Outlaws Podcast

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 ...

💡 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 exist...

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...

In this episode we share our first 'Outlaw Diaries', and Shayla sits down with Fiona McLay—a former litigation lawyer turned legal tech evangelist and author—for an honest conversation about what it really takes to change course.

Fiona shares how she moved from the traditional path of legal practice into something far more aligned with who she is today. They talk about the messy middle of reinvention, the fear and worries, and the ...

In this episode of Outlaws, 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 ...

You followed the rules. You ticked all the boxes. You built the “successful” career. So… why does it still feel like something’s missing or that you're not really happy?

In this first episode of Outlaws, your hosts Shayla and Kate (two former lawyers turned question-askers and life-redesigners) get real about what brought them here — from burnout and breakdowns to career pivots and messy in-betweens.

We talk:

• Walking away fro...