Harnessing Design Thinking in Reentry: Lessons from Reentry Summit Miami

The challenge of reentry — the process of transitioning people from incarceration back into society — presents a unique interplay of complexity and opportunity. It requires more than providing basic needs like housing, transportation, and employment. Instead, it necessitates a holistic approach encompassing education, mental health, medical needs, substance use, and legal issues. The recent Reentry Summit in Miami, co-hosted by The Umbrella of Hope Coalition and the University of Miami, offered a fresh perspective on tackling this multi-faceted challenge, employing a framework centered on values, problems, solutions, and actions embedded with design thinking principles.

In curating this framework for the Reentry Summit Miami, I emphasized design thinking principles, especially its focus on the user — in this case, the justice-impacted individuals. This approach allowed us to truly understand their unique challenges and needs, enabling the creation of effective, adaptable, and scalable solutions.

I recently had the invaluable opportunity to delve into the realm of Design Thinking as part of the Executive Program in Social Impact Strategy at the University of Pennsylvania. This enlightening experience has equipped me with the necessary tools to approach and solve “wicked problems.”

“Wicked problems” is a concept introduced to Design Thinking by Richard Buchanan, a notable design theorist and academic, in his seminal 1992 paper “Wicked Problems in Design Thinking.” Such problems are complex, ill-defined, or unknown, resisting resolution through traditional problem-solving methodologies.

Design Thinking, with its iterative process, serves as an adept mechanism to address these wicked problems. It allows for the reframing of these issues in a human-centric way, providing a more comprehensive and empathetic understanding of the problem. The process promotes ideation through brainstorming sessions, encouraging diverse solution generation. It also favors a hands-on approach in prototyping and testing, facilitating continual learning, adaptation, and refinement of solutions based on real-world feedback and testing.

The introduction to Design Thinking during the Executive Program in Social Impact Strategy was particularly transformative, particularly when considering the multifaceted challenge of reentry. The complexity of reentry, with its intricate array of individual, societal, and systemic factors, characterizes it as a wicked problem. The application of Design Thinking allowed us to reframe this issue in a manner that prioritizes the needs and aspirations of justice-impacted individuals.

Design thinking has its roots in the latter half of the 20th century, with the term first being coined in the 1960s. However, it wasn’t until the 1990s and early 2000s that it began to take shape as a recognized strategy for innovation, mainly due to the work of design firm IDEO and Stanford University’s d. school. Design thinking emerged as a response to the complexity and ambiguity that traditional problem-solving methods often failed to address, offering a human-centered approach to innovation that integrates the needs of people, the possibilities of technology, and the requirements for business success.

The importance of design thinking lies in its unique approach to problem-solving. It is inherently empathetic, starting with a deep understanding of the users’ needs and experiences. This empathy allows for a more accurate definition of the problem at hand, which is often half the battle when seeking practical solutions.

Design thinking is iterative, promoting a culture of prototyping and testing, encouraging risk-taking, and learning from failure. It believes in the power of multidisciplinary teams and invites diverse perspectives, fostering creativity and innovation. Above all, it is an action-oriented approach, always aiming toward creating a viable solution.

In the context of reentry, this empathetic and action-oriented approach is particularly valuable. It allows stakeholders to step into the shoes of those reentering society, understanding their unique challenges and needs. By working closely with these individuals, stakeholders can define the most pressing problems, ideate and prototype potential solutions, and implement actions that have a real impact.

Adding to the significance of Design Thinking, a notable case study comes from Apple’s collaboration with IDEO in 1980. Apple tasked IDEO with developing a mouse for their groundbreaking new computer, the Lisa. Prior designs by Douglas Englebart and Xerox PARC had proven too expensive and complex to manufacture. Apple’s mouse needed to be more reliable and less than 10 percent of the cost of the earlier versions.

The IDEO design team, embodying the principles of Design Thinking, started by creating a cost-effective and improved mouse operation mechanism. They innovatively used a complex plastic “ribcage” structure to hold the components together. The team then tested and refined other key components of the mouse, such as the audible and tactile click of the button and the rubberized coating on the ball. They even used a record turntable spinning for days, mimicking “mouse miles,” to check the reliability of the electromechanical assembly.

The resulting product was a mouse that was both mechanically sound and economically viable. The design was only slightly altered when adapted for the first Macintosh computer, and it served as the basis for virtually all mechanical mice produced since then.

This collaboration between Apple and IDEO serves as a powerful example of how Design Thinking can lead to groundbreaking solutions that meet both user needs and economic requirements. It also underscores how Design Thinking, much like we experienced in the Executive Program in Social Impact Strategy, can be instrumental in tackling “wicked problems.” It provides valuable insights into our intricate, multifaceted challenges and enables us to devise innovative, effective, and sustainable solutions.

Indeed, the application of Design Thinking extends far beyond the development of Apple’s mouse. Many of the world’s leading companies and institutions have used Design Thinking to create or improve their products, services, and processes.

Airbnb, for instance, used Design Thinking to reinvent its business strategy when the company was struggling in its early days. They redefined the user experience from a human-centered perspective, resulting in a resurgence of their business.

