Shannon Lee Simmons: How To Stop Feeling Broke | #415

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—and what to do instead. (0:20:32) Her four-bucket framework for worry-free spending and maintaining financial flexibility. (0:22:35) A practical test for deciding whether a large purchase is truly affordable. (0:25:01) Aligning spending decisions with personal values using an "emotional return on investment." (0:28:12) Helping couples navigate different financial priorities without turning disagreements into conflict. (0:30:28) Separating good decisions from bad outcomes to overcome financial regret. (0:33:48) The major financial decision crises people commonly face—from divorce to illness to retirement. (0:35:16) Using "micro financial plans," guardrails, and scenario planning during periods of uncertainty. (0:37:45) The three phases of a financial decision crisis and how planners can help through each stage. (0:41:41) Why retirement often reveals differences in couples' relationships with money that never surfaced while saving. (0:45:19) The psychological challenge of withdrawing from investment portfolios after decades of accumulation. (0:46:41) Using cash wedges and realistic retirement projections to reduce anxiety around spending in retirement. (0:49:42) How saver-versus-spender dynamics can evolve into power struggles during retirement. (0:53:12) The question almost every client is really asking: "Am I going to be okay?" (0:54:41) Why planners should ask about clients' hidden DIY investment accounts. <p d