Episode 279

We are allowed to say the F word, right? Navigating Transitions With Staacy Cannon

Published on: 19th April, 2025

On this episode of I Date Money, Lisa sits down with Staacy Cannon, a powerhouse midlife mentor helping women navigate major life transitions like perimenopause, divorce, and burnout. Together, they explore the intersection between health, hormones, and your financial story—and how reframing your relationship with money can change everything.


Lisa shares personal stories of growing up with a financially stressed entrepreneur mom, her imaginary friend (money!), and the roots of her Money Multiplier System. Staacy opens up about overcoming scarcity, going through a high-stakes divorce, and how a healing retreat in Hawaii helped her redefine abundance.


✨ Topics Discussed:

  • Hormones, health, and money: how they’re all connected
  • Budgeting vs. a spending plan (and why words matter)
  • Emotional triggers around money and childhood memories
  • The real ROI of self-care and retreating to recharge
  • Money buckets, tax planning, and the truth about financial peace

If you’ve ever felt like there’s never enough or struggled to separate personal and business finances—this episode will feel like a big exhale.

Want to reconnect with yourself and rediscover your joy?

Check out Stacey’s 10-day retreat in Hawaii: www.lahiretreats.com

Thank you for tuning into this week’s episode of I Date Money! 🗝🌬💖💸

If today’s conversation sparked an aha moment or gave you a new perspective on your relationship with money, we’d love to hear from you! Your journey to financial empowerment starts here.

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Remember, it doesn't matter how much money you make; it's what you do with it

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Intro/Outro music "IDM" by Christa Lily

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About the Podcast

I Date Money

Fall head over heels in love with money! Lisa and her guest share their money stories, the rollercoaster ride we take with finances, money management, tips, and strategies to multiply the money you already have. We're talking about activating wealth to unlock your financial genius. 💸Receive money with grace 💸 Support causes you love with generosity 💸 Save money with ease 💸 Design your financial future with confidence. It doesn't matter how much money you have; it's what you do with it 🗝️ 🌬️ 💖 💸

About your host

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Lisa Drennon

Lisa Drennon, Wealth Activator & founder of I Date Money™️ has been in the finance & insurance industry since 1987. Her unconventional Money Multiplier System transformed her money relationship to become a self-made millionaire, retire 2 ½ years early, pay $100K of debt in 6 months, & relocate to her beachfront dream home.