THE OMNI SHOW

Ryan Briggs: I think I would struggle to design a product where it can be something that I could pick up when I'm 20 and looking for something, and then just absorb the load as I move through my life and do thousands more tasks per year. At this point, everything is in it. So, all this stuff for my kids is in it. I just don't remember things. I don't try to because my memory is not that good. And so, it's everything.

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 Ryan Briggs uses OmniFocus. Well, welcome everybody to this episode of The Omni Show. My name's Andrew J. Mason, and today we are super honored to be able to have Ryan Briggs with us. He's a social scientist and associate professor at Guelph Institute of Developmental Studies and Department of Political Science at the University of Guelph. Very excited to be able to have that slice of the knowledge show up here for us in this conversation too. But first, before we jump into any of that, welcome. Thank you for joining us today.

Ryan Briggs: Thank you for having me. Really happy to be here.

Andrew J. Mason: I'm super excited to hear a bit more about your experience in social science and being an associate professor as well. But let's jump into what's number one maybe, where do you find yourself? But then number two, what does a typical day-to-day look like for you there?

Ryan Briggs: Yeah. Sure. So, I live in Toronto. My university is a little bit outside the city, so I go there when I teach. Typical days for me are all over the map. So, if it's one of the typically two days that I'm teaching September through April, I go out to the university, I teach courses, I have all of my meetings, which is service things, running the university stuff that happens when you get more senior, and then meeting with grad students to do a lot of advising. And so that dominates some days and then other days are I basically try to save them for research, which for me, research is me on a laptop. I'm a quantitative social scientist and so I'm just writing code.

Andrew J. Mason: This is a loaded question, so feel free to just take it in any direction that you want to. This is zero knowledge of quantitative science, anything.

Ryan Briggs: Go for it.

Andrew J. Mason: What are some interesting slices that you're researching now or things that you're digging into these days?

Ryan Briggs: Yeah. Sure. I had a grab your answers to this a few years ago before I started doing metascience, which is basically studies, science of science, this kind of thing. The stuff I used to do. The stuff I was trained to do as a political scientist was political behavior type questions. Trying to understand how people act often in democracies, why they're voting certain ways. The thing that I was doing, which I found to be really fun and interesting is I was studying these questions often in low income countries, where the data that we have is really bad. And so you often haven't had a census done in a long time. You may not really know where people are. You can't really trust the GDP figures. It's not that they're manipulated. It's just the data quality is not very good because it's expensive to collect good data. And so then you find yourself, as someone who's trying to analyze things, having to figure out alternative ways to make data. And so this was what I spent a lot of my time doing originally. So, for example, you might not have a good sense as to where there's economic activity inside most low income countries. But we know that as soon as people can, they tend to want light at night because it sucks not being able to see. We have weather satellites that have been up looking down on earth, detecting luminosity for a long time because cloud cover, like sun bouncing off clouds is a good indicator of clouds, and then you can use that for weather forecasting. Turns out you can do that at night and you can pick up where there's light at night and you can see all over the world. As places industrialize and start putting up streetlights, all of sudden, boom, boom, boom, you see this lighting up. And you can pick that up from satellites even if the country is not collecting good data. And so there was a big boom when I was a grad student of people realizing we have all of these alternative sources of data and all we need to do is be creative about how we use cell phone pings off towers, or light at night. Or later, machine learning to identify buildings and you can build little data sets of seeing this stuff build up over time.

Andrew J. Mason: That's really incredible.

Ryan Briggs: That's what we used to do. Yeah. That's fun. It's an interesting way to try to figure out how can we learn these things in, I don't know, the Democratic Republic of the Congo, where there hasn't been a good census since the '80s. It's just no good information. It's not like, I don't know, I'm in Canada. I can't just go on Stats Can or the equivalent in any other high income country, just pull the data down.

Andrew J. Mason: That's right.

Ryan Briggs: But that's interesting. There's a certain kind of person that finds that challenge to be really fun.

Andrew J. Mason: Do you have any recollection of any times that you have dug into the data? And it is so far beyond when it was originally captured that the delta in either changed behavior or changed findings of the data have really surprised you. You're like, "Oh man, it's been 10 years. I thought it would be one way." It turns out it is way over here instead.