Uber Eats also leveraged Design Thinking to enhance their food delivery service, optimizing the process to ensure it was user-friendly, efficient, and met the needs of both the restaurants and the consumers.

At Stanford Hospital, Design Thinking was implemented to improve patient experiences and care processes, focusing on the human element of healthcare to create a more compassionate and efficient system.

Nike has used Design Thinking to drive innovation in their products, creating shoes and apparel that meet athletes’ functional needs and resonate emotionally with their consumers.

Netflix, a pioneer in the streaming industry, used Design Thinking to constantly refine its user interface and recommendation algorithms, ensuring a personalized and seamless experience for each subscriber.


In the context of reentry, values hold a profound significance beyond conventional understanding. They are not merely abstract principles or standards of behavior; instead, they serve as a compass guiding the reentry journey, shaping judgments on what is important in life for those transitioning back into society.

At the heart of these values is the inherent dignity of every individual and their potential to contribute meaningfully to society. This perspective was a central theme during the Reentry Summit in Miami, as we aimed to transform the narrative around individuals affected by the justice system.

We endeavored to view individuals not as ex-offenders marked by their past mistakes but as potential assets brimming with untapped potential. Regardless of their past, each person holds the potential to become an employee contributing their skills to the workforce, an entrepreneur innovating and creating jobs, a mentor guiding others through similar experiences, or a positive contributor to making their community a better place.

By reinforcing these values, we aren’t just promoting a shift in societal perceptions but also fostering a change from within these individuals. We’re helping them redefine their self-image and understand that their past does not dictate their future. These values serve as a foundation for their self-esteem, encouraging them to see themselves not through the lens of their past mistakes but through the lens of their potential and the possibilities that lie ahead.

In this way, values become an integral part of the reentry journey. They shape how we approach reentry — it’s not just about integrating individuals back into society but about supporting them in realizing their potential and contributing meaningfully to their communities. By putting values at the core of our approach, we create an empathetic environment that supports individuals in their journey toward rebuilding their lives post-incarceration.

This approach to values, deeply rooted in respect for individual dignity and potential, aligns with design thinking principles. As we continue to center justice-impacted individuals as the users of our reentry programs, we make sure that our strategies and interventions are responsive to their needs and aspirations, fostering an environment of empathy, dignity, and potential growth.

In essence, by aligning our values with those of the individuals we aim to serve, we ensure that our approach to reentry is not just about providing services but about empowering individuals to lead fulfilling, productive lives post-incarceration.


The problems facing reentry are multi-layered and complex, involving a myriad of interconnected issues. The Reentry Summit Miami underscored that housing, transportation, education, employment, mental health, medical needs, substance use, and legal issues are significant barriers to successful reentry. For instance, obtaining housing or employment can be tremendously challenging for individuals with a criminal record. Simultaneously, managing mental health or medical issues or dealing with substance use only adds to the burden.


Design thinking offers an innovative and empathetic approach to developing solutions to these problems. This user-centric methodology emphasizes understanding the individuals’ experiences, needs, and challenges in their unique context. It involves iterative ideation, prototyping, and testing processes to create solutions that are effective, adaptable, and scalable.

Design thinking principles were applied at the Reentry Summit Miami to brainstorm novel solutions for reentry challenges. For example, creating partnerships with businesses to provide employment opportunities, developing supportive housing models, implementing education and skill training programs, and providing comprehensive mental health services. Legal issues were tackled through advocacy for policy changes, promoting social justice and equity.


The design thinking framework culminates in actions — taking concrete steps to implement the solutions. This involves collaboration between various stakeholders, including policymakers, community organizations, businesses, and individuals. The actions foster a community-led, systemic approach to reentry, encouraging everyone to support individuals in their transition back into society.

At the summit, the discussions were centered on creating strategic action plans to implement the proposed solutions. Emphasizing the need for concerted efforts, the summit concluded with a call to action for all stakeholders to collaborate and contribute towards making the reentry process smoother and more effective.

A standout feature of the Reentry Summit in Miami was the leadership of justice-impacted individuals. They headed most, if not all, the working groups, a purposeful and strategic move. This was a true testament to the values we wanted to emphasize: the inherent dignity of every individual and their potential to contribute meaningfully to society and the reentry process itself.

Having justice-impacted individuals lead and participate in these working groups was powerful on multiple levels. First, it affirmed their value as leaders, as individuals with unique insights and experiences who could guide the conversation and steer the direction of the solutions. Second, it served as a potent symbol of change and potential — a demonstration that past experiences do not limit one’s ability to contribute significantly to society.

Moreover, this leadership structure encouraged collaboration in a way that traditional setups may not have. Justice-impacted leaders brought first-hand knowledge and experiences, ensuring the conversations, decisions, and actions were rooted in reality. Their leadership fostered an environment of empathy and understanding, encouraging stakeholders to view the reentry process from the perspective of those experiencing it.

Stakeholders from all areas of the community were present at these tables — government, community organizations, businesses, and justice-impacted individuals themselves. This broad representation created a rich tapestry of perspectives and ideas, enabling a holistic view of the challenges and potential solutions. It encouraged an understanding that successful reentry is a community effort, requiring the active participation and collaboration of all sectors of society.

