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April 9, 2024, 6 a.m.
Learn OmniFocus Founder Tim Stringer Returns

In this episode of The Omni Show, we reconnect with Tim Stringer, the founder of Learn OmniFocus and Technically Simple. Tim, an expert in OmniFocus coaching and consulting since 2010, shares how his approach has remained consistent, with an emphasis on refinement and efficiency even while testing the latest OmniFocus updates.

Show Notes:

We delve into OmniFocus 4 advancements, Tim's shift towards mobile usage, and the importance of a clean, actionable system within OmniFocus. We also discuss common pitfalls in task management and the significance of having a dedicated space for idea capture and project planning. Our conversation wraps up with a vision for increased human connection within the productivity community, transcending geographical boundaries.

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 Tim Stringer returns to talk about how he uses OmniFocus. Well, welcome, everybody, to this episode of The Omni Show. My name's Andrew J. Mason, and today, we're talking to the founder of and Technically Simple, Tim Stringer. Tim's been providing OmniFocus coaching and consulting and training to people since 2010, and he first appeared on The Omni Show in episode 78 three years ago. And it is great to have you back on the show, Tim. Thanks for joining us.

Tim Stringer: Yeah, thanks very much, Andrew. It's great to be back and yeah, really looking forward to our conversation today.

Andrew J. Mason: Me too. And it's been a couple of years since we've chatted, at least on this show. And dare I say, a lot of stuff has happened since then, not the least of which is a fresh version of OmniFocus out in the wild now. We've got things like spatial computing happening, and we also know that you've been honing Learn OmniFocus and Technically Simple along the way, so really broad brush strokes, but feel free to dive in as deep as you like and just share what's been happening over the last couple of years for you in any of these spaces.

Tim Stringer: In some ways things have stayed the same, in other ways they've changed significantly. Maybe I'll start with what is the same as when we last spoke. And I would say my approach to using OmniFocus is essentially the same. That's something I've honed over the years and have gotten to a place where it really works well. So when there are major developments like OmniFocus 4, for instance, that's really adding an enhancement to what I'm already doing with OmniFocus. And it's making it more convenient, even more enjoyable to use things like that. But the sort of fundamental way that I use OmniFocus, interestingly enough, probably hasn't changed in 10 years or more. It's been more kind of a refinement of the way I've been using it since the very early days. What has really added value to it is certainly the features that have come with OmniFocus 4, and just being able to dial it in so that it's a really accurate representation of my life and my work. And I think especially just getting what I need in the moment and not getting overwhelmed with additional details. So that's where things like custom layouts are very valuable. For certain perspectives, I only need to know the due date and the name of the action or something like that. I don't need to put tags on the screen and things like that. So it's very nice to have that really clean view that I could put as kind of a sidebar on my Mac. And there are other times where I'm maybe doing a review and I do want to know all those parameters so I can really dial it in. And I think that's, especially for people who've been using OmniFocus for a while, it's great to start simple, kind of use things the way they're set up out-of-the-box, but then as you get more experience just to say, "How can I make this even more attractive and convenient and things like that?"

Andrew J. Mason: Hmm. Now that's interesting. I actually hadn't heard that perspective before about how it helps minimize the cognitive fatigue that says, "Just show me the things I only care to see about in this perspective here." What else shows up for you when you think of, "Hey, this is new and it's something that's really helped me along the journey"? And you actually got into TestFlight maybe even before TestFlight. You were one of the first users of OmniFocus as it was being developed in the beta. Talk to me about that journey a little bit. What showed up? What are you excited about in the new version, and what's helped you along the way?