Ryan Briggs: This wasn't my result, but there was, it's probably 10 years ago now. Coming back to the GDP question, a pretty fundamental question is the size of a country's economy, but it's hard to measure this stuff. Even in rich countries, it's really hard to measure, because the quality of goods changes over time and how are you going to count all the free stuff that tech companies give us? It's a genuinely tricky question, but there were lots of countries in Africa where GDP estimates were off by, I think, over 20% or 30%. And so people went back at their own stats agencies, they went back because they were realizing, "Oh, we probably weren't counting stuff exactly right." And we were estimating and extrapolating and the whole economy changed a lot in that time, so the extrapolations maybe were good. And everyone thought they'd change a little bit. It changed a lot, like a lot, a lot. And so it's one of these really weird situations where you're like, "What do we know here?"

Andrew J. Mason: That's fascinating. That is fascinating. Okay. So, I feel like I got a more decent grasp other than 0%, which is what I had going into this admittedly. So, hopefully that helps people get their heads around a little bit of what you're into. Which also I think in a corollary, we'll jump back into that here in just a minute, but explains a little bit of the email that you had sent me prior to this conversation too. So, that puts a lot of that back into perspective there for me. Let's do a parallel track here real quick though and talk to me a little bit about, do you have any recollection when you first came across OmniFocus or Omni Group more broadly? Do you have any like, "Oh yeah, that was just something that grew over time," or, "This was really the space and time, and I remember seeing that software and there it was and it was something for me?"

Ryan Briggs: Right. Yeah. So, I had to stretch my brain on this one. I knew this question was coming and I was just thinking, "When was it exactly?" I can't peg it to a month, but I know it was 2006. I was an undergraduate student. I remember that I bought the Black Plastic MacBook Pro, MacBook, not the Pro, the MacBook Because I remember thinking I was such an idiot. How could I justify spending, I don't know if it was like 50 or 100 bucks more just for the color. And then every single time I used it, I felt like James Bond and it was the best 50 bucks I ever spent. So, it was that computer, it was great. And so I'm pretty sure if my memory is right, that should have been 2006. I was in the middle of my undergrad degree and I remember thinking that I finally hit a point in my life where I could not just manage things in my head. And so I don't remember everything that I tried, but I remember going through a very intentional exploration phase to just figure out, do I want to put everything in a calendar? Do I want to write stuff down? There was enough of the internet at that point that you could search around and find good things. And so there were a lot of different ways of coming at this that I explored, just different, I don't know, ways of working and ways of tracking my work. And at some point, I don't remember how I came across the GTD thing and that seemed pretty good. But I really didn't want to have a stack of index cards, which was a common recommended way to manage this whole thing.

Andrew J. Mason: That's right.

Ryan Briggs: And my MacBook had OmniOutliner pre-installed, I think. I don't remember ever buying it, but I'm pretty sure it was pre-installed and I was using it to take notes in all of my courses. And at some point in 2006, I came across the Kinkless GTD series of scripts or something for managing. And so I started using that and then I have consistently used every iteration of OmniFocus from 2006 until today.

Andrew J. Mason: That is crazy.

Ryan Briggs: I'm 40, so that is half of my life. That is essentially my entire adult life. I would've been, I guess, 20 and now it's 2026. So, for a solid 20 years.

Andrew J. Mason: 100% feel the same way. Where I've been doing this for longer than I haven't been doing this now. So, I can't really imagine what the behaviors look like torn apart from that as software. Fun facts, you mentioned it being pre-installed. I think it was at that time. OmniOutliner was pre-installed as Mac software at that point. And it's interesting too, you mentioned everything that's happened since then over the last 20 year, the story arc of your career. And I don't know causation correlation there in your behavior set and how that lands you in the spot that you are now, but do you have any advice for somebody that is they're in that place of expansion, maybe they've either bit off more than they currently know how to chew? Or they're in this space where they're like, "I have an additional role there's another hat that's showing up that I need to wear right now and I don't know how I'm going to be able to start pulling that together." And they haven't yet adopted any behavior set, Omni or not, that allows them to track it, stack it and keep tabs on what their commitments currently are? Do you have any advice for somebody that's in that space where it's like, what's a good first step in that direction? Because it's like, I can't climb the mountain yet. I don't know how to do that, but how do I start taking steps in that space, in that direction?

