Outlaws Podcast: Embracing Career Freedom

From M&A Lawyer to Biotech Startup Founder: Michael Kingsbury on Uluu, Seaweed and Reinventing Your Career

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.

Designing Freedom: How Kelly Irving Rebuilt Her Business to Work 20 Hours a Year (& Travel the World!)

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
 

How to Make Big Decisions Without Overthinking with Bethan Winn

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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Burnout, Rest and Recovery: A Doctor’s Story

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 whose own experience of burnout stopped her in her tracks and ultimately reshaped her entire understanding of care, success, and sustainability.
Emily spent 15 years in medicine, building a thriving practice and supporting others through some of their most vulnerable moments. From the outside, she was capable, calm, and deeply competent. Inside, she was running on adrenaline, guilt, and a relentless sense of responsibility, until her body finally said no.
What followed was not a neat recovery story, but a profound reckoning with rest, identity, and the cost of always being the strong one.
This is a powerful conversation about burnout in caring professions, why capable people often miss the warning signs, and what real recovery actually looks like when you stop trying to outpace yourself.
In this episode
Emily’s path into medicine and why general practice is as much about life as it is about illness
The slow, invisible build-up to burnout and why she didn’t see it coming
The moment everything stopped, and why her body became the final boundary
The difference between altruism and self-sacrifice, and why self-awareness matters
How perfectionism and identity can trap high achievers in unsustainable patterns
Why rest is essential, not indulgent, especially in helping professions
What changed when Emily redefined success around inner capacity, not output
How Whole Hearted Medicine was born, and why practitioner wellbeing is not optional
This conversation explores burnout, rest and recovery in medicine, but the themes will resonate with anyone in law, healthcare, leadership, or any role where being capable has become part of your identity.
Connect with Emily:
 Whole Hearted MedicineW: www.dremilyamos.comIG: @dremilyamos 
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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Hosted and produced by Shayla Strapps and Kate Offer

Imposter Syndrome - what it is, why it shows up and how to break free - with Alison Shamir

In this episode, Kate and Shayla sit down with author and imposter syndrome expert Alison Shamir to unpack one of the most universal, misunderstood experiences in modern work: that persistent belief that you don’t deserve your success.
Alison breaks down what imposter syndrome actually is, why high achievers are especially prone to it, and how those old origin stories from childhood quietly shape our confidence, our careers, and our sense of belonging. Together they explore why external success never fixes the internal narrative, how perfectionism and overworking keep the cycle alive, and what it really takes to rewrite the story that keeps so many brilliant people stuck.
From self-worth to self-confidence to the “trilogy of selves,” this conversation goes deep into the psychology, the patterns, and the practical tools that help people move beyond self-doubt and into grounded, evidence-based confidence. 
If you’ve ever found yourself minimising your achievements, waiting to be found out, or discounting every win… this episode will feel like someone finally turned the lights on.
In this episode
What imposter syndrome is
Why competence isn’t the antidote and why confidence alone can’t save you
The origin story: how early experiences shape adult self-belief
The difference between self-worth, self-esteem, and self-confidence
Why high-performing professionals mask their doubt so well
The imposter cycles and self-sabotaging patterns Alison sees in her coaching
How to build an evidence bank that your brain will actually believe
The surprising role of authenticity and psychological safety at work
What it takes to rewrite the internal narrative… and why it changes everything
Resources:
Buy the book: https://amzn.to/48yQYSP 
Clance Imposter Scale test - https://paulineroseclance.com/pdf/IPTestandscoring.pdf
Connect with Alison Shamir:
Linkedin - https://au.linkedin.com/in/alison-shamir-67440b17
Instagram - https://www.instagram.com/alisonshamir/
Websites - https://alisonshamir.com/ 
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 usInstagram: @the.outlaws.podcast - https://www.instagram.com/the.outlaws.podcastFacebook Group: Outlaws Podcast Community - https://www.facebook.com/groups/the.outlaws.podcastLinkedIn: Outlaws Podcast - https://www.linkedin.com/company/106681587Email: contact@outlawspodcast.com
Hosted and produced by Shayla Strapps and Kate Offer

The Voices in Your Head Are Lying to You: Conquer Your Imposter Syndrome (feat. Alison Shamir)

