Streetwise — Chapter 4: Lawyer, Briefly

1. 1. The author liked tax law for its intricacy but grew to hate it for the same reason.
2. 2. The author and his girlfriend Debbie took a cheap trip to Europe using standby tickets on Freddie Laker's airline, staying in youth hostels.
3. 3. The author worked on tax refund claims for record companies arguing that 'mothers' (stamping disks) were tangible property eligible for the investment tax credit, including royalty costs.
4. 4. The author spent two years living mostly in Los Angeles, working sixteen-hour days on the tax case, while shuttling back to New York every few weeks.
5. 5. John Baity, the author's boss, mentored him on professional appearance, advising him to buy collar stays and Hermès ties.
6. 6. The author reflects on how digital technology and AI have transformed legal work, such as Shepardizing, which used to take days in a law library.
7. 7. The author won the tax case but felt the work had no continuing relevance because the law and technology had changed.
8. 8. The author met his wife Laura through a blind date arranged by his officemate Emily Sherman, who systematically went through her Rolodex.
9. 9. Laura's father was a left-wing academic called before HUAC, and her mother died when she was six; she attended Fieldston on scholarship and faced classism.
10. 10. The author proposed after Laura demanded a ring in exchange for continued use of her air-conditioned apartment.
11. 11. The author realized he would never be as good at tax law as colleagues like Tim O'Neill, who eagerly awaited advance sheets of new tax cases.
12. 12. The author felt that becoming a partner at a big law firm would lead to a 'horrible and bourgeois' life, recalling the existential ending of The Heartbreak Kid.