Jordan Moore Intuition-led Designer

The Park Editor Made Me Do It

We tend to build a story out of past events to make sense of the present, with varying degrees of accuracy, but I’m almost certain that I can attribute my career path to the skatepark editor from Tony Hawk’s Pro Skater 2 on PC. This is my short ode to a game that I believe changed the course of my life.

It was the Christmas of 1999 when the lesser-known PC port of THPS2 arrived in the Moore household. I was completely obsessed with that game. After blitzing through the career modes of all the skaters, and all bonus characters, my sights were set on finding all of the gaps in the game (for the uninitiated, a gap is linking two or more objects together via a trick, eg jumping between two buildings). Gaps, in hindsight, was an excellent mechanism way to extend the game beyond the core gameplay of achieving the goals and scores for each level, and it certainly gave me many extra hours of enjoyment out of the main game.

Practical Paradigm Shifts

But I still wasn’t done with the game yet. I wasn’t ready to let go. Luckily I found an early online community within a site called Planet Tony Hawk. If memory serves me correctly, Planet Tony Hawk linked to a forum provider called Delphi Forums where there was a dedicated community to Tony Hawk’s Pro Skater 2 for PC. There I met people who had found ways of hacking the game files to adjust things like view distance, add new tricks, and insert new graphics into the game.

This wasn’t straightforward at all. I recall being frustrated with these fan-made tools that came packaged with plenty of warnings that it could corrupt save files and it was enough to put me off for a while and retreat to the in-game park editor and come up with creations that the community had been sharing with each other.

Pro Skater 2’s park editor was a superb example of creative constraints. You had limited space to work with, limited tools (ramps, pipes, benches, rails, and trees), and limited themes. Still, the community around the game found ways of building some really creative levels that had me going back to my grid paper at the time (mostly during class) and rethinking a lot of ideas.

My grand goal at the time was to recreate Camp Woodward from Dave Mirra’s Freestyle BMX. I got as close as I could using the building blocks provided, but the pre-packaged themes meant that a lot of imagination was required if I was to share this park online and seriously have people believe that it bore any sort of resemblance to the real thing.

The overriding image of Camp Woodward from Dave Mirra’s game was the “WOODWARD” sticker emblazoned on all half and quarter pipes. If I could get that graphic alone on the pipe texture, that would be enough to give the map some credibility. I returned to the fan-made tools to try and figure out how to make this a reality. This led me down a path of needing to learn a graphics editor other than MS Paint that could export TIFF images, which was the format required by the tool to insert into the game. I had to learn now to export the wooden pipe texture, add the Woodward logo as a layer and resize to fit, export as TIFF, import to the game and hope for the best.

Any hobbyist pushing their skills beyond their comfort zone and getting the outcome they were looking for knows the sense of satisfaction I got seeing that it actually worked.

Then I wanted to share the map AND the texture pack with the world which meant that I needed to build my first website. Thankfully, the early web had Geocities - the tool that launched a million careers in the industry. I had no idea what I was doing at the time (which is still true in what I do today), and I had no idea that there was even a career path in making web things with digital tools.

Many people talk about how the Pro Skater series created paradigm shifts in terms of openness to different music genres, which it did for me too, but my shift looked like discovering an entirely new hobby, building upon new web design skills through tutorial sites like Pinoy71 to try and replicate a lot of the wonderfully overly-skeuomorphic interfaces of the time period.

Subjective Paradigm Shifts

The secondary, more subtle paradigm shift that these games imposed on their players isn’t spoken about so much, perhaps because it’s not as in-your-face obvious as the prior examples.

Skaters see the world differently than the rest of us. Where we look at an unremarkable urban area, a skater can see the potentiality of the environment as a skateable space with lines linking objects, surfaces like benches and ledges being repurposed for entirely new uses. When the line works and things become effortless for the skater navigating the terrain, they are undoubtedly in a flow state in an environment that was otherwise entirely dull to any other human walking through the same space.

The level design in the Pro Skater series subtly encourages you to see things this way. The first time you grind a rail in the game, you don’t look at the pixelated rail the same way again. It’s not something to hold on to, it’s something you can use to navigate the environment in different ways.

This exceptional video breakdown of the THPS series produced by Liam Triforce contains a slightly modified quote from the Godfather of flatland skating, Rodney Mullen:

…Mullen once described skating as connecting disparate information and bringing it together in unexpected ways.

— Liam Triforce

Sounds fancy, but it’s exactly how the world looks through the eyes of a skater. And it’s something Neversoft’s developers integrated deeply into the level design. Ramps lead to rails, then to ledges which can be a short manual away to a quarter pipe creating a nice line for a combo to rack up extra points.

It is quite literally a paradigm shift, i.e a change in how you view the world around you. Everything becomes remarkable and new again because you notice the new potential in the environment. The game, skating in real life, and just walking around looking at things becomes borderline meditative. It’s hard to think of any other game in gaming history that achieves a similar effect.

I like to think this helps stimulate the creative mind. Rodney Mullen’s TED talk that contains the previous quote was actually aimed an audience comprising of people from the tech industry. “Connecting disparate information and bringing it together in unexpected ways” is firmly in the realm of working backwards from magic and creating new value.

What I’m trying to say is: I feel like I owe a lot to this game. There are probably even more subtle subconscious shifts induced by the game that I haven’t recognised yet, and I can’t say for certain that the developers intended all of this by design, but I can say with some degree of certainty that if I hadn’t played this game, I wouldn’t have ventured near Paint Shop Pro, then explored Photoshop for some additional power, or had any reason to create a website on Geocities and try to improve it for a small audience.

Bonus: A Few of My Favourite Levels

My original intention for this was to put together something detailing what I like about some of my favourite levels from the game, but I’ve ended up detouring slightly with a short ode to the series which hopefully makes the whole thing a little more interesting than some guy’s boring list. Note that I’m only listing levels from the original 4 games rather than the Underground series and beyond. Anyway, here’s that boring list…

  1. Marseilles: THPS 2 — A small, contained map which far surpasses all of the pure skatepark competition levels. This level is my happy, Zen-like place. It just feels peaceful. Head to the bowls for intense trick linking, but rolling up towards the road side of the park finds a neat, open urban space at a completely difference pace.

  2. School II: THPS 2 — There are two iconic levels in this list, in that if you mention the game, this is doubtlessly one of the levels that will spring to mind. School II has several different pockets and moving from the start of the level at the top of the map to the bottom and anywhere around is effortless. It boasts two additional secret areas too which add to an expansive map without it playing as something too bloated.

  3. Alcatraz: THPS 4 — I could make an argument for this taking the top spot. I find that the levels in Pro Skater 4 tend to be overshadowed by 2 and 3, yet some of the most creative level design takes place in the 4th game. Alcatraz is the standout. It pays enough homage to the real world location with an unforgettable start area with long stretches of grinable curbs to push both manual and grind balance to the limit.

