Outlaws Podcast: Embracing Career Freedom
Episodes
Ditch the Shoulds: The Biggest Lessons from Season 2
05 Apr 2026
Contributed by Lukas
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 Seas...
Mattering Matters: Rethinking Burnout, Success and Connection
29 Mar 2026
Contributed by Lukas
In this Outlawbrary episode, Kate and Shayla discuss Mattering: The Secret to Building a Life of Deep Purpose and Connection by Jennifer Breheny Walla...
Leaving Law for Hollywood
22 Mar 2026
Contributed by Lukas
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 traditio...
From Global Finance to Somatic Therapist: Reinventing Success
15 Mar 2026
Contributed by Lukas
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 ye...
Are You Actually Not Ready, Or Just Overthinking Your Career Change?
08 Mar 2026
Contributed by Lukas
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 block...
From Litigation to Legal Tech: How Sam Flynn Built Josef
28 Feb 2026
Contributed by Lukas
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 l...
Outlawbrary: Stop Measuring Your Life by Money
22 Feb 2026
Contributed by Lukas
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 financia...
Truth Over Career, When Speaking Up Is the Outlaw Move
15 Feb 2026
Contributed by Lukas
What happens when telling the truth could cost you your career? In this Outlaws Diary episode, Kate and Shayla sit down with Rabia Siddique, internati...
Stop thinking, Start making, How a side hustle awakens creativity
08 Feb 2026
Contributed by Lukas
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 joi...
Leaving Law to Understand It: How systems affect wellbeing
01 Feb 2026
Contributed by Lukas
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 Aus...
From M&A Lawyer to Biotech Startup Founder: Michael Kingsbury on Uluu, Seaweed and Reinventing Your Career
25 Jan 2026
Contributed by Lukas
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 climat...
Designing Freedom: How Kelly Irving Rebuilt Her Business to Work 20 Hours a Year (and Travel the World)
18 Jan 2026
Contributed by Lukas
What if career freedom isn’t about walking away from work altogether, but about consciously redesigning how you work? In this Outlaws Escapes episod...
How to Make Big Decisions Without Overthinking with Bethan Winn
11 Jan 2026
Contributed by Lukas
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 overth...
Burnout, Rest and Recovery: A Doctor’s Story
04 Jan 2026
Contributed by Lukas
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 wh...
Imposter Syndrome - what it is, why it shows up and how to break free - with Alison Shamir
14 Dec 2025
Contributed by Lukas
In this episode, Kate and Shayla sit down with author and imposter syndrome expert Alison Shamir to unpack one of the most universal, misunderstood ex...
The Voices in Your Head Are Lying to You: Conquer Your Imposter Syndrome (feat. Alison Shamir)
07 Dec 2025
Contributed by Lukas
What if that familiar “I’m about to be found out” feeling isn’t the truth… but a story your brain has rehearsed for years? In this Outlawbra...
Getting Unstuck: What to do when you feel trapped in your own life or career
30 Nov 2025
Contributed by Lukas
What happens when your life looks perfectly fine on paper, but you're quietly trapped in a life or career that no longer fits? This episode began with...
How to Leave Law for Writing: Emily Tsokos Purtill’s Leap Into Fiction
23 Nov 2025
Contributed by Lukas
What happens when a lawyer turned author finally stops waiting for the “right time” and writes the story she’s been carrying for decades? In thi...
Outlaw Escapes: Taking a Career Break and Living With Less: Kate Cranney
16 Nov 2025
Contributed by Lukas
What if taking time off wasn’t a luxury, but a smart, sustainable part of your career? In this episode of Outlaws Escapes, Shayla and Kate chat with...
From Burnout to Viral: How One Lawyer Used Content to Call Out Corporate Life: Henry Nelson Case
09 Nov 2025
Contributed by Lukas
What happens when a lawyer calls out the legal and corporate world for what it really is - often unhealthy, unsustainable, and quietly breaking people...
Career Change, Career Freedom, and Work-Life Balance - what we've learnt so far
28 Sep 2025
Contributed by Lukas
20 episodes. Countless conversations. One big Outlaw experiment. In this special wrap-up episode, hosts Shayla Strapps and Kate Offer look back on Sea...
How to Get Better Sleep: Why Rest Is the Most Rebellious Act. With Psychologist Alicia Visser
21 Sep 2025
Contributed by Lukas
Sleep isn’t wasted time. It’s the secret weapon for clarity, creativity, resilience - and not being permanently cranky. And if you’re not gettin...
Learning to Breathe: How Burnout Recovery Led to Leaving Law
14 Sep 2025
Contributed by Lukas
Breathwork. Can sounds a bit woo woo, right? Even Alicia thought so, until it became the one thing that helped her crawl out of burnout and rebuild h...
