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Midlife Money Dilemmas: Worth It… or Not? with Financial Expert Hayley Dickson

March 5

13 mins

Episode Description

What happens when you take real-life financial decisions women face in midlife… and turn them into a game?

In this bonus episode of The Iconic Midlife, I’m joined again by wealth advisor and financial life designer Hayley Dickson for a rapid-fire round of “Worth It… or Not?”

We put some of the most common midlife money dilemmas on the table — the kinds of choices many women quietly wrestle with:

Should you prioritize experiences now or build more long-term wealth?

Is it worth staying in a high-paying job you’ve outgrown?

How much risk actually makes sense in midlife?

And when does a financial decision stop being strategic… and start being emotional?

There aren’t always obvious answers — which is exactly why these conversations matter.

Hayley shares how she helps clients think through these trade-offs so their financial decisions support the life they actually want to live.

Because at the end of the day, money isn’t just about accumulating wealth.

It’s about designing a life.

About Hayley Dickson

Hayley 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 Listeners

Hayley 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 podcast 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