Things Go Sideways

KiKi L'Italien
  • 5.0 (8)
  • MENTAL HEALTH
  • UPDATED 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. 6D AGO

    What Is Digital Nomad Life Really Like? The Real Story

    What is digital nomad life really like? For Katherine Tuominen — marketing strategist and founder of Catalyst Brand Strategy — it looked nothing like the Instagram version: visa battles, reverse culture shock, lost friendships, and the slow realization that a beautiful destination doesn't outrun an unhealed self. It started during Melbourne's hardest lockdown, when she couldn't leave her house without a grocery receipt and made a quiet promise to herself: she would never feel that trapped again. In this conversation, Katherine talks with KiKi about what the lifestyle actually costs, why the nine-to-five script makes any other path feel reckless to the people around you, how she landed on a travel rhythm that worked for her after almost three years of trial and error, and how the cultural fluency she's built abroad now shapes the brand work she does with founders in the health and wellness space. The thread running through it: when you strip away the titles, the resume, the corporate version of yourself nobody calls you by overseas, what's left tends to be what was already there — the kid who wrote plays, drew on lunch breaks, made up worlds. The life she designed didn't invent a new Katherine. It handed back the original one. Resources Catalyst Brand Strategy — Katherine Tuominen (website): https://catalystbrandstrategy.com Katherine Tuominen (LinkedIn): https://www.linkedin.com/in/katherine-tuominen/ Catalyst Brand Strategy (Instagram): https://www.instagram.com/catalyst_brandstrategy/ HIGHLIGHTS 00:00 — KiKi opens with the gap between designed life and lived life 01:15 — Katherine on what a digital nomad actually is 02:48 — Melbourne lockdown becomes the non-negotiable turning point 04:18 — Making the jump: backlash, lost friendships, going against the grain 06:53 — The Instagram version meets the laptop on the beach 08:55 — First real hurdle: baggage travels with you 10:25 — Finding her travel rhythm after almost three years of trial and error 13:18 — How cultural nuance reshaped her brand work with clients 16:39 — The third culture kid origin: Finland, China, Australia 20:08 — Identity stripped of titles: who you were as a kid is who you are 24:30 — Fear as guide, and breaking the leap into bite-sized starts 30:11 — Closing: you don't have to resolve everything, just stop pretending If you've been suspecting the life you carefully designed is starting to design you back, Katherine's story is a steady, honest look at what happens when you stop performing the version that's been working. Listen & Subscribe Substack: https://thetrustproject.substack.com/  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

    33 min
  2. Finding Direction After Roads End

    MAY 7

    Finding Direction After Roads End

    He Built a $25 Million Business. Then Everything Collapsed. 🔴 JOIN on SUBSTACK: 👉https://thetrustproject.substack.com/  Shane Barker thought he was building something that mattered. His company grew fast during the mortgage crisis by helping people challenge predatory loans. Within two years, the business exploded to 130 employees and a reported $25 million valuation. Then everything shifted. A $62 million lawsuit, frozen bank accounts, public attacks, and years of uncertainty forced him into a fight he never expected. In this episode, Shane Barker talks with KiKi L'Italien about what it feels like when your name, your business, and your future all come under pressure at once. They discuss the emotional toll of public scrutiny, the collapse of professional trust, losing opportunities because of online narratives, and the strange reality of trying to rebuild while still in the middle of the storm. This conversation also explores how that experience eventually led Shane into online reputation management and the creation of TraceFuse.ai. Underneath the business story is something more human: what happens when survival replaces strategy, and the only way forward is one day at a time. Resources Website — Shane Barker: https://shanebarker.com/ TraceFuse.ai — Shane Barker: https://tracefuse.ai/ LinkedIn — Shane Barker: https://www.linkedin.com/in/shanebarker 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 Me On Other Platforms: Substack: https://thetrustproject.substack.com/  YouTube: https://www.youtube.com/@WhenThingsGoSideways/shorts  LinkedIn:  https://www.linkedin.com/in/kikilitalien/  Instagram: https://www.instagram.com/kikilitalien/  For Business Inquiries: KiKi@ThingsGoSideways.com

