Former first lady Michelle Obama is a self-proclaimed “box checker” of achievements. Proud of her South Side Chicago roots, she earned degrees from Princeton University and Harvard Law School. She returned to her hometown in 1988 to an associate position at Sidley Austin.

But as Obama, nee Michelle Robinson, enjoyed the spoils of her hefty associate paycheck in Big Law, a nagging realization was forming: She didn’t enjoy being a lawyer.

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