The Power of Making a Third List: Lessons from Chicago’s Riverwalk on Shaping the Future

Chunka Mui
8 min readFeb 13, 2024

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When I was growing up on Chicago’s South Side, I often rode my bike over a stretch of the Chicago River known as “Bubbly Creek.” Chicago lore has it that the namesake bubbles came from decomposing cattle entrails dumped into the river by the nearby stockyards. Decades earlier, in his muckraking classic, The Jungle, Upton Sinclair had described the river as “a great open sewer.”

Indeed, the river was so polluted that it required one of the great civil engineering feats of the early 20th century-the reversal of the river’s flow away from Lake Michigan-to stop the river’s contamination of Chicago’s drinking water. By my time, the river was still dark, ominous, and effectively devoid of life, with a murky brownish-green hue interlaced with an oily sheen. Sadly, the decrepit river fit too well with the disappearing stockyards and decaying industry that dominated its banks.

Today, the Chicago River is transformed. Its cleaner waters and healthier ecosystems encourage the return of nature, community engagement, and economic vitality. The river is now home to dozens of species of fish and supports a variety of other wildlife. It is increasingly lined with walkways, parks, and recreational areas. The river has become a social and cultural hub, hosting kayakers, boaters, river taxis, boat tours, art installations, and community gatherings. New residential, commercial, and mixed-use developments are emerging, capitalizing on the river’s appeal and contributing to the city’s economy

The crown jewel of the Chicago River’s restoration is the Chicago Riverwalk, a scenic promenade in the heart of downtown Chicago where the river meets Lake Michigan.

Before the Riverwalk, the river’s downtown stretches were barely accessible. That span of the riverbank was little more than a concrete embankment on the edge of the highly trafficked, double-decked Wacker Drive.

Wacker Drive and the River’s Edge Before the Riverwalk

Lower Wacker Drive, which ran along the river’s edge, was built to get traffic around downtown Chicago as quickly as possible. It was both a symbolic and concrete barrier separating the city from its eponymous river. Few ventured beyond it to the river’s isolated, trash-strewn docks and landings.

Vision and Leadership Matters

Credit for the restoration of the Chicago River belongs to multiple generations of civic leaders, urban planners, civil engineers, environmental advocates, community groups, and volunteers who played vital roles in the decades-long transformation. Architect and urban planner Daniel Burnham, in his 1909 “Plan of Chicago,” first proposed transforming the river into a recreational waterway. Though long delayed, Burnham’s vision still inspires the ongoing restoration.

Richard M. Daley, who also grew up not too far from Bubbly Creek and served as mayor from 1989 to 2011, deserves immense credit for energizing Burnham’s vision. It was a key part of Daley’s broader hope for urban green spaces and sustainable development. In addition to promoting an optimistic vision for the river, Daley’s administration promulgated a series of forward-looking development plans, design guidelines, and zoning ordinances that encouraged and shaped riverfront development towards this vision.

Rahm Emanuel, who followed Daley as Chicago’s Mayor from 2011 to 2019, deserves ultimate credit for building the Chicago Riverwalk. Emanuel leveraged Daley’s foundation to realize this key part of Burnham’s vision. How Emanuel accomplished this urban transformation is interesting in its own right and instructive for how to shape the future.

Rahm Emanuel’s Three Lists

During his two terms as Mayor, as he has recounted, Emanuel always kept two to-do lists in his coat pockets. One was a daily list filled with urgent, attention-needing items for that day. The second was a weekly list filled with critical items he needed to address that week.

Emanuel also kept a third list. This third list, which he kept in his top desk drawer, dealt with his biggest, most ambitious 10, 20, and 30-year goals for his hometown. But the list wasn’t just about long-term wishful thinking; it focused Emanuel on things he could accomplish in his term that could materially address the opportunities and challenges that he knew Chicago would face in that longer timeframe.

For example, Emanuel’s Third List aspirations included providing free universal Pre-K and college education for Chicago residents; eliminating gaping health, wealth, and opportunity inequities; modernizing O’Hare airport; solving the city’s pension problem; and, addressing climate change. He recognized most of these critical issues were unlikely to be completely solved during his stint as mayor; but, he was always looking for opportunities to make progress. If he did not do so, he reasoned, the prospects would significantly worsen.

Also high on Emanuel’s Third List was the restoration of the Chicago River.

From Vision to Obsession to Reality

Emanuel started by thinking big. He made a campaign pledge to fulfill Daniel Burnham’s vision to turn Chicago, which sat on the shore of Lake Michigan, into a “two waterfront city.” Soon after his election, he declared he would make the Chicago River “the city’s next recreational frontier.”

Some might say Emanuel was focused on the Riverwalk; one Chicago newspaper called it an obsession. Leaning on his significant experience, influence, and connections (he had previously been a senior leader in the U.S. Congress and then Chief of Staff to U.S. President Obama), Emanuel was always looking for “exactly the right time” to push the Riverwalk forward.