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 Outlawbrary episode, Shayla and Kate dive into Conquer Your Imposter by confidence and imposter syndrome expert Alison Shamir. It’s a book packed with research-backed insights, personal stories, and practical tools for anyone who’s ever questioned their capability, underestimated their achievements, or secretly worried they’re “winging it.”
They unpack the history of imposter syndrome, the surprising statistics behind it, the ADHD connection, the trilogy of selves (self-confidence, self-esteem and self-worth), and the five imposter syndrome types that show up in high-achievers. They also share their test results from the Clance Imposter Phenomenon Scale and reveal what they learned about their own patterns of self-doubt.
Then, in a special guest appearance, Alison Shamir joins the conversation to talk about why she wrote Conquer Your Imposter, how her personal story shaped the book, and what she hopes readers will take away from it.
If you’ve ever wondered why capable people feel like frauds, or you’re curious about how imposter syndrome shows up in your own life, this episode offers clarity, compassion and a heap of practical insight.
In this episode
– What Conquer Your Imposter teaches us about understanding imposter syndrome – Why Shayla and Kate scored higher than expected on the imposter syndrome test – The overlap between ADHD and imposter syndrome – The five imposter syndrome types and how to spot your dominant pattern – How perfectionism, identity and self-talk keep imposter syndrome alive – Alison’s personal journey and why she decided to write the book – The biggest myths about imposter syndrome and what actually helps
Resources:
Buy the book: https://amzn.to/48yQYSP 
Clance Imposter Scale test - https://paulineroseclance.com/pdf/IPTestandscoring.pdf
Connect with Alison Shamir:
Linkedin - https://au.linkedin.com/in/alison-shamir-67440b17
Instagram - https://www.instagram.com/alisonshamir/
Websites - https://alisonshamir.com/ 
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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Hosted and produced by Shayla Strapps and Kate Offer

Getting Unstuck: What to do when you feel trapped in your own life or career

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 an email from a listener. She is accomplished, respected, highly capable, and yet she feels like she has no room to breathe, no time to think, and no idea how to get unstuck. She told us she feels weighed down by the golden handcuffs, unsure whether she can take a step backward in seniority, afraid of starting again, worried about losing flexibility, and pulled between gratitude for what she has and a growing sense that something needs to change.
These feelings are more common than most people realise. So today, we wanted to talk about what being stuck really looks like, why it happens to smart people with good careers, and how you can begin to loosen the grip without blowing up your life.
We unpack the emotional, financial, practical and psychological forces that keep people exactly where they are. From the sunk cost fallacy to confidence dips, cognitive load, the fear of making a wrong move, the weight of responsibility, and the false belief that flexibility and fulfilling work cannot coexist, this episode goes deep into the real barriers that make change so hard.
And then we talk through ideas and small, practical moves to help you start shifting things. Because getting unstuck is rarely one big leap. It is usually small, intentional changes that slowly make space for clarity, courage and choice.
Whether you are feeling trapped in your job, sitting in the discomfort of "fine", craving more fulfilment, or just needing permission to question the rules you have internalised, this conversation will meet you where you are and offer gentle ways forward.
In this episode
The reality of feeling stuck in your career
Why cognitive load makes it impossible to plan a way out
Finding micro-moments of time when life feels full
The sunk cost fallacy and why your brain fights against change
Golden handcuffs and the fear of going backwards
Using the Backwards Budget to understand what you actually need
Rebuilding confidence after a break or big life shift
The devil you know and the myth that change is always riskier
How to experiment, test ideas and make decisions with less fear
Why small shifts are often more powerful than dramatic ones
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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Hosted and produced by Shayla Strapps

