Designfulness (Part I): What if Design Thinking isn’t ultimately about Designing?

Jason "TOGA" Trew, PhD
7 min readOct 8, 2022

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“We don’t meditate to get better at meditating; we meditate to get better at life.” Sharon Salzberg

I love this quote. It easily applies to other practices as well. For example, while I find intrinsic joy in exercise, I also know there are benefits that stay with me well after I leave the pool or track or weight room.

I think games contain a similar duality. The “magic circle” of a game — the space in which play is formally condoned and expected — is a scene of pleasurable engagement. The players, however, have also strengthened their capacity for playfulness, which has advantages beyond our physical and metaphorical playgrounds (e.g., creativity, resilience, etc.)

When I set out to learn about Design Thinking, the reason was practical and direct. I was learning a method to approach messy problems, including how to teach Design Thinking to others who, like me, are not professional designers. Instead, students at Squadron Officer School (SOS) came from every career field in the US Air Force, including the medical corps, engineering, administrative support, and aircrew.

I had attended SOS myself about a decade earlier while in between assignments as a fighter pilot. Design Thinking was not part of the course at the time, but creative problem solving and experiential learning definitely were ingrained at SOS, the US Air Force’s premier leadership school.

I had earlier glimpses of Design Thinking. During my doctoral research into innovation and organizational culture I came across references to it. I knew enough to know it was different from the Operational Design taught in professional military education, but not much else. Now, in my pivot from the cockpit to the classroom, I found myself responsible for the curriculum that was heavily influenced by Stanford’s d.school and IDEO. And so that’s where I started.

After going through hundreds of articles, dozens of books, a handful of design sprints, and a few courses from IDEO and the d.school, I felt confident enough to facilitate workshops on my own and even start writing about the topic.[1]

Image Source: https://dschool.stanford.edu/our-impact/

When a major organization in the Department of Defense asked me to start an innovation and design school, I took the opportunity to reflect on my own journey as a non-designer-doing-design.[2] That’s when it dawned on me: applying Design Thinking to wicked problems can be, like meditation or games, a means to something more fulfilling…but also more difficult to explain.

To capture the distinction I was sensing, I borrowed a construct from another field I enjoy exploring: play versus playfulness. The two are related, but not synonymous. Play is an activity while playfulness is an attitude that can exist outside of play. Likewise, the attitude that comes with the activity of design — but can exist outside of the formal activity — would be designfulness.

As examples, Design Thinking emphasizes empathy, a bias-to-action, and creative confidence. Of course, participating in design is not the only way to cultivate those characteristics. But it was key to my own personal growth in these areas; it is how I learned to be more empathic, more confident, and more willing to take bold, creative risks.

The best analogy I know to explain the growth I experienced goes back to the metaphors of exercise and play. One of the benefits of participating in sports, especially for children, is that it can also be a practice field for sportsmanship. Repeatedly testing yourself against others while still treating them with respect inculcates an attitude that hopefully carries over to other arenas of life. Likewise, Design Thinking gave me the “reps and sets” to hone a collection of designful qualities that enhance my performance as a leader, coach, and educator. Honestly, I think I’m an overall better person for it.

In fact, I have come to wonder if this is actually the best reason for any group of non-designers to engage with Design Thinking. In other words, meaningful participation in design still matters, but not solely to solve a specific problem. Rather, the strategic value of practicing design in schools may be to create problem solvers ready to creatively and collaboratively tackle any problem with empathy, initiative, and confidence.[3]

To be honest, my reflections on designfulness raised more questions than it answered. Foremost, I was wondering if others have experienced this as well. So, I asked and here are some of the responses I received:

“Previously, I thought that Design Thinking was a set of mechanics for consultants. But now I know, deep down, that it is a galaxy of big and small approaches to embrace the unchartered territories of humans. Let’s consider Design’s famous first step: empathy. I used to think that empathy was only about the others, I now understand that it also means knowing oneself better; unchartered territories also lay within. For example, I never start a course with new students without a session on self-empathy; this is key to combining skills and trust and it is key to quality teamwork. ’Designfulness’ is a way of life, a mindset and a daily wonder…”

