This report is a celebration of the incredible progress we’ve made together and the pathways we’ve built for hundreds of individuals seeking a way forward.

In this report, you will see some amazing milestones achieved – like job seekers placed in 1,229 total jobs; 2,488 tons of trash collected by our Cleanslate crews; 2,075 volunteer hours supporting our job seekers; and 138 jobs created by our Cara Plus affiliates, to name just a few.

We also share impactful stories of participants who have transformed their lives, uplift the work of a few key partners, and share accomplishments from our recently completed three-year strategic plan.

Behind every accomplishment are the people who make this work possible: our job seekers, who inspire us with their resilience; our partners and donors, whose belief in our mission fuels our progress; and our dedicated staff and volunteers, who bring compassion and expertise to every interaction. Together, we are proving that when we invest in people, we invest in stronger families, neighborhoods, and economies.

Thank you for contributing to these amazing outcomes and for being part of our community.

Your Friends at Cara Collective

The post Read Our 2025 Annual Report appeared first on Cara Collective.

For the past two years, Phillips has served as Chair of Cara Collective’s Board of Directors. He first joined the Board in 2016 and brings a wealth of experience and deep commitment to our mission. During this time, he has been an active advisor in the expansion strategy for the enterprise, the rollout of the enterprise’s FY23–FY25 Strategic Plan, and the reshaping of the Board of Directors to bring more diverse experiences and skillsets.

In addition to his Board leadership, Phillips is the founder and CEO of Parson Partners, a boutique management consulting and business services firm. In his 25-year career, he has advised C-suites and Boards of Directors for mid- and large-sized firms, Fortune 500 companies, government agencies, hospitals, and large universities throughout the United States as they seek to define and implement transformational business change. Prior to founding Parson, Phillips spent more than 12 years as a senior executive at three of the nation’s largest health insurance carriers.

“Cara Collective has always stood for transformation and opportunity, and I am honored to step into this role during such a pivotal time,” said Phillips. “Together, we will continue to build pathways for individuals to realize their potential and strengthen our community.”

This appointment comes after former Cara Collective President & CEO, Dr. Kathleen St. Louis Caliento, completed her four-and-a-half-year chapter leading the workforce development enterprise. Click here to read our announcement of her transition.

Cara Collective’s Board of Directors has formed a search committee and engaged Russell Reynolds Associates, a nationally recognized executive search firm, to assist in finding the next CEO. An announcement is expected in early 2026.

The post J. Todd Phillips Named Interim CEO appeared first on Cara Collective.

“Unable to find a job for the first time in my life, I struggled with depression. I was trying to shelter in place and protect myself from a disease that was spreading like wildfire. But, I was alone in a room with nobody to talk to and had no social interaction. Then I was forcibly evicted from my home and I had to make the hard decision to enter a homeless shelter.

“It’s very hard to live in a shelter. You’re with more than 150 other men. It’s kind of dormitory style. You eat together, you sleep together, you shower together. And they have a lot of strict rules that make it even harder to find and keep a job.

“But that’s also how I learned about Cara Collective.

“The first thing that Cara did for me was lift me out of my depressive state. Cara has counselors you can meet with free of charge. I learned several techniques to cope with my situation and rediscover my positivity.

“In the classes at Cara and with the support of my coach, I was freely able to communicate my struggles and received nothing but positivity and encouragement. I also received a wealth of information and opportunities to reinvent myself to get back into the job market. And on top of that, they provide transit cards to all the job seekers. With the seven-day pass from Cara, I was not only able to get to my training, I was also able to travel to look for work and see friends and family around the city.

“Without Cara, I don’t know how long I would’ve struggled with my depression.

“Because of my experience in facilities and maintenance, once I finished the training at Cara, I was offered a position on the Cara facilities team. It wasn’t an easy job, there were always problems to be addressed, but it helped me rediscover my self-worth. I was happy to be helping other people and it helped me to relearn how to socialize after the isolation of the pandemic. And to my surprise, through one of my Cara coworkers, I was able to find permanent housing. They had a personal relationship with the landlord and made the introduction. I met with the landlord and got the keys the same day!