  4. Canada: THPS 3 — This is the definitive Pro Skater 3 level for me. After the underwhelming Foundry opening level, we’re straight into the diverse design of Canada which features 3 distinct pockets: the car park, the skatepark, and the woodland area which really sold THPS 3 on next gen consoles for me. Where the Foundry level was rigid, blocky, and uninspiring, Canada is big, organic, and is where the 3rd game in the series truly gets started.

  5. New York: THPS 2 — Like Alcatraz, it’s another overlooked real-world level. New York is 3 levels in one but it doesn’t quite flow as well as other levels — in a timed run, you really need to commit to an area at a time rather than achieving all the goals in one run. The central park area is gorgeous and a contrast to the concrete start area, then grinding the subway rails leads to a rewarding traditional NYC bricked area walled off from the rest of the map.

  6. Venice Beach: THPS 2 — I know my list is a little heavy on Pro Skater 2 levels, but I simply can’t leave Venice Beach off this list. It leans slightly more towards street skate styles in a map that has vert areas dotted around the perimiter, but as far as levels with a distinct visual identity go, Venice Beach is very memorable.

  7. College: THPS 4 — One of only two starting levels on my list, College feels very different than anything before it in the previous games. It sprawls to the point of appearing like an open world THPS game and it’s nostagia bright just like your actual college years.

  8. Warehouse: THPS — Iconic. Along with School II, this is one of the levels that will spring to mind for people when you mention Tony Hawk’s Pro Skater. I personally prefer the Hangar from THPS 2 as an opening level that does a very similar job across a similar(ish) layout, but I can’t not have Warehouse on a top 10.

  9. Airport: THPS 3 — I’m not massively into downhill levels. Typically they need a reset to bring the player back to the start when they reach the end of the level which, in my opinion, feels like a cop-out in terms of figuring out a level design problem. Airport is reminicent of the Mall from the first Pro Skater game, yet it avoids the reset issue altogether by ending the decent in a departure lounge area with skateable ramps, rails surrounding the area, and a lower level with more ramps. Heading back to the start of this level is nowhere near as arduous as other downhill levels.

  10. Downhill Jam: THPS — Even though this suffers all of the afforementioned problems with downhill levels, Downhill Jam is FUN. It’s short, it stretches your stats that you’ve accumulated up until this point to the absolute limit with some really challenging gaps and goals, and it still plays well in the modern remakes.

  1. I’m linking specifically to the pipe joints tutorial which was the first place that I can recall doing any sort of UI design resembling skeuomorphic design. This stuff was mind-blowing to me at the time. 

Digital Minimalism

My brother bought me a copy of Cal Newport’s book, Digital Minimalism, a few years ago—long before I realised it was an unexpected antidote to a nagging feeling that I’ve had for quite some time now: the feeling that the colours, vibrancy, and general aliveness of life and everything in it seemed brighter when I was younger.

The world tells you to write thoughts like that off as seeing things through “rose-tinted glasses” or that it’s just nostalgia talking and you’re only remembering the highlight reel rather than the mundane, but I believe that this quiet dissatisfaction was more than just a longing for the “good ol’ days.” For instance, how come I can recall the feeling and texture of the door that led into my late granny’s house? I can’t recall my own front door that easily.

As you’ve probably guessed, this is another “phones = bad” piece, but I want to bypass the usual talk of addiction and how these things are rewiring our brains in unhealthy ways and share my experience in adopting digital minimalism and the unexpected upshot of cultivating something that feels like real-time nostalgia.

Technology Constrains Awareness

Again, I don’t want to cover the angles that Cal has expertly documented, like social media’s repeated spiking and exhausting of our dopamine receptors. Instead, I’ve noticed how my own device addiction has constrained my awareness.

When we cup our devices in our hands, they reduce sensory inputs down to a limited, one-dimensional nature. The screen is flat, there is no variance in texture, no associated smell—it’s mostly just visual representations of things in a small box with no additional senses apart from sound on occasion. Our awareness becomes confined and tunnel-like as the world around us just passes us by.

By contrast, the awareness I had as a child was the opposite. It was multi-sensory, big, wide, open, bright. The act of noticing happened because it was a muscle that couldn’t help but be trained every day. There was no living in a physical world as well as the barely noticeable transition to living in a virtual world that we make every day in the present world. Awareness was unbound, alive, connected.

Integrating Digital Minimalism

I was likely living in denial about phone addiction. I knew I had a habit of using it a lot during the day, but as I started going down the digital minimalism rabbit hole and reading up everything I could put my hands on, something about my screen time seemed off compared to the numbers that various authors were reporting. I was easily clocking up a minimum of 5+ hours of usage a day, which I had thought was an average amount… turns out it wasn’t anywhere near average.

My stomach sank thinking about what I would do if I could get all of that time back. It was the perfect kick up the ass to start living out the ideas and practices in the book. Cal Newport’s suggested 30-day social media fast exercise inadvertently became a 5 months and 23 days fast (and counting) through the sheer power of an integrated habit1.

Then I started getting fiercely protective over my attention—and I needed to go there mentally otherwise it wouldn’t work and old behaviours would take over. Integration had to be brutal to be effective. I adopted language with regards to attention being “stolen” which reframed any culprits with disgust and a burning desire cut them out.

Steps included:

  • Removing all apps except messaging and calls
  • Blocking all notifications from my Apple Watch except for Activity. (The Apple Watch itself might be next in line to go in favour of an analog watch)
  • Mass unsubscribing from all newsletters (apart from the ones I really care to read). This took weeks to complete and was oddly satisfying. Do yourself a favour and don’t use a service to do this for you. The action of pressing the unsubscribe button feels like another micro-commitment to the cause
  • Adding the Screen Time widget to my home screen as a reminder of how much attention has been stolen today
  • Buying a phone safe. Not a novelty one, a proper heavy one that I can’t open until the timer expires.
  • Finding alternative habits. This is one of those things that people say in a breezy manner, but again this requires a brutal change in your identity for it to really stick

During the first few weeks, I found myself reaching for my phone even when it wasn’t in my pocket, which really hammered home the fact that I had some unhealthy, unconscious addictive behaviours associated with my phone that I wasn’t fully aware of until I stopped using it. This happened a lot when I found myself waiting for something.

To remedy this particularly tricky habit, instead of trying to use willpower to stop the action, I bought a nice soft cover A6 notebook that fits neatly in my pocket. Now when I reach for my phone, I pull the notebook out instead and write. And I’ll shamefully admit, I have got significant mileage out of doing the judgey thing of looking at others in a waiting situation with their heads craned down and locked on their device—it gives me a little kick of feeling superior which further helps my integration. The books don’t tell you that part, and I shouldn’t have told you that part, but I’ll admit it here because it works for me and my fragile ego and it might help break the spell for you too.

Progress Report

I’m about 6 months into the journey, and as I mentioned at the beginning, it has been something of an antidote to the numbing of experience that comes with constraining awareness.

