You’re Following the Crowd Without Realizing It— Toni Will | Ep 225

On this episode of Relatable Wisdom, I had the pleasure of sitting down with Toni Will, a trailblazer who lives by Mark Twain’s mantra: “Whenever you find yourself on the side of the majority, it is time to pause and reflect.” Toni’s journey—from the banking world to becoming the general manager and only female governor of a men’s professional hockey team—is full of bold, rebellious decisions and powerful self-reflection. We talk about what it feels like to be the only woman in high-pressure rooms, how choosing sobriety (not because of crisis, but for clarity and more intentional success) changed her life, and the importance of “coloring outside the lines.” Toni’s insights will help you question default thinking, redefine success on your terms, and trust your ability to weather tough moments. If you’ve ever wondered how to make unconventional choices or stick to your values even when it’s uncomfortable, this conversation will give you both inspiration and practical strategies. Plus, learn how Toni’s upcoming book, Rebellious Success, and her leadership philosophy can fuel your own growth and gutsy decisions.Connect With Toni WillWebsite: https://toniwill.comWomen In Podcast: https://toniwill.com/women-in-podcastIf Relatable Wisdom speaks to you—if a quote shared makes you pause, smile, or see things differently—consider subscribing so you never miss an episode. And if you have a minute, leaving a review helps more people discover these everyday voices and the wisdom they carry. Your support means the world.Every episode has more to it than what you hear. Join the Relatable Wisdom newsletter to get thoughtful reflections, behind-the-scenes extras, and personal notes that don’t make it into the show. It’s a calm space to stay inspired between listens.Sign up here: https://relatablewisdom.com/joinChapters00:00 Introduction And Welcome01:20 Toni’s Life-Changing Quote02:24 Choosing Sobriety And Standing Apart03:47 Breaking Barriers In Hockey Leadership05:28 Navigating Microaggressions And Speaking Up06:49 Building Confidence And Overcoming Internal Barriers08:45 Leading Authentically And Her Leadership Pillars10:08 Embracing Career Detours12:37 Recognizing Opportunities And Following Breadcrumbs13:58 Facing Fear And The Power Of Challenge16:22 The “More” Behind Going Alcohol-Free17:58 Surprising Lessons From Sobriety20:05 Defining Rebellious Success21:42 How Her Definition Of Success Changed23:51 The Value Of Failure And Trying25:12 Fill-In-The-Blank Wisdom Game27:18 Healthy Rebellion Versus Contrarian Sabotage28:34 Pausing Before Responding29:57 Where To Find Toni Online30:22 Closing Reflections And Farewell