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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this deeply personal solo episode, Lewis Howes confronts the painful reality that trying to please everyone actually diminishes respect rather than building it. He opens up about his childhood struggles, sharing a vulnerable memory of literally paying five dollars to join a "club" with classmates who ultimately ignored him anyway. (30:00) This experience created psychological wounds that led to decades of people-pleasing behavior that drained his energy and fractured his sense of self.
Lewis Howes is a New York Times bestselling author, entrepreneur, and host of The School of Greatness podcast. He's written multiple books including "Make Money Easy," "The Greatness Mindset," and "The Mask of Masculinity." As a former professional athlete turned business mentor, Lewis has built a multimillion-dollar media company focused on helping ambitious professionals achieve greatness in all areas of their lives.
Lewis emphasizes that if you can't say no, your yes becomes meaningless. (01:44) The key is communicating with kindness and clarity rather than guilt-driven responses. He suggests using phrases like "I appreciate you thinking of me, but I can't take that on right now" instead of lengthy justifications. This boundary-setting will initially ruffle feathers, especially from people accustomed to your constant availability, but it's essential for reclaiming your power and self-respect.
Confidence in your tone creates confidence in others' responses to you. (10:09) Lewis shares how he transformed from mumbling and constantly apologizing to speaking with deliberate clarity and presence. During a recent workshop with billion-dollar company executives, someone interrupted to comment on his powerful eye contact and presence. The practical step is replacing phrases like "Sorry, can I say something?" with direct statements like "Here's what I think."
The more you justify yourself, the less power you hold within yourself. (18:28) Lewis admits he used to spend hours crafting replies to requests, trying to create perfect excuses that wouldn't upset anyone. This exhausting pattern drained his energy and made him appear unsure and easy to argue with. The solution is stating your decision once and then stopping - silence after stating your boundary commands more respect than any explanation.
People test your boundaries not by what you say but by what you do, and consistency builds respect. (22:40) Lewis shares a painful lesson about lending money to friends despite initially saying no, which ultimately ruined relationships and created resentment. He learned that when you cave on boundaries due to guilt, you're doing something out of alignment with yourself, which fractures you psychologically and emotionally. The key is identifying where people are crossing your boundaries and taking immediate action.
If you're always the doormat, you're in the wrong house - the fastest way to gain respect is being around people who already respect themselves. (27:43) Lewis emphasizes that you become the average of the five people you spend most time with. He suggests auditing your relationships by asking who makes you feel drained versus who lifts you up, then doubling down on empowering relationships while creating distance from energy vampires. This might mean having conscious conversations about shifting activities from bars to hiking or basketball.