Episode
Shannon Lee Simmons: How To Stop Feeling Broke | #415
- Published
- Jun 25, 2026
- Duration seconds
- 4778
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Summary
In this episode, we are joined by Shannon Lee Simmons—Certified Financial Planner, Chartered Investment Manager, bestselling author, and founder of the New School of Finance—for a wide-ranging conversation about the emotional side of money. Drawing on more than two decades of working directly with Canadians, Shannon explains why financial stress has become so pervasive, how social comparison shapes spending habits, and why a well-built financial plan can be one of the most powerful antidotes to money anxiety. We also explore decision-making during financial crises, the psychology of regret, why traditional budgeting often fails, and how couples navigate money differently—particularly in retirement. Shannon shares practical frameworks for aligning spending with personal values, avoiding emotional financial mistakes, and helping households make confident decisions through life's biggest transitions. Key Points From This Episode: (0:03:56) Why people worry about money—and why financial uncertainty often feels like uncertainty about life itself. (0:04:24) Why so many middle- and upper-income Canadians still feel broke despite earning good incomes. (0:05:18) The importance of having a financial plan and reducing harmful social comparison. (0:06:55) How social media fuels overspending, comparison, and "financial dysmorphia." (0:08:35) Why cashless spending has fundamentally changed our relationship with money. (0:11:52) How perceived life milestones—especially home ownership—shape financial decisions and expectations. (0:13:36) Practical ways to manage financial stress, restore confidence, and build resilience. (0:15:55) The growing "spending arms race" and how rising expectations have redefined what's considered normal. (0:18:09) Why Shannon dislikes traditional budgeting—a…