THE OMNI SHOW

Jorge Arango: And this is the other thing. At the beginning, you're not going to be very skillful in using the tools, so you're going to be architecting a system whose affordances and constraints you don't really understand yet. So it's much better to just work with a tool, even if unskillfully at first, and then learn about how you use it and what your needs are so that you can adapt it to your needs.

Andrew J. Mason: You're 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 Jorge Arango uses OmniFocus. Well, welcome everybody to this episode of The Omni Show. My name is Andrew J. Mason, and today we're beyond thrilled to be able to have Jorge Arango with us. He's longed to help architect digital products that people trust, and today he uses that expertise to design AI-powered systems that free people to focus on work that matters. In co-founding, Unfinishe_, he helps small and mid-sized businesses do just that. Jorge, we're so excited to have you with us. Thank you so much for joining us today.

Jorge Arango: Andrew, it's such a treat to be here. I'm a big fan of Omni products. I'm happy to talk about them.

Andrew J. Mason: I'm so grateful to have you with us too. How did you first discover OmniFocus? You've mentioned that it was a part of your workflow in your life. What about it has kind of kept central to your workflow over these years?

Jorge Arango: I'm going to go to a place that is going to immediately date me. So I came to know about The Omni Group in general in the early 2000s when Apple released macOS X. That operating system, as I recall, came bundled with OmniOutliner and perhaps a version of OmniGraffle. I'm not entirely sure about that, but for sure OmniOutliner. And I remember there not being a lot of native apps for macOS X when it first launched because everything was coming over from the Mac classic world. And I loved the Outliners and I thought, "Well, here's an Outliner." And I started using it and I have been a happy customer of Omni products ever since. The way that I got your question was about OmniFocus in particular. So right around that time, the hotness in the personal productivity space was an approach to productivity called Getting Things Done, based on a book by David Allen. Although that approach is kind of technology neutral, there were not many GTD specific tools on macOS X that you could use to practice this approach to productivity, to managing your to-dos. And at the time, I remember, I think it was Merlin Mann released a set of scripts. I think he called it Kinkless GTD or kGTD.

Andrew J. Mason: This is right. This is true.

Jorge Arango: Yeah. It was a set of scripts that worked with the pro version of OmniOutliner, and basically turned it into a tool for GTD. And I used that for as long as it was a thing and it was a thing until ... This is the way that I think it happened. I think that Omni ... So it's like, "Oh, look at what people are doing with our tools." And they're like, "Maybe we should make one of these, like an Outliner specifically designed for this." And so OmniFocus came out. So I've been an OmniFocus customer since day zero because ... So I've been using it since before it was OmniFocus I think.

Andrew J. Mason: And forgive me, it just hit me Merlin Mann popularized it, but it was Ethan Schoonover I think that was, that actually had created the kGTD. You're absolutely right about that though. My gosh. So even prior to version one and I remember, yeah, Omni Group started saying, "My gosh, people are starting to use this in the GTD way. Let's go ahead and build a product that backs them up in that way." So maybe zoom it out a little bit and talk to me about what sorts of things have you used OmniFocus for in your work and life?

Jorge Arango: If anyone listening and knows about what the Getting Things Done methodology entails, the idea is to get all the things that you have to do, all the commitments that you have to get them out of your head and onto a trusted system where you can keep track of what you've committed to do either to others or to yourselves. And that's how I use OmniFocus. I think I use it for its intended purpose, which is to keep track of the things that I've committed to. That manifests on two levels. So one level is projects and we can talk about what that means, because there's technical definitions about what a project is. And projects have tasks or commitments or things that I'm waiting other people to do for the project to move forward, and I keep track of all of those things using OmniFocus. I'll add one final thing. I don't use it exclusively to get things done. I also write my daily, like the things that I need to do every day. I do write them by hand. I find that writing them by hand helps me internalize them better. OmniFocus is like my source of truth. And then as I'm going about through the day, I'm just kind of crossing things out either on my iPad with the Apple Pencil or on a piece of paper, and then in the evening I'll just go into OmniFocus and check them off.

Andrew J. Mason: Yeah. We have heard this use case before too, this analog meets digital where the digital is the source of truth that brings forward the information and then the analog shows up where it's like I really need to get this as part of me and also have the focus that it's just limited by the canvas of the one sheet or the one notepad that I have and it doesn't expand into infinity or anything. I'd stopped you there. Keep going, I'm sorry.

