Outlaws Podcast: Embracing Career Freedom
by Shayla Strapps & Kate Offer | Outlaws Podcast
Career change, career pivot, work life balance, career freedom — if you’re craving any of these, Outlaws is the podcast for you. Hosted by Shayla Strapps and Kate Offer, two out[of]laws who walked away from traditional legal careers, this show is for professionals who look successful on paper but feel stuck inside.Each episode explores bold career shifts, honest stories of uncertainty, and practical tools for rewriting the rules of work and life. Whether you’re questioning your job, dreaming of more freedom, trying to find better work life balance, or navigating a big transition, Outlaws offers real talk for people ready to redefine success on their own terms.Subscribe now and start your own Outlaw journey.📬 Get updates: www.outlawspodcast.com📘 Join the Facebook Group: Outlaws Podcast Community📸 Follow on Instagram: @the.outlaws.podcast💼 Connect on LinkedIn: Outlaws Podcast
Episodes
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Ditch the Shoulds: The Biggest Lessons from Season 2
What if the real lesson from this season is that you’re allowed to change your mind about your career? In this episode, Shayla and Kate wrap up Season 2 of the Outlaws podcast, reflecting on the biggest themes across the season, from career change and career pivots to leaving corporate and...
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Mattering Matters: Rethinking Burnout, Success and Connection
In this Outlawbrary episode, Kate and Shayla discuss Mattering: The Secret to Building a Life of Deep Purpose and Connection by Jennifer Breheny Wallace and explore a deceptively simple idea: feeling valued and adding value is a fundamental human need. From burnout and loneliness to leadership…
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Leaving Law for Hollywood
In this episode of Outlaws, Kate and Shayla sit down with Hollywood talent manager Rob Marsala—a former Perth lawyer who walked away from a traditional legal career to build a life in the entertainment industry. Rob shares his unconventional journey from law school (which he admits he never…
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From Global Finance to Somatic Therapist: Reinventing Success
What happens when the career you spent decades building no longer feels like success? In this episode, Kate and Shayla speak with a guest who spent years at the highest levels of global banking, finance and corporate risk. From investment banking in London to senior roles across Australia’s major...
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Are You Actually Not Ready, Or Just Overthinking Your Career Change?
In this episode, Shayla and Kate sit down with career counsellor and founder of Career Wisdom, Lois Keay-Smith, to unpack one of the most common blockers in professional life: readiness. So many smart, capable people tell themselves they’ll make the move, apply for the role, start the business…
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From Litigation to Legal Tech: How Sam Flynn Built Josef
In this episode of Outlaws, we sit down with Sam Flynn, former litigation lawyer and co-founder of Josef, an AI automation platform transforming how legal work gets done around the world. Sam started on the traditional legal path. Law school. Top firm. Supreme Court clerkship. The funnel was...
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Outlawbrary: Stop Measuring Your Life by Money
In this Outlawbrary episode, Kate and Shayla dive into The Five Types of Wealth by Sahil Bloom and ask a deceptively simple question: what if financial wealth isn’t the only kind of wealth that matters? Sahil Bloom’s Five Pillars of Wealth framework challenges the traditional scoreboard of…
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Truth Over Career, When Speaking Up Is the Outlaw Move
What happens when telling the truth could cost you your career? In this Outlaws Diary episode, Kate and Shayla sit down with Rabia Siddique, international human rights lawyer, former British Army officer, and leadership consultant, to explore what it really means to choose truth over safety. From…
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Stop thinking, Start making, How a side hustle awakens creativity
What if your side hustle wasn’t about making money, but about becoming more of yourself? In this Outlaws After Dark episode, Kate and Shayla are joined by Sandrine Alexandre-Hughes, a lawyer and mum of three who built a creative side hustle while working full time, not to chase millions, but to...
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Leaving Law to Understand It: How systems affect wellbeing
In this episode of Outlaws, Kate and Shayla are joined by Dr Carly Schrever, a former lawyer who retrained as a psychologist and went on to become Australia’s first dedicated judicial wellbeing adviser. Carly shares her own journey from law to psychology, including the moment she realised she was...
