the real gifts Questions this conversation answers: What was Lisa Conway's sideways moment? She lost all memory of driving to a shopping center and couldn't find her car. It followed years of memory gaps during menopause, and it made her finally take her health seriously. How did Lisa find out she has ADHD? During EMDR therapy, her therapist suggested she might have "a sprinkling of ADHD." A psychiatrist confirmed it within minutes of meeting her. What advice does Lisa give someone who's overwhelmed? Listen to yourself, and treat small symptoms as "taps on the shoulder" before something bigger forces you to stop. Clearing your mind, whether through meditation, swimming, walking, or gratitude, is as basic as brushing your teeth. How does Lisa define success now? Working with people she wants to work with, and not measuring her worth by how much she produces or how she looks. Chapters 00:00 Welcome & Introduction 02:46 Growing Up & Finding Beauty 06:41 Building a Business & Losing Herself 14:28 The Toxic Overload 24:35 ADHD Diagnosis 32:58 Redefining Success 38:12 Life in Bali & Spirituality 43:29 Final Advice & Closing Connect with Lisa Conway: Website: https://salonconversation.com Instagram: https://www.instagram.com/lisa.conway_ Resources: https://bit.ly/4uXzmKn About Things Go Sideways Things Go Sideways is a podcast hosted by KiKi L'Italien about what happens when your world gets shaken up and pushing through stops working. Subscribe here: https://thingsgosideways.com/ Things Go Sideways Substack: https://thingsgosideways.substack.com/welcome Things Go Sideways Book Club: https://bookclubs.com/kikis-library-hour/meetings #ThingsGoSideways #ADHD #Menopause #Burnout #LateDiagnosis #SalonOwner #Reinvention #LisaConway   Subscribe for weekly conversations about navigating the sideways moments in your career and life. What is one lesson from your own professional path that you wish you learned sooner? Subscribe here: https://thingsgosideways.com/   About Lisa Conway Lisa Conway is a hair and beauty business coach, founder of The Salon Mentors, and host of the Salon Conversation podcast. She is the bestselling author of The Naked Salon, Your Salon Team, and Your Salon Retail. She helps salon, spa, and clinic owners attract better clients, build stronger teams, increase profitability, and reclaim their time. Connect with Lisa: Website: https://salonconversation.com Instagram:   / lisa.conway_   Resources: https://bit.ly/4uXzmKn About Things Go Sideways Things Go Sideways is a podcast hosted by KiKi L'Italien about what happens when your world gets shaken up and pushing through stops working. Subscribe here: https://thingsgosideways.com/

  3. Aug 2

    From Corporate Burnout to Reading the Body's Signals: Sara Nakamura

    What if the stress you're managing isn't the problem — it's information you haven't learned to read yet? Sara Nakamura, well-being consultant and founder of StressXperts, spent years running three Starbucks locations in Las Vegas, working herself into heart palpitations, hair loss, and an autoimmune condition before her body forced a reckoning she couldn't out-hustle. Sarah's the moment stress stopped being just part of the job arrived while she was managing three Starbucks locations — burnt out, running point-of-sale systems, opening new stores fast — and a 5:30 a.m. phone call brought news that her dog had died of an aggressive cancer the same morning her boss screamed at a colleague over a coffee break. In this episode, Sara and KiKi talk about what happens in the body long before a breaking point becomes visible — heart palpitations, hair loss, an autoimmune skin condition — and why "you're so sensitive" is often the last thing said before someone's body forces the decision their mind wouldn't make. Sara shares the "I CARE" framework she teaches leaders and clients (Inside, Contain, Awareness, Realign, Energize) for reading stress signals before they become a crisis, why she calls it "adaptive intelligence" — the human operating system nobody teaches us to update — and how she helps high-performing executives see that the stress showing up at home is data about what's not working at all. In this episode: The 5:30 a.m. call that ended Sara's corporate career Why "thin-skinned" was the last thing anyone said to her before her body forced the exit Stress as data, not dysfunction — and how to tell healthy stress from harmful stress The "I CARE" method for catching a stress spiral before it becomes a health event The "six areas of life" audit (C.Fresh) for finding where you're actually out of alignment Why leaders are often "great in the office" and falling apart at home — and what that gap is really telling them Resources & Links: Sara's book, Stressed Out and Don't Know What To Do: https://amzn.to/3RVP9Lx Free gift from Sara (10-minute audio, "Relax to Ease Pain"): https://stressxpert.com/free-gift-from-sara Sara's website: https://stressxpert.com Connect with Sara on LinkedIn: https://www.linkedin.com/in/sara-nakamura-901a5b3

  4. Jul 27

    She Swore She'd Never Build a Company Again. Then Her Grandmother Fell.

