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- Forty year old divorcée Julie started a new downtown life following her marriage breakup, but her downtown chic attitude has been with her since childhood, when she used her lunch money to take cabs to school. Having worked her entire life in the service industry, she recently moved from a management position to service since she could make more money via the cash tips, that cash which just prompts her to spend on indulgences for herself. Her father and stepmother, Larry and Audrey, have been her cushion, bailing her out financially more than once, as Julie has panic attacks whenever she has to deal with issues of debt. Now reaching retirement, Larry and Audrey don't want to have to bail her out anymore. Despite liking being forty, Julie has not even considered her golden years which are creeping up faster than she imagines. Larry had set up a $25,000 stock investment for Julie in a non retirement account, but she is currently $20,000 in debt. Gail's challenges specific to Julie are: cutting the proverbial apron strings with Larry, who may be more of a problem than Julie; planning for emergencies and retirement; testing to see if certain indulgences actually net her more money in the service industry; and turning certain dreams into realities by making them priorities in spending. Gail's final challenges test whether Julie is truly on the road to recovery from her princess ways.