THE OMNI SHOW

Maggie Delano: The first time I started using OmniFocus, I just really didn't have a good way of organizing my life. I didn't think about things as projects or as areas of responsibility. And this is why I'm saying I can't really think back to how I though about them before because I think I just wasn't thinking about them at all in that way.

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 Maggie Delano uses OmniFocus. Well, welcome to the Omni Show everybody. My name's Andrew J. Mason and today we get to listen to how Maggie Delano gets to use OmniFocus. They're an engineering professor at Swarthmore, they design medical devices for people living with chronic diseases, and Maggie does great work on inclusive engineering. Also happens to keep the whole faculty life in OmniFocus, which is exactly the kind of story that the Omni Show is built around. Maggie, thank you so much for joining us today.

Maggie Delano: Thanks for having me.

Andrew J. Mason: Well, tell us a bit more about yourself. It's kind of a giant question, but what your day-to-day happens to look like.

Maggie Delano: So Swarthmore is in Delaware County, right outside Philadelphia. So I actually live in Philly and I do a reverse commute, which is really nice. It's a small liberal arts college, and so I teach in the engineering department here. And because we're a liberal arts school, we have actually a general engineering program, which is really unique. We don't major in any particular subdiscipline of engineering and there's no graduate students, it's all undergraduate students. But I really love it here. I moved here in January 2018 and actually one of the big reasons I started using OmniFocus was to kind of help me prepare for this job, but I really like it. And then outside of faculty life, I also like spending time with my partner, doing puzzles, playing chess, all that stuff.

Andrew J. Mason: Awesome. Awesome. And you say Delaware County actually coming from the state of Delaware, so we're not too far apart. Do you have any recollection as to when you first came across OmniFocus or even the Omni Group a little bit more broadly? That the day, that was the time, or was it just more of a growing general awareness that showed up for you?

Maggie Delano: Yeah, I think it was probably in the late 2010s, maybe early 2020s. So I was pretty into the quantified self movement and productivity technology in general. So I was in grad school from 2012 to 2018. So I think it was kind of around grad school when I started getting more into productivity software, especially because I was having a hard time just keeping up with all the tasks that I needed to do. It was less from an overwhelmed point of view and more from a motivation point of view. So I was really into the Pomodaro technique, so I tracked thousands of Pomodaros during my PhD, but when I transitioned into the faculty life, I was doing a lot more with overwhelm, all the different areas of responsibility that I had, and I really felt like I needed to find a better system. And so during the lockdown period, I took Thiago Forte's Building a Second Brain online course, and it was during that process that I was really looking for things that I could stress test. And OmniFocus was one of the ones that I heard about and I tried it out in 2021, and then I just went back and reread my blog post about it earlier today and I still use the system in almost exactly the same way five years later.

Andrew J. Mason: Wow, wow. Speaking of stress tests, okay. What stood the test of time there? That's crazy. And I've heard of Thiago's method, but was it the PARA method? Is that how it works?

Maggie Delano: Yeah. So projects, areas, resources and archive. So I implement some version of that in Omnifocus.

Andrew J. Mason: That's fantastic. And for those people that are listening to this going through collegiate life thinking, "Oh, well, things will get easier when I get out of college," it's like, well, maybe not necessarily. What advice do you have for somebody that maybe knows they need to be doing something, maybe more to keeping track of their ideas or their workload or roles or responsibilities start to expand? What's a great first tip? It can be software-agnostic. It can have to do with OmniFocus if you want to, but just in general, what's your first go to for when you see somebody struggling, but they know they need to do something?

