DLGP

Doctor of Leadership in Global Perspectives: Crafting Ministry in an Interconnected World

From Free Birds to Jail Birds: Wicked Problems

Written by: on February 26, 2025

I love watching birds, especially now that my kids bought me one of those fancy feeders with a camera that sends live stream images to my phone. Seeing each one flitting in and out, pecking at seeds with a calm purpose, makes me smile. The simplicity of their actions is a peaceful backdrop to the complexity of the world beyond, where problems often seem as chaotic as the flapping of bird wings.

Yet, just as birds instinctively know how to navigate their environment, we, too, must learn how to approach the challenges of our time. Capitalizing on earlier research by Horst Rittel and Melvin Webber, who first organized problems into categories labeled “tame” or “wicked,” Joseph Bentley and Michael Toth sought to explore how contemporary challenges could benefit from the findings of those studies. Problems defined as tame “lend themselves to straightforward solutions while wicked problems were inherently difficult to solve.” Examples include building a website for a company or optimizing staff scheduling for greater efficiency.[1] Examples of wicked problems include improving education or reducing mass incarceration, but these don’t have straightforward solutions. They are interconnected with many different factors and often require a combination of strategies that must evolve over time.[2]

In Exploring Wicked Problems, Bentley and Toth examine wicked problems, including their systems, stakeholder conflicts, and the idea that a flexible, iterative solution could provide the best solution.

The Tame Problem: Easy Peasy

When we think about tame problems, it’s easy to feel comforted by how simple they seem. They are usually pretty straightforward, with a clear scope, and the solutions are either already known or easy to figure out. For example, building a website for a small business will require a layout design, assurance that it’s user-friendly and that basic functionality is included. Luckily, many tools, templates, and “off-the-shelf” models make this much easier. You can also test iterations in a controlled environment to see how they perform quickly.

Adding More Wickedness to Complex and Unpredictable Problems

On the other hand, wicked problems are large, messy issues that don’t have easy fixes. Mass incarceration is a classic wicked problem because it is tied to so many different factors—economic inequality, racial disparities, outdated policies, and even the influence of private prisons that incarcerate people for profit. In her book, The New Jim Crow: Mass Incarceration in the Age of Colorblindness, Michelle Alexander said, “The system of mass incarceration is not a system that can be fixed with a single solution or a quick fix. It is a complex, interconnected problem with deep roots in our history, culture, and politics. To truly dismantle it, we need a fundamental transformation in how we think about race, justice, and equality in this country.”[3]

Mass incarceration is a wicked problem that will need more than simply tweaking laws or making minimal reforms; it will require a significant systemic change in how we think about justice to address social and economic inequalities. There is no one-size-fits-all solution, and progress will be slow with a lot of circular debate. Also, what works in one community might not work in another, and what seems like a step forward can sometimes bring even more significant problems or, as Bently and Toth say, “Add more wickedness”[4] that needs flexible, evolving strategies to adapt as we learn more and realize new hurdles.

Conclusion

While the distinction between tame and wicked problems may be helpful to some, I didn’t find the categorization or this book particularly helpful. Real-world problems are rarely as neat and clean as these categories. Challenges can feel tame initially but evolve into wicked problems over time.

Furthermore, wicked problems aren’t necessarily impossible to solve. They may require ongoing attention but often involve incremental improvements rather than looking for a single, final solution. Bentley and Toth argue that while wicked problems are complex, people addressing them can benefit from applying systems thinking—considering each issue holistically and exploring various solutions from different angles.[5]

Whether solving a tame problem like building a small business website or addressing a wicked challenge like mass incarceration, the key lies in understanding the nature of the problem. For tame problems, clear guidelines and established solutions can lead to success. However, when addressing a wicked problem, flexibility, collaboration, and long-term commitment to meaningful, incremental change will be important. Bentley and Toth’s exploration of wicked problems reminds us that while we may not have all the answers, approaching them with patience and adaptability can lead us closer to solutions[6]—just like birds finding their way back to the feeder time and again.


[1] Bentley, Joseph C., and Michael A. Toth. Exploring Wicked Problems: What They Are and Why They Are Important. Bloomington, IN: Archway Publishing, 2020.

[2] Wedell-Wedellsborg, Thomas. What’s Your Problem? To Solve Your Toughest Problems, Change the Problems You Solve. La Vergne: Harvard Business Review Press, 2020.

[3] Alexander, Michelle. The New Jim Crow: Mass Incarceration in the Age of Colorblindness. Tenth anniversary edition. New York London: The New Press, 2020.

