Outlaws Podcast: Embracing Career Freedom

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

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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:

What career freedom really means (and what it doesn’t)

Redesigning work to reduce burnout and protect energy

Why working on your business matters more than working in it

Delegation, community, and letting others step up

Family travel as a catalyst for perspective and change

The power of intention, discomfort, and starting before you feel ready

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
– Why most professionals were taught how to analyse, not how to decide
– The myth of the “good decision” and why the real work starts after you choose
– What’s really happening when you feel stuck between two good options
– Gut instinct, what it is, what it isn’t, and why it matters even in rational professions
– How overthinking is often a sign of fear, not lack of intelligence
– “Nibble rather than scoff”, making big decisions through small, reversible steps
– A practical decision-making framework built around permission, values, data, noise, and testing
– Why values sit underneath every decision, whether you name them or not
– How to reflect on decisions without self-blame when things don’t go to plan
– Creating space to think in a noisy, fast-moving world

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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