Maggie Delano: Yeah, so I think there's a lot of different systems out there, and I think a lot of it is finding what resonates with you, but also what the issue is. So one of the big things in the academic world is there's a faculty success program from the National Center for Faculty Diversity and Development, I think it is, NCFDD. And they talk about there's three different categories of things that you have going wrong. So one is a technical error. If someone just explains to you, "Well, you're just doing this wrong and here's a better way to do it," and then you do it that way and everything works. But a lot of times advice is not always as helpful because it's actually more of a psychological block. It's you know what you should be doing, but you're a perfectionist or you're afraid of failure, or there's something else going on and so you can't take a step. So it's sort of like you need therapy or something to really take the step that you need to take. And the other one is external factors. So basically you know what you need to do, there's no psychological block, but you just can't do it. Maybe you've just had a kid or you don't have enough time in the day, you're overloaded, you've been given too many responsibilities, and so there needs to be something else that's not you that needs to change to address it. So usually I try to understand that first, because I think the most common thing is people want to give someone advice that's around a technical error. It's much easier to talk to people about, "Well, just use this tool and then everything will be better." But in a lot of cases that doesn't actually address the issue. If it is a technical error, I think that's much easier to give people advice on, because I know lots of things about various productivity software. But if it's more of a psychological error or even an external factor, I think that's harder, but also maybe more useful to give people advice on.

Andrew J. Mason: I love that preliminary question that shows up first saying, let's tailor this to the individual first because one size doesn't necessarily always fit all. Do you mind, for yourself, thinking through OmniFocus and where it sits in your life, placing it in an overall context? Do you have other software that flows into or information from OmniFocus that flows out of that software? You mentioned the PARA method as a piece of the puzzle. Maybe just give us a tour of what else is happening around it.

Maggie Delano: Yeah, sure. So I use OmniFocus among other tools too. So OmniFocus is basically where most of my tasks live. So the one exception is that sometimes if I'm working on a research task, it makes more sense to store that in my note-taking system. And actually I've experimented with a lot of different note-taking systems. The main one that I'm using right now is Obsidian, although I also still use Rome Research a little bit for really divergent thinking types of things. So Rome Research is an outliner and it's really good for having lots of different information all over the place. So I like that specifically for if I'm writing a paper or something like that. Sometimes I keep some to dos in there because it's very fluid, whereas OmniFocus is a little bit more focused. So I think that's useful for a lot of tasks, especially things where you have a clear template about exactly what you need to be doing. If you want to work through things, I find that it's more helpful to do that than an outliner or something like that. But basically all the project management stuff is in OmniFocus in some form. But then also because I'm the chair of my department right now, I also have an Airtable that basically I just use a Kanban board to see a high level what's going on, because there's some things that are in the Airtable that aren't really my personal tasks that I need to do, so I don't want to have them in OmniFocus. But then I think also when it comes to the day-to-day, I keep so much in OmniFocus. I think I have 130 projects or something like that. A lot of that's not actually relevant. It's on hold because it's relevant in the fall, or it's something I want to come back to someday. And so I want to have just what am I doing exactly today? And so what I usually do is I use the plan date feature and then I filter down, well, what are the things that I'm going to do today? And then once I have the plan stuff just for today, I actually take a lot of that out and I put it in Intend. It used to be called Complice, but it's basically a very lightweight thing where it's basically just a text editor and you just put in all the tasks that you're going to do that day, but you can color code them so you have different areas of responsibility. So I can, at a glance, see is my day going to be more teaching focused? Is it going to be more service-focused right now because I'm chair, it's a lot more service-focused and then not as much research-focused, so I can see all of that. And I think the one benefit of that is it also has daily tasks and things like that. I don't really want to clutter up OmniFocus with floss every day kinds of things. It's just not necessary to put it in there. But then I do go back and reconcile things. So every day I go and I clean out, well, what is I planning on doing that day? If I did it, great, I'll just take it off. And if I didn't do it, I can move it to a different day. I try not to leave things as overdue.

Andrew J. Mason: How does capture show up for you? When you're going throughout your day, it sounds like things are fairly fast-paced. Are you capturing from your phone? Are you talking to your watch? Do you have just a block of time where, "Hey, there's a five-minute breather between meetings here, and this is the time that I'm going to empty my head." How does that typically show up for you when you're moving throughout your day?

