Live Show Announcements

• Steven Dubner announces two upcoming live shows
  • January 3rd in San Francisco
  • February 13th in Los Angeles
• Tickets available at freeconomics.com/liveshows

Adam Moss Background and Career

• Lifelong editor, recently author and painter
• Founding editor of 7 Days magazine (transgressive arts/culture weekly)
• Editor at New York Times Magazine for many years
• Editor-in-chief of New York Magazine (radically remade for digital era)
• Won all major editorial awards
• Shaped careers of hundreds of writers/editors
• Left New York Magazine in 2019 (feeling burned out, ready for something new)

Early Magazine Career and Mentorship

• Started at Esquire under Lee Eisenberg
• Eisenberg took interest, taught him through apprenticeship model
  • Had him set up tape recorders for interviews
  • Gave him transcripts to analyze
  • Shared process of constructing conversations for print
• Learned through doing older editor's work (controversial but effective)
• Brought generational perspective/fresh eyes to Eisenberg
• Magazine form appealed to him since late 1960s/early 1970s
  • Heyday of magazines during cultural upheaval
  • Loved smartass, funny publications like New York, Mad Magazine
  • Attracted to distinct personality/voice of publications

Role of Magazine Editor-in-Chief

• Decides magazine direction and coverage
• Shapes magazine identity and reader relationship
• Manager role coordinating group enterprise
  • Story editors, visual people, copy editors, production
• Like conductor of orchestra
• Rarely about fixing sentences (common misconception)
• Overall direction and vision setting

Management Philosophy and Style

• Described as "exacting" with high but elusive standards
• Balance of grandiosity and humility
• Getting people to care as much as he did
• Hiring crucial, but also day-to-day familial approach
• Helping people find independence as thinkers
• Relished when story editors would fight with him (showed they "got it")
• Parenting analogy - different relationships with each person
• Recognized as form of mentorship/teaching

Dubner's Experience Working for Moss

• Worked as story editor at New York Times Magazine (late 1990s)
• Found editing excellent training for writing
• Shocked by quality of big-name writers' first drafts
• Took 6-month leave to work on first book
• Returned with plan to stay one more year before leaving to write
• Relationship changed once he became "lame duck"
• Left because didn't want to be promoted to boss role
• Now recognizes he became similar type of boss in his own company

Generational Differences in Workplace Culture

• Younger employees more comfortable with adults but resent certain workplace "parenting"
• Old Esquire model: people would cry after brutal story meetings
• Moss tried similar approach but staff rejected it
• Had to find workarounds and different language
• Learned to praise then withhold as strategy
• Former employees described him as "withholding" but overall experience positive

Transition to Painting

• Started painting in 2019 after leaving New York Magazine
• Began with no training, painting one per day in Cape Cod
• Connected with Maria De Los Angeles (recent art school graduate) as teacher
• Focused on technique and confidence building
• Kindness important in mentorship relationship
• Considers himself "mediocre" painter, not good enough for his exacting standards

"The Work of Art" Book Project

• 43 cases of building something from first notion to finished product
• Interviews with creators: Stephen Sondheim, Twyla Tharp, David Simon, Samin Nosrat, Will Shortz
• Visual format like giant magazine with sketches, graphics, sidebars, footnotes
• Part 1: Engaging artists as collaborators to show their process
• Part 2: Writing (described as "hell" due to loneliness)
• Recreated group creation context he loved in magazines

Creative Process Insights

• Book explores personality attributes for artistic success
• Not self-help - many traits can't be learned (focus, obsession, drive, taste)
• Encourages artists that they don't need to be Joyce/Picasso
• Art making comes down to learning to fail and get back up
• Addresses survivorship bias - only shows successful outcomes
• Wanted to give permission to fail

The "Bounce" Method

• Collaborative improvement through back-and-forth dialogue
• Works in group settings (magazines, TV shows)
• Solo artists must have this conversation in their own head
• David Simon example of internal dialogue process

Artist Satisfaction and Work vs. Product

• Moss expected "big firework" moments of completion from subjects
• Artists consistently expressed relief when work was done, not exaltation
• Realized it's about the work itself, not the end product
• Artists get up every day because they like/need to work that way
• Changed his own relationship to painting - found pleasure in process rather than outcome
• Verb of making vs. noun of final product

Self-Awareness and Experience

• Rates himself 2-4 on self-awareness scale (out of 5)
• Became more self-aware over time as editor
• Sometimes experience can be hindrance - stops you from trying things that previously failed
• Samin Nosrat example: "beginner's eyes" advantage
• Need to maintain belief you can succeed to move forward