The right time came in a 2012 meeting with U.S. Department of Transportation (DoT) Secretary Ray LaHood, a former Illinois Republican Congressman and long-time Emanuel acquaintance. LaHood oversaw the Transportation Infrastructure Finance and Innovation Act (TIFIA), which provided long-term, low-interest loans to help jumpstart significant local and regional transportation infrastructure projects. Emanuel, as he tells the story, improvised “from thin air” a pitch to LaHood and his team for the Riverwalk as a pedestrian and bike transportation infrastructure project that fit TIFIA goals, and got the go-ahead to submit a formal proposal.

Opportunity in hand, Emanuel directed a task force of city departments and outside planners to devise a plan to finance and build a long-envisioned path system connecting the lakefront and a prominent downtown stretch of the river. Less than a year later, in 2013, Emanuel secured a $98.7 million 35-year, low-interest loan from federal government to build the Chicago Riverwalk. With those funds the city launched into a high-profile, multi-year construction project in the heart of downtown Chicago.

Emanuel then used his and the city’s considerable sway to establish the public/private partnerships that have made the Riverwalk so successful.

The city attracted vendors to provide a range of public amenities, including restaurants, wineries, gift shops, boat tours and kayak rentals. Lease payments and revenue sharing from these deals were core to successfully making the federal loan payments. Locals and tourists from all over the world loved it.

Over time, as the Riverwalk became more successful, Riverwalk vendors made considerable capital improvements at their locations, such as adding restrooms, enhancing decor and upgrading utilities, with these improvements reverting back to the city at the end of their lease periods.

Throughout the construction of the Riverwalk and after its successful public opening, Emanuel was a tireless champion.

Visiting dignitaries often got a personal tour. If Emanuel had a meeting or appearance nearby, he’d frequently walk to it along the Riverwalk. He was also known to drop in on weekends for a drink, and often followed up his visits with rapid fire emails to staff with items for their to-do lists. And, he rarely made a public appearance without finding some way to promote the Riverwalk.

With Sadiq Khan, the Mayor of London, During His Visit to Chicago
With Construction Workers During a Lunch Break
Mayor Rahm Emanuel on Chicago Riverwalk

The success of the Riverwalk attracted developers to nearby areas as well. Those projects were governed by Riverfront design guidelines and zoning ordinances that further expanded pedestrian walkways and public access to the river.

For example, there’s the dramatic building at 150 N. Riverside. It has a dramatic “tuning fork” shape that seems to barely touch the ground in order to comply with the city-mandated 30-foot setback and the requirement to provide another stretch of Riverwalk. Before the success of the Riverwalk drew developers to it, that building site had been vacant for decades.

The stunning Vista Tower, now the third tallest building in Chicago, was built further east along the river. It also has a walkway that connects the tower with the Riverwalk. The developers also built a glass elevator structure that takes pedestrians from upper Wacker Drive down to the Riverwalk, which previously had three handicap-accessible ramps but no elevators.

The Vista Tower (The tallest one on the left bank of the river.)

By 2019, as Emanuel was finishing up his second and last term as mayor, the Riverwalk had triggered a waterfront building boom with five new office towers and six new apartment buildings. Chicago generated an estimated $4–6 billion in investment along the river, as Emanuel proudly noted, “with zero down payment from Chicago taxpayers.”

The Chicago Tribune observed, “the riverwalk, which has brilliantly transformed a harsh industrial-era waterfront into an inviting postindustrial playground, is among [Emanuel’s] finest achievements.”

Even in a mixed retrospective of his performance as mayor, the Chicago Sun Times concluded that “Chicago is better today because Rahm Emanuel was mayor.” Exhibit number one was his pivotal role in the Riverwalk:

Then came Mayor Rahm Emanuel, who ran with the [River]Walk. He found the necessary money and was born with the necessary impatience. Nothing was going to stop him from crossing this achievement off a “to-do” list that he keeps in the top right-hand drawer of his desk at City Hall.

What’s on Your Third List?

Not all of us will spearhead multi-million-dollar projects, steer the redevelopment of cities, or change the course of rivers. Yet, we each hold the power to influence our own corners of the future.

We each have personal and professional influence over the realms we inhabit. Such responsibility inevitably fills our daily and weekly to-do lists with tasks big and small. But beyond these immediate tasks lie the potential for something greater. What visions and aspirations do you harbor for the next 5, 10, or even 25 years? These are not just idle daydreams; they form your Third List-the repository of your most audacious goals and transformative aspirations.

Engage with your Third List as a strategic map for long-term impact. Look for what you can do in the present to carve a path toward your desired futures. How can you lay the groundwork and advance those goals and aspirations? What steps will you take to ensure that your biggest dreams don’t just remain visions, but evolve into the chapters of your legacy?

If you enjoyed this article, please give it a clap up and a repost. Thanks! — Chunka Mui

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Don’t Fall for the Hype or Hysteria About AI. Don’t be Complacent, Either.

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A Brief History of a Perfect Future: Inventing the world we can proudly leave our kids by 2050

Originally published at https://www.linkedin.com.

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Chunka Mui
Chunka Mui

Written by Chunka Mui

Futurist and Innovation Advisor. I try to carry out Alan Kay’s exhortation that “the best way to predict the future is to invent it.”