Thinking About: Design Thinking & The Fear of Failure

Updated: May 19

Failure isn't an option. It isn't even a word I recognise anymore: The story of almost a thousand press-ups and the birth of Design Thinning™.


Trying is difficult and failure is frightening. Like most people, I don't like difficult or frightening things and am inclined to avoid them. This can prove somewhat detrimental to one's flourishing.


Failure is particularly pernicious. It's how final it feels. And how permanent and perhaps shameful. Like a face tattoo. But it shouldn't be like this.


Now, imagine a system that made children view every stage of their learning journey through such a threatening lens. Pass or fail. Or worse, they're ranked indiscriminately against friends (and enemies). A system where an innocent future can pivot on the exact recalling of a trigonometry equation, a misspelled COAGULANT or not being bored by sitting in chair all day while the big wide world frolics with infinite wonder just outside the stale classroom's window. Disturbing.


Probably you're not struggling to imagine such a thing. You likely lived a similar life of year groups, timetables, exams, little star stickers pasted to your forehead, corner standing, results days, abject fear, unexplained time dilation and endless homework. And if you were born in Northern Ireland like me, a test which determined the entire trajectory of your life at age 11.


So, WTF society? Well, presumably it makes for easier sorting, doing things that way.



Anyway, I'm thinking about failure because I just failed a 1000 pushup, 28-day solo lockdown challenge (it was close, but [excuses]).


Well, that last sentence would have been the internal language old-me would have used.


New-me no longer knows such language. New-me is trying something different. Something I hope will increase my chances of success. Something that should help me better understand myself and maybe even modulate (for the better) the way I think. Step one: I don't say failure, I say iteration now.




"Don't think of it as failure, think of it as designing experiments through which you’re going to learn." - Tim Brown (CEO, IDEO)


Well, Empathise, Define, Ideate, Prototype, Test, then Iterate to be precise. What I've been trailing is applying a framework of Design Thinking to my lonely lockdown health challenge. Design Thinking is a problem-focused framework that is particularly suited to dealing with "unknown unknowns" (as early 21st Century philosopher Dick Cheney would say).


“If I had an hour to solve a problem, I'd spend 55 minutes thinking about the problem and 5 minutes thinking about solutions.” A. Einstein

Design Thinking as outlined by Stanford University's d.School.

Empathise: Who am I Dealing With?

The first practical step in applying Design Thinking to any challenge is to develop a deep understanding of the end user. This proved harder that it initially sounded. The Human-Centered Design Toolkit is a good starting point if you are hoping to learn more about others. If I was working with students I could run a Launch Cycle as proposed by the endlessly inspiring John Spencer or open up IDEO's Design Thinking for Educators. Heck, if I was trying to change culture within schools and communities I could deploy the Co-designing schools toolkit.


I turned to the Waking Up mindfulness app to help me get in touch with my inner self. This is what I discovered:


  • I was forced to do sports I derived almost no joy from growing up. However, when I partook in physcial activities I was interested/intrinsically motivated in (javelin & cycling), I would throw myself at them and could even excel.

  • I really enjoy food and drink.

  • I'm quite heavy

  • My general fitness is low following a recent bout of pandemic lockdown

  • I spend too long working at the computer each day


Define a: Just what is my Real Challenge?

From these insights I am now able to redefine my real challenge or more likely, real challenges.


These are the challenges I identified by applying my experience of the first iteration against what I had learned about myself in the empathise stage:

  • I don't really care about press-ups hence I'm not massively motivated to do them.

  • I lack a discipline for consistency.

  • I'm taking too much of a treat-yoself attitude at the weekends.

  • As I'm quite heavy and press-ups are hard. I may have needed more practice to complete the challenge. Hopefully the first challenge has provided me that.

Define b: Practical Pressures

There may also be practical pressures opposing my ability to complete the challenge eg, work commitments, travel, family etc... Some of these will be predictable and some unpredictable. Considering, and weighing the effect of the unpredictable is an area our human brains appear particularity poor and we tend to be overly optimistic about the unknown. This inherent bias is detailed in the work of psychologist and economist Daniel Kahneman and featured in his dense yet hugely rewarding best-seller Thinking, Fast and Slow. I will try to keep this in mind when planning and try to over estimate this risk by a factor of x3 (as Prof. Kahneman suggests).


Having a clear understanding of my objectives (and hopefully some useful insights) I could now begin ideating some strategies to improve my chances of success.


Ideation: Time to get Creative

This is my favourite stage of the Design Thinking process to facilitate, particularly when working with younger students who throw themselves at the challenge with gusto. That said, I've noticed (as with other creative or self-guided tasks) as ages creep up to around 12-14, heavy resistance to being any way vulnerable in front of peers starts to manifest. The old, safe ways of doing things are gripped tightly.


