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May 26, 2025 63 mins

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What do you do when the work that once lit you up now leaves you cold? If you're in midlife or a career cul-de-sac and wondering what next, this episode is for you. Midlife Career Change Coach, Josh Peck, joins us to unpack the real conversations that help people move from stuck to clear, and from disempowered to energised. His methods help bring you and your career back into alignment.

In this illuminating conversation, we talk about fear, identity, money, confidence, and how to ask for what you want - even when you're not sure where to start. Josh shares the three conversations everyone should have before making a career change and explains why most of us are "pre-failing" before we even begin.

Whether you're burnt out, bored, or just ready for something more meaningful, this is a practical and hopeful listen.

In this episode, we explore:

  • How to recognise when you're experiencing "Sunday night dread, probably every night of the week"
  • The three essential conversations for successful career transitions
  • Why career changes rarely happen overnight and how to approach transitions realistically
  • How to handle the identity destabilisation that comes with career shifts
  • The concept of "pre-failing" and how it keeps us stuck
  • Why you're 7x more likely to get a job through conversations than applications
  • Setting a target number of conversations to move your career forward
  • How to choose conversations wisely and hold them gently
  • Navigating financial anxiety during career transitions
  • Building your second career on the shoulders of your first

About Josh Peck: Josh Peck is the founder of Your Best Life and the Align career change programme. After 20 years as a corporate lobbyist, Josh made his own midlife career transition and now specializes in helping people navigate career changes that align with who they are, what they do best, and how they want to live.

Running order

00:24 – Why this episode matters: conversations that get you hired
02:33 – Josh’s career pivot: from politics to coaching
06:10 – The Amy Winehouse moment that changed everything
08:36 – The 3 conversations everyone needs to have
13:09 – Why money fear keeps us stuck (and how to manage it)
19:49 – How to deal with unsupportive partners or sceptics
25:41 – Why 50 conversations can unlock your next job
29:11 – “Pre-failing” and how to stop sabotaging yourself
33:48 – How to craft a narrative that makes people want to help
46:46 – Why networking events don’t work (and what to do instead)

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