Ditch the Shoulds: The Biggest Lessons from Season 2

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 Season 2 of the Outlaws podcast, reflecting on the biggest themes across the season, from career change and career pivots to leaving corporate and redesigning work in a way that actually fits your life.

This season has been full of conversations with people who stepped off the expected path. Lawyers building careers that didn’t exist 10 years ago. Professionals walking away from corporate roles. People making bold shifts, and others making small, steady changes that led somewhere completely different.

What becomes clear is this, career change doesn’t always look like a dramatic leap. Sometimes it’s a pivot. Sometimes it’s a slow burn. And sometimes it starts with simply questioning whether the path you’re on still makes sense.

We talk about:

– Why some of the most interesting careers today didn’t exist a decade ago – What it really looks like to leave corporate, and what comes after – The difference between overthinking and actually being “not ready” – Why intuition is pattern recognition, not something mystical – The concept of burnout beyond long hours, including misalignment and moral injury – How small decisions, made consistently, can lead to big career shifts

Whether you’re thinking about a career change, curious about a career pivot, or quietly wondering if leaving corporate might be an option, this episode brings together the insights, stories and lessons from a season of people doing work differently.

In this episode – The top episodes of Season 2 and why they resonated – Lessons from guests who left traditional paths to build something new – Why “procrasti-learning” keeps people stuck in careers that don’t fit – The idea that there’s no perfect decision, only the one you make work – Real examples of redesigning work without burning everything down – Why career change is more possible, and more varied, than it seems

🔧 Resources & Links 📩 Got ideas for Season 3? Email us: [e-mail] 💬 Connect with us on social media and share your favourite episode from this season

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Hosted and produced by Shayla Strapps and Kate Offer