Are You Actually Not Ready, Or Just Overthinking Your Career Change?

In this episode, Shayla and Kate sit down with career counsellor and founder of Career Wisdom, Lois Keay-Smith, to unpack one of the most common blockers in professional life: readiness. So many smart, capable people tell themselves they’ll make the move, apply for the role, start the business, or ask for the conversation “when I feel ready.” But what does ready actually mean? And how long are we allowed to wait for it? This conversation explores the uncomfortable truth about readiness and career change. Often, what we call preparation is actually overthinking. What we call learning is sometimes procrasti-learning. And what we’re really waiting for is certainty that rarely arrives. Lois shares what she’s seen across 20 years of supporting executives, elite athletes, and professionals navigating major transitions, from voluntary career pivots to forced change through redundancy or illness. The pattern is clear: action creates clarity, not the other way around. In this episode – Why “I’m not ready” often really means “I don’t know where to start” – The perfectionism trap that fuels overthinking career change – Procrasti-learning, and when more courses are helping versus hiding – How MOOCs (massive open online courses) can be a low-stakes way to test ideas – The power of getting “oot naboot” and having real-world conversations – How to ask better networking questions that actually generate opportunities – The career theory of “planned happenstance” and why serendipity needs movement – Why forced change sharpens clarity fast – The small scripts that make asking for help less awkward One of the most powerful ideas from the episode is this: you don’t feel ready and then act. You act, and then you start to feel ready. If you’ve been stuck in analysis mode, researching, planning, mapping, learning, and still not moving, this episode will gently (and sometimes directly) challenge you to consider whether readiness is the real issue, or whether it’s fear wearing a very professional disguise. 🔧 Resources & Links Career Wisdom – Lois Keay-Smith Search “MOOC + [your topic]” to explore free or low-cost university courses 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 - https://www.facebook.com/groups/the.outlaws.podcast LinkedIn: Outlaws Podcast - https://www.linkedin.com/company/106681587 Email: [email protected] Hosted and produced by Shayla Strapps and Kate Offer