I have noticed that:

  • My attention span expanded after learning to lean into boredom again. Remember boredom?
  • My awareness expanded from the tunnelled version that came with my device usage towards something much broader and much more present
  • Instead of feeling nostalgic for childhood experiences (or, controversially, Lockdown #1), I noticed I started to get that same feeling about last week, yesterday, and sometimes, that feeling about this very morning
  • Feelings of time slowing down

Much of the Buddhist literature points out that thinking (or more specifically, the identification with thought) is the source of suffering, and—that sense of dissatisfaction that has crept into my own life the further I get from childhood. I’d add that device usage falls into a very similar category with regard to obscuring our awareness in the immediate now. Thankfully, there seems to be an undo button.

  1. I find a lot of the talk about habits is quite surface-level, not really getting into how powerful and identity-changing actually integrating these habits can be. 

The Illusory Internet

I have been using Twitter less frequently than I used to, and now I find myself in a situation where I’m torn between not wanting to engage with the platform at all, and experiencing a sense of loss aversion that Twitter seems to evoke through its various psychological design levers it enjoys pulling (I have a hunch that they do an awful lot more than dopamine spiking through engagement buttons).

I tend to find that during these drier periods, I’ll get random notifications from people engaging with some of my older tweets. Today, someone engaged with a monologue I shared from Hideo Kojima’s Metal Gear Solid 2 released in 2001 which features horrifyingly accurate predictions about social media before social media even existed as well as some correlations with the 2016 election 15 years before it happened, and it covers the nature of memes before the word entered the broader public lexicon.

  • “The digital society furthers human flaws and selectively rewards development of convenient half-truths.”
  • “The untested truths spun by different interests continue to churn and accumulate in the sandbox of political correctness and value systems.”
  • “Everyone withdrawals into their own small gated community, afraid of a larger forum; they stay inside their little ponds leaking what ever “truth” suits them into the growing cesspool of society at large.”
  • “The different cardinal truths neither clash nor mesh, no one is invalidated but no one is right.”
  • “The world is being engulfed in “Truth”. And this is the way the world ends. Not with a BANG, but with a whimper.”

After rewatching the video on the lazy Saturday afternoon that it arrived in my notifications, I decided to look into the story behind the monologue and found myself in a dark little corner of the web called “Agora Road’s Macintosh Cafe” which hosted a provocative thread called the Dead Internet Theory, written by someone calling themselves “IlluminatiPirate”, referenced the aforementioned scene from Metal Gear Solid.

Some choice language and expressions aside1, the thread raises some interesting points that are worth revisiting at this point in the history of the web. Many outlets have dismissed the theory in previous years, but now that we’re getting a bit of a feel of where this whole artificial intelligence thing is going.

“The internet feels empty and devoid of people”

Initially, I also dismissed the theory, particularly this part of the author’s thread, but I quickly remembered what brought me here - a notification on an old tweet that followed a pattern I noticed that arises when I spent time away from Twitter. The pattern roughly goes: time passes, an old tweet with an ok-ish amount of engagement for an account of my small size is liked or shared by an account that I have never heard of before with no real person in the avatar and a similar-looking bio to others that follow this pattern.


The Dead Internet Theory thread goes on to make a number of claims, some seemingly outlandish and difficult to verify, some unmistakably true such as the claim that bots are generating more conversations and generating more content on social networks than humans than we realise. Elon Musk’s public sounding of the alarm bell/attempt to back out of the Twitter deal/attempt to drive down the value of the Twitter deal, or some combination of all 3 came to mind when reading through the theory.

As it turns out, bots account for 5% of Twitter users2, which doesn’t sound too scary until you read that they account for 21%-29% of the content on the platform. Close to a third of the content isn’t made by humans.

“Ah but that’s just a problem with Twitter” you might say, to which I was shocked to hear that the problem is worse outside of Twitter’s walled garden - 64% of all internet traffic is bots3. Or to put it another way, humans are the minority on the web.

⌘+C, ⌘+V Opinions

We like to be liked. The Dead Internet Theory thread author made the following observation on human behaviour and how we interface with the web, and how it is prone to hijacking:

The internet is a fast way to get info, and info is what moves the mind, and the thing is, the mind likes recognition. When the “likes” were introduced without negative feedback they created a copy-feedback subconscious, they made it so only “positive” opinions be propagated (also accepted), and in it’s way negative opinions to be obsolete.

Now everyone is too cowardly to have an opinion so they copy others they like, they are more likely to follow trends and say what others said, you can also see it with the paranoia of always wanting to listen to experts.

The fast feedback system of the net created a human obsession to be in with trends, getting away from it makes it so you always feel like you are missing out, to play it safe in a trend is more easy as you can copy what already is accepted. In this way, the internet and social media, which was supposed to democratise media by allowing users to create whatever content they wanted, has instead been hijacked by a powerful few.

Creation of original content is how the internet used to work. Anonymous people were willing to express their opinions and try radical or experimental things. More truly original content, uninfluenced by bots or paid influencers, was created due to anonymity as protection against negative feedback. On the old internet, you could start anew every time you posted something.

Now add bots to this. Make it so an opinion be repeated more and more, they are faster than us, so the positive feedback makes is so we copy the bots, and anonymity can’t do anything against it because we can’t influence the bot like we would a human, this is an easy weapon to manipulate people, so anyone with an agenda can use a bot, is designed in a way compared to how clickbaits are made, most won’t read the content, this creates tv-like propaganda where they aren’t influenced by the user and that puts bots at a great advantage over any other opinion because it wont change, and we are copying that.

To summarise: consensus can be manufactured and propagated into the collective networked mind of social media, which will then proceed to reward those who echo the sentiment back into the network, reciting their predefined opinions.

I genuinely set out without the intention of talking about ChatGPT because everybody has it well covered. And we’ve done so well to get to this point in a piece like this without a clichéd nod to it, but we have to at this point, because no doubt you’ve drawn those conclusions already - the “oh dear God, what happens when we let that become part of this?” type of conclusion. It turns out, there is already a subreddit populated purely by ChatGPT both in terms of posts and replies to itself. The two things that worried me the most about that were learning that:

  1. If the usernames didn’t contain the letters “GPT” you could swear that it was normal human beings having a conversation on the web
  2. And these conversations are running on the old version of GPT: GPT2 (the vastly inferior model)

A few months ago, an interaction on Twitter left me very pissed. I have negative interactions from time to time and they genuinely don’t bother me, but this one did. I posted a UI concept for reading multiple branches of a conversation on Twitter - purely as something I would like to see, and by no means a suggestion for Twitter to take seriously as a solution.

It gained a decent amount of attention (once again, for an account of my humble size) and that was 99% positive for the first few days. Then about a week later, I woke up from a sleep and carried out my usual bad habit of checking email, Reddit, and Twitter first thing after waking and noticed that I had 20+ notifications. Again - for an account of my size, 20+ means either: something amazing has happened - likely some big account has shared something, or something bad has happened.

It was the latter. Sentiment had completely changed on the tweet. Every single new notification took the shape of either personal insult, or sniping at the UI concept - no constructive critique, just some variation of “L take” and other short quote tweets and responses.

