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What happens when life hands you a sliding-doors moment and you choose courage instead of certainty?
In this deeply relatable and energising conversation, I sit down with Naomi Holmes, founder of Her Money Matters, to explore what it really looks like to start over in your 50s.
After a 30-year corporate career and an unexpected redundancy, Naomi found herself at a crossroads many women quietly face: return to what’s familiar or listen to the pull towards a burning desire.
What followed was a deep reckoning and the decision to build a business on her own terms.
This episode goes far beyond money. It’s about the stories we inherit, the beliefs that keep us playing safe, what happens when your “who-ness” gets rattled, and why Gen X women are uniquely positioned to create powerful second acts…if they’re willing to take the courage pill and step into the unknown.
We also unpack why women are so often sidelined in money conversations, how “not deciding” shapes our future, and what becomes possible when money feels lighter and less intimidating.
If you’ve ever wondered whether it’s too late, too risky, or too uncomfortable to choose something new… this conversation might help you see what’s possible.
Key takeaways:
o How everything shifts when a long-held corporate identity suddenly disappears.
o Why women over 50 are starting businesses faster than ever and why this stage is so powerful.
o How your early money story shapes your confidence, decisions, and sense of control.
o Why imposter syndrome often appears right before real growth.
o How women can stop being sidelined in money conversations.
o Why choosing not to learn about money is a decision which has real consequences.
o How making money lighter and more human can change your entire relationship with it.
Get in touch with Naomi:
Website: Her Money Matters
LinkedIn: Naomi Holmes
Instagram: @her_moneymatters
Facebook: Her Money Matters
Podcast: Her Money Matters
Find out more about Her Money Matters courses.
COURAGEOUS ME – THE BOOK
Grab your copy of Courageous Me – The courage to turn someday into today.
Where to find me:
Website: Kim Payne
LinkedIn: Kim Payne
Instagram: @iamkimpayne
Facebook: KimPayneBiz
COURAGEOUS SHIFT
Want to make the impact you know is possible without having everything figured out?
Get access now to The Courageous Shift – a FREE 90 min audio mini-series to work out your next move.
Want to get clear on your next steps in your business or career?
Book a FREE 45 min Call to Action to help you get to the starting line.
By Kim Payne5
22 ratings
What happens when life hands you a sliding-doors moment and you choose courage instead of certainty?
In this deeply relatable and energising conversation, I sit down with Naomi Holmes, founder of Her Money Matters, to explore what it really looks like to start over in your 50s.
After a 30-year corporate career and an unexpected redundancy, Naomi found herself at a crossroads many women quietly face: return to what’s familiar or listen to the pull towards a burning desire.
What followed was a deep reckoning and the decision to build a business on her own terms.
This episode goes far beyond money. It’s about the stories we inherit, the beliefs that keep us playing safe, what happens when your “who-ness” gets rattled, and why Gen X women are uniquely positioned to create powerful second acts…if they’re willing to take the courage pill and step into the unknown.
We also unpack why women are so often sidelined in money conversations, how “not deciding” shapes our future, and what becomes possible when money feels lighter and less intimidating.
If you’ve ever wondered whether it’s too late, too risky, or too uncomfortable to choose something new… this conversation might help you see what’s possible.
Key takeaways:
o How everything shifts when a long-held corporate identity suddenly disappears.
o Why women over 50 are starting businesses faster than ever and why this stage is so powerful.
o How your early money story shapes your confidence, decisions, and sense of control.
o Why imposter syndrome often appears right before real growth.
o How women can stop being sidelined in money conversations.
o Why choosing not to learn about money is a decision which has real consequences.
o How making money lighter and more human can change your entire relationship with it.
Get in touch with Naomi:
Website: Her Money Matters
LinkedIn: Naomi Holmes
Instagram: @her_moneymatters
Facebook: Her Money Matters
Podcast: Her Money Matters
Find out more about Her Money Matters courses.
COURAGEOUS ME – THE BOOK
Grab your copy of Courageous Me – The courage to turn someday into today.
Where to find me:
Website: Kim Payne
LinkedIn: Kim Payne
Instagram: @iamkimpayne
Facebook: KimPayneBiz
COURAGEOUS SHIFT
Want to make the impact you know is possible without having everything figured out?
Get access now to The Courageous Shift – a FREE 90 min audio mini-series to work out your next move.
Want to get clear on your next steps in your business or career?
Book a FREE 45 min Call to Action to help you get to the starting line.

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