Job #3: LISC & the Chicago Chronicles
In October 2003, I packed up a half-full moving truck in front of my mom’s house on Liberty St (my Inkster people know about Liberty St) and headed to Chicago for my first move outside Michigan. Moving back home after I quit my job at the Greater Lansing Urban League was humbling, but gave me a soft landing that positioned me for what was on the horizon. I didn’t have much to take with me… a full-size bed, my aunt’s furniture, and lots of books.
In hindsight, I knew very little about Chicago. I had only visited a couple of times, most notably in high school with the Wayne State Upward Bound program for our end-of-summer trip. I remember being enamored by the historic architecture and saying to myself that if New York wasn’t in the cards for me, I would move to Chicago. Nine years after making that declaration, my independence from Inkster was finally taking place.
My new job was located on the corner of Madison and LaSalle in the heart of the financial district of the Chicago Loop, but I made the unwise decision to live in Oakbrook, 20 miles west of the city. And while I knew very little about Chicago, this Inkster girl had no frame of reference for living in an affluent suburb. My logic at the time was to make sure my family wasn’t worried about my safety. I also justified it because I was pretty lopsided on my high-interest car loan which would take another 18 months to pay off, so I was keeping my car. Thanks to the high-functioning transit system in the Chicagoland region and the transportation stipend offered by my employer, I was able to use public transportation every day which has always been my preference for commuting.
While I knew very little about Chicagoland, I knew even less about community development or the new organization I would be working for. LISC is a national community development finance institution (CDFI) that helps local organizations revitalize their communities. They provide financing to community development corporations and other local groups with more favorable terms than what banks typically offer. Their efforts touch both urban and rural communities across the country. They’re often the first ones in on a development deal, which then attracts other resources. Both the Urban League and United Way gave me a glimpse into the field of community development by working on a YouthBuild grant application and by seeing the efforts of local organizations connected to Community Development Advocates of Detroit. But the details of what comprehensive community development work looked like, I had no clue. I just knew that I came from a community that could benefit from an organization like LISC, and I wanted to learn what they were doing in other locations in case I ever had the chance to do it in my hometown. I also knew the job included travel, with trips to New York, DC, and other sites, something I absolutely desired in a job.
Although my new boss Evelyn assured me that I would receive ample training to familiarize me with my role, the organization, and the 12 sites I would be assisting her with managing, I knew I needed to know more about the field of community development. So I did what I always do when I want know more about something, I bought the book. I was an early Amazon user, back when all they sold were books. When I found A Guide to Community Development Careers on Amazon, I was confident I had a roadmap for my new job. The book was useful in helping me situate CDFI’s and other intermediaries into the broader community development landscape, and making sense of the barrage of acronyms that would soon be coming my way (CDBG, HOME, NMTC, LIHTC, to name a few). The book also helped me consider the various career pathways available should I choose to build community development expertise. While the book didn’t explain to me what I would be doing in my new job as an Assistant Program Officer (APO), it definitely helped me understand what questions I should be asking about the organization’s work and the broader field. From the beginning, Evelyn let me know I would likely outgrow my position in a couple of years, and that I should be considering which path in community development I wanted to pursue: real estate finance or organizational development.
As Evelyn promised, I received an abundance of training upon arrival at LISC: Real Estate Underwriting, Organizational Development 101, Managing Government Contracts, and CDBG Basics. Most trainings took place in New York, where LISC was headquartered. There was also the time we got to tag along with the Chicago LISC office for a meeting at the MacArthur Foundation to learn all about chaos theory and how it helps explain neighborhood change. I needed all the training I had access to because the work at LISC was fast-paced and more complex than anything I’d experienced in my prior jobs. There were dozens of real estate deals and capacity-building projects of varying amounts from different geographies across the country that my boss had to review and usher through our internal process each week. My primary role was to make sure each project within Evelyn’s portfolio was properly approved and tracked in the system.
There were other projects: measuring the impact and mapping the capacity of each site and providing support during times of financial challenge. It was significant work for the local sites we supported, but I often struggled with whether or not I was personally making a true contribution to the actual communities. Although I was in the field of community development, I felt so far removed from the neighborhood and residents where the work was truly situated. Although I had read the book and understood that community work happens at different levels, I didn’t realize how the work I was doing would make me feel until I was in the role. I thought I should be doing more. There were also days I was equally intimidated or fascinated by the work. I was surrounded by so many employees that were smart in very specific ways, whereas I had thought of myself as a generalist. It was an inspiring place to work early in my career. My boss Evelyn was extremely gracious with me as I navigated my new home and work life. This was important to me because I was absolutely a fish out of water in a city (and region!) that was unforgiving to me as a newcomer.