I tried to find the source - the one who had flipped the sentiment from 99% good to 100% bad, and I couldn’t find them. I looked at the profiles of the people who were behind the more vitriolic responses, and they all followed a similar pattern:

  • No real face in the avatar (or AI generated face for that matter)
  • Poor ratio of following to followers
  • Followers always capped around the 100 mark
  • VAST majority of interactions on their timeline were the same sort of replies to other people

I am now entirely convinced that the interaction I had, that left me rattled in a way that I haven’t felt in quite some time on social media, was either entirely bots, or mostly orchestrated by bots in terms of setting the sentiment for others to follow. This reframing has been both helpful and unsettling.

I’ll try and bring this home to some sort of optimistic outlook. It seems that there is at least some degree of validity to the Dead Internet Theory in that bots are starting to run the show, and set narratives to follow. The fact that you rarely see the words “this changed my mind, thank you” in online discussions is something of a red flag to indicate that perhaps the web isn’t the best place to be having these types of discussions anyway. And, in a way, it’s slightly meditative to detach from the emotion of a fuelled discussion online knowing that there is a significant chance you’re talking to machine code.

The alternative path is to pivot towards true, human connection. I’m having more phone calls with people I know from Twitter than I ever have before, and it’s refreshing to have those conversations that aren’t being watched and scored by others.

The friction of the dial-up web where technology kept us from being extremely online was a flavour of how these things should have worked, so maybe it’s time to exercise some self-control and disconnect. Bots don’t have to be a problem in your everyday life if you don’t spend all of your every life with them.

  1. Slightly meta sub point: I believe we need to get better at separating message from messenger. Pre-filtering happens all the time across online discussions where the source determines people’s views on any particular topic to the point that the viewpoint itself rarely gets past the pre-filtering for an honest assessment against the reader’s own values. 

  2. According to research conducted by Similarweb - 

  3. According to research by Barracuda - 

How to Dismantle a Creative Wall

Zen and the Art of Motorcycle Maintenance by Robert M. Pirsig is one of those books, like Self-Renewal by John Gardner, where I come away from it receiving a completely different message from the author than most of the people I talk to about the piece.

The centrepiece of the book, for me, happens around a relatively obscure passage around the halfway point of the book where Pirsig’s character, Phaedrus, grows increasingly agitated with one of his students who was struggling to complete a 500 word assignment about the United States.

She was suffering from a classic case of a creative blockage in the form of writer’s block. She didn’t know where to start and the size of the task at hand had become so daunting and that familiar feeling of imposter syndrome when faced with the empty canvas staring back at her. The subject was too broad to latch onto a good starting point.

When it came to the due date, the student still hadn’t produced a word. Her creative blockage also impeded Phaedrus when he tried to help her. He suggested narrowing the subject down from the wide topic of the United States down to the main street in Bozeman.

Still nothing.

Phaedrus became angry and shouted “You’re not looking!” at the student. The character remembered a time where he too had too much to say on a subject, and the fact that there are an infinite number of things to say in all directions. The more you look, the more you see.

“Narrow it down to the front of one building on the main street of Bozeman. The Opera House. Start with the upper left-hand brick.” The student returned to the next class looking shellshocked as she handed in a five thousand word essay.

Pirsig’s Brick

Pirsig’s Brick demonstrates the idea that depth of knowledge can lead to greater understanding at the breadth, or put another way: looking closely at the micro level can unblock you for understanding the macro level.

Another way of looking at the issue faced by the student (and any time we face similar creative blockages in our work) is that there is some unseen force getting in the way of flow. In Pirsig’s example, the impediment to flow was the sheer breadth of the topic to begin with. The book also added that:

She was blocked because she was trying to repeat, in her writing, things she had already heard, just as on the first day he had tried to repeat things he had already decided to say. She couldn’t think of anything to write about Bozeman because she couldn’t recall anything she had heard worth repeating. She was strangely unaware that she could look and see freshly for herself, as she wrote, without primary regard for what had been said before. The narrowing down to one brick destroyed the blockage because it was so obvious she had to do some original and direct seeing.

— Robert M. Pirsig, Zen and the Art of Motorcycle Maintenance

Pirsig’s Brick is a tool for seeing things freshly “without primary regard for what has been said before” which creates that perfect tension of challenge and ability enabling flow. Former chess player and martial arts champion, Josh Waitzkin, is one of the few people I have noticed who has made reference to Pirsig’s Brick in his book “The Art of Learning”.

After referencing Pirsig’s Brick, he notes on understanding:

The learning principle is to plunge into the detailed mystery of the micro in order to understand what makes the macro tick.

— Josh Waitzkin, “The Art of Learning”

And followed up immediately after by taking aim at the blockages of creative flow…

Our obstacle is that we live in an attention-deficit culture. We are bombarded with more and more information on television, radio, cell phones, video games, the Internet. The constant supply of stimulus has the potential to turn us into addicts, always hungering for something new and prefabricated to keep us entertained. When nothing exciting is going on, we might get bored, distracted, separated from the moment. So we look for new entertainment, surf channels, flip through magazines. If caught in these rhythms, we are like tiny current-bound surface fish, floating along a two-dimensional world without any sense for the gorgeous abyss below. When these societally induced tendencies translate into the learning process, they have devastating effect.

— Josh Waitzkin, “The Art of Learning”

I have come to learn over time that most of the art of staying in creative flow is just getting obstacles out of the way to let the process unfold on its own. Robert M. Pirsig has provided us with an incredibly effective tool for not only removing these obstacles, but one that also has the added benefit of opening up new ways of thinking and looking at things deeply in the abyss with the intention of bringing new value and insights up to the surface.

Working Backwards from Magic

I have wanted to write about working backwards from magic for quite a while now, partially from a place of laying claim to the idea as some smart minds are taking note of the idea, but I didn’t want to rush out a half-baked take on a concept that I truly believe has the power to change the world.

My ego temporarily entertained the idea of writing a book about the concept, however, even though I believe that working backwards from magic is an extremely powerful approach to creative problem-solving, it would be disingenuous to package a relatively simple idea with 200+ pages of padding to make a quick buck in the self-help/productivity niche. The concept really doesn’t need that much unpacking, it’s almost laughably simple and it has the capacity (at least in my experience) to make conventional approaches to problem-solving look ridiculously convoluted by comparison.

I feel that as an industry (and I’d perhaps extend this towards society as a whole) that we are sleepwalking into a level of comfort where big, bold, radical thinking has made way for safe, tried and tested systems and processes that produce reliably similar results and more of what the world already has. The industry seems as though it is short on new ideas and bravery, and big on conventional thinking and mass-producing more of the same. It’s tilting towards anti-progress. Working backwards from magic is the pushback against this mode of thinking.

What is Working Backwards from Magic?

Put simply: working backwards from magic is an approach to creative problems by using the suspension of belief and any limiting factors to unlock new value.

It is a tool that can be turned towards design and development problems, product ideas and/or improvements, essentially anything that would benefit from thinking from new directions and perspectives. It’s an incredibly simple process to describe and, in my opinion, easier to apply than the prescribed templates of conventional creative processes and approaches.

