Night Owls at Apple: The Untold Stories of Late-Night Creativity
Keara Fallon Recalls the Intense and Humorous Moments of Apple's Design Marathons
In an evocative reunion, former Apple colleagues Michael Darius and Keara Fallon reminisce about their groundbreaking work at Apple during the late 1990s and early 2000s. This period, marked by intense creativity and innovation, saw them contributing significantly to Apple's design philosophy. Michael reflects on his journey from interface engineering to a design leadership role, emphasizing his early adoption of skeuomorphic design principles under the guidance of Keara. Keara, on her part, recounts her transition from smaller studios to the influential environment of CKS Group and her role in integrating music and design, which significantly influenced Apple's aesthetic. Their discussion reveals deep insights into the ethos of Apple's design team, showcasing a time of relentless work, passionate creativity, and the forging of a design language that would become iconic in the tech world.
The interview delves into personal anecdotes and professional milestones, highlighting the duo's experiences working under Steve Jobs' leadership. Michael and Keara candidly share the challenges and exhilaration of meeting Jobs' exacting standards, shaping products that resonated with millions. They discuss the evolution of their design practices, from Keara's influence by her time at a MIT Media Lab startup to Michael's focus on internet-enabled applications. The conversation also touches upon the personal cost of their dedication, from Keara's late nights and Michael's sacrifices for the job. Both designers reflect on the legacy of their work at Apple, recognizing the impact of their contributions on modern design and the enduring influence of their experiences during that transformative era in Apple’s history.
Keara Fallon: Well hello Michael! It's been nice reconnecting with you 20 something years after the most rigorous job in my career! (well ok, maybe not the most - but it's definitely up there). I know we reconnected in person last year, but would love to recap where we left off. Of course, when I think of that time back then, there was a very small circle of people working on some very big efforts. What were you up to when I arrived on the scene at Village Green? (and it only took me 20+ years to realize that was a reference to The Kinks - Village Green Preservation Society song and LP)
Michael Darius: Keara! It's indeed a pleasure to reconnect after all these years. Reflecting back on those times, they were certainly intense and rewarding. While we were working at Valley Green, I was deeply immersed in a variety of projects, pivotal to shaping Apple's design ethos during that period. You were one of the first real introductions I had to skeuomorphic design principles. Before I moved into more of a design leadership role, I enjoyed doing the interface engineering for designs of yours. You always had great taste in music, and I remember countless late nights working our asses off to some pretty glaring music at times before I took some ownership of the studio atmosphere.
Keara Fallon: Oh how funny that is your memory! And how bad mine is to think it was Village Green. There I go channeling Steve's need to have Easter Eggs in everything... I was convinced it was Village Green. Did I tell you about the iMusic Review page where he said he loved it but the background sheet music has to be "Yesterday" by The Beatles?! I think I did... anyway... it was right around when Apple Corp was negotiating with Apple Music (The Beatles) to have a music service. I think it was a bit faster to negotiate the copyright on the background image than the rights to Apple Music! haha. But yes, I came from smaller studios before I entered the machine of CKS Group - we knew them as the CKS Partners... the guys who led Apple design internally before he left for Next... and the same partners who came back with their design company when Steve came back. I entered that world around late 1998. We listened to a lot of music anytime we worked on design. That's just what creatives do, ya know! I was also helping manage a few major label bands and around that time started my own indie label, so I was a bit into the music scene back then. How did you end up with so much responsibility at Apple?
Michael Darius: After the success of iTools when Apple finally came out and introduced its "Internet Strategy", there was no shortage of projects that had a need for someone who understood how to design 'Internet-Enabled Apps".
Keara Fallon: (For the record, I didn't even know what Skeomorphism was at the time - to me it was 'digital realism')
Michael Darius: Well, the CKS group came from the print world which at the time meant pulling protruding (real world objects) stock imagery into web pages which looked more like they were designed in Adobe Pagemaker than they were like an application. But there was this interesting hybrid between what a web app could be and ways the print world could protect important design principles that most dot coms at the time simply didn't understand.
