Connect with the amazing community surrounding the Omni Group’s award-winning products.

March 4, 2024, 6 a.m.
How Michael Darius Uses Omni Software

In this episode of The Omni Show, we dive into the world of design with the Michael Darius, a protege of Steve Jobs and a pioneering Apple designer. Michael, whose journey with Apple spanned key years of explosive growth, shares his rich history.

Show Notes:

He also delves into his deep connection with Omni software, highlighting how OmniGraffle and OmniFocus have been integral tools in his and his colleagues' processes. Michael's story takes us from his early days of using a koala pad on an Apple IIe, through his persistent efforts to join Apple, to his significant contributions as a senior interface engineer and the first official in-house application designer since Steve Jobs' return.

Some other people, places, and things mentioned in this episode:


Andrew J. Mason: You are listening to the Omni Show where we connect with the amazing community surrounding the Omni Group's award-winning products. My name's Andrew J. Mason, and today we learn how designer Michael Darius uses Omni Software. Welcome everybody to this episode of the Omni Show, and today we have Michael Darius. He's an Apple pioneer, and honestly, if you don't know who he is in the Apple design community, it's my honor to be able to introduce him. A protege of Steve Jobs, he's worked with Apple from 1999 to 2005. Maybe lesser known in his portfolio is that he's done photography work for brands like Macy's and Forbes and TechCrunch. And Michael, you've just got such a rich history and I'm so glad that you've been talking about all of it in the recent months. And man, I can't wait to dive in and just excited to have you on the show with us.

Michael Darius: Thank you. That was a thoughtful introduction. It's a pleasure to be here.

Andrew J. Mason: Absolutely.

Michael Darius: Well, just to preface this, I think I still have Ken Casey's business card around here somewhere, and the Omni Group has been like family to me for over 20 years. I feel like I need to name some people who use OmniGraffle religiously that I've worked with, and maybe we can do that at the end. But a number of us, especially the producers, all of our functional specifications were designed using the OmniGraffle. I'm in Omni Apple Vision Pro right now, and I've got OmniPlan pulled up and Gantt charts and the way you've got the Zoom functionality working with the... We've done a great job for right out of the box getting in the map store, so congratulations on that.

Andrew J. Mason: Thank you for that. Absolutely. And Michael, I would love for you to wind back the clock for us. Think back to when you're first getting the job at Apple, was there a catalytic event? Do you remember a series of things that happened, a timeline? And when you actually stepped foot inside, were you aware of the significance of what was happening in that moment?

Michael Darius: I don't know if I've ever not been at Apple. When I was younger, I was using a KoalaPad on an Apple IIe, so it felt like I was at Apple. It felt like I was at the company, I'm using the computer. So once I got a job at Sony, that was one of my first design jobs, and I was like, "Well, if I can get a job at Sony, then I'm going to make the leap and move to Cupertino area to see if I can get a job at Apple." Because I was like, "Well, I'm going to make this happen." So I was sending my resume in every month at least once a month, which was probably the stupidity, and I was determined that they were shredding my resume in the fax machine. Back then they had fax machines. So I finally gave up and I was like, "Ah, all right, they're ignoring me."

Andrew J. Mason: So it feels like the end of the story, but what happens?

Michael Darius: About six months later, after I gave up on sending my resume in, I get a call from Shandra Rica who's a good friend of mine now. She was running the HR department, and I come in and Robert Kondrk, Elizabeth d'Errico, Eric Bailey gave me my technical interview. Eric Bailey basically built WebObjects for NeXT, and I just had the privilege of coming in and beating whoever I was competing against. And that was the day that I met my spiritual family in life. And I would've taken a much less prestigious position, but I got to join as the senior interface engineer, and then I transitioned into the design group because all of my code kept getting thrown away because all the strategic business decisions wasn't very accommodating of how much code we were writing every week. So I was like, "I need to be a little bit more involved on the strategic side." So I, technically speaking, was the first official in-house application designer because we were working with CKS who was still external at the time. So eventually, they ended up getting brought into the company and they built the internal communications department. But the applications group started with me, myself, and we brought in Brian Frick, Oliver Krevet, who died a few years back and remains a true brother and friend of mine. He ended up building out the interface engineering group, and we worked very closely. He would build the designs that I was working on, and they ended up building quite a team. I should mention a few names, because they love OmniGraffle and Apple still very religiously. Some of the processes have been replaced by Keynote designers as soon as Keynote came on the scene. But there are definitely some people who are very true to Omni Group who are internal. I know Tanya Washburn. She loves working on OmniGraffle, Jay Holdsworth, Alec Marshall, Brian Larson. These were producers who had a lot of say over what the functional spec was going to include, and we had this process, so... Oh, Chi Lan-Chi Lam, she designed our whole layout for our design room. Well, we called it the Eye Dungeon, and it had a changing table and all these things, and she did all the furniture for it. It was a lot of fun. We had so much fun with OmniGraffle, the team.