Step 1: Identify the Problem

In order to know where we’re going, we need to understand the problem we’re trying to solve. How deeply you understand it doesn’t necessarily matter, this is more about having something to aim at rather than nothing.

Step 2: Remove all limitations

Leave conventional thinking at the door. It’s of no use to us in this process. Removes all limitations from the problem, all assumptions, all technical restrictions, all preconceived notions and concepts, get all of that out of the way and start from this point because by default, you’re making something new and therefore more valuable. What you won’t want to do is see how others are solving the problem - this gets you back into conventional thinking and solving problems with existing solutions.

Let’s look at the problem Uber were faced with. It didn’t require any deeper definition other than “how do we get people from A to B?”

If Uber looked at what everyone else was doing (reasoning by analogy/conventional thinking using preexisting ideas) they would just have a shinier interface on top of a regular taxi firm website offering a contact form and/or a phone number to call a taxi.

Instead, Uber decided to work backwards from magic and started from impossible. How could you get someone from A to B if this worked like magic? “Teleportation!” Obviously that’s not doable, yet at least, so if not teleportation then what? You would have a personal driver to take you from A to B. You wouldn’t need to be somewhere in particular, this service would know where you are, and you would know how long it would be until your driver gets here - etc etc, and so Uber is born.

By moving all of the limitations out of the way (current understanding of how taxis work, technical limitations, society’s expectations of what a taxi does), Uber was able to create something new and of significantly greater value than the existing solutions to the problem.

The world is full of secrets like this left to discover. We’re lucky we are in software because most of the hardware secrets have been discovered. The web is just getting started and there are millions of life-changing ideas in waiting.

Step 3: Introduce Reality and Meet Magic in the Middle

As we’ve just discussed in the Uber example, it’s not enough to start from magic and leave it at that. There is a need to get real which involves remaining disciplined about keeping conventional thinking at arm’s length.

Working backwards from magic requires you to start from impossible and slowly introduce just enough reality until your solution is as close to magic as possible.

Before Apple took over the world, the old saying was “nobody gets fired for choosing IBM”. Risk-averse people and conformists get left for dust in the long run.

Conventional Thinking vs Working Backwards From Magic

My intention isn’t to encourage a complete rejection of conventional thinking altogether. Tried and tested solutions have their time and place, but at a time where design is self-commoditising in software I can’t help but feel that the industry is declaring “mission complete” and systemising too soon.

Conventional thinking in digital design adopts the generic process of discovery through to completion by passing through all the usual stops along the way: user stories, competitive analysis, personas, wireframes and so on. Such processes are rapidly becoming checklists, or worse - ass-covering exercises so that the designer can blame the process if their work doesn’t quite return on the investment.

  Conventional Thinking Working Backwards from Magic
Starting Point Find existing examples Start from impossible
Process Pre-planned, detailed Whatever it requires
Solutions Already exist, may be combinations of existing solutions Typically new, unlikely to exist
Worldview No secrets left to find The world is full of secrets left to be discovered

The issue with conventional thinking is that it often involves an abundance of rules and processes that rarely produce the insanely valuable outcomes. The possibility space is artificially limited from the start. Ideas that create companies like Uber are left for other daring adventurers and the conventional thinker can only watch from the sidelines and wait for ideas to become mainstream before integrating them.

Working backwards from magic starts from a completely different and grander possibility space. It begins with the simple question: “if this worked like magic, what would that look like?”

“It’ll never work”

For this approach to work, it needs to live in a culture that is open to risk, making mistakes, and learning from failure quickly. We are taught from an early age that mistakes are bad and that learning to repeat answers from books is how to progress in life - in essence: do what everybody else is doing, DON’T think different. I can’t help but think that this leads to the type of ass-covering through a plethora of rules, conventions and processes that have become the norm in creative work.

I have found that, in my experience, working backwards from magic democratises design more than existing approaches which seem to revel in the authority of a UX leader type bringing the timid, naive client and others through the dangerous world of design. In contrast, asking a client “if this worked like magic, what would that look like?” brings them to the table without the need to jump through hoops, or worry about saying the right technical terms or have concerns about whether something can or can’t be achieved.

I have also started to become comfortable with the idea that “it’ll never work” is a good indication that I’m on the right track towards creating new value. “It’ll never work” simply means that it doesn’t exist (yet) and you’re firmly in working backwards from magic territory. Your possibility space is infinitely bigger.

Intentional and Emergent Design Systems II

I believe Robin Rendle’s Systems, Mistakes, and the Sea was a catalyst for several enjoyable articles on design systems since the beginning of the year. Notably Jeremy Keith’s Web standards, dictionaries, and design systems, Frank Chimero’s Gardening vs Architecture, a subsequent, deeper dive in Jeremy’s Architects, gardeners, and design systems, and Dave Rupert’s The Web is Industrialized and I helped industrialize it.

What follows is a contribution to this discussion. I’m still unpacking it but it feels timely to push some thoughts out into the open whether they’re ready or not.

I believe that we are collectively tapping into something important within the design system discourse. Something felt, but difficult to uncover and put into words. However, it is gaining shape with some common themes around the role of humans and machines, order and chaos, industry and liberty.

I’m going to dive deeper into the conversation through the framing I believe helps me most by elaborating on Intentional and Emergent Design Systems.

Recapping Intentional and Emergent Design Systems

It helps to read the original, short article first, but as a brief summary:

Intentional design systems are the typical approach to building design systems: design system first → design/build solutions from the system, i.e intentionally designing a system regardless of the solution.

Emergent design systems start from solutions and work backwards to find emerging, reusable patterns for the system.

The Reach & Scope of Design Systems

As far as I am aware, there is no collective understanding of the desirable reach of a design system. The intentional camp believes that everything must come from the system. By default, the system permeates the entire product.

In an intentional design system, there is no room for chaos. Only order. If something doesn’t fit the system it doesn’t belong in the system. If something cannot be born out of the system, it will not belong in the system. Intentional systems are authoritarian by nature.

Their liberal counterpart, the emergent design system, begins with creativity and chaos deriving patterns for the system later. Decisions start from user outcomes (the sum of all parts) and work backwards to find reusable parts. It’s hard to quantify the reach of emergent systems. It may cover a small amount of the product, and it may cover a lot of the product. It’s not all-encompassing. There is likely a correlation between the number of unique user problems encountered and the overall coverage of the system.

The scope of an intentional design system is large by default and requires some degree of conjectural bloat (code for scenarios that have yet to occur). When components are front-loaded into the process you get wastage as a byproduct. Guesswork and assumptions are part of the product’s DNA. I don’t blame anyone in thinking that this approach is the sensible direction. We’ve been conditioned to believe the next new thing should come first in the chain of events, whether it’s mobile-first, content first, users first - when it comes to building products in design and code, you can be forgiven for adopting a design system first approach.