Keara Fallon: Very good points that maybe are easier to see now in hindsight!
Michael Darius: What do you remember the most about that time period? It was intense for all of us! I remember tearing conference rooms down and turning them into war rooms until projects were out the door. Indeed.
Keara Fallon: I mostly remember getting home between 2AM and 4AM with my cute tuxedo black cat, Oliver, hearing my car engine and running to greet me and walk me home from my parked car. He was typically starving for food and attention. I didn't have much of a life except for seeing my bands on weekends. I came home to shower. It was a time when there was an unspoken competition of who would stay the latest... and the first person to leave lost. I also remember the insanely funny moments. And my eye twitch that lasted 9 mos after we launched at Macworld January 2000. It was the start of a new century... It was Y2K... it felt big and meaningful. We were at the beginning of a very long journey. We were trailblazers and could feel it! It was special!
Michael Darius: I remember it referred to as "visual metaphor research". Hahaha, my eyes still twitch to this day!
Keara Fallon: Yah, I actually did nerve damage and have a droopy eyelid (insert image of Thom Yorke here). Did you know what the hell we were doing back then? Or like me, were you just trying to be useful and were you as addicted to the work as I was?
Michael Darius: I found that when I knew I had someone important to impress (SJ) and that if I didn't pass the Steve test that it meant my work would probably not see the light of day I worked harder to get it right the first time. Looking back at your work on some of the greatest design teams around, what project or achievement are you most proud of and why? How has this experience shaped which projects you've agreed to take on since?
Keara Fallon: Well, I suppose I am still the most proud of this work and the work before it. I had come from an MIT Media Lab startup called Perspecta - we were breaking the interwebs doing fly through 3D interfaces, 5 channels of video, etc. I was the lead there and learning how to code while being paid to design. It was amazing. Apple via CKS was more tame comparatively when you look at what we were making, but in terms of household impact, nothing I've done since was as impactful as what we did then. Come to think of it, the work we did in 1999 has paved the way for no less than a million startups... Evite and Yelp come to mind, Squarespace, etc... anything that had a template or a review. I suppose we also started Mac.com and the iDisk which really was the beginning of Public Cloud storage. We designed all of those experiences! We had no clue where it would go but we knew it would be big. Look at the Cloud now...
Michael Darius: What was the most nerve-wracking part about having Steve Jobs as the biggest client you've ever had?
Keara Fallon: Yah, it was like some sort of father figure. We were shielded a bit from the wrath thanks to Hiroki Asai and Andy Dreyfus, and had our daily visits from Robert and Eddy... to make sure we weren't slacking. Or maybe just to make sure we were still breathing! The room was very small and we never left for food. I suppose it modeled all the FAANG companies since that brought in cafeterias so their workers would not leave. They knew if they brought food to us, our addictive design brains were like bats in a cave and we would work until it was perfect.
Michael Darius: I remember treating him like a big baby who didn't know how to use a computer to get the reactions we wanted out of him.
Keara Fallon: Yah, there was some idiot savant going on there for sure! But let's be clear... we wanted to be there. We didn't want to miss out on the feedback. We wanted to make cool design. You were down the hall from us - and why do I have a memory of some weird glass room. Did they airlock you?
Michael Darius: You're right, and Apple was just a little better at taking creative risks than other companies.
Keara Fallon: And here we were like... this is so tame. But what is interesting is I remember him pushing us to experiment on some weird UI. I did a hexagonal interface for something... and only just realized the other day when I came across an image you posted, that my idea actually saw the light of day. Now if I can remember what it was... that's age for ya.
Michael Darius: They moved us around a lot, once interface engineering had more than just me and John Baily and we brought Oliver Krevet on board they moved us into what would eventually be branded as the 'iDungeon'.
Keara Fallon: The creativity was palpable. We had to suspend any sense of HR violations to get through those crazy long hours. Language, jokes, references... everything was game. The delirium fed the creativity!
