Resolve Magazine Spotlights Why Not Prosper



On a chilly spring morning in Philadelphia, Michelle Simmons unlocks the door to the building she owns on Chelten Avenue, not far from her old middle school.


She owns three buildings in Germantown, actually. More accurately, her nonprofit owns them.

But Simmons and her organization, Why Not Prosper, are basically synonymous.


Once inside the building, she moves quickly, flipping light switches, sorting paperwork, stuffing goodie bags, talking herself through each to-do. She tackles detail after detail, always moving forward, building her dream to help formerly incarcerated women like herself.


Twenty years ago, Simmons had no keys. Instead of unlocking doors for women, doors closed in her face, just as she wanted to charge ahead. “As I was reentering society, I ran into barrier after barrier after barrier,” she says. “I got tired of people telling me no.”


After serving six years on and off in the California Institute for Women, Simmons was released in 1999. She left prison determined to rebuild her life, but felony convictions for possession, prostitution, and receiving stolen property followed her everywhere.


Simmons wanted to regain custody of her children, but she needed stable housing and steady employment before a judge would consider it. When government housing turned her away, she found a church in Norristown willing to give her a room.


“It was in that house that God said: open up a program for women coming from prison,” she says. “That’s where Why Not Prosper was born. In that house, on that day.”


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