Getting Past the Label: Fortune’s General Counsel Doesn’t Let Her Justice History Stand In the Way of Her Dreams

Getting Past the Label: Fortune’s General Counsel Doesn’t Let Her Justice History Stand In the Way of Her Dreams


Michele Weinstat holds two high-powered titles: General Counsel at the Fortune Society and author of three successful novels. Her experience as a formerly incarcerated woman comes to the forefront as she reflects her previous traumas in her writing. She serves as a role model to  Fortune participants just beginning to navigate life after justice involvement.  

Michele was introduced to Fortune through a drug treatment program in the 1980s before moving on to a 25-year career in public interest law. In 2020, she returned to Fortune as the Senior Director of Employee Relations; soon after, she was promoted to General Counsel. 

“I have never felt as rewarded in a career as I do at Fortune,” said Michele. “I have never felt so sure that I did the right thing by going to law school in the first place. Being here satisfied all of the things that I wanted out of a career: to feel directly helpful in achieving the agency’s mission and making the lives of the people I work with better. I can do both of those things at Fortune.”

Before coming to Fortune, she felt limited in her success because of her conviction history. “For most of my career, I had to ‘check the box,’ and I never got past the box.” She noted that once she admitted her prior justice involvement, she was often denied employment opportunities.  She also laments at how much more difficult it is for men and women of color coming out of the justice system.  

Despite her relative privilege as a white woman, she was often unable to overcome the barriers presented by her history. 

“I still have to discuss my drug use in my twenties, even after twenty-five years of practicing law. And when I go into an interview, I still have to strategically decide how to talk about it, even though it has no bearing on how well I can do the job.” 

She appreciates how Fortune embraces participants and staff alike who come to the organization with criminal justice backgrounds: “It is a wonderful thing to be at a place like Fortune where I can be completely open about my story.”  

Michele also acknowledges the ways her past enables her to relate to current participants in a more meaningful way.  

“I had always hoped that I could provide that inspiration for people, and I get to do that at Fortune. I get to say to somebody who is just coming in the door, you know, ‘me, too,’ and ‘it’s okay, you can be doing what I am doing now if you just keep showing up for yourself.’”  

Michele’s background informs not only her work at Fortune but the topics she explores as an author. She notes that even though she had not directly worked in the criminal justice sphere when she began writing fiction, her own experience with the justice system informs her work.  

“I have written three novels, and in every one of them, there is at least one chapter about incarceration and sometimes more. I think that speaks to how the trauma of incarceration is a very deep trauma that lasts a very long time. I was incarcerated…for just a few months on Rikers Island, and yet, it still comes up in my literature,” she explained. 

While there are many autobiographies written by formerly incarcerated individuals, there are few works of fiction written by those with justice involvement. Michele finds significant value in being a novelist that can relate to people with those backgrounds. 

Michele donated hardcover and audio versions of her novel to the Fortune book club for participants. After the club finishes reading the novel, she plans to meet up with the group to discuss their thoughts. 

“I have been told by those who have read the book from Fortune that the novel covers some familiar territory that you don’t normally see like what the characters come up against and what it means to have a criminal justice history walking through our world,” Michele said. “It is nice to see yourself reflected in fiction.”

Gone by Morning, Michele’s most recent release, follows a formerly justice-involved woman who is seeking to untangle relationships impacted by addiction and incarceration. It is available to purchase now

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