Michael Darius: I remember you and Meg Frost sitting side by side with Hiroki and computers facing back to back with myself and John Baily sitting opposite you.
Keara Fallon: And who was our silent programmer guy... CKS guy... long hair?
Michael Darius: I don't remember.
Michael Darius: John Baily was the development lead for Apple.com so getting to work beside him was like getting to work with one of my heroes.
Keara Fallon: All I know is we did it by divide and conquer. We put Easter Eggs in everything. Meg was queen of cute (founder of CuteOverload.com too!) and so she did many templates that were playful. That rubbed off on my more information design style, having come from the MIT thing. I did a rigid but mod resume template but also a whimsical party invite. I remember designing the Music, Sports, and News pages... These templates were so novel at the time. How did you code them when we were still in HTML 1.0 land?!
Michael Darius: Lots of iframes and nested tables, LiveStage Pro was a QuickTime authoring environment that I was known for designing more resource-intensive apps. I think we were at HTML 4.0 at that junction.
Keara Fallon: Now you're getting ahead of yourself - HTML4 in 1999?
How were you able to sustain work-life balance? Were you also doing 20-hour days with us or did that calm down after MacWorld every year? You stayed for 8 years... what was it like after that initial CKS integration?
Michael Darius: Netscape had been around for a few years, the W3C had a spec for HTML 4.0 in 1997.
Keara Fallon: I know Meg and Kevin Angel went on to lead Apple.com - you seemed to go onto a bit of everything. What were some of your official roles there after the mac.com launch?
Michael Darius: To be specific, I left on my 5-year anniversary which we can get into later but yes, 20-hour days were standard. I lost a marriage to it because she thought I was cheating on her. It never calmed down, after 5 years I was ready to take better care of my health. After we launched iTools, I inherited two areas that I'd become the design gatekeeper for. Compliance for Internet functionality in desktop apps and Aqua compliance for third-party developers like Virex who wanted to know how to make their apps Aqua compliant. My official title changed to 'Senior Designer' immediately after you left which remained the same for the following 5 years, but none of us took official titles very seriously. I was just glad to get to work on the things that I wanted to without having to get too heavily involved in management politics (even though pictures of me as a child were in the slides for the 100 Managers Meeting when iPicture was being presented).
Michael Darius: I'd love to know more about the paradigm shifts you went through from working with MIT's Media Lab to working with CKS group, I imagine the working processes shaped your design sensibilities into the impressive work you've done to date.
Keara Fallon: Well, when I think back to the MIT startup, it was founded by three people who were engineers that loved design... obviously! because they went to the Media Lab. So they just 'got' me. I was raised by an engineer dad, teaching me coding Basic and we also built a 486 PC. I always had the technical in mind. That served me well with Lisa Strausfeld, Earl Rennison, and Nicolas St. Arnaud - the founders of Perspecta. They were backed by Negroponte... so I was used to the R&D and Enterprise atmosphere and the endless hours of experimentation. It was in our DNA. That translated well to Apple, but I just needed to put a plastic coating on it to make it Consumer ready.... which leads me to post Apple...Apple trained me to make technical things look friendly and inviting. We excelled at hiding the technical and normalizing the web for ma and pa. Steve used to say "make it so my mother will understand it".
Michael Darius: A question (revised) you may have missed from earlier: What was the most nerve-wracking part about having Steve Jobs as the biggest client you've ever had, and how did working for him affect the quality of the output that your clients can count on from you in 2024?
Keara Fallon: I'll be honest... Steve was just a leader back then, not a legend yet. It's like knowing the lead singer of a band before they've made it big. We didn't know he'd be as big as The Beatles. He was more like Beck at that point. Plenty of people knew him and loved him, but he didn't own the world... yet.