    54 min

  3. APR 29

    When the Caregiving Season Costs You Yourself

    If you're the one everyone leans on… this conversation with brain health coach Barbara Gustavson is worth your time. Barbara's path to becoming a brain health coach started with a piece of paper handed to her at a Cracker Barrel on Thanksgiving Day — a document that revealed a family history of covered-up crimes, mental illness, and Huntington's Disease. That moment didn't end anything. It started something. What followed was fifteen years of navigating caregiving alongside a career just beginning to take shape, children, a marriage, and a growing awareness that her own brain was carrying more than she'd admitted. In this conversation, Barbara walks through the difference between resetting and regrouping — why you can sleep eight hours and still wake up depleted, and what it takes to actually address the root causes. We also talk about the limbo season: that stretch of time after something shifts where the old rules don't work and the new ones haven't formed. Barbara doesn't frame it as a problem to solve. She frames it as a pause that asks you to listen differently. The conversation also covers the window of tolerance, what it costs to work outside it, and how learning the language your brain actually speaks — signals, not shoulds — changed how Barbara made decisions, set limits, and stayed present through the hardest stretch of her life. Her book is Regroup: How to Reset Your Mind to Unlock Hidden Energy, Enjoy Productive Peace, and Feel Like Yourself Again. Resources mentioned the following during the episode: Regroup (Audiobook) — Barbara Gustavson: https://amzn.to/48AWdCw  Welcome to Your Crisis: https://amzn.to/3QJpyVc  Think Again — Adam Grant: https://amzn.to/3P2SxTg  Calm — mindfulness app: https://www.calm.com  Five Minutes' Peace — Jill Murphy (children's book): https://amzn.to/4w536G8  Connect With Things Go Sideways On Other Platforms: Substack: https://thetrustproject.substack.com/  LinkedIn: https://www.linkedin.com/in/kikilitalien/  Instagram: https://www.instagram.com/kikilitalien/  For Business Inquiries: kiki@amplifiedgrowth.net  00:04 — Show opens; KiKi introduces today's guest 01:53 — The Thanksgiving moment that changed everything 06:18 — Caregiving guilt: the feelings we don't name out loud 09:17 — What limbo season actually is and why it isn't a mistake 11:24 — From quicksand to surrender: reframing the stuck feeling 14:40 — Survival mode is biology, not a character flaw 18:32 — Regroup isn't reset: the difference and why it matters 23:30 — Listen to the whisper before it becomes the two by four 25:59 — The window of tolerance and the cost of ignoring it 31:12 — The principle Barbara still wrestles with: negativity bias 34:30 — Staying present in the current season, not the last one 36:32 — What to do when you're in the middle of your own limbo 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.

    41 min

  4. APR 22

    He Built a Company Inside the Limits His Body Set

    Justin Brown was diagnosed with Crohn's disease at 12, and for years he found ways to keep going anyway — ski life in Utah, cooking professionally, staying physically active. Then around 2005 his body stopped cooperating in ways that couldn't be pushed through. A bowel resection changed the baseline. Some of what he'd assumed about himself didn't come back. 👤 Connect With Me On Other Platforms: Substack: https://thetrustproject.substack.com/  LinkedIn:  https://www.linkedin.com/in/kikilitalien/  Instagram: https://www.instagram.com/kikilitalien/    For Business Inquiries: kiki@amplifiedgrowth.net  In this conversation, Justin talks about the slow process of understanding what his body could and couldn't do — not as a limitation on who he was, but as information he had to work with. He's the founder and CEO of Rhino Skin Solutions, a company built around durability and staying in the game longer. It's hard not to notice how directly that philosophy tracks back to his own story. Want to check out the promo pack for Rhino Skin? Justin shared this great offer for our audience! https://rhinoskinsolutions.com/products/podcast-starter-pack The conversation covers: the year things broke down before surgery; what "identity" actually means when it's not tethered to a condition or a sport; the craftsman approach to illness, work, and incremental improvement; how Jiu Jitsu gave him a kind of community that cooking never quite did; and what he says when someone asks if it's going to get better. Join the Things Go Sideways Substack!  HIGHLIGHTS 00:04 — KiKi sets the episode premise and introduces Justin 01:15 — Justin describes the body breaking down: two good hours a day 03:58 — Self-discovery before surgery; the physical paths that closed off 06:17 — Being diagnosed at 12 and what it did to his sense of self 08:32 — Justin explains what Crohn's disease is and how it works 10:24 — The cultural story about strength, and when it stopped fitting 11:04 — The craftsman philosophy: illness, cooking, Rhino, all one approach 13:25 — Why identity shouldn't be tethered to a condition or an object 15:37 — Wondering if disability was the path; what pointed him toward Rhino 22:09 — Two pieces of family wisdom he still carries 24:07 — His annual resolution: no complaining without a solution 25:30 — Jiu Jitsu and the kind of community that earns your trust 29:53 — The honest answer: it's not going to get better for everybody 31:26 — What passion looks like today: family, Rhino, incremental improvement Resources Rhino Skin Solutions: https://rhinoskinsolutions.com/ Podcast Starter Pack — Rhino Skin Solutions: https://rhinoskinsolutions.com/products/podcast-starter-pack Justin Brown on LinkedIn: https://www.linkedin.com/in/justin-brown-772717105/   Things Go Sideways Podcast Libsyn RSS Feed: https://feeds.libsyn.com/597715/rss Libsyn Podcast Page: https://sites.libsyn.com/597715/site 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 Book Club: https://bookclubs.com/clubs/6100919/join/4db79195 YouTube: https://youtube.com/playlist?list=PLRiPZ_HubKQpcbMaCYtlJN9D6qTv4tOrb&si=85aYxvab0LAD8LKj Spotify: https://open.spotify.com/show/0AToVdda4omlLpG9KpQ0Hj?si=6f32814b56004eab 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?source_code=ASSGB149080119000H&share_location=pdp Share Your Sideways Story (Guest Intake Form): https://forms.gle/UcccE9eJBSfEc9UN9 Schedule Your Sideways Story Interview: https://calendly.com/kiki-interview/podcast-interview 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.

