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The Confidence Conversation We Need to Have with Scott Galloway | A Bit of Optimism

Scott Galloway and I don’t always see the world the same way, but our friendly debates almost always lead us back to common ground. It’s probably why we enjoy talking to each other as much as we do. If you haven’t heard my friend Scott’s name before, he’s known for being brilliant, provocative, and unapologetically himself. He’s a professor at NYU Stern School of Business, entrepreneur, bestselling author, and larger-than-life social commentator. In recent years, his work, which includes his new book Notes on Being a Man, has explored the challenges facing men today, from loneliness and dating to purpose and identity. Scott and I have different views on what “healthy masculinity” looks like. He’s not afraid to say things during this podcast that might ruffle some feathers. But inevitably, the conclusions we get to are introspective, vulnerable, and often universal. That’s certainly true for one revelation we share: confidence matters. Not the loud, performative kind. The real kind. The kind that helps people risk rejection, build meaningful relationships, and show up more generously in the world. In this episode, Scott and I talk about the “masculinity crisis,” why young people are struggling to connect, how purpose outlasts happiness, and why masculine and feminine traits are complementary rather than competing. We explore the need for good social risks like leaving the house, meeting people, pursuing relationships, and hearing “no,” and why confidence is less about ego and more about security, kindness, and connection. This is a conversation between two opposites who challenge each other, listen deeply, and ultimately agree that building real confidence may be one of the most important skills we can teach the next generation. This is... A Bit of Optimism. --------------------------- If you want to read Scott’s new book Notes on Being a Man, head to: https://www.simonandschuster.com/books/Notes-on-Being-a-Man Check out Scott’s podcast “The Prof G Pod”: https://www.youtube.com/c/TheProfGShow-ScottGalloway You can also watch his podcast “Pivot with Kara Swisher and Scott Galloway”: https://www.youtube.com/@pivot To stay up to date with all of Scott’s work, head over to: https://www.profgalloway.com/ + + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game. + + + Website: http://simonsinek.com/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek Simon’s books: The Infinite Game: https://simonsinek.com/books/the-infinite-game/ Start With Why: https://simonsinek.com/books/start-with-why/ Find Your Why: https://simonsinek.com/books/find-your-why/ Leaders Eat Last: https://simonsinek.com/books/leaders-eat-last/ Together is Better: https://simonsinek.com/books/together-is-better/ + + + #SimonSinek

Scott GallowayguestSimon Sinekhost
Feb 23, 202654mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Sinek and Galloway debate masculinity, dating, and real confidence today

  1. Galloway argues confidence is built by risking public failure—asking, applying, starting, and being rejected—then realizing the consequences are usually minor.
  2. They explore how masculinity is often misframed as either toxic aggression or “act like women,” and propose a healthier code blending provision, protection, initiation, and kindness.
  3. Both critique social media and online dating for amplifying envy, narrowing mate-selection metrics, and worsening insecurity, loneliness, and a “sex recession.”
  4. They connect confidence to leadership and relationships: confident people share credit, take blame, show appreciation, and create psychological safety.
  5. Galloway proposes structural fixes (national service, higher wages, housing, third places) alongside parenting practices (affection + guardrails) to rebuild confidence and connection.

IDEAS WORTH REMEMBERING

5 ideas

Confidence is the willingness to risk public failure.

Galloway frames success as repeatedly doing things that can fail visibly (start businesses, ask people out, pursue friendships) and discovering the “curb is two inches high”—most people quickly move on.

Appreciating others’ success is a marker of confidence, not weakness.

Laughing out loud, complimenting another man, or saying “you’re impressive” counters the zero-sum mindset younger men can carry and signals secure self-worth.

A healthy masculinity code should include provision, protection, and initiation—without cruelty.

Galloway emphasizes economic viability and physical strength as foundations, then insists they must translate into protection (making others feel safe, breaking up fights, respecting vulnerability) rather than domination.

Psychological safety is part of “protection,” not a separate, softer add-on.

Sinek broadens protection beyond physical and financial security to include conflict repair, emotional honesty, and a home where feelings aren’t punished or weaponized.

Online platforms intensify envy and narrow what “counts,” damaging confidence for both sexes.

They argue social media raises aesthetic and wealth expectations, while dating apps concentrate attention on a small share of men and reduce evaluation to height/resources signals, fueling insecurity and resentment.

WORDS WORTH SAVING

5 quotes

My goal is to live my life like I’m dancing with no one watching.

Scott Galloway

The fear of public failure is a curb that is two inches high and really doesn’t matter.

Scott Galloway

It takes tremendous self-confidence to say, ‘Thank you,’ or ‘I couldn’t have done this alone.’

Simon Sinek

The ultimate aphrodisiac on a date is… follow-up questions.

Scott Galloway

You need to reallocate your risk.

Scott Galloway

Confidence vs arrogancePublic failure and social riskHealthy masculinity and mixed cultural messagingSex differences, stereotypes, and workplace outcomesOnline dating consolidation and “six foot, six figures” filtersMale loneliness, self-harm statistics, and fear narrativesParenting: affection, discipline, sports, outdoorsNational service and rebuilding “third places”Dating initiation, safety, and respectful approachKindness practice, humor, and signaling

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