Keara Fallon: I was not intimidated by him at all. In fact, I was even more headstrong then than I am now... the world was my hamster! Part of me was constantly trying to impress him, and the other part of me was like... "What does he know about good design?!" The fact was, he DIDN'T know what good design was or how to make it. But he sure as well knew what bad design looked like. Lucky for him, he never saw it. We had a design theme happening that Hiroki helped set the tone for. We embodied it and owned it. Sure, we individually added our own flavor to it, but it was an essence that reverberated for decades. I've only recently seen it fade.
Keara Fallon: As for experiences after and how the quality of output then impacted me after... I'd say my expectations were high - both of my clients and my designers. I was (metrik + team) also embedded over the years as an auxiliary design team... funny enough, just like we were as CKS at Apple. I always instilled the rigor in the design process. Some of the in-house designers just didn't have that drive. It could be trying at times.
Michael Darius: What a profound and poignant statement: "The fact was, Steve DIDN'T know what good design was or how to make it. But he sure as well knew what bad design looked like."
Keara Fallon: Btw, that is not a slight on Steve - he just had instincts. That was what drove him. It's why we never had User Testing back then... we didn't do design by committee. It freed us up to move more swiftly. In fact, it made us more productive. I miss those days where design rhetoric and 'thinking' didn't take over our guts.
Michael Darius: In retrospect (looking back), is there anything you can say about the era of 'digital realism', 'hyper realism', and 'skeuomorphism' that you helped define that still contains design principles you find useful in your design practice today?
Keara Fallon: (thinking)
Michael Darius: Were there sacred processes that you take with you in your work today?
Michael Darius: Any particular rituals from that time period that are unique to what makes Keara's design processes special?
Keara Fallon: Thinking out loud here... I have a few 'tools' or principles, as you say, that I use and illustrate regularly to get the job done well. I feel strongly that we underutilize the depth of infinite space within the digital sphere. I say sphere because spatial computing is here, and we are still putting things on the surface. I think dimension is significantly underplayed or underutilized. Skeuomorphism has its place for reducing cognitive load and providing a safe and friendly, inviting foyer into the digital realm. But for me, it has its place. That leads me to my process...
Michael Darius: The only thing that flat earthers are most afraid of is 'Sphere Alone.'
Keara Fallon: I tend to think in terms of objects, but in the abstract, per se. For example, I firmly believe in sketching flows and objects before I ever go to the blank screen. Once I have the concept out of my head and in black ink on my non-lined, spiral-bound A5 notebook, I will take the abstract and make it more concrete. For example, If it's a screen design and it has flow, I know the generic elements of the screen and will miniaturize them into iconic form and that helps give me a reference point as I draft the user flows. It's flat detailed iconography but it does also reduce cognitive load when relaying the flow to a client. They see the abstraction of the page and it helps them get it. It also does almost 75% of the work for my wireframes!! Sketching, planning, abstracting in mini form... "is it one of these, or one of these?" and then something like "well I know I need a chart and also a description"... next thing you know, the requirements of the client are met at the high level, and you can make the sophistication come out in the visual/graphic execution stage.
Keara Fallon: I think we are seeing Skeuomorphism come alive in all of the ChatGPT renderings. In fact, it's making those infinite imagined worlds understandable. They feel like places we can go. My goal will be to not make Skeuomorphic icons but make dimensional worlds in our underutilized spatial computing. Polygons "Be gone"—the worlds of Roblox Meta—and move into traversing a Skeuomorphic environment. That is where I will embrace it again but we don't need a Skeuomorphic object sitting on the surface of a 2D screen anymore. Steve would be ok to try it in the 'New World'.
Skeuomorphic Design: Lessons from Apple's Golden Era is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
Michael Darius: I'm of the belief that there is always a designer out there that is better than me, and I embody that statement with some of my greatest design teachers being Kenya Hara, Dieter Rams, and Susan Kare. Are there any who came before you who you would like to thank or at least recognize as having shaped your values into who you are today?