I didn’t realize how drastically different the cost of living was in Chicago compared to Detroit. So while I was making double my salary from the United Way, once you factor in higher expenses and my decision to live in Oakbrook, I was making ends meet, but barely. While I was able to secure relocation expenses, I didn’t negotiate my salary coming into the job (It was another 8 jobs later before I learned how to do this), and the salary range for my position offered little room for substantial pay increase. And though I was traveling frequently, if I wasn’t traveling with Evelyn, most of the expenses I incurred were strictly reimbursed. If wanted to make more money, I needed to move up into a program officer role. But that would mean I needed to go back to school for either an MBA or master’s degree in urban planning or something similar. I knew I wasn’t ready to go back to school just yet, but if Chicago was going to work, I needed to make more money. I’m a pretty low-maintenance person, so when I began to understand the cost of living difference from Detroit to Chicago, I adjusted. I remember returning the wardrobe of new clothes I had purchased for the new job. I remember giving up my garage spot the second year of my lease because I wanted my rent to hold constant rather than go up by $100, the same amount I paid for that heated spot. My only monthly splurge was for books and occasional restaurants. Back then I was reading Suze Orman‘s Nine Steps to Financial Freedom and counting my pennies with vigilance. I still knew I was one crisis away from it not working financially, and I was intentional about avoiding any crises.
While Chicagoland was huge, what made it feel familiar was the Spartan delegation that was present. I was never one for going out and was a proudly prudent homebody. But when I did it was likely dinner, bowling, or a movie (at best, choose two). Sydney offered the most active Spartan presence throughout my time in Chicago and was often the voice of reason in my work and personal realms. She was the one who helped me understand that my role as support to Evelyn gave me ‘fly-on-the-wall access’ to work that most folks at my level and age never get to see. And she was right.
I was often in meetings with mayors, foundation presidents, bankers, and grassroots organizers discussing community development deals that had yet made their way into the local press. She was also the one who introduced me to the book Career Warfare, by David D’Alessandro. There’s a chapter in the book where the author describes knowing when to walk away from a job. He prefaces the chapter with the lyrics to Kenny Roger’s ‘The Gambler’. And to this day, whenever I’m contemplating whether I should leave a job, I turn on Kenny Rogers's “The Gambler”, and decide from there.
After my first year at LISC, I mapped out a plan to get into grad school and get promoted to a program officer position within 12 months. I began watching and learning from other program officers, I helped form a peer group of other APOs nationally who were also contemplating their career trajectories. I started taking courses at the College of Dupage to demonstrate my current commitment to academic excellence. I began looking at master’s programs in Chicago and specifically targeted the University of Illinois at Chicago’s Master’s in urban planning program. At the time I also remember reading In an Uncertain World by Robert Rubin, who was our board chair at LISC and former Secretary of the US Treasury. I wanted to know and understand complex things just as I saw the program officers at LISC doing in their roles.
Despite all my efforts, things just weren’t panning out. I had to drop the stats course because, by the time I got from the Loop to Glen Ellyn for an evening class, I was dozing off in the computer lab. And while I put forth my best effort in applying to the urban planning program, I didn’t get in. I knew I couldn’t do another year in Chicago as I had up to that point. I needed a soft reset with an even more frugal budget, so I made plans to sell my car and move into a studio apartment in Oak Park. I would reapply to grad school the following year with more work experience to make my application more competitive. But before those steps could truly take form, I was finally hit with an unavoidable crisis: my dad took his life while I was visiting him in Dallas. The magnitude of the crisis I was experiencing — emotionally, physically, and financially — was off the charts, and I could not keep pace with work. I got behind on my bills, and I didn’t see a way out. And for me, returning to Inkster was not an option. But I was thrown a lifeline.
My partner at the time was considering international education jobs in various locations. I was excited for him, because this was his dream, to live and work internationally. We had known each other and dated in undergrad and reconnected several months prior. Our relationship was already progressing, and he asked me to join him as a traveling spouse. I wouldn’t have to work unless I wanted to. All housing expenses were covered. The cost of living was minimal. I would have time to just be, and figure out what my next steps would look like, whether work, school, or both. It was a contractual position, so we could figure out if we wanted to stay, or go someplace else after.
At the time I was no stranger to international travel. I had already been overseas to study abroad, visiting several countries in Europe five years prior. I had plans to continue traveling, but the thought of living and working overseas was not something I’d ever considered. It was a big decision. Do I thug it out for another year in Chicago, or do I press pause on all things work-related and follow my heart? I chose the latter, because more than anything, I needed peace. We got engaged, and five months later in December 2005 I turned on “The Gambler”, wrote my resignation letter from my position at LISC, donated most of my books to the local library, and headed to Southeast Asia.
I was only in Chicagoland for 27 months, but at the time it felt like a decade. Maybe it was because of how long the winters lasted, and how quickly the summers flew by. Maybe it was because I spent 10 hours commuting every week, and was completely exhausted by the time I got home. Maybe it was because nothing about Oakbrook reminded me of community. But in hindsight, Chicago was truly better for me than it was hard on me. LISC was the place where I REALLY learned Excel, which has served me well throughout my career. Evelyn was my third Black female boss, and as a Senior Vice President of a National nonprofit, I now realize how rare that was. Through LISC I got to experience Cincinnati, Baton Rouge, Cleveland, Toledo, the mid-South, and Chicago; learning their history, people, culture, and community development projects in the works. Chicago was also the place where I ran my first 5K, the Bison Stampede where I surprisingly paced an 8-minute mile, something I haven’t done since. And I ate GOOD in Chicago!
I was grateful I took the leap of faith to move to Chicago. Though I packed light as I moved on, I was taking with me a treasure trove of skills and experiences I would absolutely need for the next chapter in Laos.