[4] Bentley, Joseph C., and Michael A. Toth. Exploring Wicked Problems: What They Are and Why They Are Important. Bloomington, IN: Archway Publishing, 2020. P.189.

[5] Ibid.

[6] Ibid.

About the Author

mm

Jennifer Eckert

Operations and fundraising director, people connector, believer in second chances, fights poverty, supports justice reform, lives a life integrated with Matthew 25.

9 responses to “From Free Birds to Jail Birds: Wicked Problems”

  1. mm Ryan Thorson says:

    Thank you Jennifer for your thoughtful post. Can you share an example of a time when a problem started tame and became wicked?

    • mm Jennifer Eckert says:

      Good question, Ryan. I had to think about that one. I came up with a few, so then I had to sort out which I wanted to publicly disclose on this platform. I’ll share that a few years ago, when I worked at the food bank, local city employees had a day designated to volunteer at local charities. It was very meaningful for the workers to serve alongside their neighbors at places such as the food bank, homeless shelters, etc.

      As a former state employee, I knew this option was not offered to state workers, so I collaborated with my lawmakers to draft a bill to create it. Initially the verbiage allowed 16 volunteer hours per year, which was later scaled back to 8 hours and finally landed on 4 hours annually. The bill was heard in committee and made it to the Senate floor for a hearing but ultimately failed because of the standard boilerplate language. It stated the criteria for places where employees could volunteer, including nonprofits that did not discriminate on the basis of gender, race, class, etc.

      What I learned at that moment is that LGBT is not a protected class in Oklahoma. While the bill never mentioned that group, a few lawmakers feared the public perception if state employees chose to volunteer at one of the many local organizations that serve this population. The root of the matter was less about LGBT but rather the ingrained distrust that exists for state employees. The whole thing was eye-opening, and the outcome was disappointing, especially when the intent was to build team synergy by serving together in the “mission field.”

  2. Jeff Styer says:

    Jennifer,
    Love bird watching as well. Once this semester is done, I will head up to a spot on Lake Erie to view the migrating songbirds.
    Mass incarceration is a wicked mess, not just a problem. You suggest it will require systemic changes to adequately address it. How hopeful are you that this nation will find the courage to make the necessary changes?

    • mm Jennifer Eckert says:

      That sounds lovely, Jeff. What a perfect spot to watch the awe and wonder of God’s creation. I am hopeful that incremental changes can and are happening. However, it is doubtful that in our lifetime, we’ll see mass incarceration scale back very much. Fear is a powerful emotion rooted in rhetoric to such a degree that the general public is fearful of anyone who has been in prison, no matter how minor or major the charge. People who lovingly donate to causes to restore the prisoners are also the ones funding political agendas that include tough-on-crime measures.

      It’s a mess, as you said. BUT GOD….has the power to do anything. I’ll hang my hat on that note.

  3. mm Shela Sullivan says:

    Hi Jennifer,
    In your opinion, what are the most significant factors that contribute to the complexity and “wickedness” of the mass incarceration problem?

    • mm Jennifer Eckert says:

      Hi Shela,
      Lack of education, lack of desire to learn more about the nuances of the problem, the counter forces that reignite fear once it may have been quelled a little, and a lack of the same vernacular. These are all key issues that prohibit meaningful change in the efforts to reduce mass incarceration.

  4. Adam Cheney says:

    Jennifer,
    I can’t wait to move to my new house (in God’s timing…) so that I can set up my new bird feeder with a camera. I actually have a bird feeder set up on my front porch just out my office window so that I can watch them while I am working and on zoom.
    I also appreciate your push-back a bit on the book. I agree that there is much more nuance to problems and that they can adapt and change. Do you think it is helpful to designate a problem you are working on as a tame problem or a wicked problem? Or is it helpful to designate your response as, this is something I can get done versus this is something that will take continual work?

    • mm Jennifer Eckert says:

      When you move, I will celebrate by sending you a new birdfeeder for your new home. God’s timing.

      You asked if it was helpful to designate tame or complex problems. Honestly, not really, but your question prompted me to recall that earlier today, I asked myself how much I operate with System 1 thinking vs. System 2. I think my norm is System 1, and it has mostly served me well; however, at this point, I am not motivated to learn more or apply the ideas of tame and complex problem definitions. Just dive in and work on the aspects you can leverage at the moment.

  5. Debbie Owen says:

    Jennifer, I love our Bird Buddy too! You send me a couple of your videos and I’ll send you a couple of mine. 🙂

    In tackling wicked problems like mass incarceration, what role do you believe community engagement and collaboration play? How can stakeholders ensure that diverse voices are included in the decision-making process?

Leave a Reply