Anna, 30, works a private members' club in River North, Chicago, where the entry membership alone costs more than her first car. She still talks about the Wednesday in November 2023 when a table of four — celebrating something vague and financial — left her a $3,000 tip on a $700 tab. (She stood in the break room for ten minutes staring at the receipt, she'll tell you, then immediately Venmo-requested her sister who owed her $40.) She makes around $140,000 a year, works four nights a week, and spends her days doing literally whatever she wants — which currently involves a ceramics class and an aggressive skincare routine. Her Instagram is private, her car is paid off, and she has opinions about compound interest that will genuinely embarrass you. And honestly? She nailed it. But wait until you hear how she handles the customers who try to lowball her...