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The Definition of Success with author Neil Strauss | A Bit of Optimism Podcast

In 2005, Neil Strauss published The Game, a book about his years living in the pickup artist community. The Game sold millions of copies, stirred up huge controversy, and made Neil a bestselling author.

Simon SinekhostGreat Minds Neil Straussguest

May 8, 202435mWatch on YouTube

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CHAPTERS

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Chapter summaries

Connection Skills: Worrying About Judgment and Giving Validation
Simon asks Neil which human skills help genuine connection. Neil says to stop worrying what others think of you and realize they worry about what you think of them, so you give validation instead of seeking it.
- •Neil's biggest freeing lesson is that other people are worried about being judged by you
- •Give people validation instead of taking it
- •Simon calls this insight brilliant and says making someone feel seen is the best gift
How The Game Came About
Simon asks about the history of The Game and what it was. Neil explains that as a shy, nerdy New York Times music critic he secretly joined a pickup artist community after his editor pitched a how-to book, and he led a double life under a changed name.
- •Neil was writing for The New York Times and Rolling Stone while feeling lonely and stuck in the friend zone
- •His HarperCollins editor described an undercover community of pickup artists without money, looks, or fame
- •Neil turned down the idea publicly but was secretly intrigued
- •He changed his name and feared being found out
- •He wanted to publish the book under another name
The Book Versus Its Reputation
Simon notes that women described the book as manipulative, and Neil contrasts that with what the book actually portrays. He sees it as a story about male insecurity that ends in toxicity, and argues it is about neurodivergence rather than bro culture.
- •Once something is released into the culture it is out of the creator's control
- •The book opens with the greatest pickup artist trying to kill himself over a woman
- •Neil thought women would gain confidence on seeing men's insecurity
- •It ends like Lord of the Flies with self-taught alpha males in a house
- •Neil says most people he met were neurodivergent and needed a map
Simon's Dating Struggles and Applying The Game Today
Simon shares his own dating struggles with ADHD and overcompensating with coffee. He asks why Neil couldn't write the book today and what lessons translate. Neil says the same skills can be learned without an agenda: the question is whether your goal is to connect or to take.
- •Simon overcompensated for ADHD with coffee and did all the talking on dates
- •Neil says the lessons still apply without a goal of outcome
- •The difference is whether you aim to connect or to take
- •Neil mentions salespeople, marketers, and the FBI contacting him about the book's applications
Service, Other-Orientation, and Not Being Needy
Neil gives an exercise for social anxiety: make a few people feel better each day. Simon links this to the 12th step of 12-step programs, and Neil adds that kindness should have no neediness or expectation of return.
- •The Lamborghini example: compliment someone instead of judging them
- •Exercise: say something kind to three or four people a day
- •Simon cites the 12th step of helping another alcoholic as service
- •Neil says kindness is an end in itself and neediness is the biggest turnoff
Sex Addiction Rehab and Emotional Enmeshment
Simon asks whether Neil sees himself the same as when he wrote The Game, and Neil says the bigger transformation was sex addiction rehab. He describes a therapist naming his childhood experience emotional incest and explains how enmeshment is hard to recognize.
- •Neil says the bigger transformation was going to sex addiction rehab
- •He connects his draw to pickup techniques with fear of the feminine and a narcissistic mother figure
- •His therapist named emotional incest after his timeline exercise
- •Enmeshment feels falsely elevating, unlike abandonment
- •He realized he feared being swallowed up if he was vulnerable
Openness, Healthy Shame, and Accountability
Simon asks where Neil's openness comes from. Neil credits his interviewing and his goal of being healthy, then distinguishes vulnerability from healthy shame. They discuss how wounds come from shameless people and why Neil holds himself 100% accountable, with forgiveness as the end of healing.
- •Neil's openness came from interviewing and wanting no split between who he is and who he presents
- •Healthy shame includes things like wearing clothes
- •Wounds come from people who were shameless about boundaries
- •Neil takes 100% accountability for his own stories and behavior
- •Forgiveness is the end of the healing process
Why Culture Tears People Down
Neil observes that people either lift others up or bring them down and asks why culture criticizes people as they get big, citing Mark Zuckerberg's shift in perception. Simon answers that society has lost idealistic vision, doubled down on individualism, and heroized individual CEOs.
- •Simon agrees there are two ways to feel better about yourself: lift others or bring them down
- •Neil points to Zuckerberg as an example of the culture's pendulum
- •Simon says leaders no longer speak in idealized terms
- •Insecure, lonely people find it easier to bring others down
- •Simon says success depends on others and credits friends for what he has accomplished
What Is Success? Ecclesiastes and Contribution
Neil asks what success is and says every choice of life is equally valid, citing Ecclesiastes' advice to grow your own garden. Simon pushes back that this is selfish, arguing we are also members of groups with a responsibility to leave things better than we found them.
- •Neil says all life choices are equally valid
- •He cites the Ecclesiastes advice to tend your own garden
- •Simon calls that view selfish
- •Simon says we should leave companies, countries, and families in better shape
The Parable of the Farmer and the Horse
Neil tells the Zen parable of the farmer whose fortunes keep flipping, and uses it to argue we can't know the outcomes of our actions. Simon responds that uncertainty doesn't remove responsibility for contribution.
- •The farmer answers each event with "I don't know if it's good or bad"
- •Neil says cause and effect is too complicated to know outcomes
- •Neil's saying is that the outcome is not the outcome
- •Simon says control what you can but do it with an eye to contribution
- •Neil says it's okay for some people not to contribute
Splitting Hairs: Defining Contribution and Responsibility
They debate what contribution means. Simon defines it as leaving situations slightly better, with cultural norms in mind, while Neil argues no one knows what is right for others. Neil concludes they place the boundary of responsibility at different points, with Simon adding the goal of contribution.
- •Simon's Norway story shows contribution depends on cultural norms
- •Simon defines contribution through leadership and parenting
- •Neil asks whether one can do the right thing without owning the outcome
- •Simon says intentions and means matter
- •Neil says they draw the boundary of responsibility in different places
Stories, Uncertainty, and Closing
Simon shares advice that he lives in a world with other people, and Neil frames everyone as living out different stories. Both end up agreeing that accepting uncertainty is empowering, and Simon wraps up the show.
- •Simon was told that his definition of kind must be relative to the world he lives in
- •Neil sees the world in terms of stories people tell themselves and sell to others
- •Neil says Simon has a contribution story and he has an uncertainty story
- •Both say uncertainty is where things can happen
- •Simon thanks Neil and closes the episode

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