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
iDateMoney® helps mompreneurs manage cash flow, ditch debt, and build true wealth—without shame. Hosted by Wealth Activator Lisa Drennon, creator of the Money Multiplier System. It’s not what you make—it’s what you do with it. 🗝️🌬️💖💸
Where Women Date Their Finances and Build Wealth—Without Shame.
They’ll tell you to hustle harder. Save more. Budget better. But here’s the truth: It doesn’t matter how much money you have—it’s what you do with it. 🗝️🌬️💖💸

Welcome to iDateMoney®, the podcast that helps mompreneurs take back control of their finances with clarity, strategy, and soul. Hosted by Lisa Drennon—Wealth Activator, money mindset expert, and creator of the Money Multiplier System—this show is where taboo ends and true wealth begins.

Each week, you’ll get a mix of raw conversations, mindset rewrites, spiritual insights, and practical strategies to help you crush debt without budgeting shame, master cash flow in your business and personal finances, save, spend, and give with purpose, and create a wealth plan you actually love living.

This is not your accountant’s podcast. This is real-talk money coaching for women ready to multiply what they already have and step into their financial sovereignty.

You’ll hear real stories. Tangible tools. Energetic alignment.
And the occasional money rant (because let’s be honest, some things need to be said).

Tune in, shift your money story, and start dating your finances—because wealth is your birthright, and it’s time to own 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.