Maggie Delano: Yeah, I have two main ways that I capture things. If I know it's definitely a task. I will usually just put it right in OmniFocus through the iOS app. So now that Omnifocus is all integrated through everything through Apple, that makes my life much easier. I think at one point I was avoiding paying for the separate app, but I think I just didn't pay for the iPad app, but I had it on my phone and on my laptop. Now I have it on everywhere, which is great. So I have it all on all my different devices. So if it's just a task, I will just dump that straight into Omnifocus from my phone or from my laptop. And then if it's a thought, I'm not sure if it's really a task, I put it into Drafts app, which is a Mac app that syncs between different devices. So it's usually into one of those if I can. I just still use an analog notebook sometimes, but I try not to put tasks or thoughts in there that I need to access routinely because I don't always have it with me.

Andrew J. Mason: And talk to me about the automation slice of this. It can be as extensive as programming Omni Automation or really as simple as just, hey, it's a repeating task and I know that it's going to show up these certain days of the week or these certain quarters of the year.

Maggie Delano: I don't use automation that much. I use a plugin. So I use, it's called Toggle Tag, just a plugin I found online. I really like that plugin because I want to be able to run through my tasks really fast. So if I'm processing my inbox, I have certain tags that I use really frequently, and so I want to be able to toggle between them really easily. So I basically assign them to a hot key. So if I want to tag something that thing's happening this week, then I could tag it for this week, or if it's happening next week. And then I really don't use those are the main two tags I use. I don't actually really use any other tags. I experimented with using more tags and I found that I became more bogged down in remembering to tag things than just doing things. So I really don't use other tags, but I do have a buy tag. So sometimes if I'm online and I'm buying something, I'm like, "Well, what else did I say I needed to buy?" I might go use that buy tag. But other than that, I really don't use tags. I try to use the projects and areas of responsibility as a way to keep things organized, but I also don't have that many different contexts. I use perspectives a little bit, but anyway, my point is I don't really use the automation. I don't really need to use the automation that much.

Andrew J. Mason: We talked before we started this call about, you were joking a little bit about that you've been using Omnifocus for so long that there doesn't necessarily seem to feel like a previous time, or there's the before times and then there's how things are now. And I totally get that when you're in the flow state or this is the mental framework that I've been using for so long, it's hard to put yourself back into a place where it wasn't there to begin with. I'd love to hear a little bit of ... Do you have any wisdom or if you had one bit of productivity advice that's like, "This is my billboard to the world, and if I can just wave the magic wand and everybody understands this one thing about productivity, or at least how I've reduced friction in my life as much as possible, what would that action be? What would either that framework or that mental idea be that would be, "This is probably the biggest return on investment here for me"?

Maggie Delano: This is my personal bias. To go a little bit slower to go fast. I think it's a military term or something like that. But basically move slow to go fast is actually a really good way of doing things, especially in today's day and age with technology, AI, everything. There's a lot of anxiety. People are trying to move fast, but actually taking time and being intentional is really important, and I think one of the things that I really appreciated about when I did this Building the Second Brain course in 2021 was that I took a lot of time to think about, well, what's my system and how I'm going to make it work? And now I've actually just used that system for five years and I have really been able to stress test it in a way, and I think that a lot of the time if you're not taking a little bit of time to save yourself a lot of time in the long run, you're missing out. But I think it's so hard to carve out that time, both just in terms of a technical aspect, a technical error thing, finding the time on your calendar, but then also psychologically feeling like you actually have the time and not like you're operating from this point of position of scarcity, but more from abundance. And I think again, there are structural factors obviously with that too, but I think taking time to figure out what you want and how to do it is good, but also balancing that with not spending too much time tinkering on things. So once I got my system working, I have a PKM, a personal knowledge management area in my OmniFocus, and anytime I'm like, "Hey, it would be really great if I had a script that did this thing," or, "It'd be really great if I had a thing that did this." So I would put it in that task list and then on the weekend or something I would say, "Oh, okay. Well, I have a couple hours. Maybe I will tinker with some Python scripts to improve things." So I said I didn't do any automation, but actually there's some minor things. So you can export task paper from OmniFocus, for example, and I used that feature to paste my to dos into Obsidian. So I wanted to be able to have all the notes that I had in OmniFocus. So I forward an email to myself as a task, then I could get that context in Obsidian or Rome Research or whatever. And so I did write a little Python script that just modifies the clipboard to help you do that. Or when I paste into Intend ... The way Intend works is that you basically prepend on a line with three closed parentheses. So it basically just tells you that this is the third goal that you're working on. So when I copy a list of tasks, it just prepends them with a number so that way I don't have to do it manually. So there's little things like that, but I find that you get really sucked into the idea of, "Oh, this automation's going to be really great and really helpful," or whatever. And then the next day you're like, "Actually, I'm just really busy doing all my work. I don't have time for that." So I usually write it down and then if I come back, come do it on the weekend or a couple weeks later and I'm like, "Wow, it would still really be great to do that," then I still go and do it. But a lot of the time it's just an exciting idea and I don't actually need to do it.