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From M&A Lawyer to Biotech Startup Founder: Michael Kingsbury on Uluu, Seaweed and Reinventing Your Career
In this episode of Outlaws, we’re joined by Michael Kingsbury, a former M&A lawyer who walked away from corporate law to co-found Uluu, a climate tech startup creating seaweed-based materials designed to replace fossil-fuel plastics. What began as curiosity about science, technology and impact…
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Designing Freedom: How Kelly Irving Rebuilt Her Business to Work 20 Hours a Year (& Travel the World!)
What if career freedom isn’t about walking away from work altogether, but about consciously redesigning how you work? In this Outlaws Escapes episode, Kate and Shayla are joined by editor, book coach and founder of the Expert Author Academy, Kelly Irving, who shares how she radically restructured...
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How to Make Big Decisions Without Overthinking with Bethan Winn
What if making a big decision isn’t about finding the right answer, but learning how to trust yourself? How do you make big decisions without overthinking, spinning in circles, or waiting for certainty that never comes? In this episode, Shayla and Kate are joined by Bethan Winn, one of…
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Burnout, Rest and Recovery: A Doctor’s Story
What happens when the person everyone relies on can no longer keep going? In this episode, Kate and Shayla sit down with Dr Emily Amos, a former GP whose own experience of burnout stopped her in her tracks and ultimately reshaped her entire understanding of care, success, and sustainability.…
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Imposter Syndrome - what it is, why it shows up and how to break free - with Alison Shamir
In this episode, Kate and Shayla sit down with author and imposter syndrome expert Alison Shamir to unpack one of the most universal, misunderstood experiences in modern work: that persistent belief that you don’t deserve your success. Alison breaks down what imposter syndrome actually is, why…
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The Voices in Your Head Are Lying to You: Conquer Your Imposter Syndrome (feat. Alison Shamir)
What if that familiar “I’m about to be found out” feeling isn’t the truth… but a story your brain has rehearsed for years? In this Outlawbrary episode, Shayla and Kate dive into Conquer Your Imposter by confidence and imposter syndrome expert Alison Shamir. It’s a book packed with research-backed...
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Getting Unstuck: What to do when you feel trapped in your own life or career
What happens when your life looks perfectly fine on paper, but you're quietly trapped in a life or career that no longer fits? This episode began with an email from a listener. She is accomplished, respected, highly capable, and yet she feels like she has no room to breathe, no time to think, and...
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How to Leave Law for Writing: Emily Tsokos Purtill’s Leap Into Fiction
What happens when a lawyer turned author finally stops waiting for the “right time” and writes the story she’s been carrying for decades? In this episode, Shayla and Kate sit down with Emily Tsokos Purtill, former commercial lawyer and newly crowned award-winning novelist, whose debut book Matia...
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Outlaw Escapes: Taking a Career Break and Living With Less: Kate Cranney
What if taking time off wasn’t a luxury, but a smart, sustainable part of your career? In this episode of Outlaws Escapes, Shayla and Kate chat with Kate Cranney, a scientist, artist and communicator who pressed pause on her career for eight months to travel, hike and cycle across some of the...
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From Burnout to Viral: How One Lawyer Used Content to Call Out Corporate Life: Henry Nelson Case
What happens when a lawyer calls out the legal and corporate world for what it really is - often unhealthy, unsustainable, and quietly breaking people who care? To launch Season 2, Shayla and Kate go international with UK-based lawyer, content creator and TEDx speaker Henry Nelson Case. After…
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Career Change, Career Freedom, and Work-Life Balance - what we've learnt so far
20 episodes. Countless conversations. One big Outlaw experiment. In this special wrap-up episode, hosts Shayla Strapps and Kate Offer look back on Season 1 of the Outlaws Podcast, where career change, career pivots, and the pursuit of real career freedom were front and centre. What started as two...