Although not a like-for-like comparison, it’s interesting to see that the same voices who would bemoan libraries such as jQuery and Bootstrap - two libraries full to the brim of conjectural bloat - haven’t noticed the hypocrisy in advocating for design system first approaches before building up to more complex components. The same voices who evangelise for accessibility damning jQuery for adverse effects on performance and page weight are happy to tax users for a speculative design system1.

In contrast, emergent design systems require only accepting evidence-based patterns and components into its system. It flips everything on its head asking the parts to prove themselves to be replicable and have sufficient utility. They need the gardeners Frank Chimero alluded to.

A useful lens for drawing that difficult line around the scope and reach of a design system might be around the value of tasks the UI components will provide to users. Low-value tasks (the type that provides limited utility such as a terms and conditions page) are perfect for design systems to do the heavy lifting - if not all of the lifting. High-value tasks (such as a search box on an e-commerce product) should require more human attention and deservedly so. Think of a pilot flying a plane full of passengers - the most critical (and therefore high-value) parts of a flight are: taxiing, takeoff, and landing. Autopilot can take care of the rest. You want your pilot at his or her sharpest for those key moments. Your design system is no different.

The Sunk Cost Fallacy of Design Systems

An intentional design system assumes that your design work is done. You can maintain it, of course, but making changes to the system becomes a bureaucratic process.

We’ve industrialized design and are relegated to squeezing efficiencies out of it through our design systems. All CSS changes must now have a business value and user story ticket attached to it.

Dave Rupert — The Web is Industrialized and I helped industrialize it

I remember coming up against design bureaucracy during my time working as part of a large scale product team. We were faced with many new user problems in need of solutions. The team were hellbent on shaping the solution to the problem out of the prebuilt pieces of the design system. Reasoning by analogy. The method of thinking rarely leads to new solutions for new problems. First-principles reasoning was deemed too expensive.

I was met with arguments like “That means we’re going to have to create a new rule for this component, we’ll have to get internal sign-off, the developers will have to invest extra effort, it’ll need to go through testing, do you seriously want to go through all those steps?”

It was clear that we had been designed into a corner by our design system or at least our organisation’s ideology. What if our initial assumptions were wrong? What if we didn’t have the pieces to address these new problems?

I noticed a pattern. If a problem could be easily solved, low-effort, low value, or if it had already been solved - defer to the system. Watch out for when the system pushes back. If the design system pushes back, it’s time for human intervention and invention.

Individuals commit the sunk cost fallacy when they continue a behaviour or endeavour as a result of previously invested resources (time, money or effort) (Arkes & Blumer, 1985). The same is true for design systems that grow in scope beyond a team’s ability to become dynamic to the system and its user’s needs. Decisions are deferred to the system by default, and anything that requires the system to change is met with often insurmountable objections because of the time, money, and/or effort to change the system.

Useful questions to ask when the system pushes back:

  • Do we need to amend the system?
  • Is it a unique case that should sit outside the system?
  • Is it likely to reoccur in different variations?
  • Is it something that should be governed by a design system?
  • Does the system bake in more assumptions than a different approach? (Occam’s Razor is a good guide for software decisions)
  • Does building the best thing involve building it out of the things we’ve already built? Or does it require building something new?

You can tell what type of design system you’re working with if it biases solutions towards pre-existing components or if the system gives you the freedom to invent.

Leaving Room for Creativity

The majority of systems I hear people advocate for appear to subscribe to intentional design systems. Because of this, one of my overriding fears is that design systems are designing designers out of the picture. For years we’ve pushed against the idea of design as a commodity, yet here we are commoditising design down to atomic levels.

“Sometimes you load up a show on Netflix or a song on Spotify and you can feel the algorithm in it.”

Frank Chimero — Gardening vs Architecture

I used to poke fun at the websites of the early 2010s claiming to be “handcrafted”. Now I’m thinking they were on to something. Perhaps “handcrafted” was the wrong adjective, but I think they were trying to describe something else. Something made through more effort, deliberateness, craft, and creativity. These experiences placed more of an emphasis on the importance of aesthetics, they spoke to human ideals such as affordance, familiarity, and metaphor. Flat design lends itself towards low-effort commoditisation and malleability in a design system - perhaps leading to the ideology of “everything that can be systemised, will be systemised”.

There is a certain coldness in the algorithms. You can feel the algorithm in a rigid design system that spans every corner of a product. You don’t want a design system that feels “automated” - well, you might but your users certainly don’t. Your users would rather a product designed with care (dare I say, “handcrafted?”).

The benchmark must surely be what resonates with users - and if that is an amalgamation of predefined components and rules that must work because the system says so, then fine, so be it. I firmly believe that it makes much more sense to start from resonance and work backwards treating users first and systems second.

If I could give an artificial intelligence the keys to fully automating modern design, I’d point it towards an intentional design system. An emergent approach leaves room for mystery, chaos, intuition, creativity and expression - the unpredictable, unique, innately human elements.

Do design systems limit creativity? The answer rests on what type of system you subscribe to.

The worst incarnation of a design system designs designers out of the picture. If I were building an AI tool to displace designers, I’d point them towards an all-encompassing, intentional design system. I fear that we’re blindly running towards automation and we’re giving the algorithms the template our jobs. It’s not hard to imagine a world where No Code technology complements No Design. By contrast, the best incarnation of a design system leaves room for creativity, invention, the human elements.

And my argument is exactly that - we should safeguard the human elements of the design process. There will always be a need for human intervention, the kind of which requires a human eye to correct for optical alignment when the machines produce rounding errors, or perhaps it is our all too human flaws that produce the rounding errors, either way, the goal should be to prioritise people over rules, algorithms, and automation. Ultimately you want to design systems that liberate creative teams rather than systems that constrain creative teams.

Jeremy Keith recently added colour to the idea of intentional and emergent design systems drawing ideological comparisons with language prescriptivists and language descriptivists.

Language prescriptivists attempt to define rules about what’s right or right or wrong in a language. Rules like “never end a sentence with a preposition.” Prescriptivists are generally fighting a losing battle and spend most of their time bemoaning the decline of their language because people aren’t following the rules.

Language descriptivists work the exact opposite way. They see their job as documenting existing language usage instead of defining it. Lexicographers—like Merriam-Webster or the Oxford English Dictionary—receive complaints from angry prescriptivists when dictionaries document usage like “literally” meaning “figuratively”.

Jeremy Keith - Web standards, dictionaries, and design systems

When I first read the article, I quietly took issue with where Jeremy’s interpretation landed. The reasoning up until the ending resonated, but I believed his conclusion put intentional design systems on the side of beauty at odds with the emergent design systems - accurate but not beautiful.

I think we can learn from the worlds of web standards and dictionaries here. A prescriptive approach might give you a beautiful design system, but if it doesn’t reflect the actual product, it’s fiction. A descriptive approach might give a design system with imperfections and annoying flaws, but at least it will be accurate.

I think it’s more important for a design system to be accurate than beautiful.

Jeremy Keith - Web standards, dictionaries, and design systems

How can front-loaded design systems result in more beautiful products than design systems that begin with the end in mind and work backwards?