Jorge Arango: There are a few areas in which I find OmniFocus really shines. For me, the primary one is keeping context. So if I receive an email and it's something that requires me to do something to follow up and I cannot get to it right now, I cannot get started doing that right now, I need to save that and I'm going to save it into my task list. OmniFocus makes that very easy. There's a keyboard shortcut that I've customized to ... I've got an email selected and I'll hit that keyboard shortcut and the OmniFocus' capture window will pop up and I will type out what it is that I need to do. And then a few days later or maybe a week later or whatever, when I revisit that in OmniFocus, I can very easily get back to the email. And I know that other task managers do this as well. I guess at this point, I've been using it for so long that I've built means to do it with everything in my system. So if I need to get back to an email, I can do it. If I need to get back to a particular file, I can do it. If I need to integrate this with other parts of my workflow, there are ways to do that. And you develop ... After a while of using a tool, especially a really rich featureful tool like OmniFocus, you develop customized workflows and it just makes it easy to get things done.

Andrew J. Mason: Talk to me about this two part. It may be a two part question here, but you mentioned that the tagging system in OmniFocus is almost an information architecture feature in and of itself. And I know having been with OmniFocus, as long as you have, they started with context kind of matching that GTD, you can do one thing and one place at one time to an expanded definition where tags are a feature if you want them, and different people have taken that in different routes. How has that really manifested for you over time?

Jorge Arango: Well, you've described the trajectory. Well, it might be worth backtracking. So one of the key constructs in the GTD approach is that you write down your commitments in lists that represent the context in which you can get that commitment taken care of. So if you have to clean your house, you can only do that when you're in your house. You can't do it in your office, so it doesn't make sense for you to look at that task when you're in your office. It only makes sense for you to look at it when you're in your house. So that's what is meant by contexts here. And in its first iterations, OmniFocus had baked into it the concept of context and you would select ... And I think it was a one-to-one relationship with tasks or a one-to-many relationship in that you had one context that you could apply to a task, but a task couldn't belong to multiple contexts, if I'm not mistaken. And eventually, there was a new version of OmniFocus that came out that replaced contexts with tags. And tags, I'm sure listeners are familiar with tags in other environments and other tools, one of the benefits of having tags over a more hierarchical taxonomy like context is that you can cross-reference things. You can apply multiple tasks to a single ... Sorry. You can apply multiple tags to a single task in this case. So that allows you to create sets. Well, it allows you to use filters. So the way that I use tags in OmniFocus, and this is true of context, but it's also true of tags in general. The way I use them is as filters, because one of the most intimidating things you can have when you're trying to get things done is sitting down to a list of 500 items. You look at that and you go, "I can't do this, it's too much." I'm exaggerating. I never have 500 items, but you get the gist. Whereas if you have filters, you can find ways of slicing that up so that you can determine which ones you can do right now, which ones are most urgent, which ones are most important. One of the things that differentiates it from other task management tools is that it provides many metadata constructs to tag your tasks so that you can filter them down. If I want to, I can look at a list of only the things that I need to do in my house that are urgent and that are due within the next week. So those are very three different things. One is the place, another is date range, and the third is the fact that it's something that I need to do as opposed to something that someone else is doing that I'm waiting for. So I have a tag, for example, for traditional GTD context, but I also have a tag for, it's called waiting, where it's just something that I'm waiting for someone else to complete. By default, my to-do views hide anything that is marked as waiting, because that's not up to me. I do have another list that only shows me the waiting so that I can see what is pending from other people. So that's how I use it. Yes, it is a way to ... Technically, it's an information architecture. I see it in pragmatic terms as a way to narrow down the things that I need to pay attention to, to make them more manageable and doable.

Andrew J. Mason: For somebody that's like ... I don't even have that architected or that start to be built out. Do you have any advice for them on how to really start to think about how do I group my work into the right buckets, or it shows up in a way that makes sense for me?

