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Outlaws Podcast: Embracing Career Freedom

Outlaws Podcast: Embracing Career Freedom

By: Shayla Strapps & Kate Offer | Outlaws Podcast
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Career change, career pivot, career freedom, work life balance — if you’re craving any of these, Outlaws is the podcast for you. Hosted by Shayla Strapps and Kate Offer, two out[of]laws who walked away from traditional legal careers, this show is for professionals who look successful on paper but feel stuck inside. Each episode explores bold career pivots, honest stories of uncertainty, and practical tools for rewriting the rules of work and life. Whether you’re questioning your job, dreaming of more freedom, better work life balance, or navigating a big transition, Outlaws offers real talk for people ready to redefine success on their own terms. Subscribe now and start your own Outlaw journey. 📬 Get updates: www.outlawspodcast.com 📘 Join the Facebook Group: Outlaws Podcast Community 📸 Follow on Instagram: @the.outlaws.podcast 💼 Connect on LinkedIn: Outlaws PodcastCopyright 2025 All rights reserved. Career Success Economics
Episodes
  • When a Side Gig Becomes a Movement: Career Change, Passion, and Mental Health
    Aug 17 2025

    What happens when a casual side gig turns into a global movement for mental health?

    In this episode, Shayla and Kate sit down with Nick Hudson, engineer-turned-entrepreneur and founder of The Push-Up Challenge. What began as friendly banter at the surf club became one of Australia’s biggest mental fitness events, raising over $50 million for mental health and connecting hundreds of thousands of people.

    Nick shares how open-heart surgery, a battle with depression, and the itch to create something meaningful pushed him toward a bold career change. What started as a side gig became his passion, proof that following a spark can change not just your own life but the lives of many.

    From engineering rules to outlaw moves, Nick talks about:

    – Why innovation is so hard inside traditional careers – The leap from side hustle to full-time mission – “Mental health by stealth” and how a push-up can start a conversation – Taking risks, funding your dream, and failing hard (in the best way) – The tension between being sensible and going all in when you follow your passion

    Whether you’re contemplating a career pivot, building a side gig, or wrestling with your own mental health journey, this episode is packed with real talk, risk, and resilience.

    In this episode: – How a casual push-up challenge grew into a global event – Nick’s story of depression, open-heart surgery, and recovery – The courage to walk away from a safe career in engineering – Why side gigs can scratch the creative itch your career can’t – Practical advice on risk, failure, and building something that lasts

    This episode is for you if: – You’re dreaming of a career change but stuck in the “what if” loop – You’ve got a side gig that lights you up more than your day job – You want to know how to follow your passion without burning it all down – You’re interested in practical, hopeful ways to engage with mental health

    🔧 Resources & Links 🌐 Learn more about The Push-Up Challenge 📩 Subscribe to the Outlaws newsletter for updates and extras

    ❤️ If you loved this episode… Share it with a friend who’s sitting on a “one day” idea. Rate and review us on Apple Podcasts or Spotify — it helps more Outlaws find us!

    🔗 Connect & Explore Hosted and produced by: Shayla Strapps and Kate Offer

    Website: www.outlawspodcast.com Email: contact@outlawspodcast.com

    💬 Join the conversation: 📘 Facebook Group: Outlaws Podcast Community 💼 LinkedIn

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    44 mins
  • Outlawbrary #3; How do we know how to make good decisions? Values based decision making with Greta Bradman
    Aug 10 2025

    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 right call, this episode might just help.

    In this third Outlawbrary edition, Shayla and Kate dive into Greta Bradman’s inspiring and practical book What Matters to You — exploring the big question: how do we know how to make good decisions? Greta is a psychologist, a four-time number-one classical singer, and someone who knows how powerful values based decision making can be in creating a life that actually fits you.

    Through honesty, humour, and real-life examples, Shayla and Kate unpack:

    – How to recognise when “shoulds” are steering your choices – Why threat-based values can hijack your decision making without you noticing – The difference between chasing perfection and making progress – How imposter syndrome can keep you from making values aligned choices – Practical steps to bring your values into every decision you make

    This isn’t just a book review. It’s a conversation about clarity — identifying your true values, spotting when fear is running the show, and building the confidence to make decisions you won’t regret.

    In this episode: – Shayla’s battle with perfectionism while learning French – Kate’s reflections on ADHD, avoidance, and imposter syndrome – The pull between comfort and growth in decision making – Why knowing both your core values and threat-based values is a game changer – How to put values based decision making into practice every day

    This episode is for you if: – You’ve ever wondered how do we know how to make good decisions? – You want tools for more confident, intentional decision making – You’re tired of letting fear or perfectionism dictate your path – You’re ready to make values based decisions that feel right for you

    🔧 Resources & links 📘 What Matters to You by Greta Bradman – add it to your Outlawbrary

    ❤️ If you loved this episode... Share it with someone who’s been second-guessing their choices. Rate and review us on Apple Podcasts or Spotify – it helps more Outlaws find us.

    🎧 Find out more 🌐 Website: www.outlawspodcast.com

    🔗 Connect with us Instagram: @the.outlaws.podcast Facebook Group: Outlaws Podcast Community LinkedIn: Outlaws Podcast Email: contact@outlawspodcast.com

    📩 Sign up for our newsletter for more tools and real talk

    🎧 Hosted by Shayla Strapps and Kate Offer 🎙 Produced by the Outlaws Podcast

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    38 mins
  • Unlocking Transferable Skills for Meaningful Career Change with Anna Black
    Aug 3 2025

    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 and Kate invite career counsellor Anna Black to discuss transferable skills and how to identify the ones that truly resonate with you. We're not just talking about what you're good at; we're exploring what you actually want to do - and spoiler - they are probably two different things!

    Together, they unpack the real reasons changing careers feels daunting, how to get unstuck in your career pivot, and why your next step doesn’t have to mean starting over.

    • From existential crises to actionable steps, they cover important insights:
    • Why being good at something doesn’t mean you should keep doing it
    • How to spot your burnout skills (and why people keep asking you to use them)
    • The role of transferable skills in a career pivot and strategies to pinpoint the right ones
    • What to do when your job looks great on paper but feels all wrong
    • How to find the common thread between what you’ve done and what you genuinely want to pursue.

    If you’ve ever stared at your resume and thought, “I can do all this, I just don’t want to anymore,” this episode is designed for you.

    In this conversation:

    • Anna’s journey from geophysics to career counselling
    • What your past jobs can reveal about your future direction
    • Why it can be difficult to see your own value — and how to change that
    • The surprising way career clarity often starts (hint: it's not Seek)
    • How to reconnect with what energises you

    This episode is perfect if you're stuck in a job that doesn't feel right but are unsure of your path forward, or if you’re craving a career change, a pivot, or even just a redefined work-life balance.

    🔧 Resources & Links 💬 Connect with Anna: https://www.strategiccc.com.au/ 📩 Want updates and tips? Subscribe to our newsletter for tools, stories, and outlaw encouragement.

    ❤️ If you loved this episode, share it with someone questioning their career path — they're not alone! Rate and review us on Apple Podcasts or Spotify to help more Outlaws find us.

    Find out more 🔗 Website: www.outlawspodcast.com

    📬 Email us: Outlaws Podcast Community 💼 LinkedIn: Outlaws Podcast

    Hosted and produced by: Shayla Strapps and Kate Offer

    🎧 Hosted on Podbean

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    33 mins
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