Then I realised the flaw in my thinking. Jeremy was describing the design system itself, not the fruits of the system. (The irony of my flawed thinking further highlights my own biases towards the emergent end of the spectrum!)

I feel that one further elaboration is required: an intentional design system can create beautiful design systems, an emergent design system can be created from beautiful products.

  1. I’ve been told that a speculative design system makes the point that I’m trying to make with “intentional” design systems much clearer. I really don’t care what label anyone wants to use as I mentioned in the previous article, I’m not trying to make this a “thing”. I seek no such fame. All I want to do is outline there are two competing approaches here which people aren’t talking about. 

Intentional and Emergent Design Systems

There are two competing approaches in designing design systems. I’m going to call these approaches intentional design systems and emergent design systems to create a clear distinction between both.

An intentional design system

This seems to be the default methodology in design circles. The flavour and framework may vary, but the approach generally consists of: design system first → design/build solutions.

I have a few concerns with this way of working with design systems. Front-loading design and/or build with the pieces you believe you’ll eventually need to arrive at a solution creates a limited set of outcomes. Any attempt to create more pieces in anticipation of generating a greater number of outcomes results in conjectural bloat – a cost offset to the user paid for in unnecessary data and time.

Assuming the pieces will arrange themselves into answers means that you begin by painting yourself into a corner with something yet to prove its worth. This variety of design systems thinking usually finds its authors and gatekeepers consulting with the system over answers rather than thinking from first principles. Intentional design system advocates focus primarily on the what and how rather than the why.

An emergent design system

Then there is the opposing approach, the unashamedly cart before horse way of looking at design systems.

This approach is much closer to the user needs end of the scale by beginning with creative solutions before deriving patterns and systems (i.e the system emerges from real, coded scenarios).

Emergent design systems are typically more liberal and agnostic to predefined ideas and pieces. The rules are written as the game is played, not before, which opens up more creative possibilities. The rules committed to code have been proven in the wild and earned their place in the system.

The fundamental difference between the two competing methods is the point at which design decisions become codified as part of a design system. This may seem like a minor point to get stuck on but it touches on an old CSS problem: it’s hard to remove CSS after the fact because it isn’t clear where certain style rules are used or perhaps never used. Front-loading a design system with granular, variable-like CSS rules is as good as saying those rules are immovable and any attempt to move them will have unintended consequences up the design system chain from granular to fully formed components and patterns.

Waiting for systems to emerge, through a continuous process of building and deconstructing, goes some way towards remedying the assumptions of the alternative technique.

Idea Friction

Noun The time between idea cogitation in the mind to manifestation in a sharable form.

One of the biggest challenges in any creative endeavour is manifesting ideas as close to the speed they form in the mind as possible. Ideas tend to have a half-life in that the longer we hold on to them without expressing or capturing them, the more fragmented they become from the original concept.

In general, the faster you can express and capture ideas, the more they stay true and intact. Therefore, verbalising your ideas is the fastest route to expressing and capturing them. It’s the current benchmark.

Writing down ideas, whether by pen or by typing, increases idea friction but enjoys the retrieval benefit of finding them again at a later point in time. Sketching, drawing or visualising through design tools has a much greater rate of idea friction but enjoys the benefit of higher fidelity than other methods.

Idea friction is especially true of any collaborative endeavour where you have an exchange of ideas. If the ideas are being discussed verbally you need to bank your idea, wait your turn, listen and understand ideas from other parties, contribute, notice how it affects your idea, then communicate.

It is therefore desirable where possible to reduce idea friction by shortening the time between idea conception internally and manifestation externally so ideas can be captured and acted upon.

Experience Gaps

I hold a special place in my heart for Pearl Jam’s Yield album, released in 1998. It’s a remarkable album, easily overlooked. At first glance, the cover is pretty forgettable and not unlike something you would find scrolling through Unsplash, searching for the word ‘road’. Yet I’ve heard fellow fans gushing about how the yield sign in the middle of a road that has no junction to yield to and no traffic to give way to is actually a message saying to just yield to experience and let go.

I don’t buy it. Nor did I buy the black and white photos in the booklet taken by the bassist, Jeff Ament. They were dull and uninspiring. Nevertheless, they were my access to the lyrics and the personnel involved with each song, the instruments they played, the sound engineers and producers. These details matter when you obsess about music.

Over a series of listens with headphones on, the album booklet spread out on the floor in front of me, as I often did in the late ’90s before the days of streaming music, I started to notice some unusual things with this once trivial booklet. It started when I was listening to the song ‘Given to Fly’. I took notice of the accompanying photo as it looked like a photo of a statue gazing towards the sky, spreading its wings. The strange thing was that this was the only photo in the booklet that clearly depicted the track, whereas the rest of them didn’t. I flipped through the booklet towards one of my favourite tracks, ‘Faithfull’. I was met with a photo of a concrete building viewed from the ground. Did the building represent something? It wasn’t a church or somewhere you would practice your faith. As I contemplated the meaning behind the image, I noticed that one of the windows near the top was clearly shaped like a triangle, not a rectangle like the others.

I flipped the album closed to reveal the boring cover shot of the triangular yield sign. Was this a clue of some sort? I pored over the other shots in the booklet. The next track, ‘No Way’, had a photo of birds perched on telephone wires with a backdrop of clouds. Again, uninspiring at first glance, but there it was again, hiding in plain sight – an unnaturally shaped cloud in the shape of a triangle! I searched online for ‘Pearl Jam yield signs in booklet’ and didn’t get any useful results. I kept looking and found hidden yield signs in every photo of the book, some more obvious than others; some might even have been my imagination seeing something that wasn’t there.

The band deny all knowledge of hidden signs in the album artwork. Someone was playing a game. And I loved the thrill of the chase. World-renowned computer adventure game designer Brian Moriarty calls attributing personal meaning to sequences of things ‘constellation’, as in the verb to constellate, just as ancient civilizations would have looked up at the stars and grouped them into patterns, drawing connections between points and giving them meaning.

In today’s digitally transformed music industry with streaming on demand, Yield feels one-dimensional. There is no companion booklet to tell me who wrote the words and music for each song; I don’t know what the lyrics are or the visual representation of the lyrics from the artist; I don’t know how the album artwork feels to touch; I don’t know the personnel involved; I can’t see any of the hidden yield signs within the booklet; I can’t see the album in relation to the rest of my collection; and I can’t talk my friends through my collection.

Drew Austin notes in his article ‘Cold Discovery’ for Real Life magazine that physical record collections are tools for people to ‘publically signal their identities’ and

[…] covers are part of a whole regime of organizing information and space that is now in danger of disappearing. While the design of libraries and bookstores prioritizes the coherent visual display of book covers and spines so that people can navigate collections and find the singular physical objects the covers signify, the endlessly rewritable surface of the screen dispenses with that arrangement.

In some sense, record collections were regarded as an extension of ourselves.

