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

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Hosted and produced by Shayla Strapps and Kate Offer

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.

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Hosted and produced by Shayla Strapps and Kate Offer

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.

• 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

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Hosted and produced by Shayla Strapps and Kate Offer

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/

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Hosted and produced by Shayla Strapps and Kate Offer

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 Search “MOOC + [your topic]” to explore free or low-cost university courses

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Hosted and produced by Shayla Strapps and Kate Offer

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. If you’ve wondered what else you could do with a law degree. If you’ve felt the weight of prestige pressing in.

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 – The hostage crisis in Iraq and what happened behind closed doors – The discrimination case that challenged the UK government and military – Why injustice by those you trust can cut deeper than trauma itself – What whistleblowing really costs and why it matters – How to practise ethical, values-based leadership inside rigid systems – The myth that success requires perfection and conformity – Why you don’t have to be in a war zone to feel “held hostage” by your career

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 Rabia’s book: Equal Justice Connect with Rabia via her website and social media

If you loved this episode... Share it with a friend who’s wanting a change (or just needs permission to do the thing!).

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Connect with us Instagram: @the.outlaws.podcast - https://www.instagram.com/the.outlaws.podcast Facebook Group: Outlaws Podcast Community - https://www.facebook.com/groups/the.outlaws.podcast LinkedIn: Outlaws Podcast - https://www.linkedin.com/company/106681587 Email: contact@outlawspodcast.com

Hosted and produced by Shayla Strapps and Kate Offer