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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.
Former Marine, CIA operative, and acclaimed novelist Elliot Ackerman discusses his new column "A Man Should Know" at The Free Press, exploring the small but significant skills that build masculine confidence. (02:33) The episode centers on how competence in everyday tasks creates intentionality and purpose, transforming how men carry themselves through the world.
• Core theme: Masculinity fundamentally comes down to "confident competence" - the ability to get stuff done and move through the world with purpose and skill. (02:27)
Brett is the founder and editor of The Art of Manliness, a website and podcast dedicated to helping men become better versions of themselves. He has been working in the masculine development space for almost twenty years, covering everything from practical skills to character development.
Elliot is a decorated Marine who served multiple tours in the Middle East and Southeast Asia, earning the Silver Star, Bronze Star, and Purple Heart. After his military service, he worked as a CIA paramilitary operations officer before transitioning to become a National Book Award-nominated novelist and the writer of "A Man Should Know," a column at The Free Press exploring essential masculine skills.
Ackerman emphasizes that confidence comes from competency in small, everyday tasks rather than grand gestures. (11:21) His transformation from someone who could barely do seven push-ups to becoming a Marine demonstrates how daily discipline in small areas creates broader life confidence. When young men master basic skills like tying a tie, introducing themselves properly, or maintaining their appearance, they experience what Nietzsche called "the feeling of power increasing" - the joy that comes from expanding your capabilities. (49:43) These small competencies compound over time, creating a foundation for tackling larger challenges with confidence.
Modern young men are struggling because culture has "shied away from speaking to just sort of young straight dudes with intentionality," leaving them to learn essential life skills through osmosis. (15:54) Ackerman argues that every young person needs to be "spoken to with intention by someone" who sees their potential and guides their development. Without this intentional guidance, young men lack the roadmap for basic competencies that previous generations took for granted. The solution requires deliberately teaching skills rather than expecting them to emerge naturally.
Drawing from his military experience, Ackerman explains that transformation happens through "every day just chipping away, chipping away, grinding away at something till you get there." (22:45) His six-to-nine-month physical transformation before joining the Marines taught him that accomplishment comes through "the consistent practice of small things day by day by day." (22:55) This principle applies to writing careers, building businesses, or any significant life goal - success results from daily discipline rather than sporadic bursts of effort.
Ackerman's CIA experience taught him that empathy - the ability to understand others' perspectives without agreeing with them - is crucial for masculine effectiveness. (24:10) This skill translates directly to business success, where understanding customers and negotiation partners becomes essential. Rather than viewing empathy as weakness, competent men use it strategically to navigate complex social and professional situations. The ability to "stand in somebody else's shoes" while maintaining your own principles represents sophisticated masculine capability.
Ackerman maintains a six-day-per-week workout routine not for military readiness but for "psychological well-being." (14:21) Completing the "first hard thing of the day" through exercise creates momentum for tackling other challenges. This physical discipline serves as a foundation for mental toughness and provides daily proof of your ability to push through discomfort. The habit demonstrates to yourself that "if you do the work, you get the result," building confidence for larger life challenges. (30:09)