Outlaws Podcast: Embracing Career Freedom – Details, episodes & analysis

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Outlaws Podcast: Embracing Career Freedom

Shayla Strapps & Kate Offer | Outlaws Podcast

Business

Frequency: 1 episode/8d. Total Eps: 41

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 Podcast

Recent rankings

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Apple Podcasts

🇨🇦 Canada - careers
21/05/2026
#91
🇨🇦 Canada - careers
25/07/2025
#84

Spotify

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https://paulineroseclance.com/pdf/IPTestandscoring.pdf
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Score global : 72%

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From Army to Outlaw: Leaving Certainty for Purpose After 20 Years in Uniform

Season 1 · Episode 10

Sunday, July 20, 2025 • Duration 40:44

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, Shayla and Kate sit down with David (Dave) French, former infantry officer turned leadership coach, who spent 21 years in the Australian Army, followed by a second act in corporate consulting, and now has started his own business to follow his purpose. Dave describes a deeply personal reckoning with identity, values, and purpose - and a brave decision to walk away from stability and seniority to start over.

This is not your classic “pivot” story. It’s about responsibility, guilt, family, and the hard emotional work of letting go — and what happens when you realise you don’t want to keep climbing the ladder.

Together, they talk about:

The identity shock of leaving a long-term career
Why walking away from command roles was harder than it looked
The pressure men feel to be providers — and how that shapes career choices
How networks and connection can be two very different things
What happens when your kid’s playdate leads to your next job
The tough, transformative work Dave is now doing with incarcerated veterans

This is a story about honour, courage, and values — not in war, but in everyday life. And it’s about knowing when to stay loyal… and when to let go.

In this episode:

– Dave’s story of turning down the job he thought he wanted – Why success stopped meaning rank and started meaning alignment – How military belonging compares to the identity of lawyers – Leaving consulting after confronting a values clash — and what happened next – The power of purpose, and how it guided every step that followed

Resources & Links

📚Book - Man's Search for Meaning: Viktor E Frankel

Find more episodes: www.outlawspodcast.com 📩 Subscribe to the newsletter for updates, tools & more

If you loved this episode...

– Share it with someone questioning their own career – Rate and review us on Apple or Spotify — it helps more Outlaws find us!

Connect & Explore

🌐 Website: www.outlawspodcast.com 📸 Instagram: @the.outlaws.podcast 📘 Facebook: Outlaws Podcast Community 💼 LinkedIn: Outlaws Podcast 📬 Email: contact@outlawspodcast.com

🎙️ Hosted by Shayla Strapps and Kate Offer 🎧 Produced by Shayla Strapps 🏠 Hosted on Podbean

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Outlawbrary #2: How Outlaws Stop People-Pleasing and Overthinking: The Let Them Theory by Mel Robbins

Season 1 · Episode 8

Sunday, July 6, 2025 • Duration 35:35

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 and Kate crack open Mel Robbins’ bestselling book The Let Them Theory and explore why these two tiny words are such a potent tool for living like an Outlaw. Because Outlaws don’t build their lives by managing everyone else’s opinions — they build them from the inside out.

From family expectations to tricky work politics, they dive into how letting them think, feel, and do what they want (without you trying to control it) is actually one of the most radical ways to reclaim your time, energy, and joy.

It’s not just about ignoring people. It’s about getting very clear on what’s yours to carry - and letting the rest go.

Inside, they unpack:

- Why Let Them is the ultimate Outlaw move for stopping the exhausting job of managing everyone else’s feelings - How Let Me gives you permission to take up space, rest, fail, and chase dreams (even if no one else gets it) - Why guilt, culture and gender norms can make this shift feel “selfish” — and why that’s the very reason to do it - How letting go of control doesn’t make you a doormat — it actually clarifies where your real power lies

Whether you’re a recovering people pleaser, stuck in overthinking, or just tired of asking for permission to live the way you want, this is an episode for Outlaws ready to build life on their own terms.

In this episode

- What exactly is Mel Robbins’ Let Them Theory (and why it’s a bestseller) - Shayla and Kate on people-pleasing, perfectionism, and why this has been life-changing for them - The hidden role of gender, culture & family messages that make letting go so hard - Why professionals often think they can — and must — fix everything and why it is uncomfortable to think you can't - Practical ways to start small: one let them or let me moment at a time - Scripts for when your brain spirals: “Their comfort isn’t more important than my peace.”

This episode is for you if:

– You’re tired of spending energy on what other people think – You keep bending yourself into knots to keep everyone comfortable – You want to live more from your own values (like a true Outlaw), not from guilt or expectations – You want real stories about how this simple idea helped two professionals stop burning out

Resources & Links If you loved this episode... Find out more

From Lawyer to Author: How Sulari Gentill Left Law and Found Her True Calling

Season 1 · Episode 7

Saturday, June 28, 2025 • Duration 39:45

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 pen finally let her breathe.