Andrew J. Mason: Amazing. Amazing to hear. Thank you for that too. And thank you for mentioning them. I remember one of our initial conversations a couple of months ago, I was just getting it off my chest that I hadn't been a huge fan of where more current operating systems had gone with everything just looking more flat. But the idea of skeuomorphism is a brilliant thought to me. I remember growing up, I actually had a KoalaPad myself with my parents, and just this idea that there is a real life thing that looks and acts like something that mirrors what's happening on the screen, and then getting to see it show up on that screen and suddenly you have this knowledge transfer that's not... It's just one less thing to teach you because you know what the mental model is that's happening there. Talk to me about how you first encountered this idea of interacting with tech through something that looked and sounded and felt and was just similar to something that you would encounter in real life.

Michael Darius: I think that there's a huge mistake in the way that people use the term skeuomorphism first of all. It's a term that derived from the fact that radio buttons originated from radio buttons in the car on your car radio. The real world parallel to something in the real world that allows you to make that cognitive jump and say, "Oh, okay, I get this." And the way that I hear people who are using the word skeuomorphism is more around the idea that it's this visual style that's kind of dated. And I think that the reason that it obtained that definition is because there was a lot of overly literal interpretations that may have been taken too far. But if you understand that etymology of the term, skeuomorphism, it's actually kind of being bastardized by the use of the term neumorphism or glassmorphism, that it's been popular now that Apple Vision Pro is out. But at the end of the day, everything is skeuomorphism. There's no such thing as the software interface element that lives on a screen that you understand that doesn't relate to something that you're familiar with. That's why I hate the word intuition or intuitive. I don't design intuitive experiences. I design familiar experiences. So if you're always designing for what's familiar, then you're going to work harder to find the thing that connects with a person's mind. And when I think about good software design, I actually quietly am at the back of my mind thinking about OmniGroup. You are the true craftsman of software design. There are no words to say how much is owed to the legacy at NeXT that OmniGroup created, and it was really such a privilege to get to be there so early on, and now to be talking with you is even more fun.

Andrew J. Mason: This is a blast, and thank you. When you're at Apple and you're seeing these designs or actually being a part of these designs taking shape, between when we last talked and right now, I took the liberty of listening to your Twitter space with Marc Hemeon, and to me, it sounded like you use this phrase, and as soon as I heard this phrase, I'm like, "I got to talk to Michael about this." This phrase of conscience. It's almost like after this 20-year hiatus, you've been reactivated and re-engaging with the design community, and in a sense, wanting to be a conscience around thoughtful design. Why do you feel that time has shown up for you now? And if you had a charge to lead your message to the world almost, what would that charge be?

Michael Darius: I haven't really been very active on social media and with my writing and things like that, because I didn't become a designer because I wanted to become a design influencer. I became a designer because I wanted do great work and have a private life. But it's been 20 years now, and I'm like, "Well, if I died tomorrow, there's a lot of knowledge that would be going to my grave with me, and I would be depriving a lot of people of some very important information about processes that change the world." So that's what I'm doing now. I'm making the effort. I'm not doing it because I want notoriety. I'm doing it because, if the book I'm working on doesn't end up in a book, then at least people will have access to this information.

Andrew J. Mason: In some way, I feel like that might be difficult because you're not just sharing an opinion on something, although you are, but also, "Hey, here are just the facts that I've bumped up against. This is what I've seen."

Michael Darius: Oh, no, I've got plenty of haters, believe me.

Andrew J. Mason: Well, I've read... I'm looking through it and I'm like, "Man, there are some strong opinions here. Wow."

Michael Darius: They either hate Apple or they hate designers or I don't know. It goes with the territory.

