Leaving Law for Hollywood

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 redesigning work in a way that actually fits your life. This season has been full of conversations with people who stepped off the expected path. Lawyers building careers that didn’t exist 10 years ago. Professionals walking away from corporate roles. People making bold shifts, and others making small, steady changes that led somewhere completely different. What becomes clear is this, career change doesn’t always look like a dramatic leap. Sometimes it’s a pivot. Sometimes it’s a slow burn. And sometimes it starts with simply questioning whether the path you’re on still makes sense. We talk about: – Why some of the most interesting careers today didn’t exist a decade ago – What it really looks like to leave corporate, and what comes after – The difference between overthinking and actually being “not ready” – Why intuition is pattern recognition, not something mystical – The concept of burnout beyond long hours, including misalignment and moral injury – How small decisions, made consistently, can lead to big career shifts Whether you’re thinking about a career change, curious about a career pivot, or quietly wondering if leaving corporate might be an option, this episode brings together the insights, stories and lessons from a season of people doing work differently. In this episode – The top episodes of Season 2 and why they resonated – Lessons from guests who left traditional paths to build something new – Why “procrasti-learning” keeps people stuck in careers that don’t fit – The idea that there’s no perfect decision, only the one you make work – Real examples of redesigning work without burning everything down – Why career change is more possible, and more varied, than it seems 🔧 Resources & Links 📩 Got ideas for Season 3? Email us: contact@outlawspodcast.com 💬 Connect with us on social media and share your favourite episode from this season   If you loved this episode... Share it with a friend who’s wanting a change (or just needs permission to do the thing!). Rate and review Outlaws on Apple Podcasts or Spotify — it helps more Outlaws find us Find out more Website: www.outlawspodcast.com [http://www.outlawspodcast.com] Subscribe to our newsletter for updates, tools, and more Outlawbrary picks Connect with us Instagram: @the.outlaws.podcast - https://www.instagram.com/the.outlaws.podcast [https://www.instagram.com/the.outlaws.podcast?utm_source=chatgpt.com]Facebook Group: Outlaws Podcast Community - https://www.facebook.com/groups/the.outlaws.podcast [https://www.facebook.com/groups/the.outlaws.podcast?utm_source=chatgpt.com]LinkedIn: Outlaws Podcast - https://www.linkedin.com/company/106681587 [https://www.linkedin.com/company/106681587?utm_source=chatgpt.com]Email: contact@outlawspodcast.com Hosted and produced by Shayla Strapps and Kate Offer

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 and workplace culture, they unpack why achievement alone isn’t enough and what happens when connection and contribution are missing. They reflect on: * Why “fine” might be the worst way to describe your job * The link between burnout and a lack of mattering * The tension between individual responsibility and broken systems * Why self-care matters (and not just to make you more productive) * The concept of “personal policies” and setting boundaries that stick * How small, everyday acts of recognition make the biggest difference * The risk of “mattering too much” — when everyone depends on you * Competitive workplaces vs cultures of connection * What great leadership looks like when people genuinely feel seen Kate and Shayla also share personal stories from legal practice and leadership  including what it feels like to truly matter at work, and what happens when you don’t. This episode is a reminder that mattering isn’t about grand gestures or big achievements but built in the small, relational moments of everyday life. If you loved this episode... Share it with a friend who’s wanting a change (or just needs permission to do the thing!). Rate and review Outlaws on Apple Podcasts or Spotify — it helps more Outlaws find us Find out more Website: www.outlawspodcast.com [http://www.outlawspodcast.com] Subscribe to our newsletter for updates, tools, and more Outlawbrary picks Connect with us Instagram: @the.outlaws.podcast - https://www.instagram.com/the.outlaws.podcast [https://www.instagram.com/the.outlaws.podcast?utm_source=chatgpt.com]Facebook Group: Outlaws Podcast Community - https://www.facebook.com/groups/the.outlaws.podcast [https://www.facebook.com/groups/the.outlaws.podcast?utm_source=chatgpt.com]LinkedIn: Outlaws Podcast - https://www.linkedin.com/company/106681587 [https://www.linkedin.com/company/106681587?utm_source=chatgpt.com]Email: contact@outlawspodcast.com Hosted and produced by Shayla Strapps and Kate Offer

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 really wanted to attend) to the mailroom at a major talent agency in Los Angeles—earning just $300 a week despite holding a law degree and an MBA. What follows is a story of persistence, humility, and backing yourself—even when it means starting from the very bottom. In today’s episode we cover: * Why Rob chose law (hint: it wasn’t passion) * The moment he realised legal practice wasn’t for him * Getting retrenched—and why it was the best thing that ever happened * Moving to New York and completing an MBA in media management * Starting over in Hollywood’s mailroom at 26 * The reality of “paying your dues” in a competitive industry * How legal skills became a surprising advantage in entertainment If you loved this episode... Share it with a friend who’s wanting a change (or just needs permission to do the thing!). Rate and review Outlaws on Apple Podcasts or Spotify — it helps more Outlaws find us Find out more Website: www.outlawspodcast.com [http://www.outlawspodcast.com] Subscribe to our newsletter for updates, tools, and more Outlawbrary picks Connect with us Instagram: @the.outlaws.podcast - https://www.instagram.com/the.outlaws.podcast [https://www.instagram.com/the.outlaws.podcast?utm_source=chatgpt.com]Facebook Group: Outlaws Podcast Community - https://www.facebook.com/groups/the.outlaws.podcast [https://www.facebook.com/groups/the.outlaws.podcast?utm_source=chatgpt.com]LinkedIn: Outlaws Podcast - https://www.linkedin.com/company/106681587 [https://www.linkedin.com/company/106681587?utm_source=chatgpt.com]Email: contact@outlawspodcast.com Hosted and produced by Shayla Strapps and Kate Offer