Tim Stringer: Yeah, sure. In some ways it doesn't feel like a new version to me. I was one of the first people outside of the Omni Group who was using OmniFocus 4, so I've been using it for quite some time at this point and it's really great to have it be a release product. And I'm sure for Omni as well, having that really solid foundation to build on. One of the biggest things that's changed since using OmniFocus 4 is I find I'm using a lot more on mobile devices, I'm using it a lot more on my iPhone and iPad. I used to kind of resort to my Mac in the past because there was a feature like Quick Open or Focus or the sidebar or something that I really relied on for my workflows. So it's nice to be able to sit down on the couch with my iPhone or iPad or be on the go or something and have access to all those amazing features. Quick Open is one that I use a lot. And there's some Omni automation plugins that I've been using for so long at this point they feel like features within the app. So being able to create a project based on a template when I'm using my iPhone on the go has become kind of second nature at this point. And it doesn't need to be something that I put on the list for when I get back to the office later in the day. It's that sort of a immediacy and that convenience that I think has really been a game changer.

Andrew J. Mason: I'd be interested to know, because I think you and me are probably two on a handful of, I don't know if you can count them on one hand or not, but spend a large part of our time talking to people about how they use OmniFocus. I'd be curious to know what patterns have you seen emerge over the last three years, whether in terms of workflow, how people like to set up their OmniFocus that's different than how it was three years ago? Or common hangups that people, challenges that people run into when they're setting up their workflow that has emerged over the last three years? Is there any commonalities that show up there for you?

Tim Stringer: I guess about nine, almost 10 years ago, I wrote an article on common pitfalls with OmniFocus, and I have tips for all of them on how they can be avoided. Or if you do fall into one of them, kind of how to get out of the hold there. And I went through that article again just recently as I was updating some of the content for OmniFocus 4, and it's interesting that those haven't really changed since OmniFocus 1. There are certain ways of using a task manager, it doesn't even have to be OmniFocus, it could be any task manager. There's certain pitfalls that people fall into. By far the biggest one is that they treat OmniFocus as a dumping ground, every thought they have while out walking the dog or aspirations that are 20 years away rather or whatever it is, it just kind of ends up in OmniFocus and it becomes... It sort of feels good in the moment to get it off their mind or to have somewhere to put it, but over time, it makes OmniFocus feel daunting, they don't even want to open, look at it, they don't use it. Eventually, they switch to another task manager, do the same thing with that task manager and maybe a year or two later they're back at OmniFocus willing to give it another go. So I think it's really important to define what is the purpose of OmniFocus, what is it used for and what is it not used for? And it tends to get used as a dumping ground if people don't have a designated place to put notes. So in my case, I'm using Craft. I really like the Craft note-taking app. Apple Notes has come a long way. Obsidian, I know there's a lot of fans in our community of that app. But have somewhere to capture ideas and develop them and kind of noodle on them that's not OmniFocus, and then use OmniFocus as a prompt to say, "Go and look at these ideas for 20 minutes and see if there's anything you want to extract out of them in terms of projects and actions." And it's amazing how big a difference that makes once people start to use OmniFocus really for actionable things, as a sacred space, as I'd like to say, everything in there is representing a future commitment to time and energy. Then they'll be much more selective about what they put into it. As I like to joke, people who work with me usually use OmniFocus a lot less, but they get a lot more use out of the tool because they're using it in the way I think it was really designed for as a personal task manager, a sacred space to say, "There's so much I could spend my time on, what's sort of in the queue? What am I committed to spending time on?" Not to say that everything will be done, but at least the fact that it earned its way into OmniFocus means there's an intention to do it. I've got it kind of pass the gatekeeper to say, "Yeah, this is worthy of my time and energy. It's aligned with my values, my job responsibilities," that sort of thing.

Andrew J. Mason: I'm pretty sure people have heard me bring up the concept of forced disfluency a billion times, if you've listened to this show at all. Charles Duhigg, his second book after The Power of Habit book about productivity brings up this concept of forced disfluency saying that having access to data is no longer an issue for us. We have more data than we know what to do with in the given course of a day, and now the challenge becomes really slowing down and thinking about that data. How do we do something meaningful with that data and untangle the spaghetti until we can create some meeting out of something? And I think for us, very often we settle for the checked box that shows up for us when we capture something. So we capture that 2:00 AM thought, we capture that idea, "Hey, that's a great idea." It shows up in our OmniFocus inbox. And then for us, we feel like we're done. I've finished the job, and in reality, we're no better, worse for wear if we don't do anything with that information. So yeah, you want to go through and cull the garden and figure out what's worth keeping and taking action on and what's worth throwing away. "Hey, that was a 2:00 AM thought, doesn't have any value." But what I hear you say is there's another level of elegance about keeping the lines clean and neat on what's truly actionable inside of OmniFocus versus just kind of using that inbox as a space to have just different thoughts here and there. Talk to me more about that, because there is a little bit of a trade-off. The frictionless mind of being able to capture and stay in flow, I love that. But, man, I don't like having 35 inbox items every time I swap over to the OmniFocus inbox.

