Today is a super fun interview because it was all about money — our attitudes towards it and our core beliefs about it. We segued right into the concept of ‘how do you go about spending your money, guilt-free?’

My guest today, Shannon Simmons, the author of Worry-Free Money — which just released today. She also owns The New School of Finance and she runs a series of programs online to teach the notion of financial acumen. As a new mom, she gets the pressures of the millennial, emerging entrepreneurial lifestyle and the shift that we’re seeing in our society — that is we’re moving away from the idea that everything is secure and easy to the fact that we need to have a new idea and paradigm as we approach money.

I can’t have a podcast or a business that focuses on producing healthy outcomes for people if we don’t talk about money — and that’s exactly what we did today and why I’m so excited to share this interview with you, between myself and Shannon Simmons.

Key Takeaways:

[1:46] About the interview today with Shannon Simmons.

[2:38] The consistent sources of stress I see when people come in for their intakes with me.

[4:00] How Shannon became not only an expert on finances but how she’s positioned that knowledge in a totally unique way.

[5:46] Shannon’s book on guilt-free spending and the simple things we need to look at when it comes to having a happier financial life.

[9:20] The first step to saving to appease that fear-based scarcity mindset.

[10:24] The most important side: cutting out traditional budgeting.

[13:13] What Shannon insists you do: Spend your money for you!

[15:53] Why Shannon thinks we have such complicated emotions in the relationship we have with money.

[17:57] Everyone’s inherent need to ‘keep up’ and how Shannon maintains a healthy grip on the ‘comparison game.’

[23:43] The fundamental basics of financial literacy.

[27:23] Ratios and benchmarks people should be aware of when it comes to debt.

[30:16] Allocating cash flow and paying yourself first.

[33:56] How to get that dopamine fix without spending money and avoiding that ‘f*ck it’ moment.

[36:12] Keeping open and honest with friends, family, and children in the conversation of money.

[38:35] The negative ways parents transmit their beliefs to their children about money.

[40:39] The importance of transparency.

[41:57] The first step to changing our relationship with money.

[44:45] The sentiment of success: changing your paradigm.

[46:01] What Shannon wants her legacy to be.

[46:58] How Shannon defines health.

[48:22] Rapid-fire questions for Shannon!

[55:44] Where you can find out more about Shannon.

Mentioned in This Episode:

Worry-Free Money:The guilt-free approach to managing your money and your life,

by Shannon Simmons

The New School of Finance

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More About Shannon Simmons

Shannon Simmons is the author of Worry-Free Money: The guilt-free approach to managing your money and your life. She also owns The New School of Finance and runs a series of programs online to teach the notion of financial acumen.

Shannon is a Certified Financial Planner (CFP), Chartered Investment Manager (CIM), media personality, personal finance expert and founder of the New School of FinanceTM. She is widely recognized as a trailblazer in the Canadian financial planning industry. She was named one of Canada’s Top 30 Under 30,  the Notable Award for Best In Finance and New School of Finance won the 2016 Wealth Professional Award for Digital Innovation. She is a regular financial expert in the media and has a monthly column for Globe and Mail and is a personal finance columnist for CBC’s On the Money and Metro Morning.

Connect with my Guest:

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This week’s call to action is all about creating momentum towards a healthy & happy financial situation. I challenge you to open up a savings account and commit to contributing $25 or more each month to it. This money may not change your world right now, but as it grows, your confidence and momentum will too. Share your commitment on our Entrepology Facebook page. Because when you are accountable, you are helpable.


“The problem is, is that there’s so much noise. … There’s a lot of noise coming at people to save.” — Shannon Simmons

“I basically think that budgets are broken. I think that no one should budget their money ever again — I think it’s making things worse.” — Shannon Simmons

“Look at your spending and you ensure that you’re getting the biggest emotional return on investment for your money.”
— Shannon Simmons

“Even small changes in your financial life can have a snowball effect.”
— Shannon Simmons

“Being motivated is critical.” — Shannon Simmons

“The number one thing for being financially literate is [to] start saving an emergency account.” — Shannon Simmons

“I think that making money part of honest conversations with our friends, family, and our children, is the number one key way that we can all defeat this ‘pressure cooker,’ fear-driven environment we find ourselves in.” — Shannon Simmons