    35 min

  5. APR 15

    He Renamed His Disease "Constant State of Adaptation." Then He Got Back to Work.

    Mark Wallach was diagnosed with ALS in April 2021. By then, he'd already been losing function in his right arm for years — adapting each time, finding workarounds. He's now a quadriplegic and also a working entrepreneur who recently posted about learning to drive his wheelchair with his eyes. That post reached more than 300 people outside his network. An assistive technology company in Germany reached out to send him equipment. (Could this be what happens when someone stops protecting the image and starts telling the truth about their sideways moment?) In this conversation, host of Things Go Sideways podcast, KiKi L'Italien, and Mark cover what it means to keep building when the losses keep coming — and they don't stop. They talk through the grief that doesn't end (he lost use of his right arm, then his left, then both legs), how ALS clarified rather than collapsed his sense of what matters, and what legacy actually looks like when you have a real timeline. They also get into bandwidth, delegation, AI as a genuine equalizer, and why Mark believes vulnerability isn't a soft concept — it's an access point. Mark has a name for his disease that isn't ALS. He calls it "CSA: Constant State of Adaptation." If you were hoping for tidy resolutions, you won't find them here. This episode doesn't end cleanly. It ends with a man still in the thick of it, still building, still figuring out how to receive what other people offer him. And that's where things get interesting! Timestamps 00:04 — KiKi names the premise: stories about reckoning, not highlight reels 01:45 — Mark shares his mission: earn the right to be the first call 04:01 — Mark renames ALS to CSA: constant state of adaptation 06:07 — Going public with vulnerability: unexpected reach and a $8K technology offer 09:49 — What the disease taught him that anyone could use 14:47 — Outsourcing admin, leaning on AI, and working as a quadriplegic 18:21 — Mind shift: from salesperson stigma to connector with purpose 22:34 — Why building for legacy means learning to replace yourself 26:29 — What legacy actually looks like: his wife, his reputation, pizza nights 29:54 — The first sideways moment: August 2018, a weak right arm at Whole Foods 33:28 — The diagnosis, stopping driving, and doing what he'd been putting off 38:51 — Getting out of a funk: goals matter more than self-pity — with permission for rest 40:45 — The hardest thing he's learned: accepting help and letting go of the how 44:33 — The cave question: learning to receive what others offer Resources 🔗 Mark Wallach on LinkedIn: https://www.linkedin.com/in/markwallach/ 🌐 Engagement Mobile Strategies: https://www.engagementmobile.com/ 💙 I Am ALS (advocacy organization): https://www.iamals.org/ 💙 The ALS Association: https://www.als.org/ 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.

    46 min

  6. APR 8

    He Built Companies for 30 Years. Here's What Almost Broke Him.

    Vidar Hokstad has spent more than 30 years building, scaling, and exiting tech companies. He's started price wars he couldn't win, fired people who didn't deserve it, and hit the kind of burnout that doesn't announce itself—it just slowly narrows your field of vision until all you can see is the next task. In this conversation, Vidar talks about what it's like when investors override your judgment, when a dot-com crash forces you to cut a team from 50 to 7, and what happens inside you when the company you relocated countries for starts to collapse. He also gets honest about why big corporate jobs felt like a vacation after startup life, why he kept going back to building anyway, and what finally made fractional consulting feel like the right fit—not a fallback. This episode is for anyone who's building something that looks successful from the outside but feels quietly unsustainable on the inside. Vidar doesn't offer a clean resolution. He offers what 30 years of sideways moments actually taught him: the sooner you take the break, the shorter it needs to be.

