How to setup the formerly incarcerated for success

January 12, 2022
© Christian B / Stocksy United

Ken Oliver is the executive director at the Checkr Foundation. Before joining Checkr he was the executive director at Creating Restorative Opportunities and Programs (CROP). He brings a wealth of knowledge and lived experience to issues of incarceration and rehabilitation, having served 24 years in prison.

The criminal justice system in America has created a two-tier system of citizenry, where the formerly incarcerated live with a draconian umbilical cord that prevents them from becoming a member of society and the mainstream economy again. There are 70-100 million people in America with some type of criminal record. Even if they weren't convicted of a crime, that arrest record can prevent them from accessing housing, jobs, social services. And so people who have been convicted of a crime are forced to serve this second prison sentence—this scarlet letter, if you will—that they carry around in perpetuity. 

In California, for example, there are 4,800 laws on the books today that prevent or erect barriers for people who have a criminal conviction to access basic necessities. This second-tier system of citizenry forces many to be locked into poverty. And this creates a cycle that prevents generations of Americans from opportunity and building wealth. 

It's a systemic problem that haunts anyone with a criminal record. But we can change that. Here's how.

We need to ensure people have access to dignified housing

Safe and dignified housing should be a human right. And as the formerly incarcerated re-enter society, we must make housing a priority.

Now, dignified housing doesn't mean recreating what happens in prison. We can't just take  10 individuals and stuff  them into a four-bedroom transitional facility or re-entry facility, where people are forced to live on bunk beds and share bathrooms. Providing people with dignity and centering the human experience is key. 

It's really not rocket science: when you treat people well and you treat people like they matter, the response is usually that people then act like they matter. You get a better result. On the other hand, if you treat people poorly and like they don't matter, they then tend to internalize that and act like they don't matter. They might start losing hope or stop caring, and you see all these other symptoms that occur—from substance abuse and depression to alienation and recidivism. Giving people dignified housing when they need it is a key first step to successful re-entry.

Housing costs money and it's going to take efforts across the board, from philanthropies to the government. 

I really believe philanthropy has a responsibility; a lot of these organizations have focused missions and experience on the ground to truly help people. But the government also has a responsibility to ensure that people have a pathway from prison gate to full reintegration and that starts with housing. 

We must help detox the prison experience

We haven't even begun to understand, let alone pay attention to, what happens to people in prison. Living in a six-by-nine cell with someone else where your arms can reach back and touch both sides of the wall. A toilet literally at the foot of your bed, where another person uses the bathroom for years. 

There's a true loss of dignity that occurs when you're in prison. 

The real test begins when you walk out of the prison gates. Currently, there is no meaningful handoff. The guards don't care if your mom picks you up or if you walk five miles to catch a Greyhound.Are we then going to expect somebody to transition seamlessly from a maximum security prison to a job in a cubicle at Google? It's hard to imagine that transition!

There are psychological seeds that are planted. Over years, they grow and they take their toll.  

We need full wraparound services before you leave prison: personal leadership development, technology education (15 years is a long time, especially in the smartphone era), social services—and that's just a start. 

We need to give people space when you leave prison. I think of this as a time and space to  “detox” the prison experience. People really need a chance to deconstruct the prison mindset, deconstruct the culture, and have an opportunity to adapt to a culture in the community. 

Financial literacy is essential

We must give former prisoners a very holistic and human-centered financial literacy education. How do we take people who come from cash economies historically and teach them how to buy a Subway sandwich on an Apple iPad with a piece of plastic? We need to educate people on how and why they need a savings account. Without a baseline level of financial literacy—especially for those who were incarcerated long before the rise of digital banking—it will be very difficult to access the middle class economy and break that cycle. 

We also need to educate employers

If you do all of those things I just laid out, but haven't done the work with employers, then all of that is for naught. 

 At the end of the day, if an employer doesn't hire someone that's spent time to rehabilitate and skill up, what does it matter? At CROP,  we've created an education program for employers. We go in and build partnerships with employers, including some of the biggest in the country: Google, Oracle, Microsoft. We do eight-week bootcamps and educate them about ensuring they have fair-chance hiring as the baseline for Diversity, Equity, and Inclusion hiring. Because you can't really talk about being inclusive unless you're including the most vulnerable populations, like the formerly incarcerated and those with a criminal record.  

We have worked to build those relationships, change the narrative, and deconstruct some of the false notions employers have about somebody with a criminal record.

There is no single solution, everything must work together

The most important thing is, well, everything. All of the different cogs have to work together if we want to break this cycle. We need to invest in a holistic strategy so that the formerly incarcerated have a fighting chance to join the mainstream economy and to build wealth for themselves and for the next generation.

About the Author
Ken Oliver

Ken Oliver is the executive director at the Checkr Foundation. Before joining Checkr he was the executive director at Creating Restorative Opportunities and Programs (CROP). He brings a wealth of knowledge and lived experience to issues of incarceration and rehabilitation, having served 24 years in prison.

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