“After an incredible year at Cara, I worked with the Employment Services team to find my next opportunity. Given my background, they helped me apply and interview for Environmental Service jobs at three different hospitals.

“Today, I’m an Environmental Services Technician at Advocate Illinois Masonic Hospital. In addition to my day-to-day responsibilities, I also train new associates. I really enjoy getting all of the new hires up to speed and affording them the opportunity to excel at their position. Because of my hard work and dedication, my supervisor saw my organizational skills and is working with me to advance to a lead position after only six months at the hospital.

“One of the biggest things I learned at Cara is we all have struggles in life. Cara means ‘friend’ – and that’s what everybody associated with Cara is to me. Thanks to my friends, I have a stable job that I love. I have a home again. I have returned to myself. And best of all, I have a place in the world.“

Your support this Season of Giving is critical to helping more job seekers like Rich transform their lives and find self-sufficiency through the power of employment. Click here to make a donation today.

The post Rich Finds His Place in the World appeared first on Cara Collective.

“For nearly a decade, my world revolved around my family. Those years were deeply meaningful and I would do it again in a heartbeat. But as my children grew older and more independent, I was ready to focus on me again.

“I had been the first in my family to graduate from college, I had run my own businesses from home, and I had so much knowledge and experience to offer. I thought it would be simple. With my degree, work history, and entrepreneurial experience, I expected opportunities to follow.

“Instead, I spent seven months building spreadsheets of job applications, paying professionals to rewrite my résumé, and reaching out to contacts, but the callbacks were few and far between. Even when interviews came, they led nowhere.

“The gap on my résumé seemed to overshadow everything else. I began to second guess myself. Had I made a mistake stepping away? Was I out of touch? What was I missing here?

“It began to wear me down. I felt like a failure.

“Then one day, I opened a community newsletter from Austin Coming Together and saw the name “Cara Collective.” I didn’t know what it was, but something nudged me to click.

“At first, I wasn’t convinced it was for me – especially after seeing a video of people singing in the Motivations circle. But the name kept appearing in my inbox. Eventually, I told myself, ‘If you’re going to let something like singing stop you from your goals, maybe you don’t want this as much as you say you do.’

“I came to Cara in March 2024. And that decision changed everything.

“The first week was intense. I felt out of place at first in the group assignments, unsure if I belonged. I even seriously considered quitting.

“But then I told myself: ‘How can I say I work well with all kinds of people and turn away a prime opportunity like this.’ So, I talked myself into staying. That was a turning point for me.

“I stayed. I led. I grew.

“At Cara, I rediscovered my resilience. I learned that leadership isn’t about waiting for the perfect environment; it’s about creating it. I learned that my ‘gaps’ didn’t define me—they strengthened me.

“By the end of our four-week training, my cohort voted to honor me with the Founders Award—something I never could have imagined in those first uncertain days.

“When it came time to job search again, I no longer felt alone. I had an entire team committed to my success and opening doors I couldn’t open on my own. It was empowering.

“That’s how I found my way to BMO.

“During my final interview, the market president told me she knew she wanted to hire me after seeing me in the Motivations circle – the very thing I was once running away from helped me secure my job.

“Today, I walk into my branch each morning knowing I belong. I meet with dozens of customers daily, helping them reach their financial goals and navigate their lives. The work feels natural because helping people is what I’ve always done.

“If you ask me what’s changed most since coming to Cara, I’ve become relentless about what I want to pursue in life. I no longer wait for opportunities. I create them. And I no longer question whether there’s a place for me. I know there is.”

Your support this Season of Giving is critical to helping more job seekers like LaKeita transform their lives and find self-sufficiency through the power of employment. Click here to make a donation today.

The post LaKeita Pursues the Life She Wanted appeared first on Cara Collective.

“At 18, I enlisted in the Air Force – which took me to places like Washington D.C. and Spain. Through my service, I found work in accounting and finance, I got married, and I had two beautiful daughters.