How to Leave Law for Writing: Emily Tsokos Purtill’s Leap Into Fiction

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 this episode, Shayla and Kate sit down with Emily Tsokos Purtill, former commercial lawyer and newly crowned award-winning novelist, whose debut book Matia just won the 2025 WA Premier’s Book Award for an Emerging Writer.
Emily’s story captures everything we talk about on Outlaws, the tension between safety and creativity, a career that looks great on paper but doesn’t fit anymore, and the quiet bravery of making space for the thing you’ve always wanted to do.
If you’ve ever wondered how to leave law for writing, or whether it’s too late to follow that creative itch you keep ignoring, this conversation is a beautiful invitation to rethink what’s possible.
We dive into:
– How Emily went from corporate transactions to fiction – Writing scenes in the car between school pickups – Why reading like a writer changed everything – The moment a publisher said “yes” and everything clicked into place – Letting go of productivity conditioning to create freely – What rejection taught her, and why it made her work better – Money, motherhood, and making unconventional choices – The surprising skills lawyers take with them into creative careers
In this episode
– Emily’s path from commercial law to becoming a published author – How to build a writing life when time is in short supply – The power of tiny creative acts – Why your first published book might not be your first written book – How legal skills translate surprisingly well into storytelling and publishing
To enter the competition for a copy of Emily's book, please go to www.outlawspodcast.com and sign up for our newsletter.  
See more about Emily at https://www.emilytsokospurtill.com/
To buy her book https://amzn.to/44tlPyW
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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Hosted and produced by Shayla Strapps and Kate Offer

Outlaw Escapes: Taking a Career Break and Living With Less: Kate Cranney

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 Kate Cranney, a scientist, artist and communicator who pressed pause on her career for eight months to travel, hike and cycle across some of the world’s most stunning landscapes.
From Patagonia to the Alps, Kate and her partner swapped meetings for mountains and discovered what happens when you stop working and start living deliberately. Her story isn’t about quitting everything and running away. It’s about designing a life that has space for rest, adventure and curiosity, and how that can actually make your work richer, too.
In this episode – The planning and mindset behind an eight-month career break – Living with less, and why simplicity can feel freeing, not limiting – How slow, physical travel builds patience, perspective and creativity – The real value of time off: clarity, confidence and courage – What “coming back” looks like after stepping away
🔧 Resources & Links
Kate's website -- https://katecranney.com/ 
Warm Showers -- https://www.warmshowers.org/
EuroVelo is a series of cycling networks all around Europe -- https://en.eurovelo.com/
Tim Minchin's address -- https://www.youtube.com/watch?v=yoEezZD71sc&t=1s
Ken Robinson's 'Finding your element' talk. I listen to this many times a year. I love it https://www.youtube.com/watch?v=17fbxRQgMlU 
'The Gap' by Ira Glass, I love this, on the importance on putting out a body of work https://vimeo.com/85040589 and here is the full article https://gointothestory.blcklst.com/the-gap-by-ira-glass-9651a750408f?gi=655cd32905f6 
Connect with Kate Cranney on LinkedIn: https://www.linkedin.com/in/katecranney
❤️ If you loved this episode... Share it with a friend who’s overdue for a pause (or just needs permission to take one).
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Hosted and produced by Shayla Strapps and Kate Offer

From Burnout to Viral: How One Lawyer Used Content to Call Out Corporate Life: Henry Nelson Case

What happens when a lawyer calls out the legal and corporate world for what it really is - often unhealthy, unsustainable, and quietly breaking people who care?
To launch Season 2, Shayla and Kate go international with UK-based lawyer, content creator and TEDx speaker Henry Nelson Case. After years of watching toxic behaviour get rewarded and burnout get normalised, Henry decided to stop pretending everything was fine - and start saying what everyone else was thinking.
From vomiting before work to going viral online, Henry has turned his lived experience into a platform that exposes the quiet damage of corporate culture - with humour, compassion and brutal honesty. His videos have reached millions, not because they’re flashy, but because they’re true.
In this conversation, Henry, Shayla and Kate dig into why law so often rewards overwork, how younger generations are refusing to play along, and what happens when someone finally says, “this isn’t okay.”
In this episode– The invisible toll of toxic workplaces and the myth of “just toughing it out”– What burnout looks like when you’re still performing well on paper– Why we keep mistaking exhaustion for excellence– How humour can break the silence on mental health in law– What Gen Z and younger lawyers are teaching the profession about boundaries and wellbeing– Why content can shift culture faster than any policy ever will
🔧 Resources & Links🎥 Watch Henry’s TEDx talk on toxic masculinity and men’s mental health📱 Follow Henry on Instagram,  TikTok, Linkedin and Youtube for more of his corporate-law truth bombs or visit his website🗣 Join the conversation in the Outlaws Podcast Facebook group
If you loved this episode...Share it with someone who’s quietly burning out under “business as usual.”Rate and review us on Apple Podcasts or Spotify — it helps more Outlaws find us.
Find out moreWebsite: www.outlawspodcast.com
🔗 Connect & ExploreHosted and produced by: Shayla Strapps and Kate Offer
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