What the hell is Design Thinking Anyway?

Jaime Medina
7 min readFeb 13, 2020

“What the hell is Design Thinking anyway?”

The question was ejaculated out during a discussion group with the same pessimistic impulse as a deflating balloon zipping across the room - first soaring to an apex, then landing flaccidly on the floor. The tone of the question seemed to imply “Design Thinking” has had the very same trajectory: once a vaunted concept, now all but entirely dismissed. Yet it was said in the same way a child would while listening to the grownups talking shop — spastically interjecting an idea filled with equal parts bravado and naiveté, but wanting attention and an answer — immediately.

It was a perfectly valid question and I stopped for a movement to roll the idea of the thing around in my head, wondering if it was like a box that needed to be opened and its contents extracted and then enumerated one by one, or if it was, perhaps, more like a room into which one enters and is surrounded by an atmosphere of secret knowledge.

What does it mean? The question was relentless and infectious. After all, shouldn’t I be able to convey all the implications of the term right there and then? Shouldn’t I be able to clearly articulate a tenant or two? I went to art school after all. And then I went to engineering school, didn’t I? I have written about it, spoken about it, lectured on it, driven workshops through it, and built teams around it. I can whip up a PowerPoint slide stack with the best of ’em (apologies to the Tufte crowd.)

I got home and looked over the pile of notebooks I’ve filled with sketches of UI’s and blobs of code, and thoughts of thoughts. I skimmed over the smeared graphite, and drawings of diagrams comingled with figurative sketches, and words of verse, and stacks of dog-eared texts bursting with post its, and outlines in UML, and all the other fucking yadda-yadda-yadda that has consumed me to no small extent over the last 28 years of designing products and applications, and writing code.

But what is it? The nagging was insistent as if somewhere deep down in the bowels that sit between the limbic mind and the frontal lobe there was some Jungian archetypal entity calling bullshit on the whole thing.

I dismissed the creature immediately but that did little to quell my uncertainty.

And so I did what I always do when working through a problem: I grabbed a pen and one of those afore-mentioned notebooks still having an empty page or two and started writing.

Certainly, Design Thinking (capital D, capital T) is all the rage, with no shortage of proponents. But it is not a new idea. I leafed through my copy of Productive Thinking by Max Wertheimer who explored the thought experiments and visual-thinking process of Albert Einstein, and who advocated for learning by understanding the essence of the problem rather than by rote. Published in 1945, so much of the text still rings true.

I rifled through the small library of texts I’ve amassed over the years and made like Solomon — cleaving them in two general groups. On the one hand, Design Thinking seemed to want to be a discrete set of problem-solving tools from which one could choose and apply to a given problem. On the other hand, it claimed to be almost a state of mind in which one must exist and by which one can produce novel solutions that have hitherto proved elusive. A kind of Design Ontology. But the primal “I” inside me quickly pointed out that the truth of it all most likely lies somewhere in between. And so I set about the task of surrounding the concept with a few concepts of my own to help define, once again, what design thinking means to me.

Design thinking is Collaborative

“And those who were seen dancing were thought to be insane by those who could not hear the music.”

– Megan Fox tattoo.

I’m not a big believer in designing alone. Design is a team sport. Yes, team dynamics are complex, there’s always a contrarian; there’s always ‘that person’ who derails the conversation, but a good design lead can take control and guide the conversation — culling where needed, digging where appropriate, and exploring where there’s an opportunity.

There is a collective intelligence that emerges from a team that often can transcend the efforts of any single individual. This is not to disparage all the one-person design shops out there that produce genius every day. But building a responsive design team is one of the most valuable things an organization can do. Whether it’s product design, web UI’s, or application development, a self-collaborating team is a great way to suss out design problems and reign-in effective design strategies.

Design Thinking Is a Process

“Life ain’t all sunshine and rainbows.”

– Rocky Balboa.

Designing is no different than any other creative effort: cobble something together, look at it from every perspective possible, kick the tires here and there, cutaway, join together, build-up, tear down, spit and polish, rinse and repeat — over and over and over again. Or at least as long as the deadline will allow.

The saying ‘Don’t let the perfect be the enemy of the good’ is often bandied about, and for good reason. Well-earned design chops are all about knowing where to edit, and when to abandon.

Adding structure to the process is helpful, but so is knowing when to diverge from it. Codifying the structure is recommended and helps to inculcate new designers and to track utility and productivity.

Design Thinking is Iterative

“Repetition is the mother of learning, the father of action, which makes it the architect of accomplishment.”

– Zig Ziglar

I like to think of design as a process of convergence. The vicissitudes of designing are often sinusoidal — hitting above the mark at times, then below it — all the while trying to manage the delta. Little by little, you get there. Little by little you shorten the great distance between the initial glimpse of an idea and the long winding path to get there. What begins as a spark serves as the driving force that guides a team to that instinctive locus.

How a team gets there is often a speculative process of putting forth a proof of concept, a straw man, a mock-up, or a design candidate and then ruthlessly tearing it down.

How a team converges on the solution is at the very heart of design.

Design Thinking is Stoic

“Of each particular thing ask: what is it in itself? What is its nature?”

– Hannibal Lector quoting Marcus Aurelius

What?

Yep.

Design thinking is Stoic; that is to say, designing is often the process of maintaining control, of keeping emotions in check, of cultivating an ethos and an understanding of the very nature of things. That is not to say that raw emotion has no place in design. Good design can be filled with rage or passion or joy or sorrow. But stoicism in the design process can help one capture the very essence of the thing in an applicable way.

The Meditations by Marcus Aurelius is as good a text on Design Thinking as anything ever written since. Where ever I see the tool-box approach, I see stoic heuristics at work. I’ve built my own set of rules over the years and continue to refine them as I move from design to design. I often hear mention of Occam’s razor which strives not to complicate matters, but rather to find the simplest solution. I have found that there is something akin to a stoic lantern that exists to help guide us by the light of our experiences — good and bad. I find this approach to be invaluable from the diagnostics perspective.

Design Thinking is Merciless

“If you meet the Buddha, kill him”

- Linji Yixuan

I abhor the sentimental. Or, insofar as designers tend to fall in love with their designs, I abhor the sentimental tendency toward attachment to a design. I call it Masterpiece Syndrome. I’m sure this is a malapropism on my part, and I’m sure another definition for this term exists somewhere. But I’m co-opting it here.

We often get sentimental about the things we create. Don’t. Keep the essence of the design, or better yet, find the kernel and then find 100 other ways to express it. After the 100th, go for 101. Here is where a team is invaluable. In all things that constellate around design: function, color, form, meaning, and connotation — there is most likely another way. Find it, build it, tear it down, and build it again. This is the act of discovery.

Design Thinking Embraces Failure

“…Experience is frequently the result of bad judgment.”

― Henry Petroski

Design is the opportunity to be fearless. Take it and run with it. Design is the opportunity to discover failure, to learn from it, and then, to overcome it. Where else can you find the line step over it, smirk, then step right back behind it?

Design is luxury. Revel in it. Devour it. Disrespect if a bit and then revere it. Acknowledge the history of design, and then completely ignore it. Somewhere in between all the hours of failure, you’ll find it, pick it up off the floor inflate it and let it go.

At the root of it all, Design Thinking is a tool and a mindset. It gives us the tools to reason about a problem and find a path to solve it.

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