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How to Get Better Sleep: Why Rest Is the Most Rebellious Act. With Psychologist Alicia Visser
Sleep isn’t wasted time. It’s the secret weapon for clarity, creativity, resilience - and not being permanently cranky. And if you’re not getting enough, it is probably making you sick. But in a world where pulling an all-nighter is treated like a badge of honour, no wonder so many of us are...
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Learning to Breathe: How Burnout Recovery Led to Leaving Law
Breathwork. Can sounds a bit woo woo, right? Even Alicia thought so, until it became the one thing that helped her crawl out of burnout and rebuild her life. In this episode, Shayla and Kate sit down with Alicia Snijders, a former corporate lawyer who spent eight years chasing promotions and pay...
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You don’t need a 5 year plan. You need to experiment. Outlawbrary #4 | Tiny Experiments byAnne-Laure Le Cunff
What if you could learn how to stop chasing goals and instead start running tiny experiments? In this Outlawbrary episode, Shayla and Kate dive into Tiny Experiments: How to Live Freely in a Goal-Obsessed World by Anne-Laure Le Cunff. It’s part science, part storytelling, and part permission slip...
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Side Hustle Ideas: From Courtrooms to Cattle with Katie Sierakowski
What if your “side gig” was more than just extra cash, what if it was your way out, or your way to more joy and fulfillment? In this episode of Outlaws, Shayla and Kate kick off a brand-new semi regular series on side hustles. From bold experiments to quiet projects done late at night, side…
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How to Live Overseas for a Year and Make Career Break Travel Possible: Outlaw Escapes
What if taking a year to live overseas wasn’t a fantasy, but a plan you could actually pull off? In the first episode of our new semi regular episodes of 'Outlaw Escapes', Shayla and Kate talk with lawyer and mum Melissa Hii, who moved her family to Bordeaux and ran her law practice from France.…
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When a Side Hustle Becomes a Movement: Career Change, Passion, and Mental Health
What happens when a casual side hustle turns into a global movement for mental health? In this episode, Shayla and Kate sit down with Nick Hudson, engineer-turned-entrepreneur and founder of The Push-Up Challenge. What began as friendly banter at the surf club became one of Australia’s biggest...
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Outlawbrary #3; How do we know how to make good decisions? Values based decision making with Greta Bradman
Need to make a decision but not sure how to start? If you’ve ever felt stuck, second-guessed yourself, or wondered whether you’re making the right call, this episode might just help. In this third Outlawbrary edition, Shayla and Kate dive into Greta Bradman’s inspiring and practical book What...
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Unlocking Transferable Skills for Meaningful Career Change with Anna Black
What if the skills that made you successful are the same ones making you miserable? In this episode focused on career change and career pivots, Shayla and Kate invite career counsellor Anna Black to discuss transferable skills and how to identify the ones that truly resonate with you. We're not...
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Navigating Career Change Uncertainty: Sitting with Discomfort
What if sitting in the discomfort of "I don’t know" was the first real step in your career change? In this episode, Shayla and Kate delve into the liminal, messy, and often uncomfortable space that exists between knowing what you don’t want and having any clue what comes next in your career…
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From Army to Outlaw: Leaving Certainty for Purpose After 20 Years in Uniform
What happens when the job you thought you'd stay in forever — the identity you've carried since age 17 — stops feeling right? In this episode, Shayla and Kate sit down with David (Dave) French, former infantry officer turned leadership coach, who spent 21 years in the Australian Army, followed by…
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Burnout Prevention & Sustainable Work: How to Make Work Work with Sally Clarke
In this episode, Shayla and Kate sit down with global burnout expert Sally Clarke to discuss burnout prevention and how to achieve sustainable work-life balance. Chronic stress can hijack our energy and identity, but through actionable insights, we uncover how to reboot before we break. Drawing…
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Outlawbrary #2: How Outlaws Stop People-Pleasing and Overthinking: The Let Them Theory by Mel Robbins
What if the most rebellious thing you could do wasn’t to break the rules — but to stop worrying what everyone else thinks? In this episode, Shayla and Kate crack open Mel Robbins’ bestselling book The Let Them Theory and explore why these two tiny words are such a potent tool for living like an...