Andrew J. Mason: Well, I love that you appreciate the idea for what it is, but it's like, yeah, it's not really attaching to whether or not I'm actually going to take the action associated with that idea. I think that can, in the long run, probably save us a couple of hours here and there and rabbit trails without really necessarily saying, "Well, my system is what it is." I think the fact that you're able to spend some time working on it, but without the all-in kind of methodology, where it's like, "I'm going to spend three hours on a Saturday and completely..." Yeah, you're right. As soon as the flu hits or something where your day just gets so fast and furious, you're not able to go through and work out the system in the new way that you're hoping for. So there's these little baby steps, these little tiny improvements that show up over time, I think really have a cumulative result. Any thoughts show up as I was talking through there?

Maggie Delano: Yeah. And I think the other thing I think that's kind of cool about the professor job is that you have a seasonality built into the cadence of your work. And so I try to make really intentional use of that in between time. So the time between the fall and the spring semester, I take some time off for vacation, but then I try to spend some time thinking about my systems. Are things working for me? I check my PKM list. Are there things in there that I really want to work on? And sometimes there's a more heavy lifting project that I want to do, maybe some improvements for some obsidian setup that I have and I might spend a couple hours working on them and then I have that ready to go. But I'm really focused on doing that in January between semesters or maybe in August over the summer. So I have these designated times where I'm working on these things and then outside those times I'm really trying to avoid it. I was dealing ... The past year I had to be in physical therapy for my hands, so I couldn't really use the computer as much. So one of the things I was focused on was, well, how do I really keep my workflows focused on things that I'm the only one who can really personally do them, and then I can also do them as efficiently as possible? So I was thinking a little bit about, okay, well, I don't really want to click 100 times because that hurts my hands. So maybe there's a better way I can write to do this or I can get someone else to do it sometimes. Not everyone has that luxury. So I think that was the other thing is thinking, okay, well, do I even need to do it this way? There's a lot of teaching tasks that professors do by hand, things like grading, but there's actually a lot of great educational technology tools that can make that easier for people like GradeScope. And so I said, okay, well, I'm having a hard time using my hands a lot, but so I can scan a bunch of PDFs and they can put them on GradeScope and then I can just click and it's much easier to grade, but it's not degrading the experience for the students at all. If anything, they get the feedback faster because the grading software makes it much faster to go through everything. So I think a lot of that could help too.

Andrew J. Mason: That's fantastic. Not everybody has the same rhythm of the year, but I think what you're calling out is everybody does have a rhythm. And so being able to find when are times a little bit more lax or when are times a little bit more just crazy, fast furious get through it, survive it. And then to your point as well about sometimes environment forces, or gives us a new opportunity to respond to a change there. And that's another additional perspective sometimes that we don't come up with on our own. And that's really exciting too, to think about it in that way. So different stage of life, different environment, different place, all of these things can equal a new perspective on the way that we do things and the way that we execute our work. So thank you for that. That's awesome.

