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 lightbulb moment: when Sam and his collaborators built a simple legal tool to help people navigate Victoria’s infringement system, 30,000 people used it on day one. Within a month, 60,000 people had accessed it. The law eventually changed.

That experience sparked Josef. Today, the platform is used by organisations like Bumble, L’Oreal and Bupa, as well as community legal centres and universities, to automate legal questions, generate documents and streamline workflows. At its core is a belief that self-service legal tools, when properly supervised, can help close the access to justice gap rather than widen it.

But this conversation isn’t just about legal tech.

Sam talks openly about what he had to unlearn from legal training. The obsession with risk. The fear of embarrassment. The idea that failure defines you. He shares the moment he realised that striving is far less embarrassing than staying small to avoid criticism.

We explore identity shifts, burnout, creativity, storytelling in business, and why lawyers statistically make “bad founders” unless they learn to turn down the risk dial.

If you’ve ever felt pulled toward something different.

This episode is your reminder: you can follow your curiosity. You can build something new. You can strive anyway.

If you’re a lawyer wondering whether the traditional path is right for you, or you’re curious about legal tech, AI in law, or alternative career options for law graduates, this episode offers both inspiration and practical insight.

You don’t have to abandon law to reinvent it. Sometimes you just have to step into the arena.

Theodore Roosevelt’s speech - The Man in the Arena

Sam on LinkedIn 

Sam’s newsletter: https://www.linkedin.com/newsletters/scooped-7183318477628223488/

Sam's Fireside Chat series with Tom Dreyfus https://open.spotify.com/show/2tBSFrxTSO30Pknjmyb7RG

Josef

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Hosted and produced by Shayla Strapps and Kate Offer

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, social wealth, mental wealth and physical wealth.

For high performers, especially lawyers and professionals trained to optimise for achievement, this conversation hits close to home.

We also explore whether this kind of framework feels obvious… or whether it’s exactly what people stuck in high-pressure careers need to hear.

And yes, we share honest thoughts about what worked in the book, what didn’t, and whether we’d recommend it.

If you’ve been quietly wondering whether the ladder you’re climbing is leaning against the right wall, this episode is for you.

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Hosted and produced by Shayla Strapps and Kate Offer

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 is universal: what do you do when the system tells you to stay quiet?

This episode explores courageous leadership, workplace discrimination, whistleblowing, and what it really means to speak truth to power. Rabia shares the personal and professional cost of challenging authority, and why values-based leadership often requires breaking the rules that protect powerful institutions.

We talk about what happens when silence feels like complicity, why speaking up can feel career-ending, and how real leadership sometimes begins the moment you refuse to comply.

– Rabia’s journey from Legal Aid lawyer to the British Army

This conversation moves beyond the extraordinary circumstances of a military hostage situation and into something far more familiar: the moments in our own careers where we feel stuck, silenced, or pressured to conform.

And sometimes, the real outlaw move is this: speak up anyway.

Resources & Links

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Hosted and produced by Shayla Strapps and Kate Offer

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 felt compelled to act. Instead of approaching the problem with fear or lectures, she asked a different question: if the problem is dark, does the solution have to be? That question led to All the Likes, a card game that teaches online safety through play, followed by Smoke, Mirrors and Filters, a conversation game about our digital habits and the conversations we avoid.

What followed wasn’t overnight success or financial freedom. It was exposure to creativity, manufacturing, education, media, and whole new worlds that sit well outside the legal profession. This episode is an honest look at starting a side hustle without quitting your job, and what can open up when you stop overthinking and start making.

 In this episode

🔧 Resources & Links

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Hosted and produced by Shayla Strapps and Kate Offer

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 judicial stress and wellbeing, including her role in the National Judicial Stress and Wellbeing Study.

In this episode, Carly shares what the data actually tells us about stress in the legal profession and why judicial officers, despite deep job satisfaction and commitment, experience alarmingly high levels of burnout and secondary trauma. Carly explains why judges aren’t ‘above’ stress, why lower courts are under the greatest pressure and how systemic injustice itself becomes a source of psychological harm.

