Ladder Up: Steps to a New Life




By Judy Carmack Bross





Saluting how Chicago non-profits live out their mission is one of this magazine’s whole-hearted goals. How Ladder Up connects tax assistance to community need is something to celebrate as well as how they get ahead of tax time is something to emulate.


Ladder Up’s annual Tax-a-Thon is an extended length free tax preparation event to kick off the tax season. Photo Credit: Isabella Kadowaki 

Ladder Up’s Tax Assistance Project swings into gear on February 3rd with their annual Tax-a-Thon at Olive-Harvey College when over 35 Ladder Up staff members and volunteers, will be helping clients who live at or below the poverty line from across Chicago, preparing their tax returns and helping navigate other financial challenges.


Phyllis Cavallone-Jurek 

We spoke with Executive Director Phyllis Cavallone-Jurek about the almost 30-year-old Chicago organization which provides free tax completion, representation on identity theft, IRS, and IDOR issues, help for students seeking financial aid, and solutions to financial challenges, that allow those who are treading financial water to turn the corner.

“The name “Ladder Up” really captures the essence of the work. We hope to empower others to access resources and ladder up to where they see themselves in the future,” said Cavallone-Jurek. “Tax-a-Thon is really an uplifting day. We provide little goodies for our clients and most importantly want to make sure that at the end of the day every dollar that should be going into our clients’ pockets do so. We work with the very vulnerable, many who are elderly or have language differences. There is so much terminology you have to understand when doing taxes and quite often it can be overwhelming. People deserve an advocate, someone in their corner.”


Ladder Up will provide tax assistance at 13 locations throughout the city and six surrounding suburbs. Photo Credit: Jasmin Shah

“In the last fiscal year, Ladder Up was able to return an estimated $45.5 million in economic benefits across all of our programs. In 2023, Ladder Up prepared over 13,500 tax returns to secure more than $19.3 million in refunds for hardworking families and individuals. In our 29 plus years of existence, Ladder Up has served over 770,000 individuals, prepared over 625,000 tax returns, returned over $1 billion in refunds to the community, and helped secure an estimated $375 million in financial aid.


“Currently, we focus our work in underserved Chicago area communities where trustworthy financial services are scarce or predatory. Nearly all our clients live at or below 200 percent of the Federal Poverty Level, the average household income is $21,871, and 72 percent identify as persons of color. In 2023, Ladder Up clients qualified for an average refund of $1,428 and over 75 percent qualified for a federal tax refund. Tax refunds are often used to help with housing, medical expenses, groceries, and give these taxpayers a rare opportunity to save.

“During tax season we have 700-1000 volunteers, which includes young retirees, college and graduate students, CPAs and other professionals from financial institutions and corporations. We provide help in 13 different locations from Waukegan through Chicago neighborhoods and in several suburbs, using community spaces such as libraries, junior high schools, and centers. On Tax-a-Thon Day I will be at Olive-Harvey College but throughout the year, I like to be an extra pair of hands at multiple places.”


Certified Ladder Up volunteers help taxpayers claim credits and refunds that may otherwise remain unclaimed. Photo Credit: Jasmin Shah

A resident of Beverly where she lives with her “husband, two adult sons, and several fur children,” she is a native Chicagoan.

“Previously, I served as the chief of academics for the Office of Catholic Schools for the Archdiocese of Chicago. In this role, I led work which fostered excellence in teaching and learning through the support of instructional initiatives, curriculum formation/development, school improvement/accreditation, teacher/principal evaluation, student assessment and ongoing professional development for teachers and professional staff for nearly 170 schools.”

“Additionally, I was a principal at St. Therese Chinese Catholic School. During my 14-year tenure, I led the once-struggling inner-city school and transformed it into an international model of academic excellence and cultural expression. I have been recognized for my work in leadership as the 2017 Stanley C. Golder Leadership Award winner by the Golden Apple Foundation, among others and I was named a National Distinguished Principal of the Year, also of that same year.”

“After nearly 30 years in education, I was approached with the wonderful opportunity to lead and serve Ladder Up. In many ways, I believe the work is similar. Educators care about the whole person and their growth. And I truly enjoy helping others. I have dedicated myself to strong mission-centered work and helping under-resourced communities and individuals who need support seemed very much aligned to my personal passions. Also, given my mathematics education background and interest in personal finances, I thought the work would be exciting. I am very appreciative to the chairman and founder for this opportunity.”


CCM:  What most appeals to you about your work and makes you happy to meet with your clients and offer these services?

PCJ: I find working directly with the clients most appealing because I witness our impact in action. Seeing and feeling the important role Ladder Up plays in our client’s lives is rewarding. Giving financial workshops and working at a tax site during the season also gives me joy. The interactions we have instill a sense of making a tangible difference, both in terms of what we can directly do to impact their financial situation and in the personal connections we establish with those we serve.


CCM: Are there particular examples of clients that you serve that you would like to share?

PCJ: Every day we engage with clients and those interactions are truly heartwarming and uplifting. Our clients inspire me so much. Many older clients make do with very limited incomes, yet they talk about their own dedication to their church and family. Some families with young children get a bit emotional when they discover they qualify for credits they did not know about as this is a means for them to buy their kids clothes, school items, catch up on medical expenses, etc. One client particularly struck me last year. She called the library tax site to confirm availability and wanted assurance that we would work with her. She just lost her daughter, a college student. She knew it was near the end of tax season and needed to file. Suffering from such a recent loss, even going out of the house was still very hard for her. She just wanted some help because mentally she couldn’t do this on her own. When she arrived, our team worked with her as quickly as possible, providing compassion throughout the process. I remember watching her hold her daughter’s papers and driver’s license in her hand. She just held them, gently feeling them. Serving her was very special to our whole team that day. We will not forget that experience. I still get quite emotional thinking about that moment.