Digital streaming favours speed over the old process, which was accidentally meditative in that it was slow and it coerced you into being present in the experience. Perhaps digital is also hampered by the limitations of the screen eliminating the other senses that played supporting roles in this experience, such as touch and smell. As a result, streaming music feels shallow, a little like 360° panoramic photos of a landmark. It looks great for a moment, the novelty of the technology excites you for a moment, but you’re not really there.

New adventures in Wi-Fi

I try not to be a back-in-my-day kind of guy. I’m actually quite optimistic that digital lowers the barrier for creators to make meaningful experiences, and we are yet to see the full array of possibilities in front of us. Brendan Dawes has been exploring such possibilities. His Plastic Player project is a wooden box with purpose-built slots along the top to house a series of slides containing album art, similar to how vinyl is displayed in a record store, and a space to place your chosen card.

Dropping a slide in place triggers a sequence of events beginning with the internal Arduino Yun with an NFC (near-field communication) shield read the NFC sticker on the back of the slide. Once the tag is identified over Wi-Fi, the Pi MusicBox API plays the selected album from Spotify through the connected speakers. To me, Brendan’s Plastic Player is the perfect example of analogue and digital music experiences coexisting in balance and harmony with each other. Other senses are brought back into play – the speed of digital (as a bug, not a feature) is eliminated by the time it takes you to leaf through the collection of slides, select one, and play. It’s not easy to skip tracks, browse, and add thousands to your collection by design. It’s thoughtfully paced; it leaves room for meaning. Decisions are slower and more deliberate.

Brendan’s Plastic Player project makes a screen look like a limitation rather than an optimal interface in this more considered approach to digital music. It’s easy to imagine how we could take the idea further – you could trade the physical slides with your friends and family; you would be able to gift them, as they’re a tangible analogue interface to a digital medium; you could even imagine music clubs sending you random slides each month with the kind of excitement and anticipation experienced when opening Panini football stickers. Best of all, the slides themselves could enable the yield triangles to exist and set up opportunities for another person to constellate and find personal meaning in an analogue space. All of these offshoots let the listener spend time with the complete work of the artist rather than skipping through it or past it. This thought experiment makes room beyond the screen for new ideas.

If we don’t look beyond the screen, we get the benefit of instantaneous delivery but we are left with experience gaps: Areas of potential where digital transformation left behind the meaning and soul of something. I haven’t come here with ready-made tips or techniques for plugging these experience gaps, and if I did I’m not sure I’d want to give them to you either. I’d rather see what you come up with, reasoning from first principles rather than by analogy, through creative invention rather than imitation.

Originally published in New Adventures Paper 2019

Unpacking Design Problems

The best puzzles are the ones that demand more of you. When the answer appears obvious, but you second guess yourself. When you know there’s more to it than meets the eye.

Nob Yoshigahara’s infamous number tree puzzle is certainly one of my personal favourites for just these reasons. It gives you a set of information and asks, What do you make of this?

Puzzles are a great tool for strengthening mental muscles that can help unpack design problems. They push you to adopt a different mindset and perspective, challenge assumptions, study intently, and look closely. Like a puzzle, difficult design problems evoke that same moment of epiphany when you peel back the layers to find hidden truths.

But design challenges are not quite as easy as puzzles, which have the answers hidden in plain sight. With puzzles, all the pieces are available to you: You just need to put it together. With design problems, you need to find the pieces first, then put everything together.

This can be daunting, but there are methods, tactics, and techniques you can reach for to help facilitate these discoveries.

First principles

Although used heavily in the field of physics, Aristotle’s method of reasoning known as “first principles” originated as a means for organic reasoning (as opposed to looking at analogies, which are often riddled with errors).

When applied to design problems, you start with an observation, such as a requirement in a project brief. Then you ask why until you arrive at the most basic understanding of the truth of the problem. This provides a solid foundation to build upon.

First principles force you to look at the problem without using other people’s preconceived ideas and attempts on how to solve it. When you use this approach, you automatically generate new value. It’s certainly cognitively more intense, but in my experience it produces more original and valuable results.

What happens if you arrive at the same conclusion others have already reached? Is this method a waste of time?

Mike Bithell, an independent game developer, sums this up nicely:

“Oftentimes, when trying to reinvent the wheel, you end up with a wheel. But there is a nice moment of ‘huh, I guess that’s why people just use wheels’… that process of justifying the standard is satisfying, if massively wasteful. Still. Cool wheel.”

For a good example of first principles in action, try this Wikipedia experiment. Click on the first non-parenthesized link in any random article and follow the chain. It will lead you down a path toward the most basic understanding of any concept. Strangely, approximately 80% of articles deconstructed in this manner bring you back to the Wikipedia article about philosophy.

Question everything

“Judge a man by his questions rather than by his answers.” –Voltaire

A design problem is only as difficult as the questions you ask of it.

Good questions don’t necessarily lead to definitive answers, but rather further questions. The amount of additional questions tends to correlate with the value hidden within the problem. If a question is easily snuffed out and the conversation cut short, it might not be as provocative as you originally suspected.

Some good starting points for exploratory questioning are:

  • Why is this a problem?
  • What makes you believe this is true?
  • What is your biggest challenge?
  • Who does this well?
  • What question did I not ask that would be valuable to know?

Feel free to use why liberally. Why is like a jackhammer for drilling through a problem’s layers. Why is flexible enough to get to the basic fundamentals (see: first principles), but can also be used to dig deeper into the problem you’re facing.

Sometimes, the best follow-up question is no question at all. A tactical silence can encourage your client to fill in the gap and reveal additional knowledge that might have otherwise been overlooked.

Collaborative understanding

Your strength as a product designer is determined by your ability to provide valuable solutions that address your client’s business goals and objectives. This can only be achieved if you deeply understand the original problem.

I find it beneficial to collaborate intensely with the client to define the problem(s) you’re going to address. Don’t take the version defined in the brief as the be all, end all. Explore it completely, break it down to first principles, build it back up, and communicate the problem back to the client.

This demonstrates your understanding of your client’s problems, your ability to grapple with problems, and your client’s understanding of their own problems. It creates a good starting point, and it’s the perfect time to demonstrate exactly how you’re going to test assumptions and measure success.

“A design lives and dies by its designer’s understanding of the problem. Understand the problem.” –Jared Erondu

A few more back-pocket methods

There are always more ways to test your solutions.

For example, Occam’s Razor is a mental model that suggests that the simplest solution—the path of least resistance—tends to be the right one. Although it isn’t always indicative of the truth, it’s a good technique to help avoid assumptions and analogies.

It’s also worth implementing techniques that help remove biases and ensure objectivity. One of my particular favourites is “steelmanning,” or building the strongest possible counter-argument to your solution. Adopting both for- and against-mindsets as you pursue a solution is hugely valuable; it not only produces a better solution, but arms you with a defence against the alternative.

The path to delivering value in product design isn’t through shiny user interfaces. Like a good puzzle, it lies in your ability to approach the problem from an inquisitive perspective, assemble the pieces of information you need, explore fundamentals and truths, and build back up to the definitive solution.

No one said it would be easy.