“Two years after my service ended, my husband and I divorced. At that point, I needed a clean break. My daughters and I moved back to Illinois, and I raised them as a single mom.

“Starting over was difficult, even a little lonely. But it also pushed me to become strong. I had to for my daughters. I had to figure out everything from scratch.

“I was able to find work for the IL Department of Commerce and Economic Opportunity and then left to become a code enforcement officer. I built a good life for my daughters and I. They graduated high school as valedictorians and went on to earn degrees, start careers, and eventually settled in California and Germany. I think I did a great job.

“Then in 2020, my entire department was eliminated at the height of the COVID pandemic. On top of that I had also lost a neighbor to COVID very suddenly. That left me scared to even venture outside, let alone search for a new job.

“I moved into my friend’s house to be his in-home caretaker. I thought it would be a good opportunity to have a place to live and to make some money. But after a while, he became aggressive and it was not a safe environment for me.

“I knew things had to change. So, for my own safety, I chose to live out of my car. I never imagined my life leading to homelessness, but I also didn’t lose hope. I knew I had way more fight in me.

“I contacted the Veterans Affairs office and was able to receive housing assistance. At this point I was also referred to Cara.

“Stepping into Cara’s doors, I knew this program would help me. I saw so much warmth. I saw so much diversity. I saw a community. As someone who was a loner much of their life, I had never had community like that before.

“Cara also pushed me; to get uncomfortable in sharing. During the Transformations classes, I was asked to look in the mirror and share what I saw. Initially, I saw a lost soul, but I could also see parts of my old self. The exercise made me realize I get to determine who I am, not experiences that made me feel like nothing. During the Forgiveness Exercise, I was able to forgive my friend and then forgive myself.

“I had lost my identity after being in such a dangerous situation with nowhere to go. Cara helped me get back to myself. My confidence started to come back.

“I worked a few transitional jobs, one for a property management company and then one at Cara’s South Side Campus. When a permanent role opened on Cara’s operations team, I immediately applied and got the job.

“This role pushed me to develop my customer service skills, and connect and build relationships with participants, guests, and staff – a softer side of me I wasn’t used to showing in past jobs. The most challenging part was managing the front desk transitional workers because they would eventually leave after they got a permanent job. I advocated for the position to become a full-time role, and Cara made it happen. This allowed me to move into my current role as an Administrative Specialist, with a larger focus on directly supporting my colleagues.

“Today, I am so grateful for Cara. I am in a much more stable place. I am happy. I am planning for my future, saving up for retirement, and I get to take trips to see my daughters and grandbabies. But most of all, Cara helped me heal and reclaim my strength and my self-worth when I needed it most.”

Your support this Season of Giving is critical to helping more job seekers like Bernita transform their lives and find self-sufficiency through the power of employment. Click here to make a donation today.

The post Bernita Reclaims Her Strength appeared first on Cara Collective.

“I endured a rough upbringing. However, I was always an overachiever. I pushed myself and graduated high school 12th in my class. I was accepted into the University of Illinois Springfield’s Honors program in 2020, with all my room, board, and tuition covered.

“However, a few months into school, I suffered a severe mental breakdown.

“Over the next three years I was diagnosed with major depression, anxiety, and borderline personality disorder. I attended therapy and took medications to cope. But in December 2023, my depression became so great I stopped attending class. I dropped out to avoid having a transcript full of “Fs.”

“Fearing for my future, I reached out to Cara and was recruited into its March 2024 Cohort. I remember spending the majority of my orientation trying not to cry. I felt ashamed for being unable to find a job on my own and I was afraid because my community had repeatedly let me down. I didn’t know what to expect from Cara, but then my recruiter introduced me to the Great Wall.

“The Great Wall is a powerful symbol in Cara’s main classroom. It’s a display of plaques honoring participants who’ve completed a year on the job. Each plaque bears a name, a workplace, and a date — and each represents a story of perseverance. Every day I walked into Cara, I saw that wall, and it gave me hope. It reminded me that I wasn’t alone, and that success was possible. Every day, I showed up at Cara, I saw the Great Wall, and I was fueled by it.

