Outlaws Podcast: Embracing Career Freedom

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 re...

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 M...

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 defini...

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 conver...

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 working exactly as designed. But along the way, something shifted.

What began as volunteering with civil liberties organisations led to a ligh...

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 success. Instead of measuring life purely by income, status or external validation, he argues that we should also be investing in time wealth, s...

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 a hostage crisis in Iraq to a discrimination case against the UK government, Rabia’s story is extraordinary. But the tension at its core ...

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 explore something her legal career simply couldn’t offer.

After hearing devastating stories about online grooming and bullying, Sandrine fe...

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 more interested in the human dynamics of the courtroom than legal argument. That pivot ultimately led her to groundbreaking research on j...

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 has become a globally significant attempt to tackle plastic pollution, climate change and ocean health—using seaweed.

Michael shares his...

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 her business to avoid burnout, reclaim her time, and create a life that worked for her family.

A few years ago, Kelly and her family pack...

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 Australia’s leading experts in critical thinking and human skills, to unpack how decisions actually get made, and why so many high-achievers feel st...

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.

Emily spent 15 years in medicine, building a thriving practice and supporting others through some of their most vulnerable moments. From the o...

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 high achievers are especially prone to it, and how those old origin stories from childhood quietly shape our confidence, our careers, and ou...

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 insights, personal stories, and practical tools for anyone who’s ever questioned their capability, underestimated their achievements, or ...

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 no idea how to get unstuck. She told us she feels weighed down by the golden handcuffs, unsure whether she can take a step backward in se...

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 just won the 2025 WA Premier’s Book Award for an Emerging Writer.

Emily’s story captures everything we talk about on Outlaws, the tension ...

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 world’s most stunning landscapes.

From Patagonia to the Alps, Kate and her partner swapped meetings for mountains and discovered what happens...

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 years of watching toxic behaviour get rewarded and burnout get normalised, Henry decided to stop pretending everything was fine - and start s...