The challenge is simple: In 3 minutes (this can be shorter but rarely longer) write down as many ideas as possible to solve one of the design problems. I stress to the participants: "I don't want good answers, I want many answers. Any idea that comes into your head, write it down. There will be a prize for the person/team with the most answers".


Once we have our (hopefully long) list of ideas we can begin to parse out the good ones. A good first step I have found is to have all ideas presented, examined and discussed. Often many esoteric ideas heard together can trigger a cascade of fresh thinking and new, more coherent, finely tuned [better-adapted] ideas.


Below are the sum of my proposed solutions for my identified challenges:


  • Implementing Trello for management of the project

  • Better timetabling

  • <strike> Read self-help book about discipline <strike>

  • Clearly outline what is required on a day-by-day basis

  • <strike> ignore weekends entirely </strike>

  • <strike>Do more practice </strike>

  • <strike>ignore weekends entirely </strike>

  • <strike>Give up </strike>

  • <strike> Change Technique</strike>

  • <strike>Change terms of challenge </strike>

  • <strike> Wait until pandemic is over to continue </strike>

  • <strike>Get a personal trainer </strike>

  • <strike>Engage other people in the task </strike>

  • Public shaming

  • <strike> Writing a personal contract </strike>

  • <strike> Tell a friend </strike>

  • Commencing a second iteration of the challenge with same conditions.


Note that although I have decided not to go with certain ideas, it doesn't mean they are excluded for consideration in future iterations.


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There are many tactics for winnowing the hopeful ideas from the brain farts including small group discussion, voting, Dragon's Den etc... The context, project objectives, time constrains and number of participants will play an important role here. It is worth considering that the d.School put an emphasis on rapid prototyping, particularly in the ideating, prototype and testing phases.


Prototype, Testing and Iteration

The most important aspect of Design Thinking is perhaps its iterative nature where ideas are prototyped, tested and reexamined. Returning to any stage of the Design Thinking process is reasonable including revisiting the Empathise stage. What Design Thinking empowers us to do is to learn from each attempt, increasing our understanding of the challenge, the world in which it is occurring and ultimately ourselves. It is a process that revolves us towards a multi-dimensional, real solution with ever greater fidelity. One way to imagine it is to think of the Golden Ratio where we are spiraling from the outside in.


Is the Golden Ratio related to Design Thinking? Maybe.


The Learning Journey

Returning to reminisce of our inflexible, classroom entombed youths, perhaps re-imagine a process that embraced some of the ideas embodied in Design Thinking. Particularly in how they could be employed in relation to assessment. Imagine a journey where the learner is at the center of the experience and engaged emotionally in its development and the quality of its outcomes (to whatever degree). Imagine they took (and were allowed to take) responsibility for those outcomes because they chose the path. Imagine when they fall we don't turn to a dusty file to note that Thom fell over, but rather reach down with compassion and a helping hand and ask, "What happened there champ? Did we learn anything about using cycling as a method for returning from the pub? Shall we have a think about how we can do better next time? Is there anything that I can get to help you?" or say "Don't worry mate, I'll still love you for who you are whatever decisions you decide to make in your life. I believe in you. Anyway I think they can laser those things right off these days."


I'll wrap up by saying that I'm not unaware the world isn't tough and that there may be pragmatic reasons for society and the job market to outline demands and parse competencies, but a process of learning that weaves failure into its pedagogical fabric is one that I believe, at worst recklessly and dispassionately handles learners' psyches, and at best handicaps their ability to reach their full potential.


The fact that certain people have flourished does not evidence the system isn't broken but rather makes me wonder what geniuses have we squeezed out, and how many content, actualized lives have we stymied by feeding the fear of failure throughout our development.


Design Thinking solo is to the disadvantage that I don't have the shared wisdom and experience of a group to draw from to inform ideas and next steps, but I am at least very well practiced at self-criticism.


The final question might be, then how do we implement this. What is the alternative? And that's a great question that I don't have the immediate answer to it. I would love to hear your thoughts about it.



Addendum - My 1000 Press-up Challenge Journey so Far

My experience so far (22/04 - iteration 2) has been revelatory. Not only am I delighted to not find myself under the covers shaking, crying and eyeballing a stark sense of worthlessness as I'd expect with a failed challenge, I'm feeling kinda good. In fact, I'm feeling sorta exhilarated and empowered. I'm optimistic. I'm feeling genuinely engaged with the process and curious to see if my changes will actually effect a difference. I find myself almost looking forward for the next round. I can do this!

I'm Design Thinning if you will.


I will update my first Design Thinning challenge as it continues.












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