Ryan Briggs: So, I talk to students all the time and these are people that were at the age when I started this. And everyone has trouble managing their time, but this is often the time when people realize whatever systems I had, they don't work quite as well. The advice that I give students is there's a real explore, exploit thing going on here. And so especially if you're younger or you think you have a lot of career ahead of you, I just think there's enormous value in figuring out a system that works well for you. I don't know what system that will be. I think it's different for different people, but I think at least I have found it to be incredibly useful to find a system that works well with my brain and then just stop changing. And once you find it, then go into the exploit phase and just use that forever. Presumably lots of people are not like me and change over time and at some point you have to go back, but I haven't. And so what I typically advise students to do is just spend some time, maybe a month with a system trying to hold to it or two weeks with a system trying to hold to it, and see how it goes and then try something else and then try something else. I think it's a mistake to jump into something really, really quickly because you don't know what's out there yet. You should order a bunch of things off the menu first and then find the thing that is the thing that works for you, and then try to double or triple down on that.

Andrew J. Mason: That's right.

Ryan Briggs: So, that's advice I commonly give students and I think it tends to work pretty well. The one risk of that is that doing things is work. And so it's possible to cycle through a whole bunch of different ways to approach managing your time and structuring to do lists and stuff and realize I don't really like any of them because they all expect me to do things.

Andrew J. Mason: That's a great point.

Ryan Briggs: Yeah. And so there is a sense in which at a certain point, the problem is you and you need to actually realize doing work sometimes involves doing tasks that are aversive and that's just how it goes. And every job is like that, every phase of life is like that, even when there's lots of good things. And so there's a little bit of you're never going to find a system that makes aversive tasks not be aversive. And then you need to accept that and just realize that's part of, not even living, that's just part of being alive. But I do think there are ways to structure this that can be better or worse for different people and finding that match is really valuable. Especially if you are earlier in a career and then you can just cash in on it for decade and decade and decade.

Andrew J. Mason: There is a point of diminishing returns. I think also too, the whole, David Allen always talks about people blame me for what's on their list kind of a thing. Where at some point, there is a piece to be made and once that piece is made, you double, triple, quadruple down. I think of Jim Collins' bullets before cannonball. You do want to experiment a little bit and try, but at some point, the answer isn't always out there. It might be you are with you wherever you go, and so maybe the answer is I should have to decide that maybe what I need to do is just to do the thing, do the task that's associated with it and not try and... And there is probably some conflation that happens that shows up where it's like, "Maybe it's the task manager and it's not me." And then we get stuck in this loop. I would love for you to place OmniFocus in an overall context for us, whether there's some corollary software that helps information get into it, or whether you use data that exports out of it or really it just sits on its own. But if you would permit me, I'd love to read the contents of that email that you just sent because I think it's hilarious, number one. Because it's a unique vantage point that you don't get otherwise outside of having this long sided view. But before I read it, if you don't mind, let me let you tee it up for us.

Ryan Briggs: Yeah. Sure. I have been using the software since 2006. I, at one point, lost a database when I was transferring from one version to another or something like that, and so I only have a consistent dataset from 2014 forward. One thing I've been really impressed with really just fell in the background and never noticed it. But when I realized I was going to do this interview, I was reflecting on it, and I became very impressed, is I started using this when I was 20 as an undergrad and I felt like I was swamped with tasks and I had no tasks. It just makes no sense. I had enormous free time and nothing demanding my time. And then I went to grad school and I had more tasks. I'm like, I can see this. I'm looking at the graph right now of how many things I did in a year. So, I had more tasks and they were all done at these weird hours between... I got more tasks done between 5:00 PM and 2:00 AM during grad school than during the day. And then I started my first job and I had more tasks. And then I had kids and I had more tasks, and then eventually got tenured and you think, "Well, then you're set," but then you just get more tasks. But it's been fine. The whole thing has just been fine. I really think part of the reason it's been fine is I just don't carry any of this stuff with me. Everything just gets dumped in. Not only it hasn't felt stressful, it just doesn't feel like weighty. I've just been really, really impressed. I think I would struggle to design a product where it can be something that I could pick up when I'm 20 and looking for something, and then just absorb the load as I move through my life and do thousands more tasks per year. And at this point, everything is in it. So, all this stuff for my kids is in it, I just don't remember things. I don't try to because my memory is not that good. And so it's everything and it's just handled that really well.