The conversation also explores moral injury, intentional hope, and what it really takes to build a sustainable legal career inside an imperfect system. Rather than focusing solely on individual resilience, Carly makes a compelling case for systemic change  and for leaders being willing to speak honestly about the human cost of legal work.

This is a thoughtful, rigorous discussion about law, justice, and what it means to stay human while working inside systems that are often broken.

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Hosted and produced by Shayla Strapps and Kate Offer

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 journey from law school to top-tier firms, through strategy and innovation roles, and into the uncertain, exhilarating world of startups. We talk about leaving law, redesigning work, and why legal skills like problem-solving, clarity of thinking and working under pressure can be powerful assets far beyond the profession.

This is a conversation about career reinvention, calculated risk, and the courage to follow what genuinely interests you—even when the path isn’t obvious. For lawyers questioning the traditional trajectory, professionals craving career freedom, or anyone wondering whether meaningful work can look radically different from what they were taught to expect, this episode offers both inspiration and permission.

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 packed up their lives and travelled through 11 countries — all while she reduced her one-to-one workload and experimented with working just 20 hours across an entire year. In this conversation, Kelly unpacks what redesigning work actually looks like in practice, from delegation and community-led business models to letting go of perfection and the myth of indispensability.

Together, they explore career freedom, the courage to tolerate discomfort, and why bold change rarely comes from having a perfect plan — but often starts with simply naming what you want and beginning.

This episode is for anyone questioning traditional definitions of success, feeling the early signs of burnout, or wondering whether there might be another way to work, live, and lead.

In this episode, we discuss:

More about Kelly Irving

Connect with Kelly at www.kellyirving.com or www.expertauthor.community

Follow on LinkedIn and Instagram. 

Nail your best book idea with the Book Canvas here.

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Hosted and produced by Shayla Strapps and Kate Offer

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 stuck when it matters most.

From intuition and values to analysis paralysis and permission, this conversation reframes decision making as a skill you can build, not a personality trait you either have or don’t.

In this episode

More about Bethan Winn

https://www.linkedin.com/in/bethanwinn/

https://www.instagram.com/bethan_winn_critical_thinking/

https://www.facebook.com/bethanwinn.com.au/

The book is available www.bethanwinn.com.au/shop or on Amazon and soon from any good bookshop 

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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 outside, she was capable, calm, and deeply competent. Inside, she was running on adrenaline, guilt, and a relentless sense of responsibility, until her body finally said no.

What followed was not a neat recovery story, but a profound reckoning with rest, identity, and the cost of always being the strong one.

This is a powerful conversation about burnout in caring professions, why capable people often miss the warning signs, and what real recovery actually looks like when you stop trying to outpace yourself.

In this episode

This conversation explores burnout, rest and recovery in medicine, but the themes will resonate with anyone in law, healthcare, leadership, or any role where being capable has become part of your identity.

Connect with Emily:

 Whole Hearted Medicine

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Hosted and produced by Shayla Strapps and Kate Offer

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 our sense of belonging. Together they explore why external success never fixes the internal narrative, how perfectionism and overworking keep the cycle alive, and what it really takes to rewrite the story that keeps so many brilliant people stuck.

From self-worth to self-confidence to the “trilogy of selves,” this conversation goes deep into the psychology, the patterns, and the practical tools that help people move beyond self-doubt and into grounded, evidence-based confidence. 

If you’ve ever found yourself minimising your achievements, waiting to be found out, or discounting every win… this episode will feel like someone finally turned the lights on.

In this episode

Resources:

Buy the book: https://amzn.to/48yQYSP 

Clance Imposter Scale test - https://paulineroseclance.com/pdf/IPTestandscoring.pdf

Connect with Alison Shamir:

Linkedin - https://au.linkedin.com/in/alison-shamir-67440b17

Instagram - https://www.instagram.com/alisonshamir/

Websites - https://alisonshamir.com/ 

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Hosted and produced by Shayla Strapps and Kate Offer