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 financial institutions, her career was built on structure, certainty, status and performance. From the outside, it looked like the definition of success. Inside, something was slowly dimming. What followed was not one dramatic leap, but a long and honest career change from corporate life. Burnout, severe migraines, and a growing sense of disconnection forced a reckoning with the life she had built. A sabbatical opened the first real space to question whether success had been defined by the wrong metrics all along. What began as curiosity, volunteering at Lifeline, exploring psychology, and learning to trust instinct over certainty eventually led her somewhere completely unexpected: becoming a therapist specialising in somatic psychotherapy. This is a conversation about burnout in corporate careers, identity, uncertainty, and the uncomfortable but powerful space between the life you had and the life you are still figuring out. In this episode – Building a high-powered career in global banking, finance and risk – Why corporate environments reward certainty, status and performance – The quiet “dimmer switch” of burnout in high-achieving careers – How volunteering at Lifeline became the turning point in a corporate career change – Following curiosity and learning to trust instinct rather than certainty – Redefining success around meaning, flexibility and being excited for the day ahead This episode will resonate with anyone in banking, finance, law, consulting or other high-pressure professional environments who has ever wondered why a successful career can still feel misaligned. It is an honest look at what happens when the identity built around work begins to shift, and the slow process of reinventing success on your own terms.   Find Jo at https://www.linkedin.com/in/jo-bowles/ [https://www.linkedin.com/in/jo-bowles/]  If you loved this episode... Share it with a friend who’s wanting a change (or just needs permission to do the thing!). Rate and review Outlaws on Apple Podcasts or Spotify — it helps more Outlaws find us Find out more Website: www.outlawspodcast.com [http://www.outlawspodcast.com] Subscribe to our newsletter for updates, tools, and more Outlawbrary picks Connect with us Instagram: @the.outlaws.podcast - https://www.instagram.com/the.outlaws.podcast [https://www.instagram.com/the.outlaws.podcast?utm_source=chatgpt.com]Facebook Group: Outlaws Podcast Community - https://www.facebook.com/groups/the.outlaws.podcast [https://www.facebook.com/groups/the.outlaws.podcast?utm_source=chatgpt.com]LinkedIn: Outlaws Podcast - https://www.linkedin.com/company/106681587 [https://www.linkedin.com/company/106681587?utm_source=chatgpt.com]Email: contact@outlawspodcast.com Hosted and produced by Shayla Strapps and Kate Offer

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, or ask for the conversation “when I feel ready.” But what does ready actually mean? And how long are we allowed to wait for it? This conversation explores the uncomfortable truth about readiness and career change. Often, what we call preparation is actually overthinking. What we call learning is sometimes procrasti-learning. And what we’re really waiting for is certainty that rarely arrives. Lois shares what she’s seen across 20 years of supporting executives, elite athletes, and professionals navigating major transitions, from voluntary career pivots to forced change through redundancy or illness. The pattern is clear: action creates clarity, not the other way around. In this episode – Why “I’m not ready” often really means “I don’t know where to start” – The perfectionism trap that fuels overthinking career change – Procrasti-learning, and when more courses are helping versus hiding – How MOOCs (massive open online courses) can be a low-stakes way to test ideas – The power of getting “oot naboot” and having real-world conversations – How to ask better networking questions that actually generate opportunities – The career theory of “planned happenstance” and why serendipity needs movement – Why forced change sharpens clarity fast – The small scripts that make asking for help less awkward One of the most powerful ideas from the episode is this: you don’t feel ready and then act. You act, and then you start to feel ready. If you’ve been stuck in analysis mode, researching, planning, mapping, learning, and still not moving, this episode will gently (and sometimes directly) challenge you to consider whether readiness is the real issue, or whether it’s fear wearing a very professional disguise. 🔧 Resources & Links Career Wisdom – Lois Keay-Smith [https://www.careerwisdom.com.au/]Search “MOOC + [your topic]” to explore free or low-cost university courses If you loved this episode... Share it with a friend who’s wanting a change (or just needs permission to do the thing!). Rate and review Outlaws on Apple Podcasts or Spotify — it helps more Outlaws find us Find out more Website: www.outlawspodcast.com [http://www.outlawspodcast.com] Subscribe to our newsletter for updates, tools, and more Outlawbrary picks Connect with us Instagram: @the.outlaws.podcast - https://www.instagram.com/the.outlaws.podcast [https://www.instagram.com/the.outlaws.podcast?utm_source=chatgpt.com]Facebook Group: Outlaws Podcast Community - https://www.facebook.com/groups/the.outlaws.podcast [https://www.facebook.com/groups/the.outlaws.podcast?utm_source=chatgpt.com]LinkedIn: Outlaws Podcast - https://www.linkedin.com/company/106681587 [https://www.linkedin.com/company/106681587?utm_source=chatgpt.com]Email: contact@outlawspodcast.com Hosted and produced by Shayla Strapps and Kate Offer