Andrew J. Mason: Thank you for sharing too. Grateful that you said that. But also let me read that paragraph that you had just sent. So, this is Ryan throwing a lot of the contents of his database into an LLM, and then having it just summarize what do you see statistically? What's showing up here for you? And so it says, "Across 22,987 tasks over 11.8 years," so this is the data set from July 14th to April 2026. It says, "you've built an unusually consistent productivity record. Around 1,500 to 2,500 completions every year with peaks of 25, 34 in 2021 and 2,490 tasks in 2025, and a 59% on time rate against due dates. But the real story here is that late almost never means late. 95% of the late tasks are closed within 24 hours of time, and only seven tasks and the entire archive were more than a week overdue." That's insane. I don't know if you get a back pat for that, but I think you should be patting your own back for that. That's crazy. The volume is dominated by personal/family buckets, miscellaneous personal 7,800, 1,900, mostly on a Mac 7,000, at home, 3,000 with Mondays the heaviest day and weekends lower. Here's the fun part here. The most striking find is how visibly your kids reshape your workday. 2014 to 2016, you are a night owl peaking at 17:00 to 02:00 AM. And then the second kid in March 2017, flips the peak permanently 12:00 to 14:00 hours and pushes the workday share near 34% to 60% by 2024. Third kid in November 2022 lights up in early AM, 5:00 to 8:00 AM bump, that hit 7.3% in 2023 and fades as the baby starts sleeping later. That long record must be interesting you were saying to me. I think that's, number one, hilarious that it's able to do that much analysis on it. But number two, kudos to you for having... This is the story arc not only of your career, but also of your life as it's informed by these different events that are happening, and it's so cool to be able to have this entire data set. I wouldn't expect anything else from somebody who does data analysis, but it's just an interesting perspective intake that I hadn't heard elsewhere. So, thank you for sharing that with us, number one. Which is so cool to be able to see all of that data flowing through it and then have this consistent story arc for your life and career show up here. So, talk to me a little bit about, obviously there's some LLM interaction for the sake of this story, but is there other software that either is on the giving or receiving end of OmniFocus for you?

Ryan Briggs: Not a lot. I've increasingly just tried to make the setup as simple as possible. And so earlier on, I had experimented with all different kinds of little things, wiring things up and that. And now it's quick entry on my Mac. It's just dictation on my phone to get things in. I clip an enormous amount of emails because I just get too many emails and I don't want them to live in my inbox, and so I just click them into tasks all the time. And then I have an email address set up for my wife, which lets her just insert tasks into my to do list, which is a little bit dangerous, because I don't have a great memory genuinely. And so I treat my to do list like Ron Burgundy's teleprompter. And so I just do the tasks. I don't reflect on, I just do them, and she hasn't abused this yet and set me off to kill her enemies. But it has been very helpful to have the ability of she needs me to do something. I really genuinely try really hard not to reflect on the tasks once they're in there because I already put the thought-

Andrew J. Mason: It's the flow state, that's right.

Ryan Briggs: ... of them there and I just want to do them. And so having someone else have the ability to stick them even in just your inbox is a little weird, but it hasn't been abused yet.

Andrew J. Mason: It's trust and I appreciate that. I think that's awesome. Like you said, I haven't seen the abuse happen yet and I think you're good, especially after as many years as you're doing there, it shouldn't be a concern at this point. I am curious too about the automation factor. Are there any ways in which you use automation? It can be OmniAutomation, like the JavaScript-based language, or even something as simple as repeating tasks that show up. So, I have to clean the air filter once every six months, I don't need to think about that, repeat.

Ryan Briggs: Yeah. So, again, I've just shifted everything to be as vanilla as possible and that's been great. Now I'm plugging everything, but the updates to repeated tasks have actually been really useful for me. So, saying repeat a thing 10 times or whatever, I don't know. So, where does that come up? I have very, very mini tasks that are repeated weekly or monthly just that I don't want to remember. I have a bunch that are repeated annually because every time there's a birthday or an anniversary, I have a task to tell the person happy birthday, but also a task if I'm getting a gift or something, I need to do that in advance. So, I just constantly update that, which is fun because now I have all of these birthday reminders from people that I knew 15 years ago, which I'd never remember otherwise. Because I don't usually take them out because why would you? Just send the person a text. It's nice.

Andrew J. Mason: But it's cool too because you're the one that remembers, you're the happy birthday guy. And they're like, "How does he know?"