CCM: What are the challenges you face when delivering your mission?

PCJ: Serving all those that need the services. While we are so very proud of our impact and its significance, we recognize that there is a greater demand for our services in more communities in Chicagoland and throughout the state of Illinois. Our ability to serve is two-fold: the first is that it relies on the number of volunteers we have. We bounced back from COVID to about 750 volunteers in 2023 and we are on-track to recruiting about 900 this year. The second aspect, as with any nonprofit, is funding. We prioritize efficiency in utilizing our resources and hold great respect for all our funding sources, aiming to be responsible stewards of the financial support we receive. To grow and scale our work so we can reach more individuals and families and increase our volunteers requires continuous dedication and effort.


CCM: Tell me a little about the history of Ladder Up.

PCJ: Our founder, Robert (Bob) Burke, was only a 22-year-old Chicago business analyst when he founded Ladder Up. Bob was a volunteer coach at the time when he noticed the struggles of his west-side basketball team’s families and wondered how he could help them. So, he recruited 90 colleagues to prepare tax returns at no cost. The efforts paid off, returning over $150,000 in tax refunds to 120 families. Today, Ladder Up is led by expert staff and dedicated volunteers who carry Bob’s passion forward.

Ladder Up recognizes the intersectionality of our clients’ backgrounds and experiences. We provide a wide range of accommodations at our tax sites and legal clinic, including wheelchair accessibility, support for over 115 languages, including American Sign Language, and help for those with limited English proficiency.


CCM: Describe the Tax-a-Thon and what makes it a terrific event.

PCJ: We view Tax-a-Thon as our official kick-off to the tax season. The event brings awareness to eligible credits, such as the Earned Income Tax Credit (EITC) and Child Tax Credit (CTC). These credits support nearly 10 million people, including 5 million children, out of poverty each year. Research from the Center on Budget and Policy Priorities shows that the EITC and CTC improve employment rates, infant and maternal health, school performance, college enrollment, and future earnings for children of recipients. Thousands of low-income households in Chicagoland rely on Ladder Up each year to access these critical funds and to ensure their taxes are done correctly, on time, and at no cost.


CCM: Tell us a little about the volunteers that day?

PCJ: Oh my goodness, we love our volunteers so much! Over 35 volunteers will dedicate their day to collectively preparing probably over 80 clients’ taxes at our Olive Harvey tax site! Isn’t that a beautiful thing – to spend a day doing taxes?

We operate an IRS Volunteer Income Tax Assistance (VITA) program. The Internal Revenue Service (IRS) has offered VITA programs since 1969. Many VITA programs operate through universities, churches, community-based organizations, and nonprofit organizations like us. We are proud to say that we operate the largest VITA program in Illinois and one of the largest in the United States. The VITA program has become vital in delivering free tax preparation services to individuals who need assistance and cannot afford the services of a paid tax preparer.

Our volunteers are an important part of delivering this VITA program to the areas Ladder Up serves. I’m grateful for their dedication, as they invest time obtaining IRS certification and provide unbelievable, compassionate service to our clients. Our Tax-a-Thon volunteers bring a lot of energy and help set a great tone for the season.


CCM: Tell us about the need for your VITA Tax Assistance Program within the communities you serve?

PCJ: Over 100 million tax filers are eligible for this program, which is the majority of tax filers, but only 2 percent of those eligible actually use this program. Nearly 35 million households use tax software to prepare their returns, and 14 million of these households paid for software they should have received for free. An additional 67 million households instead went to a brick-and-mortar tax preparation service. These are funds many people do not need to spend.

However, federal tax refunds represent a large portion of the budgets of low-income individuals and families and are, therefore, significant to this taxpayer group. Such tax refunds are used to help with housing, medical expenses, and pay for clothing and give these taxpayers a rare opportunity to save. Supporting low-income individuals by filing their taxes at no cost enables them to maximize their ability to access the entire amount of their eligible tax credits. (reference for above two paragraphs: 

The benefits of a VITA tax prep program are many. VITA volunteers who prepare tax returns utilize tax breaks unbeknownst to many qualifying clients, resulting in greater tax refunds that are much in need. By spending several hours with each client during the tax preparation process, volunteers can cultivate a unique bond and opportunity for mentorship and rapport. The success of these one-on-one relationships and tax return benefits received by clients undoubtedly spurs word-of-mouth referrals, which extends trust in the communities served, increasing the number of clients seeking service. Lastly, free tax preparation provides a safe service to low-income tax filers who often reside in communities where trusted tax preparation help is limited or predatory in nature.


A Ladder Up volunteer assists a client with tax preparation at the organization’s annual Tax-a-Thon event at Olive Harvey College. Photo Credit: Jasmin Shah 

We asked Cavallone-Jurek about general organizational techniques as we all prepare for tax time.


“We see clients who come to see us with color-coded files with everything in order and we see individuals with letters still unopened. Many gig workers and those who drive for a living may not have their expenses and mileage readily handy.


“Everyone has a different way to organize. We always say ‘check, check, check’ that you have everything,” she said. “My advice to others is to recognize how you best organize. If you are the type of person who comes in and throws your key in a certain place, maybe you want to have a folder right there where you put receipts. If you are techy and put everything on your laptop or phone, take a picture of that receipt. Be honest about how you operate. But, however, or whatever your organization style looks like, we hope that you stop by one of our tax sites for help this season.”


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