In this episode of Outlaw Diaries, we talk to the incredible Sulari Gentill — a former corporate lawyer who swapped contracts for crime fiction, and found the thing she didn’t even know she was missing. From astrophysics to cow pregnancy tests to bestseller lists, her story is a beautiful, funny, and surprisingly relatable exploration of what happens when you finally listen to that quiet itch inside you.

She shares:

– Why being a lawyer never felt wrong, but never felt whole – The moment writing made her feel like she was breathing properly for the first time

– The identity crisis that comes with leaving a high-status profession – How leaving a stable, high-status profession can make you feel untethered — and why that’s part of it – Why she “corporate-lawyered” her way into a sustainable creative career (yep, you can do that)

– How her legal background (and a bit of astrophysics) helps her write brilliant mysteries

– What happened when she tried to write literary fiction (spoiler: a body showed up)

If you’ve ever dreamed about writing a novel, leaving your profession, or just finding the thing that feels like breathing — this episode is a must-listen

💡 This episode is for you if: – You’re stuck in the “shoulds” and wondering if it’s too late or too hard to start again – You’re craving a more creative life but worried it’s impractical – You’re torn between security and soul-sparking joy – You’ve ever told yourself “I can’t afford to leave” and secretly hoped someone would prove you wrong – You need permission (and a strategy) to make your leap

🔧 Resources & Links 📚 Explore Sulari Gentill’s books — including The Mystery Writer and the award-winning Crossing the Lines (due to be released in August) https://ultimopress.com.au/collections/sulari-gentill

What Does Success Really Mean? Start With How You Spend Your Time

Season 1 · Episode 6

Sunday, June 22, 2025 • Duration 34:07

What if success wasn’t about ticking boxes, climbing ladders, or polishing your LinkedIn profile — but about something quieter, deeper, and more you?

In this episode, a follow up to our very popular Backwards Budget episode, Shayla and Kate take the conversation beyond the Backwards Budget and dive into the real question underneath it all: What does success actually mean to you?

Spoiler: it’s probably not “I worked 80 hours a week and missed all the good bits.”

From French school lunches to flow states, from joyful routines to redefining ambition, this is an invitation to slow down and think about how you really want to live — and how to put that in the budget.

🎧 In this episode, we talk about: – Why your version of success might be totally different (and why that’s a good thing) – The difference between happiness and fulfillment – How daily routines, small pleasures, and deeper conversations can signal what really matters – Cultural differences in how we value time, connection, and work – The power of “flow” — and how to know when you’re in it – Practical steps for weaving more meaning into your days — without burning everything down

💥 This episode is for you if: – You’re tired of chasing someone else’s dream – You want to feel more joy, energy, and purpose in your everyday life – You’re craving space to ask bigger questions – You want to shift how you spend your time, not just how you spend your money – You’re ready to start building a life that feels like yours

🎶 Bonus inspo from the episode 📚 Flow by Mihaly Csikszentmihalyi → Penguin link 🎵 Turn! Turn! Turn! by The Byrds → Listen on YouTube

📚 2025 Personal Planning Template by Grace Clarke at (grace-clarke.com)

Budgeting for a Life You Love: How to Use the Backwards Budget to Change Your Life and Career

Season 1 · Episode 5

Sunday, June 15, 2025 • Duration 30:01

💡 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 but transformative tool: the Backwards Budget. Born out of Shayla’s own burnout and a desire to live more deliberately, this approach flips traditional financial planning on its head — starting not with income, but with the kind of life you actually want to live.

From spreadsheets to existential questions, they talk about:

– The real cost of the life you want (and how to calculate it) – Why your gut reaction to “what would you do with $70 million?” matters – The slow, doable steps toward change — even when quitting your job feels impossible – How financial clarity can give you emotional and creative freedom

🎧 Whether you're contemplating a career shift, craving more time for your family, or dreaming about becoming an author, this episode will help you turn that dream into a budget — and then a plan.

💥 In this episode – Shayla’s story of burnout and rebuilding her life from the budget up – The power of starting with what you want and working backwards – Kate’s thoughts on financial fear and practical freedom – The emotional side of money — and how budgeting can be liberating, not limiting – Why this isn’t just for rebels and risk-takers — but for anyone who wants to live with more intention

💡 This episode is for you if: – You’re constantly dreaming of quitting your job – You want more time, more freedom, or more space to breathe – You’re curious about how to start over — without starting from scratch – You’re craving real, grounded conversations about life design and money – You’ve ever said “I can’t afford to change” and wished it weren’t true

🔧 Resources & Links 🎁 Download the Backwards Budget Tool: Sign up on our website to get the spreadsheet as soon as it’s ready! 💬 Join the conversation in our Facebook Group: Share your budget stories, ask questions, or just lurk for inspo. 📩 Want updates and tips? Subscribe to our newsletter to stay in the loop.