Ryan Briggs: No, I know. I really seem like someone who has a phenomenal memory and I have a terrible memory, but I don't have to remember stuff. A kid had a minor infection that had to get medicine. It was so nice to be able to say, "He's supposed to do however many mils, however many times a day," and you just work it out, and you're like, "He's going to do this thing 30 times." I don't want to have to try to remember that. So, just being able to put that in and say, "Just do this 30 times," was excellent. I use that stuff all the time. I don't really know how much because it's such a reflex. I'm constantly dumping things in.

Andrew J. Mason: Again, the flow state, and people are like, "Aren't you bothered by that?" No, because I have trust in my system. It just happens.

Ryan Briggs: It bothered me at the beginning. I've been doing this now for 20 years. It really felt frustrating at the start because there is a tax on your time on the way in. It takes time to put it in and it takes time to organize and it's not obvious, or it wasn't obvious to me at the beginning, that that would actually pay off. And so it felt frustrating. However well-designed something is, there's still a friction to getting it in and organizing. You don't want to be the person that just prunes their to do list garden, that can't be the point. By this point, I'm just completely converted. I don't know another way to live. And there is a tiny task on the way in, but there's a huge benefit of just never having to remember this stuff. I can just think about my research problems or being present with my family. But that was something that took a little bit of... I remember that feeling of just can this really be worth it? Because here I am rather than doing the task, I'm typing it in to the computer.

Andrew J. Mason: Well, let's talk about the flip side of that coin though too. There's the, man, I'm so thankful. I've got the flow state, things are happening. It may be fast and furious at times, but there are things that are in and out of the system and I don't necessarily have to pay the mental tax on the backend of that knowing that it's taken care of, it's handled and it'll show up when it needs to. On the other side of that, is there anything that you tried, experimented, worked with, along your time here that you look back on? Maybe it's not a big oh, no or anything, but just something that shows up for you that says, if I were you and I was coaching you about how to live your life as a 20-year-old, maybe it's instructional or not, but I would just skip that part of it? It didn't necessarily bear fruit the way that I was hoping it would. And so if it's you, maybe next time just don't do the thing.

Ryan Briggs: No is such a ridiculous answer. I'm a bit of a weirdly selected person because I've been... It's really strange. So, if I was genuinely giving advice to me from back then, I would just be like, "Good job. Turns out this will work really well for you." It's crazy, but not everyone is like that, but if it was actually advice to me, that's literally what I would say. It's just silly. If I'm giving advice to other people, it's always about exploring because there's just no way that... I just got lucky or I wasn't so clever to know this would work so well for me, but it just really did. And so with the benefit of hindsight on this specific little aspect of my life, no, it would just be high-fives. The one thing I found that is really strange and it's a thing that I did very religiously and has fallen away. I think it's a structural feature of the world and not anything else. So, I've been saying I've been doing this for 20 years and I had fairly clear five-year plans the whole way through. And so I would plan at this higher level, I would then break it down to one-year plans and break it down to monthly plan. I would do the thing. I did that in a very serious way through undergrad, through grad school, through my first job before I had tenure, and then I moved universities. I used to live in Virginia and I moved back home to Toronto. And so this was all something that was fairly concretely planned out and I have no five-year plan right now. And some of that is maybe a life cycle thing, but I don't think that's actually it. I think it's a function of AI. I just genuinely don't know what my... It feels crazy to make a five-year plan and this is the first time it's felt that way in my life, but I don't have a five-year plan anymore.

Andrew J. Mason: Ryan, I love this conversation. I think this has been incredibly fruitful. Hopefully people hear a bit of themselves in your story arc or inspired by the way that you have conducted your career thus far in that slice. So, thank you for that. And then for folks that are interested in staying in your orbit or finding out more about what you're up to, how can they connect with you?

Ryan Briggs: So, the easiest way is just to go to my webpage, which is ryancbriggs.net, and then that has links to Twitter and BlueSky and I don't know, all my research. You can find my email on there and everything is on the webpage.

Andrew J. Mason: That's perfect. Ryan, much appreciated. Thank you so much for hanging out with us today.

Ryan Briggs: Thanks for having me. This has been fun.

Andrew J. Mason: Thank all of you for listening today too. You can find us on Mastodon at the omnishow@omnigroup.com. You can also find out everything that's happening with the Omni Group at omnigroup.com/blog.