Tim Stringer: It gives me the freedom to have ideas. I've heard people talk about how they have so many ideas, almost like it's a curse because they're just sort of clogging up their inbox. But once they have a place to park those ideas where they can revisit them in the future, then, yeah, they can do great things with them or pass them along to somebody else. I actually do most of my capturing into Drafts for that reason, and Drafts is kind of the entry point into my digital system. And then I have a very convenient way of sending things off to OmniFocus from there. I will go into OmniFocus directly with the control option space bar if I know for sure I need to send a document to a client or make a phone call or something, those go right into OmniFocus. But if I'm out for a walk and I have a thought about something, Drafts is kind of the entry point to the hospital where you need to be assessed to say, "Do you need immediate attention or can you come back next week and see somebody?" And you don't want to leave that. There needs to be sort of a collection point that's where you don't need to decide is this actionable, or is this important? Is this a silly thought I had when I was feeling tired yesterday and it's have no value the next day? Or is it brilliant? So taking that pressure off. I think in the past, people would've just scribbled it on a pad of paper and that can still be very useful. So Drafts is kind of the digital equivalent of that to where I don't need to decide what to do with it in the moment. And then certain Drafts, things that start in Drafts will end up in OmniFocus, other ones will be sent off to Craft, but I've got a place where I can just let the ideas fly without worrying about compromising OmniFocus.

Andrew J. Mason: I think it's wise, Tim, just the martial art of doing air traffic controller with Drafts and using that as the first space before you decide where the data goes, whether or not it's actionable, then it shows up in the OmniFocus versus just thoughts that I'm collecting for no good reason and then kind of muddying up the task management system. It's a wise way to do it.

Tim Stringer: I'll just add one makes Drafts special too, is it really removes friction to doing something with this stuff. So you can have actions configured where I can just tap on a button and it's off to OmniFocus, or tap on another button and it's off to Craft or it could be Obsidian or Notes or something like that. Otherwise, it becomes this growing list that potentially has important things, but it just feels like too much work to do something with it. It's anytime where that friction can be relieved, and this is where getting more advanced with OmniFocus as well, the system suddenly becomes more attractive and there's less time spent managing the system, more time available to actually do the work and to fulfill the actions, things like that.

Andrew J. Mason: As you look back over the last 36 months, the last three years, Tim, what do you see that was your largest project that you had to work on and that OmniFocus helped in? But personal or professional project I took on in this space, OmniFocus helped me see it through?

Tim Stringer: Yeah, sure. Well, it's kind of Meta because my biggest project is by far creating new OmniFocus 4 content and updating existing content, and I've made some great progress on there. I've got four courses specific to OmniFocus 4, and there's definitely a lot more to come. But that was pretty daunting to have to recreate the content, especially with all the added features of the iPhone and the iPad and there's just a lot more to talk about. And the approach I've took with that is not to even try to plan it all out to OmniFocus. And I also see people... Maybe another pitfall to add to the list. I see people trying to use OmniFocus as a planning tool, and I think for a very simple project that can work well, but for anything that has a large scale, a lot of moving pieces and maybe other people involved, that's where it kind of falls flat. So in my case, I keep track of all of the OmniFocus for assets, videos, courses, articles and things in Notion, and then as it's time to hit record on a piece of content, that's where it'll get a place in OmniFocus in a project. And OmniFocus is kind of where the tires meet the road. That's where things actually start to happen. Until they're in OmniFocus, it's kind of like being in a restaurant and you're looking at the menu and deciding what to order, but the order hasn't been sent off to the kitchen. OmniFocus is more like the kitchen where this is the order for pasta. I'm going to have tiramisu for dessert. It's all really defined at this point, but there needs to be a separate sort of space where the project can evolve, and kind of like a sandbox and incubator for things. So I know even what is the work and what am I going to prioritize and so forth? So in terms of learning OmniFocus, that's where Notion has proven to be a really great tool to work with alongside OmniFocus where I can get ideas, I've got many, many ideas, some came from me, some came from members of our community, and when they're ready to go, the sort of order gets sent off to the kitchen by way of an OmniFocus action or a project if it's something more involved. And then within OmniFocus, the feedback loop is kind of completed by having actions within OmniFocus to prompt me to go and review things in Notion and add notes and things like that. So the two tools are essentially talking to each other, they're co-collaborators and they each serve their own purpose overall.