“After completing Cara’s core training, the Employment Services team connected me with Rush University Medical Center’s Guest Relations Department. They saw something in me — my warmth, my attention to detail — and encouraged me to apply. A week later, I interviewed, and on June 3, 2024, I started my new role at Rush.

“Working at Rush has been the most perfect experience. As a Guest Relations Associate, I assist visitors, patients, and students of Rush hospital by giving directions, communicating with nurses on behalf of family, and checking visitors in and being a listening ear when needed. Being in a high-paced, ever-changing environment is highly enjoyable for me.

“With the support of both my Cara family and Rush family, I made the Great Wall in June of this year!

“When I saw my name on the Great Wall I was overwhelmed with feelings of gratitude and elation. I’d made it, and now, I had the opportunity to give back by sharing my story. The prompt for that morning was ‘What have you accomplished in the past year, and how did you do it?’

“I had a great first year at my dream school, Columbia College, and I qualified for a dual degree program, which allows me to start my Master’s in Strategic Communication while completing my undergrad.

“I accomplished all of this not only because of my determination, but because of the courage my Cara community gave me. If I could go back to my first day of Cara, I would tell myself, ‘You’re making the right choice.'”

Your support this Season of Giving is critical to helping more job seekers like Naila transform their lives and find self-sufficiency through the power of employment. Click here to make a donation today.

The post Naila Finds Her Motivation in the Great Wall appeared first on Cara Collective.

“Once I’d achieved a little over six months of sobriety, the recovery home I was living in referred me to Cara. I was happy to come here and get a job, but I wasn’t expecting to learn so much about myself.

“At that time, I felt like a kid who was just starting to grow up. My addiction started at a very young age and I had been in that old lifestyle for so long. I never had a voice and didn’t have many positive interactions with people. I didn’t even know myself when I first got sober, so that was one of the biggest things I had to face.

“Cara helped me start to know myself and see myself in a more positive light.

“I specifically remember the Mirror Exercise with Mr. Jesse. He put the mirror in front of me and asked me to describe myself – who I saw in the reflection. I identified with a lot of negative things, some of which I didn’t even think of as negative until Mr. Jesse pointed it out. His response made me realize I wasn’t that person anymore, and that I needed to stop selling myself short.

“That was a big turning point for me.

“But, change didn’t happen right away. As I shifted into my job search, I figured because of my lack of work history, I was only qualified for the most basic positions. Then the Cara staff suggested I apply for the Office Manager position at Chicago Survivors, a local nonprofit that provides healing of communities and families affected by violent death.

“When I first saw the job description, I questioned if I was even qualified, but I followed through on the lead and applied. It was an intense interview process, which included a panel interview, something I’d never been a part of before. It was scary, but I used everything I learned and practiced at Cara and I got the job.

“All those things I was worried I couldn’t do? I’ve been able to do it all and then some.

“I have a short-term and long-term goal list that I’m currently working on and I’m checking off things left and right. I’m the only one in the office from nine to five every day and it’s good to be counted on to be the one to run the office. I answer calls from families every day; I get referrals and make sure they get to our field staff. I really feel like I’m able to help people.

“What is even more amazing about Chicago Survivors is that our Executive Director, Jashawn Hill, is also a Cara graduate. She started as a Family Support Specialist, then she created our youth team and became the Youth Coordinator, and now she’s the executive director. It’s nice to see there’s room for growth in that organization because I look forward to going to work every day.

“I have been at Chicago Survivors for two years now and I’m super grateful for Cara’s part in my journey. I’m in a very good place, probably the best I’ve ever been in my life – mentally, spiritually, physically, and with my sobriety. Now I’m able to give my family stability and be an example of resilience and responsibility for my kids. Today, I’m motivated, confident, and happy and I’m looking forward to the next step and doing what I need to get there.”

Your support this Season of Giving is critical to helping more job seekers like Rebecca transform their lives and find self-sufficiency through the power of employment. Click here to make a donation today.

