How to Make Big Decisions Without Overthinking with Bethan Winn episode artwork

EPISODE · Jan 11, 2026 · 48 MIN

How to Make Big Decisions Without Overthinking with Bethan Winn

from Outlaws Podcast: Embracing Career Freedom · host Shayla Strapps & Kate Offer | Outlaws Podcast

What if making a big decision isn’t about finding the right answer, but learning how to trust yourself? How do you make big decisions without overthinking, spinning in circles, or waiting for certainty that never comes? In this episode, Shayla and Kate are joined by Bethan Winn, one of Australia’s leading experts in critical thinking and human skills, to unpack how decisions actually get made, and why so many high-achievers feel stuck when it matters most. From intuition and values to analysis paralysis and permission, this conversation reframes decision making as a skill you can build, not a personality trait you either have or don’t. In this episode – Why most professionals were taught how to analyse, not how to decide – The myth of the “good decision” and why the real work starts after you choose – What’s really happening when you feel stuck between two good options – Gut instinct, what it is, what it isn’t, and why it matters even in rational professions – How overthinking is often a sign of fear, not lack of intelligence – “Nibble rather than scoff”, making big decisions through small, reversible steps – A practical decision-making framework built around permission, values, data, noise, and testing – Why values sit underneath every decision, whether you name them or not – How to reflect on decisions without self-blame when things don’t go to plan – Creating space to think in a noisy, fast-moving world More about Bethan Winn https://www.linkedin.com/in/bethanwinn/ https://www.instagram.com/bethan_winn_critical_thinking/ https://www.facebook.com/bethanwinn.com.au/   The book is available www.bethanwinn.com.au/shop or on Amazon and soon from any good bookshop  If you loved this episode... Share it with a friend who’s wanting a change (or just needs permission to do the thing!). Rate and review Outlaws on Apple Podcasts or Spotify — it helps more Outlaws find us Find out more Website: www.outlawspodcast.com Subscribe to our newsletter for updates, tools, and more Outlawbrary picks Connect with us Instagram: @the.outlaws.podcast - https://www.instagram.com/the.outlaws.podcast Facebook Group: Outlaws Podcast Community

Making big decisions shouldn’t feel like endless overthinking, but for many professionals it does. In this episode, Shayla and Kate are joined by critical thinking expert Bethan Wynne to unpack why decision making feels so hard, how intuition and values actually work, and why the goal isn’t to make the perfect choice but to make the decision good. You’ll walk away with practical tools to move forward with confidence, without waiting for certainty or permission.

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How to Make Big Decisions Without Overthinking with Bethan Winn

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This episode is 48 minutes long.

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This episode was published on January 11, 2026.

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What if making a big decision isn’t about finding the right answer, but learning how to trust yourself? How do you make big decisions without overthinking, spinning in circles, or waiting for certainty that never comes? In this episode, Shayla and...

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