    Lindsay Friedman built two tech companies, walked away from the second after a patent asset sale, and swore she'd never build again. Then she became her grandmother's family caregiver — and the thing she said she'd never do again became the thing she couldn't not do. In this episode, Lindsay walks through the roller coaster of her first startup (a total failure), the patent sale that quietly ended her second, and the night her grandmother fell and broke her femur — the moment that pulled her back into building, this time for reasons that had nothing to do with return on investment. She and KiKi talk about what it's like to still be asking "who am I right now?" years into a pivot, why self-doubt kept her honest instead of stuck, and how being a self-described "control freak" collided with running a business built on things she couldn't control. Lindsay is now the founder of Care Bloom and LT Care Nav, and hosts the Caregivers Compass podcast. This one's for anyone whose "never again" turned out to be less final than it sounded. HIGHLIGHTS 01:33 — "Everything" — the roller coaster that made her say never again 02:28 — The patent sale that quietly closed the door on company #2 09:00 — She ghostwrote her grandmother's Holocaust survival story at 19 — years before it would matter 12:50 — The fall that turned "never again" into a new company 25:33 — "I still look around and go, who am I right now?" 32:39 — Why self-doubt is what keeps her on the right path, not off it Resources LT Care Nav podcast (Caregivers Compass) + book giveaway on care planning: ltcarenav.com/podcast  Things Go Sideways with KiKi L'Italien is a space for honest conversations about disruption, identity shifts, and reinvention — no tidy bows, just real stories about staying oriented when what you thought was certain collapses. 🎧 Listen on Spotify, Apple Podcasts, or YouTube — search "Things Go Sideways Podcast Lindsay Friedman" 📩 Subscribe to the newsletter at thingsgosideways.com for patterns, tools, and behind-the-scenes reflections you won't hear anywhere else 📱 Follow @kikilitalien for more

  5. Jul 24

    He Got Laid Off — and Says It Was the Best Thing That Ever Happened to Him

    Matt West didn't have one sideways moment — he's had a sideways career. Musician, graphic designer, creative director, consultant, and now leadership coach: every time he got comfortable, the context changed underneath him. In this conversation, Matt (author of Bend, Don't Break: How to Adapt in the New World of Work) talks with KiKi about the layoff he now calls one of the best things that ever happened to him, and why he doesn't recommend saying that to anyone still in the middle of theirs. They dig into the difference between healthy stress (eustress) and the kind that actually breaks people, why curiosity lowers the emotional temperature that control tends to raise, and how AI fear often has less to do with technology and more to do with losing the story we tell about who we are. Matt also opens up about "credible vulnerability," trusting himself, others, and systems in very different ways, and why he's grieved his professional identity more times than he can count. The throughline is this...bending isn't weakness. It's what happens when you're rooted in values instead of titles. And it's the difference between adjusting and shattering when the ground shifts. Read Matt West's book! Bend, Don't Break: https://amzn.to/4wlStPb 00:00 — Opening: what it means when things go sideways 00:56 — Matt West introduces Bend, Don't Break 01:34 — Why Matt calls it a sideways career, not a sideways moment 05:31 — Parenting decisions that were "imperfect, just messy" 09:38 — Where AI fear actually comes from (identity, not technology) 13:18 — Turning emotions into data instead of threats 15:32 — The layoff Matt now calls one of the best things that happened 17:56 — "The end of expertise" and why adaptability keeps you in the room 20:12 — Toxic positivity vs. healthy positivity and mental scripts 25:30 — Trust in yourself, trust in others, trust in systems 29:04 — Bend vs. break: the actual difference explained 29:43 — Eustress: the healthy stress nobody talks about 32:34 — What are you rooted to? Titles, opinions, or values? 36:17 — Why Matt wrote the book (it started as LinkedIn posts) 40:46 — Grieving identity, over and over again 43:04 — Advice for anyone feeling the ground shift right now 45:54 — Closing thought: bending is awareness, not weakness Matt West's book: Bend, Don't Break: How to Adapt in the New World of Work — benddontbreakbook.com (also available on Amazon, Barnes & Noble, and Bookshop.org) Matt West's LinkedIn: linkedin.com/in/westpractices