Andrew J. Mason: And I even wonder, I don't think it's as much a reflection on you as much as it is, people just have really strong opinions about stuff in the design space, which that makes sense. You're passionate. You do something with passion, and then that's what shows up for you. Let's shift gears into the Omni space. You mentioned being a longtime fan of OmniGraffle, OmniFocus, would you mind even just selecting whichever one makes the most sense and diving us a little bit deeper into why you say that and what your usage is?

Michael Darius: Maybe we should start with OmniFocus, because one of the things that makes me really weird at parties is that I look at everything in terms of focus perspectives and engineering perspectives. So if I'm at a party, then there's probably something that's going to come up and I'm going to relate to it as being like, "Well, does that need its own ProjectPerspective?" So I have been diagnosed by family members as being out there because of how attached I am. Actually, it's more that I'm used to working with engineers who refuse to work with you unless you're prioritizing your own to-dos in ProjectPerspectives. And so it's strange. I feel very socially awkward when I am surrounded by people who aren't expecting that from me.

Andrew J. Mason: That's incredible. So before we even have a conversation, let's really compare notes on what our OmniFocus setups look like.

Michael Darius: Exactly. You manage to build something that is an irreplaceable [inaudible 00:11:22] in personal productivity that has changed my life forever. And the way that I use OmniGraffle is a totally different story, but starting with OmniFocus, when I'm not prioritizing personal priorities on FocusPerspectives using OmniFocus, it's usually because I'm on vacation or something, or I'm trying to forget about how much work I have on my plate, but I always find that I always do my best work when I'm using OmniFocus

Andrew J. Mason: So kind. Thank you so much for that. And I remember, I think it was 2008 or so, OmniFocus first comes out and standing on the shoulders of the skeuomorphism principles of the icon is an actual folder, a purple folder with... And you get the idea that organization, some sort of mental clarity is going to be happening here. Man, gosh, I almost don't know where to take the next question because there's so many directions I want to take this.

Michael Darius: And let's circle back around to OmniGraffle also because I definitely want to answer your questions about that, but I feel like I don't know how to talk about the rest of the products in the ecosystem that you guys work on without talking about OmniFocus first, so that's why I mentioned that.

Andrew J. Mason: Great idea. Let's do that. So any examples of how you've accomplished specific tasks using OmniGraffle or just random ways, "Hey, this is how I'd like to use it."

Michael Darius: Most of the way we used it was in a way that was sort of the in-between, between the fact that we weren't permitted to use wire frames because Steve only accepted high fidelity mockups for everything. But there needed to be enough basic guidance for what was going to be a functional part of the application. So that basic guidance, OmniGraffle played and nice in between. So the designers weren't feeling like they were being micromanaged by some lofty producer who was trying to talk down to us. They were like family. They were like friends. We worked together, we were collaborative. If there was something that was left out of the functional spec, the designers helped get it in there. And if there was something that was incorrect about the way that a work process flow worked or was represented, then we had very forgiving relationships and we would figure out how to just make it work where. There was no time to fret over that. But all the functional specs that we had usually had at least one workflow, usually multiple workflows per product, and I would mock things up myself, workflows. Most of my work was done directly in Photoshop, so I was usually taking the functional specs that had been thought through by a producer and then turning those into actual pixels.

Andrew J. Mason: What a cool bit of information. I love getting to hear that too. And in one sense, I feel a little bit bad because I have the, what do they call it, the curse of knowledge of having seen your portfolio... Actually portfolio is the wrong word, a running log of just all the different things that you've gotten to work on in the Apple ecosystem. So just ILife stuff, iTunes stuff, the GarageBand stuff. There's just so much to it.

Michael Darius: When Steve returned to the company, he gutted about 30% of the staff, and I happened to be one of the people who was brought in to reinvent the company. So I was really fortunate for that. So what that meant was I got to be the one designing all the Webpoint application. As soon as I got webmail 1.0 out the door, that's when every single functional spec started heading my way. It was my job to work on all of them. And it was one of the only projects that we had that we were so much in a hurry to get out the door because Gmail already had their webmail client, Yahoo had one. Microsoft had their own. So we wanted our own and we wanted to be elegant, a lot like built in mail app, that [inaudible 00:15:09]'s team and the [inaudible 00:15:11] systems design team. We had three different design groups. So in our applications group, I got to be a part of the 1.0s. For when Emagic was acquired, I got to work on the 1.0 for GarageBand. It was such a privilege. You have no idea.