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From Lawyer to Author: How Sulari Gentill Left Law and Found Her True Calling
Ever feel like there’s something you’ve forgotten to do — but you can’t quite name it? For Sulari Gentill, leaving the law and picking up a pen finally let her breathe. In this episode of Outlaw Diaries, we talk to the incredible Sulari Gentill — a former corporate lawyer who swapped contracts…
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What Does Success Really Mean? Start With How You Spend Your Time
What if success wasn’t about ticking boxes, climbing ladders, or polishing your LinkedIn profile — but about something quieter, deeper, and more you? In this episode, a follow up to our very popular Backwards Budget episode, Shayla and Kate take the conversation beyond the Backwards Budget and…
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Budgeting for a Life You Love: How to Use the Backwards Budget to Change Your Life and Career
💡 What if your budget started with the life you want, not the one you’re stuck in? In this episode, Shayla and Kate unpack a deceptively simple but transformative tool: the Backwards Budget. Born out of Shayla’s own burnout and a desire to live more deliberately, this approach flips traditional...
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Outlawbrary #1: 4000 Weeks by Oliver Burkeman, Time Anxiety, and the Freedom of Letting Go
In this episode, Shayla and Kate crack open Oliver Burkeman’s powerful book 4,000 Weeks — and let’s be clear, it’s not about to-do lists. They explore the confronting reality that 4,000 weeks is roughly all we get in a lifetime, and how that number becomes a springboard for bigger questions: What...
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From Litigation to Legal Tech and Author: Reinventing Success with Fiona McLay
In this Outlaws episode, we kick off our first Outlaw Diaries as Shayla interviews Fiona McLay, a former litigation lawyer who made a bold career change into legal tech and authorship. Her journey shows how stepping away from the traditional legal path can lead to more balance, creativity, and a...
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The Hidden Rules of Success: What We’re Unlearning (And why you might want to, too)
In this episode of Outlaws — the career change podcast for high achievers ready to rewrite the rules — Shayla and Kate pull back the curtain on the hidden curriculum, the sneaky, unspoken rules that shape how we define success, worth, and ambition. From career ladders you never questioned to the...
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When Success Isn’t Enough: Career Change, Burnout, and Becoming an Outlaw
You followed the rules. You ticked all the boxes. You built the “successful” career. So… why does it still feel like something’s missing, or that you're not really happy? In this first episode of Outlaws — the career change podcast for high achievers rethinking success — your hosts Shayla and…
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Trailer Outlaws Podcast - Unlearning the rules of work and life
Outlaws is the podcast for professionals who look successful on paper but feel stuck inside. Hosted by two (out)laws who walked away from traditional legal careers, we explore bold career pivots, honest stories, and practical tools for rewriting the rules of work and life. If you're craving more...
About this show
Career change, career pivot, work life balance, career freedom — if you’re craving any of these, Outlaws is the podcast for you. Hosted by Shayla Strapps and Kate Offer, two out[of]laws who walked away from traditional legal careers, this show is for professionals who look successful on paper but feel stuck inside.Each episode explores bold career shifts, honest stories of uncertainty, and practical tools for rewriting the rules of work and life. Whether you’re questioning your job, dreaming of more freedom, trying to find better work life balance, or navigating a big transition, Outlaws offers real talk for people ready to redefine success on their own terms.Subscribe now and start your own Outlaw journey.📬 Get updates: www.outlawspodcast.com📘 Join the Facebook Group: Outlaws Podcast Community📸 Follow on Instagram: @the.outlaws.podcast💼 Connect on LinkedIn: Outlaws Podcast
Hosted by
Shayla Strapps & Kate Offer | Outlaws Podcast