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From Client to Facilitator

Casandra Caldwell in front of the Woodlawn Resource Center on South Cottage Grove Avenue.

Photos by Gordon Walek

On a recent Friday afternoon at the Woodlawn Resource Center, Casandra Caldwell had a difficult time walking directly from reception to a conference room at the rear of the building. At every turn she was stopped by someone wanting to chat or asking for help with a computer-related task.

“And this is one of our slow days,” she said with a laugh.

Caldwell is a LISC AmeriCorps member currently serving as a digital literacy instructor at the facility — one of 10 Financial Opportunity Centers (FOCs) operated with support from LISC Chicago. She spends her days integrating a digital education curriculum into the operations of one of the city’s most active hubs for job seekers and those looking to obtain better control of their personal finances.

Having previously struggled with her own economic wellbeing, Caldwell could never have anticipated her professional trajectory. Like many of her neighbors in the Woodlawn community, she was often forced to spend more time worrying about the means of living than the larger societal impact of her efforts.

Today, however, she plays a crucial role in lifting up her neighbors and setting them on the path to financial stability. As digital skills become increasingly necessary for managing personal finances and gaining employment, her efforts are described as indispensable by colleagues and clients alike.

“People come to the center looking for Casandra because they know they’re going to get what they need,” said Woodlawn Resource Center Site Director Sheryl Morris. “She plays a significant role in making sure our work works.”

Through her efforts to familiarize job seekers with new technology and ensure digital education is incorporated into the FOC’s efforts, Caldwell is helping lay the groundwork for fully modernized financial wellness initiatives in Chicago and beyond.

In her role as a digital instructor, Caldwell familiarizes job seekers with basic computer technology, allowing them to complete resumes and submit them to potential employers.

Digital literacy integration

FOCs offer a three-pronged approach to financial wellbeing. Clients receive job placement services, an income supports screening and individualized financial coaching. This model is rooted in the idea that employment alone isn’t enough to help struggling individuals move out of long-term poverty and indebtedness.

But as local and national economies continue to evolve, it’s crucial that FOCs evolve alongside them.

As such, LISC provides digital literacy instructors like Caldwell to the FOCs throughout the city. Its willingness to fund these positions is based, in part, on feedback from employers who say digital literacy is the missing link between job seekers and available positions.

As for the effectiveness of these burgeoning digital literacy efforts, LISC data shows that job seekers who receive some form of digital literacy education are twice as likely to stay employed for at least six months than those without the training.

“That, to me, is an indication they have the potential to advance in that job or field,” said Caroline Rendon, LISC Chicago’s assistant program officer for financial opportunities.

Like Chicago’s other FOCs, the Woodlawn Resource Center caters to the unique needs of its surrounding community. As she watches her neighborhood ready for the transformation that will likely accompany the development of the Barack Obama Presidential Library in nearby Jackson Park, Morris believes the increased focus on digital literacy is especially important.

“My vision for this work going forward is to continue providing services and skills toward employability and economic mobility,” she said. “In terms of societal norms, digital skills are crucial. If our people don’t have those core pieces of knowledge, they’ll be left behind at a faster rate and have a harder time catching up. So if we can provide those skills and make the digital world less intimidating and less mysterious, then we’re moving the needle a little at a time.”

“People come to the center looking for Casandra because they know they’re going to get what they need,” said Woodlawn Resource Center Site Director Sheryl Morris, above. “She plays a significant role in making sure our work works.”

In her effort to make digital literacy a key component of the FOC’s work, Caldwell is focused on creating both formal and informal avenues for clients to learn the skills they need for success. The formal avenues include classes that introduce job seekers to foundational skills such as Microsoft Office, e-mail etiquette and filling out online applications. The informal avenues involve one-on-one coaching by Caldwell to clients with whom she’s built a rapport.

Seniors — many of whom want to develop a familiarity with social media or who don’t feel prepared to keep up with a regularly scheduled class — are especially enthusiastic about the opportunity to sit with Caldwell and learn at their own pace.

By providing customized options for everyone from children to retired individuals, Caldwell and her team are planting the seeds for intergenerational progress in Woodlawn.

From client to leader

Casandra Caldwell first became familiar with the FOC model as a client. A Woodlawn resident since 2001, she took advantage of the resources provided by the Metropolitan Family Services FOC at Kennedy-King College in Englewood. It was there she found employment as an Affordable Care Act (ACA) ambassador and discovered her passion for community work.

The one-on-one financial coaching she received was equally important. During one session, her counselor suggested they review her credit report for errors. Caldwell was confident she knew her credit history, but upon running the report, she discovered she had been mistakenly issued a $1,000 medical bill. Having been unaware of the charge, it had gone unpaid and severely damaged her score. Working with her FOC financial coach, she was able to rectify the situation.

“That’s why I always tell people to check their credit score even if they think they know what’s going to be on there,” she said. “I thought I knew too.”

During her time as an FOC client, Caldwell also took advantage of another LISC FOC resource: the Twin Accounts program. This credit-building program allowed her to build her credit score while adding to her personal savings.

Needless to say, her experience with the FOC was personally transformative.

When her contract as an ACA promoter ended, a contact at the FOC told her about LISC AmeriCorps and suggested she apply. Although she decided to do so, she was nervous about her ability to effectively teach digital skills.

“I knew how to use a computer for myself, but I wasn’t sure I could teach it to other people,” she said.

Whether working with clients or greeting them at the Resource Center's front desk, Caldwell is a popular figure at the Financial Opportunity Center that serves the Woodlawn neighborhood.

To her surprise, however, Caldwell flourished in the position. In addition to managing the Resource Center’s computer lab, she took on various administrative responsibilities within the organization. Perhaps most importantly, she teamed up with the FOC’s core staff to ensure digital education became part and parcel of their daily work.

Her position has thus far involved a great deal of experimentation and flexibility. While Caldwell is proficient with most basic software, she’s come up against a handful of situations in which she’s had to sharpen her own skills in order to help clients tackle unique challenges in their places of employment.

Looking ahead, she plans to apply the education stipends she’s accumulating as an AmeriCorps member to the human development program at Kennedy-King College. She also intends to remain active in local community development by pushing for further integration of digital literacy education at the FOC.

That’s good news for her students, many of whom have become regulars at the Woodlawn Resource Center specifically because of their relationships with Caldwell. One such student, Linda Stewart, came to the Resource Center for retraining assistance after an injury forced her to move on from her previous career.

“Technology is moving so fast that you either get up and figure out how to do it or you get left behind,” she said. “What makes Casandra so good at what she does is her warm personality and the fact that she wears so many hats.”

Stewart has worked with Caldwell in both formal and informal settings to improve her computer skills and prepare to re-enter the workforce. Having grown up in an era before technological ability was a prerequisite for employment, Stewart said she is grateful for Caldwell’s warmth and enthusiasm.

Site Director Sheryl Morris sees the same characteristics.

“Everyone here loves Casandra,” she said. “She’s so patient. She’s also really great at innovating. She thinks of things that will help us implement our services in a deeper, more meaningful way, and she’s always willing to jump right in. She’s a key component of our success.”

To learn more about LISC AmeriCorps, check out this recent story by Stacey Rapp, Director, LISC AmeriCorps program,

For more information on LISC Chicago’s Financial Opportunity Centers, contact Jennifer McClain, Director of Financial Opportunities, at 312-422-9563 or

Posted in Financial Opportunities, Woodlawn


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