Episode 339

Money Guilt Disappears When Every Dollar Has a Job

Published on: 26th August, 2025

Do you ever feel guilty spending money—even on things you truly need? In this episode of iDateMoney®, Wealth Activator Lisa Drennon shares how money guilt is simply a signal that your money doesn’t have direction. Instead of letting shame and confusion rule, Lisa introduces her Money Multiplier System™ and Cash Flow 5-Star Formula™—simple, customizable spending plans that eliminate guilt, create flow, and put you back in charge.

Lisa reveals how she personally paid off $100K in debt in just six months, not by cutting out lattes or living in scarcity, but by giving every dollar a job. You’ll walk away with practical steps to align your money with your values, ditch restrictive budgets, and finally breathe again when it comes to your finances.


Topics Discussed

  • Why money guilt happens (and why it’s not your fault)
  • The truth about money leaks and directionless spending
  • The Money Multiplier System™ for personal finances
  • The Cash Flow 5-Star Formula™ for business income
  • Why budgets don’t work (and what to do instead)
  • How to set up money buckets that align with YOUR goals
  • The dopamine hit of paying yourself weekly
  • Why fun money is essential for lasting wealth
  • Lisa’s personal story: paying off $100K of debt in 6 months
  • Becoming the CEO of your money so it works for you

Quote to Remember

“Money guilt is really just a signal that your money doesn’t have a plan.” – Lisa Drennon


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Intro/Outro music "IDM" by Christa Lily

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About the Podcast

I Date Money
Rebuild financial stability after divorce—rewrite your money story with clarity and confidence.
Welcome to iDateMoney®, the podcast where divorced mompreneurs learn how to rebuild financial stability after divorce without spreadsheets, shame, or second-guessing every decision.

Hosted by Lisa Drennon—Wealth Activator, money strategist, and creator of the Money Multiplier System— this show is where clarity meets confidence.

Each week, Lisa shares raw stories, practical strategies, and spiritual insights to help you:

Release fear and guilt around money so you feel safe spending again.

Create steady income and financial security—even if your business feels unpredictable.

Confidently pay yourself, cover taxes, and provide stability for your kids.

Rewrite your money story so you can step into your role as a secure, empowered mom.

This isn’t your accountant’s podcast. It’s real talk for women ready to stop feeling broke, build true stability, and finally trust themselves with money.

Because it doesn’t matter how much you have—it’s what you do with it. 🗝️🌬️💖💸

About your host

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Lisa Drennon

Lisa Drennon, Wealth Activator & founder of iDateMoney® 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.