The post Rebecca Rediscovers Her Resilience appeared first on Cara Collective.

“However, I was also living with an addiction to heroin.

“I spent years in and out of prison as I struggled with addiction. But the last time I went to jail, Judge Charles Burns learned about my background and invited me to participate in the (W)RAP Program, a rehab program that was an alternative to a prison sentence.

“I spent a little over three months getting sober in the county jail and another three months going through inpatient and outpatient programs at Haymarket. I remember how horrible I felt going cold turkey the first 12 days. They were the hardest 12 days of my life. That is what motivated me to never get high again.

“When I was in recovery and ready to move back into my apartment, Judge Burns introduced me to Cara. I was skeptical at first because I had been in job training programs, and they never led me to a job. But once I got here and saw how much Vicki, Jesse, and the whole team cared, I was sold.

“In the Transformations classes, I learned there was so much more to life than getting high. I had been stagnant for a long time, but now I wanted to grow. I was determined to take all the information I learned and not just get a job but keep a job too. I learned everything about showing up and showing out: how to dress, how to work as a team, and how to get stuff done. But most importantly, I finally believed I could go places.

“Eventually I started working on a Cleanslate crew. I established myself as a good, dedicated crew member and moved from cleaning the curbs to picking up and organizing the trash bags in the truck.

“I was proud of my work because my efficiency supported our crews and made a big difference in decreasing how many times we had to stop and empty the trucks. I also felt a sense of community by bonding with my crew supervisors. Even though I don’t work at Cleanslate today, we still keep in touch.

“I kept up my work at Cleanslate until Kelly on the Employment Services team told me I’d be a great fit to work at Grainger as a Warehouse Associate. It was a good opportunity for a lot of reasons, but a big one was that Grainger provided transportation to and from work. I didn’t have my driver’s license or a vehicle then, so this was a big deal.

“When I interviewed, they were very accepting of my background. I told them my addiction was all in the past, and I was working hard to make a change and do better. They offered me the job, and it felt amazing. I got to celebrate by ringing the bell at Cara!

“I immediately loved the people at Grainger. We work hard, but we have fun doing it. At Cara, I learned the importance of teamwork, and I was able to come in ready and willing to help my teammates. I did such great work scanning shipments that they helped me get certified to become a forklift driver.

“The best part of my job is that it helped me become self-sufficient. I was able to get my driver’s license and buy a car. I don’t have to worry about having enough money to pay my rent. I can afford everything I need. It also helped me reach the (W)RAP Program’s graduation this coming December. After that, my record from the past five years will be expunged. It is going to feel so good to get my record expunged because people won’t hesitate to take a chance on me for future opportunities.

“With the support of the (W)RAP Program and Cara, I have stayed clean, I am working a great job, and I have stable housing. Now I am able to focus on my long-term goals like getting my bachelor’s degree and raising my credit score. I am just so grateful!”

Your support this Season of Giving is critical to helping more job seekers like Robbie transform their lives and find self-sufficiency through the power of employment. Click here to make a donation today.

The post Robbie Finds Stability and a New Beginning appeared first on Cara Collective.

At Cara Collective, we have always believed in the power of transformation—of individuals, of communities, and of ourselves. Today, we share news of an important transformation within our leadership.

After more than four years of dedicated service as our President & CEO, Dr. Kathleen St. Louis Caliento will move on from Cara Collective at the end of this year. Kathleen’s last day will be Friday, December 5. While this news brings a mix of emotions, we are filled with immense gratitude for her leadership and excited anticipation for what lies ahead—for her and for Cara Collective.

Before stepping into the role of CEO, Kathleen was already deeply connected to our mission. Her journey with Cara began not as a leader, but as a believer—in our job seekers, in our purpose, and in the power of community. From her very first experience in the Motivations circle, it was clear that the heart of Cara Collective—the stories, the courage, the shared “why”—would shape her leadership and deepen her impact.