Jorge Arango: Yeah, I think that it's important to make a distinction right off the bat between ... You used the word buckets, right? So I think of ways of organizing information for personal productivity and knowledge management. I think of there being two basic approaches you can take. One is to use what I call containers. And containers are things like directories or folders on your computer. In OmniFocus, there are groups, so you can have projects that then have tasks. And the other way that you can do it is by using tags, which we've talked about a little bit. The main difference between them is that containers have a one-to-many hierarchical relationship with the things they contain, and they tend to be exclusive. So the tasks that belong to one project in OmniFocus cannot belong to another project, and that's not true of tags. Tags can cut across. You can use multiple tags on a single task. Because of this, tags are both more flexible but also a little bit riskier, because you stamp the risk of going overboard. And this is a classic issue that people have when organizing their personal information or their task management system. There's this tendency to want to over-specify things. It's like, "I need to use all the tags." I think that the most important thing that you can do is use, if you're going to use tags, use them mindfully, know why you're using them. I wrote a book on personal knowledge management called Duly Noted, and the point of that book is using some of the learnings from information architecture in this space. And I talk about four possible uses for tags. So one used is what I call a semantic descriptor, so that's describing what the thing is. So for example, you might tag something with a book to say, "This item represents a book." That's one way of using tags. Another way of using tags is as a way to signify that the thing is part of a group. So for example, when I was writing the book, I had a tag called Duly Noted, where anytime I came across an article or I had a task that I needed to complete around the book, I would tag it with Duly Noted, and then I could get this view of everything having to do with Duly Noted. So that's another way of using tags. Third way of using tags is as an indicator of state. This is fairly common for people who write. You might tag an article as draft to differentiate it from something that's just in the very early stages of research or maybe something that you've already published or something like that. So rather than describing what the thing is, you're describing what state it's in. So that's a use for tags. And then there's a fourth category, and this one is obviously less applicable to something like OmniFocus, but more so to a personal knowledge management system such as Obsidian, which I also use. And that's to indicate that there's some action that needs to be taken. So for example, you could use the tag to-do indicate that something is a task that needs to be done. That's kind of what OmniFocus is. So I wouldn't expect you would use that kind for OmniFocus. But my point is rather than scatter shot using tags, it's much better to think it's like, "Am I trying to use this to describe what the thing is about? Am I trying to describe state? Am I trying to describe that ... Am I trying to tag as part of a group?" So that's one thing. The other thing is be very sparing. So I have a limit for myself of between one and three tags per item. And frankly, when using OmniFocus, I only use one tag per item. Even though there's a lot of flexibility there, that doesn't mean you need to use it. The more you add to it, the more complex your tax taxonomies become, and then it becomes a little unwieldy.

Andrew J. Mason: When somebody is looking at all of this possibility and all these different ways that they could architect their system. And it is meant to be that open so that people can customize it at what level that they're looking to customize it for. How do you keep from having a system that you spend more time in versus on and kind of over blowing the management? So you spend time, what do they talk about managing the forest versus chopping down the trees? Or maybe that's an awful analogy, but the spirit of working in versus working on, can you speak to a little bit about how you process that?

Jorge Arango: Yeah, I'm glad you brought that up, because it is an occupational hazard to working with tools like OmniFocus. Usually, the more powerful, flexible, featureful a tool is, the more you risk spending more time working on the systems than working on the work. I call this meta work, and it is a trap for people. And it's a trap because the time that you spend setting up a system is not time wasted. It is actually time that is going to help you down the line. It does give you a sense of accomplishment. You feel it's like, "Oh, I've done this, I've made this thing." But that's not necessarily going to help move the important things forward. I think everybody who has set up their productivity tools, I've suffered in the past from over-investing time, let's say, in setting up. "I need this to be perfect and I need to keep my tags in sync between OmniFocus and DEVONthink, or whatever, right?" There's this ideal of I'm going to get the perfect system that is going to help me just get things done so much quicker. And what ends up happening in reality is that rather than getting things done more quickly, what's happened is you've fallen in love with the tools and with the control that you have over being able to set things up, and that's not good. Personally, I think that getting started with a tool like OmniFocus must be intimidating for some folks just because of how open it is and how flexible it is. And if I were to make a recommendation to anyone getting started is start very simple. You're hearing us talk about tags and stuff. I would say don't use tags at first. Just start very simple. Just keep a few lists. Over time, you'll learn about the tool as you need it and you'll start implementing these more advanced features that let you get things done, but don't waste time just trying to set everything up from the beginning. And this is the other thing. At the beginning, you are not going to be very skillful in using the tool, so you're going to be architecting a system whose affordances and constraints you don't really understand yet. So it's much better to just work with a tool, even if unskillfully at first, and then learn about how you use it and what your needs are so that you can adapt it to your needs.

Andrew J. Mason: What do you say to somebody who says, "I keep cycling through, and maybe it is that I've fallen in love with just the product itself or the thing itself," versus they actually really truly getting the productive results out of it. Is there any way I can kind of wipe the slate clean or have a fresh start? Do I declare system bankruptcy? What do you suggest in that situation if somebody's finding like, "I've been spinning so much, I feel like my brain's mushed, and I need to do something different?"