Andrew J. Mason: Tim, right before this call, I remember the David Allen quote we were talking about where he was talking about, "You need a system that can still function when you're sick in bed with the flu at 7:00 PM and you still can roll through it. And it's not so full-featured and so many bells and whistles that it keeps you from wanting to even pay attention to it." I almost want to cross-reference that with his other quote about, "You need as many inboxes as you do need, so please have all the inboxes you need to have, but don't have more than that." Sometimes we want to just kind of trick things out with all the coulds and shoulds that a system offers and it's easy to fall into that temptation. Speak to somebody about how to have a system that's really as streamlined and elegant as it needs to be so that when things get tight and tough and difficult, they can still make it happen.

Tim Stringer: Yeah, sure. Well, that's kind of the basic litmus test is when you go to OmniFocus, do you feel sort of stress or relief? There could be some stress even if it's well organized because maybe you've got a lot going on right now. But generally speaking, the idea is to be feeling some relief because, "Thank goodness, I don't need to keep track of all these things. I don't need a reminder to contact Andrew three weeks from now," or something like that. It's just all kind of taken care. And then the ultimate test is when life goes sideways. And I've had several experiences in the past, even the past year or so where something very unexpected has come along like a death or a family member going to the hospital or something like that. And I've noticed that I lean on OmniFocus. It's something that it's kind of where I go to when things are starting to feel a little bit out of control. And the fact that I do that means OmniFocus is there to be leaned on, it's there to serve me. It's actually making my life easier. If OmniFocus were really out of dates and I hadn't processed my inbox in two weeks and had a today list with 300 items, then I would've avoided it because it would've just added complication. So it's really about keeping things up to date, keeping things relevant, useful. This is another sort of argument for not putting extraneous ideas and [inaudible 00:17:26] maybe lists and things in OmniFocus. One analogy is if you keep on top of your kitchen and after every meal you're putting things in the dishwasher and clearing the counters and making sure that the fridge is stocked and things like that, if somebody comes and visits you unexpectedly, you can say, "Oh, great to see you. I'm going to make you a nice meal. What would you like?" Versus if somebody shows up unexpectedly and you can't even see your kitchen counter and it's a real mess and you need to wash a fry pan before you can even make anything, then that person showing up is going to feel more like a stress even if you're ultimately really happy to see them. So keeping the kitchen clean and keeping OmniFocus clean and relevant, not putting things in OmniFocus that don't belong there, just like you don't keep things in your kitchen that don't belong in the kitchen because they're just going to get in the way when you're making a nice meal. And know that that is a practice. There's a whole system maintenance side that, I think, doesn't get talked about that much. But seeing OmniFocus and related apps is a system that needs to be tuned, needs to be reliable. Just like if you don't get an oil change on your car regularly, you might be stuck at the side of the road and have an expensive repair. And maybe it's at a time where you really need to get from A to B, there's an emergency or something like that, or an important event to get to.

Andrew J. Mason: Tim, I so appreciate not only the information that you provide, but also just you have such a calm delivery of that information that some of it is just an outflow of who you are. So I think you're just an authentic, "Hey, this is just me being me." So when you have somebody that's in what I consider to be a leadership role and you pay attention to the conversations that they're having, so much so that, "Okay, well what's Tim saying about productivity and OmniFocus because he's the one that's talking about it?" I like to hear from those people what inspires them? What is it that you're listening to or coming in contact with that's on the bleeding edge that, it doesn't have to be productivity related, although it can be, that's a source of inspiration to you to say, "This is one of the things that I find really exciting about all of this"?