Maggie Delano: Well, I want to say something I said earlier, which is that I think you have to know yourself first to know what that is, because I know how my brain works and I know that I get really overwhelmed. And so for me, the PARA system was really helpful because it helps you identify levels of actionability. So knowing is this a project? Is this a thing that's a one-off thing and then you're going to do it and then you're going to check it off? Or is this an ongoing area of responsibility that you're required to maintain certain level of quality of standard? I find that distinction to be really helpful for me, but I think there's other people whose brains work in different ways. And so I think I'd benefit from structure, but then other people I think might find that structure to be kind of suffocating. So you need to know where you are. So if I'm talking to someone who I think would benefit from the same things that I would, I would definitely say thinking about organizing all these different things, what capsules should they go into? The first time I started using OmniFocus, I just really didn't have a good way of organizing my life. I didn't think about things as projects or as areas of responsibility. And this is why I was saying I could really think back to how I thought about them before because I think I just wasn't thinking about them at all in that way. I was thinking, well, I'm teaching this class. And even though when you teach a class you have a lecture and then you have another lecture and you have a homework assignment, I wasn't really making a project for each of those things. Maybe there were subheadings, but it was all kind of just floating around in there. But now that I have a structure, I see everything through that lens, even things that I'm organizing for my colleagues at work. But also when I'm working with people, I can see how some of them jive with my way of thinking about looking at my Airtable and looking at my kanban board and seeing all that. And then other people are like, "I don't really work as well on computers. I really want to be able to print this out and see it." And so it's just interesting how different people work with things.

Andrew J. Mason: My one personal coaching question. As I hear you give that answer, in my mind, the follow-up is something I personally struggle with sometimes is how big do I make the buckets? When you decide, "Oh, this is a project," or, "Oh, this is a subheading, but there's some sub-actions under that," versus, "This is just a chunk that's a single action task," do you have any helpful ways to maybe think about how do you size that so it feels like it's the right kind of chunk to bite off and chew? Did I frame that okay? Does that sound understandable?

Maggie Delano: Yeah, yeah.

Andrew J. Mason: Yeah.

Maggie Delano: So just taking a class, for example, I actually have a separate template project for each lecture that I give, but then within each lecture there are subheadings. So there's things that have to happen at different times. So if I'm giving a lecture, there's some content that I need to have released before the lecture happened. Sorry, before the previous lecture, so assigning homework or whatever. And so then there's just a subheading within the same project for that. But I think that's also because I might do two to four lectures a week, depending on how many classes I'm teaching. And so the cadence of that is still pretty fast and it's a clear template, you follow the template and you take it off. So some of it's about how big the project is also. And then some of it is also, are you the kind of person that you feel like you need to have that positive momentum? There's so much satisfaction that comes from checking a project off. But if you're working on this big project and it's going to take six months, maybe it's not very motivating if you only get to tick the box at the end of the six months. But it also depends on if there's actually really discreet sub-tasks or subheadings that can be broken out because it's like, for example, I work on research papers. I probably wouldn't make multiple projects. I'd probably just have one project for a research paper, even though it might take months and months to do that project, just because I think that's the best way to organize it. So I think I generally err on the side of larger things even though checking the checkbox is satisfying.

Andrew J. Mason: It is. And I know it's a real thing for some people to be able to say like, "Oh man, it helped me make progress. I've made progress mentally, widget, cranked, checkbox, made progress." There's that feedback there. And sometimes it's difficult to know how big do I make the box so that it feels like there truly is progress being made. Love that. Love this conversation. Before we let you go, I know you're busy. If folks are interested in connecting with you, staying in your orbit, seeing what you're up to, how can they do that?

Maggie Delano: That's a great question. So I admit I have been on social media a bit less recently. You can follow, check out my personal website. That's probably the best way. But you can also send me an email if I have time. I'm happy to chat or at least respond to emails as well.

Andrew J. Mason: That's fantastic. Maggie, this has been an awesome conversation. Grateful to have you on. Thanks for sharing your wisdom with us.

Maggie Delano: Sure, absolutely. Take care.

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.