Andrew J. Mason: I really don't. I want to circle back a couple of questions ago. You mentioned this feeling when you walked into Apple and had this sense of like, "Man, I'm home. I made it." Your gut, your spirit, just something inside of you resonated almost like a heat seeking missile saying, "I need to belong here and now I found it. Here are my people."

Michael Darius: Exactly.

Andrew J. Mason: I'd love to know any thoughts, ideas, advice you might have for somebody that is maybe feeling some of those identical feelings, that heat seeking sort of feeling where it's like... Especially in 2024, what advice do you give to somebody that's starting now with app development design, just saying, "I know where I want to be. I'm not there yet."? And can Michael from 20 years ago give advice to the person that's maybe feeling that today?

Michael Darius: Well, we didn't have Twitter or Mastodon or any networks back then where we could show our work. There was no Twitter Portfolio Day. Portfolio Day on Twitter is on Fridays now. The main reason I'm on Twitter is because I get to see other people's design work and I get to see what they're working on. So I happen to have a website that I had designed with my portfolio, and I designed my portfolio specifically to be able to work at Apple. The fact that it went around to the right people, and somehow, at the end of the day, my portfolio was found online. So I ended up designing a lot of the hiring processes after that and figuring out how we wanted to hire designers. But now, if there's any one thing that all of us had in common when we were discovering new designers, it was always that there was just some piece in their portfolio that stood out really in a compelling way. So my encouragement is, just keep putting stuff out there that you're proud of, and don't put stuff out there that you're not proud of, because people will only think of you as your worst thing. They'll only look at the worst thing in your portfolio. And just put the stuff that you're proud of out there, keep it up and make sure that people are getting it out there. I look for really well-built design work, and I'll retweet your work out there. Tweet it to me and let me know what you're working on, and if I'm impressed by it, I'll definitely get it circulated [inaudible 00:17:47].

Andrew J. Mason: I just had this conversation with a buddy of mine who loves writing and he's feeling a little bit of the pressure of the internet, the content creation. He actually hates the term content creator because it puts the emphasis on the amount of content that shows up versus the value that a single slice or piece of content can provide. And so this does push back a little bit against what I would consider to be conventional wisdom of today, saying, "Hey, live stream your life, everything that's out there." And you say, hold on a second. Let's think about honoring other people with the content that we put in their direction and only put the things that we deem valuable in their direction, is that kind of the idea?

Michael Darius: Yeah. And design students, they get screwed over. We partnered with the Academy of Art, and I would go and I would interview designers there, and we brought one in who's a really good friend of mine, Wei Wang, but we used to do portfolio reviews and you'd be surprised just how much phenomenal work is out there and people don't get hired just based on their portfolio. And frankly, we would have people sending their portfolios in and we would ignore the vast majority, not because we weren't impressed, but just because people would send in boxes with these really built, gorgeous portfolio boxes. It was very clear that they had spent blood, sweat and tears making this thing, but it still didn't translate to having onto the job experience. And so the hardest leap is getting a person past their place of thinking, "I'm the best because my portfolio is the best." Into thinking, "I don't have any job on the job experience and I don't know how to get it, but this is something that I worked on." And if you have that attitude and you have a great portfolio, then you have a chance at an entry level position or at least an internship.

Andrew J. Mason: I've heard you mention before this idea of humility playing a role in ego separation and saying, "Here you go, world, this is just something I've created and I lay it at your feet."

Michael Darius: There's always someone better than you.

Andrew J. Mason: It's so appropriate that you started this call on an Apple Vision Pro and got to interact with your avatar in that way. And I'd love your take on the overall flow of design and design language with the introduction of something like spatial computing and Apple Vision Pro and pass through where you can actually see the real world behind whatever it is you're interacting with on the computer. Over time, things have really gone in a more, and this is just my opinion, but a flat direction in terms of design. Do you foresee the possibility of things starting to, in an operating system, mirror real life objects again, now that three dimensions is a greater factor?