Jorge Arango: Well, you know that the expression, the grass is always greener on the other side. There are always going to be new tools, new approaches coming out, and it's easy to become frustrated with what you have just because of the fact that you're in it. You're in it, maybe you've made a mess of things because of how complex it's become, and it becomes enticing to say, "Well, I'm going to scrap this and just start over using a new tool or what have you." Again, that used to be me about a decade ago or 15 years ago or whatever. And as I've gotten older, I've realized that it's better to get to know a few tools more deeply than to experiment around with a lot of tools. I've also developed a preference for tools that have stood the test of time. That can be tricky, especially when you work in tech, right? You hinted in the intro that I'm doing a lot of work with AI and helping clients with that stuff. So that's all new and everything's changing and it's changing really fast, but there's something to be said about tools that have been around for a while. As far as The Omni Group goes, I think that OmniFocus is still one of the newer tools, right? Because OmniOutliner I think comes from the next thing. It's a pre-macOS tool, so that one's even older. But I think of OmniFocus as kind of an evolution of OmniOutliner or a specialized use case for OmniOutliner, so in that sense, it has stood the test of time. And I would say committing to a tool and understanding that it's not going to be a hundred percent perfect, but it's going to get you most of the way there is much better than constantly jumping ship, because you think that there's another tool that is going to provide an edge case that this one doesn't do. And you might actually discover that the tool that you're coming from actually did have the functionality, you just didn't know how to use it. Give the tools a chance and give yourself a chance. Give yourself a chance to learn how to work with the tools. If you're really looking to have a system that is reliable, meaning where you know your stuff is going to be, that places a higher onus on switching. You should be a lot more hesitant to jump ship on a system that you're intending to be your long-term source of truth, because things will fall through the cracks in migration. And then if you're doing this kind of face-to-face transition, you're going to be facing the, "Oh, did I keep that in this system or did I keep that in this other system?" And all of a sudden, you've defeated the purpose of having a single source of truth. The point here is the phrase that David Allen used in the book, which I really like is what you're striving for is mind like water.

Andrew J. Mason: The phrase about energy too, where it's like a pebble goes into water and it gives out pebble-sized ripples and no more, no less, just pebble energy. That's it, that's all it is. What advice would you share where, man, if we could just get everybody on the same page about this thing, humanity as a whole, we'd be doing ... Maybe we wouldn't have everything solved, but at least this would be a step in the right direction for me.

Jorge Arango: Are you familiar with a book called Systemantics?

Andrew J. Mason: No. No.

Jorge Arango: It's an older book. The author is John Gall. And in this book, it's kind of like a tongue-in-cheek book about systems thinking. It's one of these books. It's like the Murphy's Law and that kind of thing where he's got these aphorisms about systems thinking. And there's this one piece in that book that has come to be known as Gall's Law because it's kind of central to his message. And I think that if I had a billboard, I would just print out what he says in the book about Gall's Law. I knew you were going to ask this, so I've written it here and I'm going to read it to you, because I think the whole thing is important. Okay? A complex system that works is invariably found to have evolved from a simple system that worked. A complex system designed from scratch never works and cannot be patched to make it work. You have to start over with a working simple system. I think it's of a piece of what we were talking about earlier. If you're getting started with one of these tools, don't start trying to use all the features. Start easy, make it work for you. Start simple. Maybe experiment with the integration I was talking about earlier with your email, that kind of thing. Start simple and let it grow and let it evolve to meet your needs. But I think it's also important to acknowledge that, that's the story of OmniFocus itself. It started with OmniOutliner and a series of Apple scripts, and it kind of evolved to meet particular needs. So I think that OmniFocus itself is an example of Gall's Law in action, and I think that, that's part of why it's been so long-lived and why people like myself find it so useful because it has evolved over time to do a very particular kind of job very well.

Andrew J. Mason: Jorge it's such a rich conversation, but I expected nothing less. For folks that are interested in hearing more, not only of what you're up to and involved with, but maybe even some of your thoughts du jour on everything from information to systems thinking, where can folks go to find out more about that?

Jorge Arango: Well, the best place is my website, and it's my first initial and last name, so Jarango.com.

Andrew J. Mason: Fantastic. Jorge, this has been awesome. Thank you so much again for hanging out with us today.

Jorge Arango: Thank you, Andrew. It's been such a treat.

Andrew J. Mason: Hey, and thank all of you for listening today too. You can find us on Mastodon at theomnishow@Omnigroup.com. You can also find out everything that's happening with The Omni Group at omnigroup.com/blog.