Outlaws Podcast: Embracing Career Freedom

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.

In this episode
– 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...
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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

Building a side hustle while working full time, without a grand plan or exit strategy

Why Sandrine never saw herself as creative, and how the creative process surprised her

The reality of starting a creative side hustle from scratch, sketches, designers, manufacturing, and learning as you go

How legal training both helped and hindered her ability to create

Why not all side hustles are meant to become businesses, and why that’s okay

Marketing, visibility, and the parts of a side hustle that are far less glamorous

Why boredom, rest, and stepping away often unlock the best ideas

Practical advice for starting a side hustle without quitting your job, including one small first step

🔧 Resources & Links

Team Together Online, Sandrine’s company focused on healthier online lives

All the Likes, a card game teaching online safety through play

Smoke, Mirrors and Filters, a conversation card game about digital habits

Australia’s eSafety Commissioner, online safety resources for families

If you loved this episode...
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Website: www.outlawspodcast.com

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Email: [email protected]

Hosted and produced by Shayla Strapps and Kate Offer