Original post can be found here: https://medium.com/@jasonmichaeltrew/designfulness-part-ii-undisciplined-by-design-7572c4b0542a
Designfulness — inspired by the analogy of play versus playfulness — is when the attitudes that enable design remain even apart from the activities of design. Part I offered a short list of how this has shown up in my life; for example, in being a more empathic leader and a more creative educator. Part I also included quotes from others who see designfulness in their own experiences.
Admittedly, anyone acquainted with Design Thinking would recognize the designful attitudes highlighted in Part I. “Creative confidence” and “a bias to action,” for example, are core concepts of design with obvious value in other areas of life. However, instead of delving further into those familiar ideas — many with direct and unchallenged benefits outside of design — Part II wrestles with a more fundamental, seemingly undocumented, and perhaps controversial way that designfulness plays out, at least in my life. To invoke yet another designful catchphrase, it is a “low-res prototype” of an embryonic idea about being undisciplined by design.
First, what does it mean to be “disciplined”?
In the thesaurus, “discipline” is connected regulation, control, and regiment. All three synonyms are closely linked to hierarchical organizations and the military, in particular.
In my experience as a military leader, I have witnessed how loosening strict control helps foster creativity, motivation, and innovation. Plus, while empowering others to solve problems has immediate practical benefits, it also contributes to their long-term growth as problem solvers. I credit my engagement with Design Thinking for providing that insight, as well as the confidence to act upon it. Yet, there is another, more intriguing scenario that links design and (a lack of) discipline.
Discipline implies order, as both a verb (to issue instructions) and a noun (a lack of chaos). It is also about punishment when orders are disobeyed or when disorder threatens stability. In academia, for example, a discipline establishes expectations for its disciples — which obviously shares the same root word — who risk their credentials and credibility if they violate the conventions of their field. Indeed, entry in the field is sometimes called indoctrination, which is another synonym for discipline.
Design, of course, is itself an academic discipline. Like all disciplines, it has its own unique ways of thinking and communicating that are applied to distinctive problems. Naturally, the sub-disciplines of design have multiplied and differentiated themselves in subject and style. Still, one characteristic that seems to remain across all the “designerly ways of knowing, thinking, and acting” is the inclination to be integrative.
Integration plays out in multiple ways during the design process: considering multiple perspectives to grasp the emergent context, weaving past precedents with novel challenges, co-creating solutions with others, balancing disparate criteria, and generally pulling in whatever is useful to craft “what works and what wows.”
The vital role of integration means that design may be considered an undisciplined discipline, one that balances disciplinary purity with pragmatic expedience. This is meant with all due respect to designers; indeed, it is a trait I admire, advocate, and try to emulate as a leader, educator, coach, and strategist.
I should note that — though the dictionary states otherwise — I am not equating “undisciplined” to a lack of self-control. Indeed, in the sense used here, the opposite is more accurate. Being “undisciplined” is deliberate; hence, it is by design. It is not heresy for its own sake. Instead, there is a strategic decision of when, how, and why to exercise “enlightened irreverence” (though it is still heretical and thus requires willpower to persevere once the decision has been made).
Regarding that decision, there are certainly times when following the status quo is appropriate or when morality demands one should challenge order/orders (i.e., structures or instructions). I am addressing a different possibility: when the goals are uncontested, but the “disciplined” approach is hindering, instead of helping, achieve those goals. In that case, being committed to the objective may require willingness to alter or abandon established approaches. After all, as USAF Chief Master Sergeant Ian Eishen says, “a checklist is the best way we knew how to do something yesterday.” And in a world of complexity and competition — a world that is “wicked once over” — today’s context could be much different than yesterday’s.
For instance, yesterday’s “checklist” directs me to avoid certain physical, organizational, and conceptual spaces. Yet, encouraged by designfulness, I have found myself doing all sorts of unorthodox projects, collaborating with a variety of individuals, and addressing important topics without certified expertise (e.g., resilience or emotional intelligence). Such “cheating” on my job (narrowly defined) or venturing outside my formal academic credentials has created serendipitous opportunities I never would have anticipated or accepted before adopting a Design Thinking practice (see the caption below).
Reflecting on those experiences makes me appreciate just how far designfulness has stretched me and — this is critical — enabled me to advance my organization’s strategic goals.
Of course, by helping me assess and apply yesterday’s wisdom, being undisciplined by design is working well today; but I know that tomorrow I should expect to be surprised. In fact, that ability to marinate in ambiguity and move with humility and agility through the everyday unpredictable is precisely what design has conditioned me to do. To return to the sports metaphor from Part I, it is the ready stance and athleticism honed on the field, carrying over into our lives off the field.
Naturally, whether in a sports field or an academic field (including design) or life in general, there is a place for discipline in many forms. And when the means are not an end in themselves, but simply yesterday’s wisdom offered as a useful starting point for today, the discipline that postures us for tomorrow includes a disciplined approach to being undisciplined; that is, being undisciplined by design.
Thank you to Prof Tom Hardy (SCAD) and Jeremy Van Egmond for reviewing the initial draft of this post. 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.
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.
 In Part I, I speculated that this may be the strategic reason to teach design techniques to non-designers. It is analogous to the attitude of sportsmanship we hope student athletes learn through the activity of their specific sport.
 Cross, Designerly Ways of Knowing (2006), p. 100.
 Liedtka and Ogilvie, Designing for Growth: A Design Thinking Tool Kit for Managers (2011). According to Nelson & Stolterman, designers work with “an integrated, complex whole that is not cleaved into clear, distinct, and separate taxonomies” (The Design Way, 2014, pp. 18–19).
 I hesitate to use “expedience” without heavy caveats because of the negative connotations. A “minimum viable” explanation is contained within the forthcoming Springer Handbook of Military Sciences, which also offers a novel historical basis for design as a natural human skill. This is a point, however, I hope to unpack with more rigor in a future piece.
 This speculation does not deny the rigor of design, which a SCAD professor recently described as “a systems-thinking process that is definable, repeatable, measurable, scalable and actionable” (personal correspondence with Prof Tom Hardy).
 The restriction may be externally imposed through explicit rules or implicit cultural norms. Admittedly, it can also emerge internally; we often “discipline” ourselves to live within self-imposed boundaries instead of being our “full freaky self.” For me, being undisciplined is as much about pushing against my own presumed limits as it is about “orbiting the giant hairball” of the institution.
 Personal communication, December 12, 2021. To be clear, there is much hard-won wisdom baked into the way we do things. As we say in the flying world, “training rules are written in blood,” meaning that the rules exist to prevent past mistakes.
 For example, in the USAF, that includes the charge from our Chief of Staff to “Accelerate Change.”