-Brigitte Lundin, Pedagogical Innovations and Experimentations Manager at Université De Montpellier

“Having led pilots, professional athletes, admirals, CEOs, and even 5th graders through workshops to create everything from business strategies, apps, and bioplastic to spaghetti marshmallow towers and juice flavors, we know Design Thinking is effective. It works so well it may sound like magic, but it works for those you trust: AirBnB, Google, Home Depot, Shell, IBM, Stanford, and so on. But seeing is believing, so instead of being convinced by what you read, why not start by trying it yourself, on yourself?”

-John and Johnny, www.StaleChips.com

“Working in leadership development at Air University, I happened upon Design Thinking as our faculty dove into the innovation space. I’m a natural skeptic, but I watched it break down so many of those self-imposed barriers we often find ourselves limited by when trying to create. Before my stint with Design Thinking, I was prone to say ‘yes, but …’ upon hearing a new idea, but now I like to press pause on my inner critic and allow myself to say ‘yes, and…’”

  • Megan Allison, Director of the Leadership & Innovation Institute and Assistant Professor of Leadership Studies at Air University

“I stumbled into design thinking after years of frustration as an instructor pilot. Routine tasks involved outdated processes and technologies, lacking consideration or inputs from the risk takers using them daily. There had to be a better way! Insightful courses from Harvard, UVA-Darden, Joint Special Ops University and Center for Adaptive Warfighting offered the design fundamentals I needed to launch a journey of iterative effort. These steps highlighted the need to start early, involve end users to identify the right problems and keep trying new solutions.”

  • Joe Stallings, Defense Ventures Program Alum | AF Pilot | International Affairs Strategist

I’d love to hear from others as well. Does this notion of designfulness resonate with you? What stories do you have about how design has impacted other areas of your life? If you’d like to share your stories or provide feedback (another important element of designfulness!), please contact me on LinkedIn.

Thank you to Prof Tom Hardy, Joe Stallings, Megan Allison, and Jeremy Van Egmond for reviewing earlier drafts. These ideas were first articulated in preparation for presentations at Arizona State University’s 2022 Project Management Summit, Savannah College of Art and Design, and the Design Thinking Zeal group. I’m incredibly grateful to all the individuals who invited me to share my experiences with those amazing groups.

Part II can be read here.

The views presented here do not necessarily represent the views of the United States, Department of Defense, Department of the Air Force, or their components.

[1] As one example, see “Introducing the Icarus Institute: The USAF Center for Strategic Design. ” As I started to investigate the scholarship on design more rigorously my ideas shifted. In fact, when I joined an international group of security professionals collaborating to produce a text on how design relates to militaries, I realized that “design thinking” is much broader than I initially understood. In fact, what I was first exposed to is sort of a branded version associated mainly with Stanford and IDEO (which is why I now distinguish their “Design Thinking” by capitalizing it). This is in no way a critique of their work, especially since their efforts to simplify design principles for non-designers was exactly what I needed for myself and for teaching others.

[2] The insinuation of being an imposter is intentional. Also, there is still no design school for US Space Command because I was vectored to another assignment. Before that decision was final, however, I was able to recruit some amazing individuals and we launched a low-res prototype (without any official mandate to do so). The final report is here (see the text box on page 7 for the ‘ludicrous speed tour’ of the month-long program).

[3] Around the same time these thoughts were coalescing, I was happy to find a similar sentiment expressed in the book Experiencing Design. The Designing Your Life books are also enjoyable, though the application of Design Thinking techniques to one’s life is much more direct than I’m claiming for designfulness. Finally, just before publishing this, I did find one reference to designfulness as a collision between design and mindfulness, which nicely matches the opening example.

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Jason "TOGA" Trew, PhD

Commander; Strategist; Philosopher of Technology; Air Force Pilot (F-15C/T-6); Triathlon/Fitness Coach