The leadership of justice-impacted individuals thus contributed significantly to the collaborative spirit of the summit. It highlighted the importance of inclusive conversations in problem-solving, ensuring that those who have experienced the challenges of reentry firsthand are not just participants but also drivers of the conversation.

By centering justice-impacted individuals in this way, we could live out the values we championed. We fostered an environment where individuals were seen for their potential rather than their past, and we created a collaboration platform reflecting the reentry process’s multifaceted nature. Through this, the summit served as a powerful demonstration of how values, when put into action, can contribute to effective and empathetic problem-solving.

The Reentry Summit in Miami was not just another conference; it was a dynamic gathering of minds where every element was designed to encourage meaningful dialogue and action. The morning panels played an essential role in setting the tone for the day, providing a platform for expert insights, shared experiences, and comprehensive overviews of the issues at hand. However, the true depth of the summit was realized in the working groups that followed.

The morning panels were instrumental in creating a shared understanding of the reentry landscape. Experts from various sectors — housing, transportation, education, employment, mental health, and legal services — presented a broad panorama of reentry, elucidating its complexities and interconnectedness. These discussions offered a foundational knowledge base, enabling all participants to grasp the full scope of the reentry journey.

Yet, understanding the landscape is just the first step. To truly make a difference, we needed to dive deeper to explore the intricate nuances of each issue from the perspective of those most impacted. This is where the working groups came into play and why it was crucial to place justice-impacted individuals at the center of these discussions.

Justice-impacted individuals led the dialogue in each working group, sharing their unique experiences and perspectives. They weren’t just voices in the conversation; they were the guides, leading us through the labyrinth of challenges and potential solutions inherent in the reentry process.

By centering justice-impacted individuals, we ensured that the deep dives into each issue were grounded in lived experiences. Their insights shed light on the often-overlooked realities of reentry, shaping the development of empathetic, effective solutions. Their leadership ensured that the discussion was not just about them but with and for them.

The various panels in the morning set the stage, but the working groups led by justice-impacted individuals indeed drove the narrative. This approach emphasized that successful reentry is not just about understanding the issues; it’s about engaging those most affected in the solution-building process. By doing this, we create more effective reentry strategies and affirm the value and potential of every individual in the process, embodying the values we champion.

As a formerly incarcerated individual, I know the power of inclusion. I’ve lived it. And as we continue to tackle the challenge of reentry, I am committed to ensuring that inclusion remains at the heart of our approach. Because I believe that when we value and include all voices in the conversation, we create more than just effective reentry strategies. We create a society where every individual, regardless of their past, is seen for their potential and their ability to contribute meaningfully to their community.

Inclusion, for me, goes beyond simply inviting justice-impacted individuals to the table. It’s about acknowledging and valuing their unique insights, experiences, and potential to contribute. It’s about recognizing that they are not merely recipients of services but crucial stakeholders in shaping effective reentry strategies.

This belief in the power of inclusion was a driving force behind my approach to the Reentry Summit in Miami. The panels and working groups weren’t just designed to discuss the issues. They were carefully curated to ensure that justice-impacted individuals were at the center of the conversation, leading the dialogue and driving the development of solutions.

This commitment to inclusion is deeply personal. It’s rooted in my own experiences and the understanding that successful reentry is a communal effort. It requires the active participation and collaboration of all sectors of society, including — and perhaps most importantly — those who have walked the path of reentry themselves.

The leadership of justice-impacted individuals at the summit wasn’t just symbolic; it was a testament to the power of inclusion. By placing these individuals at the center of the conversation, we created more effective strategies and affirmed their value and potential, embodying the very values we champion.

The dynamic energy and collaboration deeply moved me at the recent Reentry Summit in Miami. There was an electric air of possibility, a shared understanding that we were not merely discussing problems but actively creating solutions for challenges faced by justice-impacted individuals. Seeing the participants’ enthusiasm at the working tables, I could not help but feel a surge of hope for the future of reentry and the potential of each justice-impacted individual to lead a fulfilling life post-incarceration.

What continually astounds me is the level of engagement in the community. The summit was not an isolated event but a visible manifestation of ongoing dialogue and action. It was a space where stakeholders from all sectors — government, community organizations, businesses, and most importantly, justice-impacted individuals — came together to tackle the complex reentry issues.

The dedication and commitment of these stakeholders were evident in their proactive participation. Rather than merely attending, they brought their unique perspectives to the table, contributing to a rich tapestry of insights that deepened our understanding of the challenges and potential solutions. This active participation was a testament to the power of inclusion, affirming my belief that reentry is indeed a community effort requiring the engagement of all sectors of society.

The Reentry Summit Miami showcased the effectiveness of applying design thinking in the values-problems-solutions-actions framework. By placing justice-impacted individuals at the center of the conversation, we ensure our solutions are rooted in their lived experiences. This approach enables us to create impactful, sustainable solutions, promoting a more inclusive society and better outcomes for those transitioning back into society post-incarceration.

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