Michael Darius: There's a huge opportunity with Apple Vision Pro to make things more true to life, more real to life, because you have to deal with the fact there's a window on your wall just sitting there. And if there isn't something that... If it becomes an eyesore at some point, then you're going to be [inaudible 00:21:02] by that, right? You're not going to want to leave it there. So the more windows have to be more like furniture or the more that the objects in the environment have to have better ordinances, right now, when I go to grab a bar, one of the windows and drag it around, I don't know if that... I'm used to having the close bed on the top left of the window. Now it's at the bottom right, right next to the thing that I grab. It's a 1.0 product. You've got to give everyone credit and applause and congratulate the team for producing the first version. I don't know what 2.0 and 3.0 is going to be like. The iPhone didn't even have copy and paste when it was first released. There's a lot of things that don't go into a 1.0 product. So I worked on the gift card experience 1.0 and there's a lot of work that went on after the 1.0 version. But to say that I was involved in the pilot that went out and got to design those workflows for how a person types in their iTunes gift card code, that 1.0 is definitely not what's out there now. There's a lot of improvement. It's a worldwide thing now, but it's a 1.0. What do you expect?

Andrew J. Mason: To the Apple gift card experience, what an honor, what a really cool role to play in the slice of a larger experience like that, to the comments about 1.0, the first version of iPhone versus even 3G where you couldn't have multiple apps open at once. And just I think for people that see the Vision Pro and they say, "Okay, that's a cool trick. Great job." Back pat, and don't look at the longer term game saying, "Hey, we're just getting started." And think about the features that they wanted to put in but didn't make it into this device just yet, and what might we see in the next 24 months even? I get really inspired thinking about that. Michael, I want to create a scenario where the floor is yours, just thoughts that are floating around in your head that you'd love to share with the world. If you have a space and it's a soapbox, billboard to the world, what would you share with folks?

Michael Darius: That I break out in tears sometimes because I think about the amount of care that goes into getting something just a little bit closer to being right and being willing to put in the extra effort to figure out, I'm not going to give up on this just because I'm impatient with myself. But Steve Jobs gets this reputation of being a tyrant and a dictator, and I've been accused of being a tyrant and a dictator, and maybe I should take that as a compliment. I don't know. But I do know that he didn't get that reputation because he didn't care. He got that reputation because we had quality standards that we had to meet, and those quality standards were things that we were not willing to compromise on. That's what makes Apple great. That's what makes the company great. That bar is still something everyone is still trying to up uphold, the bar that Steve set for us. So now it's a work ethic that I bring with me in everything that I do. So the biggest haters that I get online are usually people who want to equate me with being a dictator or want to equate me with being somebody who is a tyrant or something. But all I'm trying to do is just tell the story, and I can't tell the story unless I'm allowed to talk about the people who were instrumental in making these products happen and talk about their standards as being something that's a little bit higher than the average person. Mediocrity was something that we were constantly battling. I think Guy Kawasaki has a new book out about murdering your mediocrity or something like that.

Andrew J. Mason: Very, very well said, Michael. Thank you, and I appreciate the passion that you bring to the process. It shows through. It's funny, I think because of this false dichotomy that if something is engineered or built with precision or logic, then there's no way it can have emotion applied to it, and just hearing your passion come through in that process tells me that nothing could be further from the truth. So thank you for being vulnerable in that way.

Michael Darius: The engineers at Apple are better designers than most the designers are at a lot of the other companies that I've worked at. There's no question about that.

Andrew J. Mason: How can folks connect with you and what you're up to now, what you'll be up to in the future? Are there any great ways that people can find out more about what you're doing?

Michael Darius: Oh, sure. I am @Darius on Twitter X, which I know is not a very popular platform right now, but I'm still there because it feels weird live tweeting from Threads, even though my Threads audience has grown just in the matter of a couple months to almost 8,000 people, which I know those aren't bots, so that means I'm doing something right. So I'm excited about the reaction and the response. I'm @Dariusdesign on Threads, so I'm making an effort to be equally, if not more active there, so I'm not totally supporting the Twitter community. But I am grateful for the response that I've received from Twitter. I've been on that platform since 2007, just under a year. So you don't get @Darius unless you've been on the platform since the beginning. So wherever you want to follow me. If you go to Darius.Design, you can see a bunch of my handles. I try to list a bunch of social networks on there that I'm on. You can even give my Goodreads if you want to see some of the things that I'm reading.

Andrew J. Mason: A fair warning too, to people who go down the rabbit hole, there's so much great stuff, not only from the past, but also what you're doing in terms of design that you'll probably recognize, skeuomorphism principles and the like. Michael, so glad that you did this for us. Thank you so much for hanging out with us. It's an awesome honor to be able to talk to you. Thank you.

Michael Darius: It's so much fun, Andrew. Thanks for having me.

Andrew J. Mason: Hey, and thank all of you for listening today too. You can find us on Mastodon You can also find out everything that's happening with the Omni Group at