Honest career, money and life conversations with practical tools to help high achievers design work that fits their life.
"Start before you feel ready."
Today Shayla Strapps and Kate Offer, the creators of Outlaws Podcast: Embracing Career Freedom share their story of careers podcast.
► Tell us about you and your podcast
Shayla Strapps and Kate Offer are award-winning lawyers who spent their careers meeting expectations, chasing promotions and collecting markers of conventional success. From the outside, it looked polished. Inside, it was a different story. Shayla hit full-blown burnout. Kate asked, “Is this really it?” Both realised the version of success they’d been chasing wasn’t what they wanted.
Instead of hiding those doubts, they spoke them aloud, honest, vulnerable conversations rarely heard from high-performing professionals taught to project certainty. Out of that came the Outlaws Podcast: a space to question the rules we’re taught to follow, explore new definitions of success, and share the messy middle, not just the happy ending.
Each week, they dive into career change, money, burnout, identity and designing a life that fits you, not just your résumé. They share practical tools like the Backwards Budget, and stories of bold moves and subtle shifts alike, from leaving law entirely to reshaping demanding careers into something sustainable.
Listeners are high-achieving mid life professionals, rethinking what success means for them. Ambitious but tired of the grind, they want grounded, actionable steps to create a more intentional life and work without blowing everything up. If you’ve ever thought “I can’t afford to change” but wished it weren’t true, this podcast was made for you.
► Why & how did you start this podcast?
We’ve both been big podcast listeners for years. They’ve inspired us, made us laugh, and kept us company during some of our most difficult professional moments. But when we were going through our own career turning points – burnout, identity shifts, and big questions about what we actually wanted from life – we couldn’t find exactly what we needed. Yes, we wanted inspiration, but we also wanted someone to tell the truth about how hard change can be. We wanted the kind of honest talk that doesn’t skip over the messy parts, the doubts, or the false starts. And that just wasn’t out there in the way we were looking for.
We knew we couldn’t be the only ones feeling this way. As lawyers, we’d both seen behind the curtain of high-achieving careers and knew plenty of people quietly wondering if the cost of “success” was worth it. We wanted to create a space for those conversations to happen out loud – a place where you could hear stories of people rethinking the rules, get practical tools to make change, and feel less alone in the process.
So we decided to stop waiting for the podcast we wanted to appear and just make it ourselves. In April 2025, we agreed to start, and by May 2025 we released our first episode. It took about a month from idea to launch because we work quickly and we were already clear on what it should be: real talk about the challenges of changing your life, mixed with enough practical advice to help someone take the next step.
From the start, our goal wasn’t to have the “perfect” podcast or a massive audience overnight. It was simply to start the conversation, see if it resonated, and hopefully build a community of people ready to question the old rules of work and life. The fact that listeners connected so quickly has only confirmed what we suspected - these conversations are long overdue.
► How'd you find the time and funding to do this podcast?
We release a new episode every Sunday, which means we’re always recording, editing, or planning the next one. Producing an episode takes several hours spread over the week - from shaping the conversation and recording, to editing, writing show notes, and creating the visuals and marketing materials. It’s a steady rhythm now, but in the beginning we had to figure out how to fit it in around already full lives.
The truth is, we make the time because we love it. The podcast isn’t just a side project, it’s something that lights us up, and we’ve both been intentional about designing lives that leave room for the things we care about. Outlaws Podcast is one of those things. Sometimes that means recording on weekends, or editing in the evenings, but it never feels like a chore.
We fund the podcast ourselves. Right now we spend a fairly small amount on a month on subscriptions and services - hosting, editing tools, and a few marketing platforms. We keep costs low and handle all of the production ourselves, which gives us the freedom to create exactly the kind of show we want.
Like most independent podcasters, we started with minimal equipment and a lot of enthusiasm, and built the process as we went. Now, it’s part of the fabric of our week – something we both look forward to, and a project that feels deeply aligned with the conversations we want to be having.
► What do you gain from podcasting?
Right now, we don’t have any sponsors – but we’re open to it in the future if it’s the right fit. The Outlaws Podcast is still in its early days, with just three months under our belt, but we’ve already had about 3,000 downloads and the audience is growing every week. We’re focused on building the right community first, so when we do take sponsorships, they’ll feel aligned with the conversations we’re having and the people we’re reaching.
We haven’t approached sponsors yet, so there’s no first sponsorship story to tell – just the knowledge that when we get there, we’ll be looking for partnerships that add value to our listeners rather than interrupt them.
The real gain for us so far has been personal. We love having these conversations – with each other, with our guests, and with our audience. We love the moments when someone messages to say an episode helped them take a step they’d been scared to take, or made them feel less alone in what they’re going through. Those messages are the best kind of feedback and the biggest motivation to keep going.
Podcasting has also been a learning journey. Every guest brings a new perspective, a fresh story, or a different way of looking at a familiar challenge, and we get to learn right alongside our listeners. And, on a purely selfish note, it’s just fun – a creative outlet that energises us and reminds us why these conversations matter.