Tim Stringer: Yeah, sure. I'm really grateful to be doing the work that I'm doing. Learn OmniFocus really emphasizes people gathering face-to-face on Zoom. So being able to see each other, get to know each other, and there's some people I've known for years, I've even visited them when I was traveling. And so there's a really human relationship there. And one of the things that lights me up the most is just seeing transformation within people, within teams, people really using OmniFocus and related tools. I also specialize in Asana, and I work with a lot of groups to help them improve their communications and collaborations. So that's really what gets me out of bed in the morning is just seeing those transformations and seeing people go from overwhelmed to feeling very calm and zen and pursuing things that they were maybe in sort of caught in that busy trap and things that were really important but not urgent that they maybe never would've gotten to in their lifetime if they didn't have a system in place to take the pressure off. So that's something that's inspired me for years and just continue to be grateful to be a part of other people's lives and work and everything like that.

Andrew J. Mason: Yeah, I think that's a fantastic answer, Tim. And as you look out, God forbid that it's another three years before we talk again. But assuming that that many years has passed by between now and the future, the next three years, what is it that you would like to see more of as you look across our community, OmniFocus, productivity, and you see the landscape and you say, "You know what, more of this"?

Tim Stringer: Yeah, I think more connection at the human level. We've got these amazing tools like Zoom where it's when I first did my first video call, I was living in Dublin, Ireland and it cost about $35 a minute to do a video call between Ireland and Canada. So it made me realize just how far we've come over the years. And so really using these tools, I think going beyond doing chats and forums, and both of those are very useful. I'm a regular on the Omni Groups forums, for instance. But I think there's a whole new level of value of connecting face-to-face and sharing common challenges and how those were overcome. And I think it's especially valuable that we're so connected as a planet now, and there might be people in totally different professions that come together and solve things. One of our Office Hours sessions, we had I think three pastors, a rabbi, an engineer. We were all sort of talking about some of the challenges. The engineer made a joke, of course. But yeah, just that sort of coming together of people. And it's kind of interesting that somebody who lives in Canada might have similar challenges to somebody who lives in Africa or in some other part of the world. There might be a different sort of flavor of those challenges, but they're probably dealing with some of the same overwhelm and too much information, too many ideas, that type of thing. So it's just really cool to be able to come together in a very human sort of way and just throw around ideas and see what sticks, and this worked for me and maybe some version of it will work for you. Something along those lines.

Andrew J. Mason: That is it, more human connection. Geography is no longer a limiting factor these days. I think that's a fantastic answer. Tim, how can folks get in touch with you? God forbid they haven't heard of Learn OmniFocus before, but just in case they want to get in touch with you, how can they do that?

Tim Stringer: Yeah, sure. They can go to and there's a contact form on there, and I answer all those personally currently. So if you have ideas or requests for content or questions about the service or just anything you'd like to share there and related to OmniFocus or productivity, and we tend to naturally get into other apps as well too because I rarely see OmniFocus as part of a... One of our members talked about it as a constellation of apps. So just having people fit it into sort of a broader ecosystem of apps. And one reason, I could have called it Learn Productivity or something like that, but the reason I made it Learn OmniFocus is I find it's really helpful if everybody has something in common, they all use the same task manager. And beyond that, there's all kinds of amazing ways that we can build it from there. So it is centered around OmniFocus, but the site is really about learning productivity skills, like soft skills, and I weave in a lot of GTD practices in there. I've got my own approach called Holistic Productivity, so it's really much more than OmniFocus, but OmniFocus is that sort of anchoring sort of element there.

Andrew J. Mason: Tim, thank you so much for joining us. I know your time is valuable, and it just means a lot that you would spend that much with us. And thank you for just being the pillar in the community that you are. We're grateful for that.

Tim Stringer: Yeah, thanks very much, Andrew. Really enjoyed our chat.

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