You don’t need a 5 year plan. You need to experiment. Outlawbrary #4 | Tiny Experiments byAnne-Laure Le Cunff
07 Sep 2025
Contributed by Lukas
What if you could learn how to stop chasing goals and instead start running tiny experiments? In this Outlawbrary episode, Shayla and ...
Side Hustle Ideas: From Courtrooms to Cattle with Katie Sierakowski
31 Aug 2025
Contributed by Lukas
What if your “side gig” was more than just extra cash, what if it was your way out, or your way to more joy and fulfillment? In this episode of Ou...
How to Live Overseas for a Year and Make Career Break Travel Possible: Outlaw Escapes
24 Aug 2025
Contributed by Lukas
What if taking a year to live overseas wasn’t a fantasy, but a plan you could actually pull off? In the first episode of our new semi regular ep...
When a Side Hustle Becomes a Movement: Career Change, Passion, and Mental Health
17 Aug 2025
Contributed by Lukas
What happens when a casual side hustle turns into a global movement for mental health? In this episode, Shayla and Kate sit down with Nick Hudson, eng...
Outlawbrary #3; How do we know how to make good decisions? Values based decision making with Greta Bradman
10 Aug 2025
Contributed by Lukas
Need to make a decision but not sure how to start? If you’ve ever felt stuck, second-guessed yourself, or wondered whether you’re making the rig...
Unlocking Transferable Skills for Meaningful Career Change with Anna Black
03 Aug 2025
Contributed by Lukas
What if the skills that made you successful are the same ones making you miserable? In this episode focused on career change and career pivots, Shayla...
Navigating Career Change Uncertainty: Sitting with Discomfort
27 Jul 2025
Contributed by Lukas
What if sitting in the discomfort of "I don’t know" was the first real step in your career change? In this episode, Shayla and Kate delve into...
From Army to Outlaw: Leaving Certainty for Purpose After 20 Years in Uniform
20 Jul 2025
Contributed by Lukas
What happens when the job you thought you'd stay in forever — the identity you've carried since age 17 — stops feeling right? In this episode, Sha...
Burnout Prevention & Sustainable Work: How to Make Work Work with Sally Clarke
12 Jul 2025
Contributed by Lukas
In this episode, Shayla and Kate sit down with global burnout expert Sally Clarke to discuss burnout prevention and how to achieve sustainable work-li...
Outlawbrary #2: How Outlaws Stop People-Pleasing and Overthinking: The Let Them Theory by Mel Robbins
06 Jul 2025
Contributed by Lukas
What if the most rebellious thing you could do wasn’t to break the rules — but to stop worrying what everyone else thinks? In this episode, Shayla...
From Lawyer to Author: How Sulari Gentill Left Law and Found Her True Calling
28 Jun 2025
Contributed by Lukas
Ever feel like there’s something you’ve forgotten to do — but you can’t quite name it? For Sulari Gentill, leaving the law and picking up a pe...
What Does Success Really Mean? Start With How You Spend Your Time
22 Jun 2025
Contributed by Lukas
What if success wasn’t about ticking boxes, climbing ladders, or polishing your LinkedIn profile — but about something quieter, deeper, and more y...
Budgeting for a Life You Love: How to Use the Backwards Budget to Change Your Life and Career
15 Jun 2025
Contributed by Lukas
💡 What if your budget started with the life you want, not the one you’re stuck in? In this episode, Shayla and Kate unpack a deceptively simple b...
Outlawbrary #1: 4000 Weeks by Oliver Burkeman, Time Anxiety, and the Freedom of Letting Go
08 Jun 2025
Contributed by Lukas
In this episode, Shayla and Kate crack open Oliver Burkeman’s powerful book 4,000 Weeks — and let’s be clear, it’s not about to-do lists. The...
From Litigation to Legal Tech and Author: Reinventing Success with Fiona McLay
31 May 2025
Contributed by Lukas
In this Outlaws episode, we kick off our first Outlaw Diaries as Shayla interviews Fiona McLay, a former litigation lawyer who made a bold career chan...
The Hidden Rules of Success: What We’re Unlearning (And why you might want to, too)
24 May 2025
Contributed by Lukas
In this episode of Outlaws — the career change podcast for high achievers ready to rewrite the rules — Shayla and Kate pull back the curtain on th...
When Success Isn’t Enough: Career Change, Burnout, and Becoming an Outlaw
15 May 2025
Contributed by Lukas
You followed the rules. You ticked all the boxes. You built the “successful” career. So… why does it still feel like something’s missing, or t...
Trailer Outlaws Podcast - Unlearning the rules of work and life
12 May 2025
Contributed by Lukas
Outlaws is the podcast for professionals who look successful on paper but feel stuck inside. Hosted by two (out)laws who walked away from traditional ...