Keara Fallon: We come from different reference points, and I tend not to be heavily influenced by other designers... but I'd be lying if I wasn't influenced by a few. In order, #1 Bruce Mau was a huge influence back when I was in school at CCA(c). He was heavily influenced by Architecture, as I am too. He designed for them, and I started my career doing the same. I still have Architect clients. That leads me to #2 Diller and Scofidio - Performance Architects, I like to say. They did some very cool work in their books that were on a lovely publisher back in the 90s. And an actual graphic designer #3 Lucille Tenazas - she, like myself, was heavily influenced by architecture and post-structuralist methods of design. I very much fell into that camp naturally and it shaped my sense of space and structure in all that I do.
My biggest influences are musicians, both old and new. I find it feeds my visual design. I've also spent a great deal of time recording, and the layering is so much akin to what we do visually. The difference is that music is my passion and mixing is a joy, not a job... but it's the only other thing that keeps me up a 20-hour day! If you think about it, the work I do today is architecture in a sense. I develop software from the front back. I still need to concern myself with the structural aspects and whether it's scalable or structurally sound as they say...
Keara Fallon: So what is the future for you, Michael? Clearly, you are forging into new territory with AI and graphics - which no doubt, I hope to collaborate on with you. What are your instincts for how the past has shaped your future?
Michael Darius: It's so important for a designer to master an art outside of our craft, and it's inspiring to me that you've found that in music. Photography is the art outside my craft that I try to use to give back to humanity.
Keara Fallon: Oh yes, that too - I don't carry my Minolta anymore like I used to, but I do keep my Instagram to more artsy type of pics. You are phenomenal at the visual.
Michael Darius: Thank you! I try to do something to train my eye every day. To be honest, this newsletter has uprooted a lot of emotion in a lot of people who knew SJ personally, and in many ways, it is pulling the design community together, but maybe more importantly, it's pulling the alumni community together. Even this interview with you, which I thank you for taking your time out to do, is bound to pull on people's heartstrings. It's the people that made the work worth the investment we all made, and that's the part I miss the most about not being on internal projects. What's next for me is to continue defending the legacy of the Steve Jobs family by surrounding myself with people who gave their health so that we could all enjoy the devices we use every day to go about our day. I most certainly hope we will get to work on projects together again as well.
Keara Fallon: Well, I have one lasting image in my mind I wanted to share with you. After our big launch about 6 months before I started metrik, Steve invited us to the original Richmond Pixar location for a private screening of ToyStory 2. It was informal and casual (- he was indeed wearing the black faded black turtleneck and ripped jeans. We had that in common! ) After a brief tour of the miniature models and the space, we settled into a small mini viewing theatre to watch the film. Steve sat right next to me. I thought it was cool then, but the memory is even more magical. I think that is true for many of us. The day-to-day was indeed stressful, but the legacy of Steve lives on in all of us and brings a smile to my face. I was truly lucky to have such an experience at such a young age, and he instilled a level of craft in us all. I will forever owe him that debt - one I can never repay.
Michael Darius: What a wonderful note to end on. Thank you so much for your time and friendship, Keara. I'll be sure to include case samples of any projects you'd like to draw attention to when we send this out.
Keara Fallon is Head of Product Strategy and Design at Metrik and has a wealth of experience with startups to corporate Fortune 500 clients, in all aspects of strategic product design development. From her early career at Perspecta (MIT Media Lab), CKS Group (Apple) and USWeb (Mattel, Shockwave) and then developing her own clients at Metrik (Sony, Yahoo, Motorola, Skype, Realtor.com), she has a keen sense of how to lead a team through a streamlined process of transforming business goals into intuitive and engaging customer solutions.
Keara’s studio has been a strategic force working with clients locally and internationally in the fields of Architecture, Big Data, Biotech, Cloud, Enterprise, Infotainment, Legal, Lending, Messaging, Mobile Platforms, Music, Real Estate, and Telecom. She is known for her work with Sony, Motorola, Skype, and Virtustream (Dell/EMC) and more recently, UnitedLex for helping to solve their next-gen Legal product strategy and design challenges.
Skeuomorphic Design: Lessons from Apple's Golden Era is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
Instructions on how to access my design services: