Episode Description
By the time we reach our 40s and 50s, money stops being theoretical.
It becomes personal.
It’s no longer just about income — it’s about security, freedom, legacy, reinvention, marriage, divorce, risk, and the quiet question so many smart women ask themselves:
Am I actually building wealth… or just maintaining a lifestyle?
In this episode, I sit down with wealth advisor and financial strategist Hayley Dickson to talk about what midlife women often get wrong about money — and how to reset your financial life with clarity and intention.
We unpack:
- The blind spots high-achieving women still have
- Whether it’s truly “too late” to build serious wealth after 40
- Financial independence inside marriage
- Risk in midlife — when to take it and when to protect
- Lifestyle upgrades vs. long-term wealth
- Designing a financial life that aligns with your values
This conversation isn’t about shame. It’s about ownership.
Midlife is not when you step back financially. It’s when you sharpen.
About Hayley DicksonHayley Dickson, CFP®, CEO & Founder of RIPPL Wealth Management
Hayley Dickson, CFP®, is the CEO & Founder of RIPPL Wealth Management. A former SVP of Global Acquisitions at Fremantle Media who walked away from a six-figure entertainment career to revolutionize wealth management, Dickson became the fastest-growing advisor in Northwestern Mutual's history before launching Rippl Wealth Management in 2025.
As a financial life designer, Dickson provides truly comprehensive planning, democratizing sophisticated strategies for everyone from first-generation wealth builders to self-made entrepreneurs to seasoned professionals seeking discerning counsel that’s often reserved for ultra-high-net-worth individuals. Unconventional and bold in her approach, she builds her practice on radical transparency and trust.
Exclusive Offer for ListenersHayley is offering our listeners a complimentary 30-minute one-on-one Life Design & Wealth Strategy Session (a $500 value). This private offer is capped at 30 individuals – simply mention this episode when you reach out to reserve your spot.
To claim your session, send an email to rippl@nm.com mentioning "The Iconic Midlife" in the subject line or fill out the contact form directly on their website:
https://rippl.nm.com/contact.htm
Connect with Hayley:
LinkedIn: https://www.linkedin.com/in/hayley-dickson
Instagram: @hayleywdickson
Join the Inner Circle: https://the-iconic-midlife-with-roxy-manning.kit.com/3433416614
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Listen on:
Apple Podcasts: https://podcasts.apple.com/us/podcast/the-iconic-midlife-with-roxy-manning/id1817484587
Spotify: https://open.spotify.com/show/4FRDzq3AalXaqfpfWq7dlm?si=7e91db12ba1f4bfa
Amazon Music: https://music.amazon.com/podcasts/ff905ad8-332f-430e-a040-ce1ba5047483/the-iconic-midlife-with-roxy-manning
Let’s Connect
Social media: @theiconicmidlife (show) | @redcarpetroxy (host)
• YouTube: https://youtube.com/@theiconicmidlife