❤️ If you loved this episode... Share it with a friend who’s always Googling “how to quit my job and not starve.” Rate and review us on Apple Podcasts or Spotify — it helps more Outlaws find us!

Outlawbrary #1: 4000 Weeks by Oliver Burkeman, Time Anxiety, and the Freedom of Letting Go

Season 1 · Episode 4

Sunday, June 8, 2025 • Duration 38:22

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.

They explore the confronting reality that 4,000 weeks is roughly all we get in a lifetime, and how that number becomes a springboard for bigger questions: What truly matters? Why do we equate our worth with productivity? And how can we let go of the pressure to do it all?

With personal stories, a healthy dose of irreverence, and some classic Outlaw-style reflection, this first Outlawbrary episode offers insights on how to rethink your relationship with time — and find more meaning by doing less.

🎧 Whether you’ve read the book or not, this one’s for anyone questioning the hustle, craving a slower life, or wondering how the heck to use their 4,000 weeks.

💥 In this episode – Why 4,000 weeks hits harder than any productivity hack – Time anxiety and the trap of “trying to do it all” – How accepting your limitations can actually set you free – Stories from Shayla and Kate on how this book shifted their thinking – The case for slowing down — and living better, not faster

💡 This episode is for you if: – You secretly feel like you're always behind – You’re craving more meaning but not sure how to get there – You’ve ever googled “how to be more productive” at 2am – You love a good book that messes with your worldview (in a good way) – You’re ready to rebel — gently — against the cult of busyness

Learn more about Oliver Burkeman and 4,000 Weeks:

https://www.oliverburkeman.com/books

Oliver's last Guardian column

🎧 Find out more 🔗 Website:

From Litigation to Legal Tech and Author: Reinventing Success with Fiona McLay

Season 1 · Episode 3

Saturday, May 31, 2025 • Duration 38:39

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 change into legal tech and authorship. Her journey shows how stepping away from the traditional legal path can lead to more balance, creativity, and a career that feels like your own.

Fiona shares candid stories about the messy middle of reinvention, the fears that come with pursuing a new vision of success, and the courage it takes to back yourself before you feel ready. Together, they explore:

The unexpected turning points in Fiona’s legal career
The messy process of career change and finding clarity and fulfilment
How coaching and community can support you when leaving litigation
Defining “enough” on your own terms
Merging legal tech, creativity, and your personal niche
Why stepping off the traditional legal script can open new possibilities

This Outlaws conversation is for anyone wondering if their current role is the right fit, standing at the edge of a big decision, or looking for an inspiring, real-world example of a successful career change story.

🎧 Press play to hear how Fiona transitioned from litigation to legal tech and author — and built a career that truly resonates with her.

🔗 Connect & Explore

Hosted by: Shayla Strapps and Kate Offer Produced by: Shayla Strapps

🌐 Website: www.outlawspodcast.com 📬 Get in touch: @the.outlaws.podcast

Facebook Group: Outlaws Podcast Community

LinkedIn: Outlaws Podcast

🎙️ Learn more about Fiona McLay

The Hidden Rules of Success: What We’re Unlearning (And why you might want to, too)

Season 1 · Episode 2

Saturday, May 24, 2025 • Duration 39:54

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 the hidden curriculum, the sneaky, unspoken rules that shape how we define success, worth, and ambition.

From career ladders you never questioned to the belief that being busy means you're important, they unpack the beliefs that ruled their lives (until they didn’t). They share five deeply ingrained “rules” they’re actively unlearning and how it’s changing the way they work, live, and measure success.

But this conversation goes deeper. They explore what happens when you realise you’ve been performing an identity that isn’t fully yours, the burnout that comes from trying to be palatable, professional, and perfect, the pressure to be “good” at everything, including being human, and the radical relief of asking: what if I just stopped?

💥 In this episode:

The myth of the ladder: Why climbing higher doesn't always mean going further
How we confuse busy with worthy (and how to stop)
The sunk cost fallacy: Why time spent doesn’t have to equal a lifetime commitment
External validation vs. internal clarity
The cost of performance: When “doing it all” means losing yourself
Why redefining success is a radical act, and a necessary one

💡 This episode is for you if:

You’re in the middle of a career transition or questioning your career path
You’ve ever felt guilty for not wanting more
You’ve internalised rules that no longer serve you
You’re tired of performing an identity just to “fit”
You’re ready to design success, and your life, on your own terms

🎧 Listen now and start unlearning the rules that were never yours to begin with.

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Outlaws Podcast: Embracing Career Freedom – Details, episodes & analysis

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Outlaws Podcast: Embracing Career Freedom – Details, episodes & analysis

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