  6. Jul 11

    The Satir Change Model: Making Sense of Chaos with Adrian Segar

    In this conversation, I sit down with my friend Adrian Segar to explore the Satir Model of Change—a framework for understanding why things feel so chaotic when everything is shifting (check out Adrian's great post about change models, including Satir's, on Conferences That Work. Adrian shares how foreign elements in his life (job loss, family crisis, identity shifts) eventually led to new, more authentic chapters.   Adrian Segar is known for designing gatherings that help people move from guarded to honest, and from conversation to action. But in this conversation, he's taking us on a guided tour of Virginia Satir's model of change. This model describes how change feels. Adrian walks us through: Why we start in an old status quo What happens when a foreign element hits our lives Why the messy, emotional chaos that follows is actually normal How a transforming idea emerges And how we eventually land in a new status quo Along the way, he shares very personal sideways stories. From leaving a physics career after 25 years of preparation, to losing a business overnight, to navigating the long, hard road of parenting adopted twins in crisis, Adrian shares how each of those disruptions eventually revealed unexpected silver linings. If you're in the middle of a layoff, a big transition, a family upheaval, or a season of not knowing, my hope is that this episode gives you language, context, and a little more compassion for yourself. Please enjoy this conversation with Adrian Segar.

  7. Jun 10

    When the Job Goes, Who Are You? Stan Gibson on Identity After Loss

    Stan Gibson built four decades of corporate success — and then watched it dissolve in a single phone call. When the Fortune 100 company he'd given everything to displaced his position, Stan wasn't blindsided by the job loss. He was blindsided by the question underneath it: who are you when the career that defined you is gone? In this conversation, Stan Gibson — executive coach, keynote speaker, and author of Living a Rich and Intentional Life — walks through what it actually takes to rebuild identity after disruption. He covers the moment a friend's terminal cancer diagnosis reoriented his entire understanding of what "rich" means; how his wife's stage four cancer diagnosis forced him to practice what he preached about self-care; and the coaching framework he uses with executives navigating their own identity collapse — from strengths mapping to "I am" identity statements to a reverse-engineered five-year vision process. Stan introduces a through-line he calls the "genius paragraph" — a granular translation of your five core strengths into a statement of who you are at your best. It's not motivational filler. It's a tool for people who've lost the external structure that told them who they were, and need something internal to replace it. Why Listen Now: If you've ever let a job title answer the question "who are you" — and then lost the job — this episode is a hand on the shoulder, not a blueprint. Stan's been there. He built a life from the rubble twice. If this is you… You're still carrying the weight of a disruption you didn't choose, and part of what's heavy is that you don't know who you are without it. Resources Double Down on You PDF (neuroscience-based resources: sleep, nutrition, fitness, visualization) — Stan Gibson: https://leadwithstan.com Living a Rich and Intentional Life — Stan Gibson (book) Website: https://www.stangibsonspeaks.com Speaker Reel: https://www.stangibsonspeaks.com/speaking LinkedIn: linkedin.com/in/stangibsonspeaks The Inspiration Podcasts with Stan — Stan Gibson's podcast Psycho-Cybernetics — Dr. Maxwell Maltz (referenced by Stan) About the Things Go Sideways Podcast When life or leadership goes sideways, the story's just getting interesting. Things Go Sideways with KiKi L'Italien features honest conversations with leaders, creators, and changemakers navigating disruption, uncertainty, and identity shifts. Each episode explores trust, resilience, and what it means to stay human when certainty breaks down. New episodes share real stories about rebuilding agency and meaning without rushing to quick-fixes, spiritual bypassing, or pretending clarity comes easy. Connect With Things Go Sideways: Substack: https://thingsgosideways.substack.com/welcome  Website: https://thingsgosideways.com  LinkedIn:  https://www.linkedin.com/in/kikilitalien/  Instagram: https://www.instagram.com/kikilitalien/  TikTok: https://www.tiktok.com/@thingsgosidewayspod and https://www.tiktok.com/@thingsgosideways  For Business Inquiries: kiki@thingsgosideways.com  Listen & Subscribe Substack: https://thingsgosideways.substack.com/  Website: https://thingsgosideways.com/listen  Libsyn RSS Feed: https://feeds.libsyn.com/597715/rss Libsyn Podcast Page: https://sites.libsyn.com/597715/site  Libsyn Video Feed: https://feeds.libsyn.com/597715/spotify Spotify (video): https://open.spotify.com/show/0AToVdda4omlLpG9KpQ0Hj Spotify (audio): https://open.spotify.com/show/2K6DYzLMRkbT4FfmDaFP7a?si=4b4c70c5a3a84ce2 Apple Podcasts: https://podcasts.apple.com/us/podcast/things-go-sideways/id1849510232 Amazon Music: https://music.amazon.com/podcasts/87fc90ea-455c-443d-a24f-bd3bccc2e764/things-go-sideways Audible: https://www.audible.com/podcast/Things-Go-Sideways/B0G59XM2XY YouTube: https://www.youtube.com/@WhenThingsGoSideways  Join the Community Things Go Sideways Book Club: https://bookclubs.com/clubs/6100919/join/4db79195 YouTube Playlist (Full Episodes): https://youtube.com/playlist?list=PLRiPZ_HubKQpcbMaCYtlJN9D6qTv4tOrb LinkedIn Company Page: https://www.linkedin.com/showcase/things-go-sideways/ Facebook Group: https://www.facebook.com/groups/1150721167011215 Facebook Page: https://www.facebook.com/profile.php?id=61585524425304 00:00 — KiKi introduces Stan Gibson and the episode's stakes 01:53 — Stan describes his first sideways moment: threatened with termination at 23 03:45 — Writing the plan on a piece of paper: "No one will ever dictate my future again" 05:12 — The second sideways moment: Fortune 100 layoff he didn't see coming 06:40 — "Always have a plan B" — why Stan was ready the morning after 07:30 — Jerry walks over at dinner: "When death becomes certain, life becomes rich" 09:10 — Wife's stage four cancer diagnosis changes how Stan lives his own framework 11:00 — The swim lane metaphor: knowing who you are and who belongs beside you 12:15 — Neuroscience of identity: RAS, amygdala, and why early lies become truth 15:23 — Working with a client whose career became her entire identity 17:45 — The genius paragraph: translating Clifton Strengths into who you are at your best 20:00 — Visioning backward: assuming five-year success and asking what got you there 22:10 — "I am" versus "I will someday": stating identity, not intention 23:15 — Mother's passing, wife's cancer, and using affirmations to embrace hard seasons 24:49 — Solomon's vapor: life isn't meaningless, it moves fast 29:00 — Marianne Williamson quote: it's our light, not our darkness, that frightens us most 34:46 — Stan's closing counsel: "Own the moment. Are you a victim or are you an owner?"

