Throughout her legal career, Courtney Caprio has identified the safe path and then deliberately not chosen it.

Now in her 17th year of practicing law in Miami, the gambles are paying off: last month, Caprio joined the Wynwood boutique AXS Law as a partner, a job that allows her to work from home with her 2.5-year-old daughter while continuing her practice of high-profile, high-stakes litigation.

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