Harris Voices: Libby Massey, CLA'23, on the Invisible yet Important Work of Building a Better Chicago

As a part of Harris Public Policy's and the Center for Effective Government’s celebration of the 10-year anniversary of the Civic Leadership Academy (CLA), we asked previous fellows how CLA has impacted their work as civic leaders. These are their opinions and perspectives, informed by their own life experiences and worldviews (and do not necessarily reflect the views of Harris).

The past few months have brought some of the biggest, toughest, and most complex leadership challenges of my career. At times, they have seemed insurmountable and felt heartbreaking. I’ve questioned why I continue to ride this government rollercoaster and whether it might be time to finally jump off for steadier ground. Amid trying times like these, my thoughts first turn to my 2023 CLA cohort, a group of leaders who understand the challenges I’m facing so thoroughly and uniquely. Before I even had the chance to pick up the phone and send out an “SOS” text to the 2023 fellows, I had a mountain of messages waiting for me, offering messages of support, suggestions to leave work early and grab drinks, a Starbucks gift card sending me much-needed extra caffeine, and several invitations to hop on a call to talk through everything. Nobody understands a complex bureaucracy problem quite like the CLA fellows, and boy did they show up. 

In my conversations with the fellows over several weeks, a common theme of strategy kept surfacing. I found myself thinking back to CLA lectures, quite literally dusting off the black, leather CLA notebook, and thumbing through my notes. I was reminded of the power of incremental change; the value in the strategic long game of building the alternative before abandoning the status quo; the significance of being a “realistic radical” that works strategically inside the system, building for the world we want while starting from where the world is now; the importance of pulling out your tool belt of past experience because part of being a skilled public servant is having more than a hammer to solve the problem at hand; and the necessity of simplifying the political landscape and asking, “What will this moment allow?” Our classes on strategy fundamentally changed the way I think about and approach my work every single day, and grounding myself in these familiar themes helped to unravel the twisted knots in my brain.

I’ll never forget when it dawned on me, sitting in a CLA lecture: That’s what CLA is – a long-term strategy to equip our public servants with the tools and the networks to build a better Chicago. CLA is an intensive, academic program of strategically chosen public servants, from all walks of life, in key areas of impact across our city who are able to help each other see our shared challenges in a different light, through the same lens. It was created ten years ago to build an infrastructure of civic leaders over time so that, as each of us rises in our roles and responsibilities to the city, we are all connected by our time in Hyde Park - by Machiavelli and Alinsky and Paris and institutional reform projects. It’s connections and this infrastructure that ensures we have people to reach out to who uniquely understand our professional struggles and their personal impacts. It’s the training to help each other navigate systems change, problem-solve leadership challenges, and connect each other to resources that meet the urgent needs of Chicago. This shared knowledge and collective impact is making our community work better every day. Incremental change. Bit by precious bit, as we do all we can in what each moment will allow. It matters now more than ever. 

When I think I might want to get off the rollercoaster ride, or when I question why anyone would continue to do this thankless and invisible work, I am reminded via late-night calls with my classmates: “We get to do the work that really matters. That’s why we put up with it and stick with it after so many years. In the end, we’re lucky to get to do the work that matters the most.” 

For me, I am lucky to have a network of civic leaders who support me when times are tough, who remind me of my value and our shared purpose. I am lucky to get to do the important, heartbreaking, insurmountable work that really matters.