  8. Jun 8

    She Went In for Her First Mammogram. Then Everything Changed.

    Cecilia Satovich was 40, raising three young daughters, and living inside the life she had hoped for. Then she went in for her first mammogram. What started as something routine (an appointment you know you should make, the kind you might delay because life is full and you are busy and also, let's be real, who wants to deal with it?) became the beginning of a breast cancer diagnosis right as the world was heading into the uncertainty of early 2020. In this episode of Things Go Sideways, Cecilia talks about what it felt like to hear the word cancer when her children were still small, treatment was suddenly complicated by COVID, and the future she had been counting on no longer felt guaranteed. We talk about mammograms, fear, motherhood, asking for help, saying the wrong thing, and how hard it can be to stay close to someone else's pain when you don't know what to do with your own discomfort. This is not a neat cancer-survivor story with a shiny bow on it. Cecilia's story is about what happens when the body interrupts the plan, when ordinary life becomes precious in a way that feels almost unbearable, and when surviving something changes how you show up for other people who are still in it. Because sometimes the sideways moment is not only the diagnosis. Sometimes it is realizing how much you love your life. And yes. Get the mammogram. --- What is it like when your first mammogram leads to a breast cancer diagnosis? When a first mammogram leads to a breast cancer diagnosis, the shock is not only medical. It can interrupt your sense of safety, your plans, your family life, and the future you thought you were standing inside. In this episode of Things Go Sideways, Cecilia Satovich talks about being diagnosed with breast cancer at 40, while raising three young daughters and beginning treatment during the uncertainty of early 2020. Her story is about fear, motherhood, asking for help, and what changes when your body forces you to pay attention. --- Connect With Things Go Sideways: Substack: https://thingsgosideways.substack.com/welcome  Website: https://thingsgosideways.com  LinkedIn:  https://www.linkedin.com/in/kikilitalien/  Instagram: https://www.instagram.com/kikilitalien/  TikTok: https://www.tiktok.com/@thingsgosidewayspod and https://www.tiktok.com/@thingsgosideways  For Business Inquiries: kiki@thingsgosideways.com

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5
out of 5
9 Ratings

About

When life, leadership, or the world go sideways, certainty doesn't show up on schedule. Things Go Sideways is a podcast for the middle of it — the part where the plan has cracked, but nothing new has fully formed yet. Each episode is a slow, honest conversation with someone living through change: a career ending, an identity shifting, a sense that what used to work no longer fits. We don't rush to lessons or tidy conclusions. We stay with what's real long enough to notice what's true. Hosted by KiKi L'Italien, Things Go Sideways is not pitching you advice, motivation, or transformation content. This podcast is bringing you orientation. A place to make sense of uncertainty without pretending you already know what comes next. (Because most of the time, we don't — and that's not a failure.) This podcast exists to help people stay present long enough to learn when certainty is gone.

Information

  • Creator
    KiKi L'Italien
  • Years Active
    2025 - 2026
  • Episodes
    26
  • Rating
    Explicit
  • Copyright
    © 2026
  • Show Website
    Things Go Sideways