    30 min

  7. APR 1

    She Flatlined Three Times at 28, Then Life Asked Her to Do It All Again

    At 28, Danielle Duran Baron was building the life she'd planned. Master's degree in hand, career moving, future wide open. Then routine blood work uncovered something no one expected: a massive liver tumor that would require emergency surgery within days. She flatlined three times on the operating table. Five years later, married and looking ahead, the cancer came back. In this episode, Dani talks about what it's like to be too young for the diagnosis you're given, too healthy for anyone to suspect it, and too early in life to have to tell the people you love that the future isn't guaranteed. She shares how strangers donated blood in record numbers, how her husband navigated a Brazilian hospital in a language he didn't speak, and how a neighbor's words, "it can't rain forever," became the thing she held onto when nothing else worked. This conversation sits with the reality that recovery doesn't follow a clean upward line. There are setbacks that feel like starting over. And there's a quiet, stubborn choice to keep making plans anyway...not because the fear goes away, but because the time you're here has to matter. Danielle published her debut book, "Viva para Contar," in 2020, becoming the first Portuguese-language author to delve into the topic of fibrolamellar cancer HCC and survivorship. Why Listen Now? Recovery isn't a montage. It's the days between the hard news and the next thing you try. If you're in that stretch right now, or sitting with someone who is, this conversation doesn't rush past it. Highlights 00:00  KiKi introduces Danielle Duran Baron and her sideways story 02:23  Dani describes a routine blood test that changed everything 05:03  How a cosmetic consultation uncovered something serious 06:43  The ultrasound room where the doctor's face changed 09:16  A community mobilizes to find the right surgeon 11:19  Surgery, flatlines, and a record number of blood donors 14:49  The cancer returns five years later 18:16  Why honoring the dark moments matters more than staying positive 25:22  "Make it matter"—how diagnosis reshaped her priorities 29:01  A secret blog becomes the foundation for a book 33:26  Why recovery is never the straight line we expect 35:16  The world keeps moving while yours stops 40:21  Volunteering with young cancer patients and losing some of them 43:36  "It can't rain forever"—honest words for a hard season Resources LinkedIn — Danielle Duran Baron: https://www.linkedin.com/in/danielleduranbaron/ 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.

    48 min

  8. MAR 24

    He Quit Drinking and Discovered He'd Been Masking His Whole Life

    Sometimes the blanket that keeps you warm is the same one keeping you from seeing clearly. Brian Kirkland's story is about what you find when you finally pull it off—not clarity, exactly, but the beginning of knowing what questions to ask. Brian Kirkland was a senior director at a major association, able to hold his liquor and show up at 6 a.m. for logistics meetings—and that behavior was rewarded. When he stopped drinking, the security blanket came off, and what was underneath wasn't what he expected. In this conversation, Brian talks about the long, uneven road after getting sober: chasing dopamine in new forms, walking into a job he knew was wrong within weeks, losing four people close to him in a matter of months, and eventually being told by a coworker in crisis to just leave it at home and get the work done. He also shares how diagnoses of PTSD, ADHD, and autism—arriving years apart—didn't simplify his story but gave him a way to stop calling himself broken. This isn't a recovery arc with a neat ending. Brian is still in it, still figuring out how to lead with empathy in spaces that don't always make room for it—and now building 501(booze)(free), a resource for the association community around sobriety and harm reduction. HIGHLIGHTS 00:03 — KiKi introduces Brian and the terrain of this conversation 01:30 — Brian names this chapter: "Pills and Thrills and Belly Aches" 03:43 — What rushes in when the security blanket goes away 05:05 — Chasing dopamine, shame, and the surprise of being supported 09:16 — Why Brian decided to go public about his sobriety 11:08 — What nobody tells you about what comes after you stop numbing 14:04 — The career spiral: burnout, a bad job decision, and a workplace that went Lord of the Flies 16:42 — Four losses in four months and a coworker's devastating response 19:10 — PTSD, ADHD, and autism: diagnoses that arrived years apart 22:06 — From "fundamentally broken" to understanding the wiring 25:25 — 501(booze)(free) and bringing sobriety talk into association spaces 27:42 — What feels risky—and what doesn't—about doing this publicly 33:11 — Brian's biggest takeaway: lead with empathy, not assumptions 34:23 — KiKi's closing: you don't have to be the bravest person tomorrow Resources Brian Kirkland, CAE — LinkedIn: https://www.linkedin.com/in/brian-kirkland-cae-5296774/ Ungovernable Context — Brian's LinkedIn Newsletter: https://www.linkedin.com/newsletters/7432243137835753472/ 501(booze)(free) — Substack: https://501boozefree.substack.com/   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.

    38 min
See All (16)

5
out of 5
8 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
    16
  • Rating
    Clean
  • Copyright
    © 2026
  • Show Website
    Things Go Sideways

You Might Also Like