Listen411.com: Lightning-fast, Cost-effective Podcast Transcription and Summarization - Crafted with Passion by Listen Notes.
► How does your podcasting process look like?
Our podcasting process is a mix of planning, flexibility, and a lot of talking things through. We use Riverside for both recording and editing, and Podbean for hosting and distribution. Most of our interviews are done online through Riverside – it gives us high-quality audio and video without the need to be in the same room.
We find guests mainly through our professional and personal networks. Having both worked in high-achieving, demanding industries, we know plenty of people with interesting stories to tell – but we’re also open to people approaching us if they think they’d be a good fit for the show. We look for guests who have made changes in their lives or careers, challenged the rules they were taught to follow, and can speak honestly about the process – the good, the bad, and the messy in between.
We plan our episodes a few weeks in advance and keep a running schedule so we can balance different themes and formats. The show has a few regular segments that keep it fresh and varied. Outlaw Diaries shares stories from people who’ve made shifts or changes in their work and life, giving listeners a behind-the-scenes look at how it really happened. Outlawbrary is our book club, where we talk about the books that have shaped our thinking and could help our audience do the same. We also include standalone episodes on tools and strategies, like the Backwards Budget, that people can put into practice straight away.
Before each recording, we spend time researching our guest or topic, setting up a few questions, and thinking about where we want the conversation to go – but we keep it loose enough for genuine, unscripted moments to happen. That’s often where the gold is. Our goal with every episode is to leave our listeners feeling both inspired and equipped to take the next step in creating a life and career that works for them.
► How do you market your show?
Our listeners find the show mainly through LinkedIn, which is where a lot of our audience spends their time. We both have established networks there from our professional careers, so it’s been a natural place to share episodes and spark conversations. LinkedIn posts – especially those where we share a personal insight or pull out a resonant moment from an episode – tend to get the most engagement right now.
We’re also starting to grow our presence on Instagram and Facebook, where we share audiograms, quotes, and behind-the-scenes content to reach a wider audience. Over time, we plan to expand our use of these platforms and experiment with short-form video to connect with people who may not be in our existing networks.
From a listener acquisition perspective, 41% of our plays come from iTunes, 13% from Spotify, 17% from Mobile Safari, and 16% from Apple Mail, which reflects the fact that many people are clicking through from our newsletter or social links.
Right now, our most useful marketing channels are LinkedIn for engagement and community-building, and email for getting episodes directly in front of our audience without relying on algorithms. As the show grows, we’ll keep testing what works best, but for now, organic reach through trusted networks has been key.
► What advice would you share with aspiring (new) podcasters?
Start before you feel ready. You’ll learn more in your first few episodes than you ever could by researching endlessly. We decided to launch within a month of committing to the idea, and that quick start kept us from overthinking it into oblivion. The truth is, your early episodes won’t be perfect – and that’s fine. Listeners connect to your voice, your point of view, and your consistency, not your ability to sound like a studio production straight out of the gate.
One of the biggest lessons we’ve learned is that podcasting is more work than it looks. It’s not just recording; it’s planning content, editing, writing show notes, creating graphics, posting on multiple platforms, and engaging with your audience. If you want to keep your show going, build a workflow that fits into your life. We design our lives to leave space for the things we love, and podcasting is one of those things – but it still requires structure to make it happen every week.
Don’t be afraid to share your real self. We’ve found that vulnerability, honesty, and a willingness to talk about the messy middle are what resonate most with our listeners. You don’t need to be an expert in everything – you just need to create a space for authentic conversation.
For practical resources, we’ve found value in online podcasting communities (Facebook groups, LinkedIn connections), Riverside’s own tutorials for recording and editing, and podcasts about podcasting like Podcraft and Buzzcast. They’re full of tips you can apply straight away.
Finally, remember why you’re doing it. Growth is exciting, but the most rewarding part for us has been the messages from listeners who felt seen or inspired to make a change because of something they heard. If you focus on serving your audience, the rest will follow.
► Where can we learn more about you & your podcasts?
You can find everything about us and the Outlaws Podcast at www.outlawspodcast.com — episodes, blog posts, resources, and ways to connect.
Listen to the podcast:
Apple Podcasts:
Spotify:
YouTube: https://www.youtube.com/channel/UC2olxR8PHg6Xlj8JYBtPLOw
Follow us on social:
LinkedIn: https://www.linkedin.com/company/106681587
Instagram: https://www.instagram.com/the.outlaws.podcast
Facebook Group: https://www.facebook.com/groups/the.outlaws.podcast
Email: contact@outlawspodcast.com
We’re always open to hearing from listeners, potential guests, and collaborators. Reach out any time.
Listen411.com: Lightning-fast, Cost-effective Podcast Transcription and Summarization - Crafted with Passion by Listen Notes.
Lightning-fast: Transcribe a 1-hour audio file in 1 minute.
Pay-as-you-go: USD $0.06 per minute + $1 per file. No subscription required.