In her more than four years as CEO, Kathleen has guided Cara Collective through moments of profound challenge and growth. From navigating the pandemic to launching new partnerships, expanding our reach, and deepening our commitment to equity and innovation, her leadership has helped position our enterprise for a strong and sustainable future.

Thanks to the strength, resilience, and commitment of our team, our board, and our community, Cara Collective is well-positioned for this next chapter. We will be sharing more in the coming weeks, including updates on the search process as they become more available.

To Kathleen, we offer our deepest thanks—for your vision, your service, and your belief in this community. You have helped write a powerful chapter in Cara Collective’s story, and your legacy will continue to ripple through the lives we touch every day.

With gratitude,
The Staff of Cara Collective

A Statement from Cara Collective Board Chair J. Todd Phillips

Founded by Tom Owens in 1991, Cara Collective has worked tirelessly to deliver solutions that transform lives, build thriving communities, and help break the cycle of poverty. Four years ago, Dr. Kathleen St. Louis Caliento took the helm of this amazing organization during a period of global and local uncertainty. With clarity, compassion, and strategic vision, she guided the organization through this time and positioned Cara Collective for long-term sustainability.

During Kathleen’s tenure as CEO, Cara Collective continued to expand its reach and deepen its impact, including (but not limited to):

• Reinvigorating our programming, resulting in more than 1,000 job placements annually
• Growing Cara Collective’s annual operating budget from $12 million to more than $17 million
• Expanding our reach and impact on Chicago’s South Side through Cleanslate’s move to the Englewood community, including a 57% increase in transitional jobs created annually
• Elevating our local and national profile through innovative partnerships and initiatives that broaden our impact and advance a more inclusive economy

The Cara Collective Board of Directors is deeply grateful for Kathleen’s leadership and proud of the many accomplishments she and the team have achieved together. At the same time, we are equally excited about the opportunity to build on Cara Collective’s strong foundation as we continue to pursue our mission of advancing transformative individual and community success.

Cara Collective’s leadership team and staff are strong, experienced, and already working to ensure a smooth transition. The Board has formed a search committee and engaged Russell Reynolds Associates, a nationally recognized executive search firm, to identify our next CEO. We will also appoint an interim CEO to manage day-to-day executive responsibilities during this process. I look forward to sharing updates in the coming months.

Thank you for your continued belief in Cara Collective. Community has always been at the heart of our work, and your ongoing support remains critical to our continued success.

In friendship,
J. Todd Phillips
Chair, Board of Directors
Cara Collective

The post A Special Update from Cara Collective appeared first on Cara Collective.

“Deep down, I wanted stability and a chance to prove myself, but I didn’t know where to start.

“Then I found Cara. I’ll never forget that first phone call. The person on the other end said, ‘We can help you.’ I thought, really? With everything on my record? But she explained the program and told me about Cleanslate. That was the beginning of my new life.

“Cleanslate was hard at first. I was cleaning streets every day. It pushed me physically and mentally. But it also taught me discipline. It taught me that if you want change, you have to show up and work for it. I showed up every day, on time, and that changed me.

“From there, Cara prepared me for something bigger. They trained me, coached me, and helped me believe in myself again.

“When I interviewed for a job at Northwestern Hospital, I was ready. I studied their mission statement, practiced my answers, and nailed the interview. When I got the job, it felt like Christmas morning. For the first time in years, I had benefits, a 401(k), and financial stability.

“A few years later, I lost my job due to the COVID pandemic. I felt myself slipping backwards. So, I reached out to Cara and I was able to come back. Once again, Cara was there for me. They helped me transition into the CTA’s Second Chance program and eventually into my current position as a Customer Service Agent.

“Today, I wake up happy to go to work. I have the means to stand on my own. I was able to put my kids through their proms. I’m putting my money in the bank. I’m saving for a car. I’m planning to get my own apartment.

“Cara didn’t just help me find a job. They gave me hope, confidence, and a second chance. Cara is helping me become who I am meant to be!”

Your support of Cara Collective means more job seekers like Harold get their chance at a new beginning. Click here to make a financial gift today.

The post Harold Believes in Himself Again appeared first on Cara Collective.