Outlaws Podcast: Embracing Career Freedom

Thinking about a career change or leaving corporate? In this Season 2 recap, Shayla and Kate share the biggest lessons from a season of bold career pivots, burnout wake-up calls and people redesigning work on their own terms.

What happens when you realise the career you worked so hard for isn’t the one you want? Rob Marsala went from Perth lawyer to Hollywood talent manager—starting over in the mailroom at 26. This is a story about risk, reinvention, and why you shouldn’t stay in a job just for the money.

Are you actually not ready, or just overthinking your career change? In this episode, Shayla and Kate sit down with career counsellor Lois Keay-Smith to unpack readiness and career change, procrasti-learning, and why action creates clarity. If you’ve been waiting to feel ready, this one might gently challenge that idea.

In this Outlaw Brary episode, we unpack Sahil Bloom’s Five Pillars of Wealth and explore what it really means to redefine success beyond money. If you’ve built financial success but feel time-poor, stretched or quietly unsatisfied, this conversation challenges the scoreboard you’ve been using.

What if your side hustle isn’t meant to replace your job, but to expand your life? In this Outlaws After Dark episode, Kate and Shayla talk with lawyer and creator Sandrine Alexandre-Hughes about building a creative side hustle while working full time. Sandrine shares what she learned about the creative process, why starting a side hustle without quitting your job can open unexpected doors, and how making something for meaning, not money, changed how she sees her career.

In this episode of Outlaws, we speak with Michael Kingsbury, a former M&A lawyer who left corporate law to co-found Uluu, a climate tech startup creating seaweed-based alternatives to plastic. Michael shares how curiosity, transferable legal skills and a willingness to de-risk career decisions led him from law to climate entrepreneurship. This conversation explores leaving law, redesigning work, and building a career aligned with impact—without having all the answers upfront.

Making big decisions shouldn’t feel like endless overthinking, but for many professionals it does. In this episode, Shayla and Kate are joined by critical thinking expert Bethan Wynne to unpack why decision making feels so hard, how intuition and values actually work, and why the goal isn’t to make the perfect choice but to make the decision good. You’ll walk away with practical tools to move forward with confidence, without waiting for certainty or permission.

Why do the most capable people feel like frauds? In this episode, we sit down with author Alison Shamir to break down the real psychology of imposter syndrome, why it thrives in high-achieving professions, and how your childhood origin story quietly shapes your confidence at work. Alison shares practical tools for rewriting the internal narrative, breaking self-sabotaging cycles, and building evidence-based confidence that finally feels real.

Feeling stuck in your job or life? You’re not alone. In this episode, Shayla and Kate break down the real reasons people get stuck and share practical, realistic ways to start moving again. From finding time to think, to navigating golden handcuffs, rebuilding confidence, challenging the sunk cost fallacy, and figuring out what you actually need, they offer small, doable steps to help you get unstuck without blowing up your life.

What really happens when you step away from work for a while? Scientist, artist and communicator Kate Cranney joins Shayla and Kate to talk about her eight-month career break, from cycling through Europe to hiking Patagonia, and how living with less gave her more clarity, creativity and courage. A practical look at how pressing pause can sometimes move you forward.

In this special season finale, we look back on the conversations, quotes, and surprises that shaped our first season. From tiny experiments and side hustles to the Backwards Budget and Outlawbrary favourites like 4,000 Weeks and Tiny Experiments, we reflect on the moments that resonated most with our listeners and with us. Along the way we revisit guest stories that pushed us to rethink what career pivots and career freedom really look like, from leaving law to breathwork, sabbaticals, and sleep science. We share the quotes that stuck, the themes that kept coming up, and the laughter that kept us going - including Kate’s instant classic quote, “discomfort is uncomfortable,” which might just end up on a mug. It’s a chance to pause, celebrate, and take stock of how far we’ve come in 20 weeks of honest conversations about career change, career freedom, and work-life balance. And it’s also a preview of what’s coming in Season 2, from tackling imposter syndrome to decision-making to Outlaws going international.

Alicia Snijders spent eight years climbing the corporate law ladder, chasing titles and pay rises, until burnout and trauma forced her to stop. In this honest conversation, Alicia shares how leaving law and discovering breathwork helped her recover, rebuild her health, and find a new path. We talk burnout recovery, identity loss, small steps toward change, and why listening to your body matters long before crisis hits.

In this episode of Outlaws, Shayla and Kate kick off a new series on side hustles with a story that’s anything but ordinary. Their guest, lawyer Katie Sierakowski, spends her weekdays in the courtroom and her weekends running a cattle business with her family. Katie shows how the best side hustle ideas often start with joy, not money. If you’re looking for side hustle ideas, craving more creativity, or wondering how others fit passion projects into a busy life, this episode is packed with inspiration and real talk.