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

June 17, 2024, 6 a.m.
How Brian Hogan Uses OmniFocus

In this episode, we interview Brian Hogan, the Director of Developer Education at Temporal Technologies. He shares how Omni software allows him to manage his workload and template his lesson plans to teach more effectively.  We also discuss the value of capturing tasks for accountability, using the Eisenhower Matrix to prioritize, and utilizing OmniFocus to create clarity.


Brian Hogan: You can only get by so long with having somebody else nudge you before they start having questions about your capabilities and your competence. If I go back in time, I think that that's the thing I try to get by myself really hard is you get things out of your brain earlier, become more accountable to yourself, become more accountable to others by getting things out of your brain and onto some kind of secondary place.

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 learned how Brian Hogan uses OmniFocus. Welcome, everybody to this episode of The Omni Show. My name's Andrew J. Mason, and I'm super excited because today we've got Brian Hogan with us. Brian's a dynamic leader in technology and education, currently serving as the director of developer education at Temporal Technologies. Brian's got a rich background as a formal editorial manager at DigitalOcean and a development editor at the Pragmatic Programmers where he's made significant contributions to the tech community through books, tutorials, open source stuff. We will talk all about that I'm sure, but let me jump into it. Brian, it is so great to know you. Thanks for hanging out with us today.

Brian Hogan: Thank you, Andrew. Thanks for inviting me to come on. This is really cool. I was really excited about this.

Andrew J. Mason: Yeah, thank you for joining us. If you don't mind, go ahead and level set a little bit about what you currently do and where you find yourself maybe geographically, and then we'll start diving in.

Brian Hogan: Yeah, sure. I'm in a little town called Eau Claire, Wisconsin. I lead the developer education teams, and so I work at Temporal Technologies where my team creates tutorials, courses, self-paced ones, online ones, and ones that you would deliver in live delivery methods through our developer education program, which is also our developer documentation, and it's all in support of helping developers solve some of the most challenging problems that they have in software. So it's a really fun and challenging job. You get to see some really big situations that people run into and some big problems, and so it's really fun to be involved with that. And when I'm not doing that, working on books, I'm actually working on a book right now. I've been editing books for quite a while. But before all this, I spent some time in the classroom teaching software developers. And then before that, I was a software developer myself. So I've learned that what I'm really good at is developing people, so that's why I find myself in these roles where I'm either teaching people or leading people, but throughout all of these things, whether I was doing software, I had to do documentation, or whether I was doing classroom work, or whether I'm working on book projects or whatever, I find myself using several of the Omni tools as part of that. And it's been really interesting how they're always there no matter what job I'm in, one of those tools is always tagging along for the ride.

Andrew J. Mason: Very cool. Yeah. Thank you for connecting the dots there, and I would love to know a little bit too about what made you transition into the online space. So you're teaching in live environments, and then suddenly over time, was there a moment where you're like, "Hey, Temporal Technologies, this is going to happen online for us," versus it's just a slow transition and over time it just seemed like the thing to do?

Brian Hogan: Well, honestly, when I was teaching full-time, half of my load was online load, and the other half was hybrid, so it was in-person part of the time, and then online the rest. And it gives you a really interesting way of learning how to teach. You've heard about the idea of the flipped classroom where you do lecture as video or asynchronously, and then everyone comes together. And doing that for four years taught me the value of in-person. Don't bring people together in-person just to be in-person. When you have people together in-person, don't just monologue at them, talk at them, lecture at them, bring them together, give them opportunities to learn, especially if they're adult learners, give them opportunities to learn.

The thing is that when I left DigitalOcean and came over to Temporal, we were thinking about our courses as part of empowerment, like how do we empower our developers to use our products. And a lot of teams are distributed, so getting people together in a day for a workshop, whatever, that's going to be less in demand than online asynchronous.

We build our courses to be the gold master of the course, and then we'll deliver that course in different formats, whether it needs to be self-based online through our LMS, or whether it's an in-person workshop. And Temporal has an annual conference called Replay. It'll happen in Seattle. I think it's the 18th of September this year for anybody who's interested in the kind of work that we do. And then my team will be there delivering these courses live. We'll be doing our live delivery of these courses for the attendees, too. It's more of a demand. We had the idea that we were going to do some of these courses that were going to be, "Oh, we're going to be on-site with all these customers. It'll be a great opportunity," but the demand wasn't there. It was more of, "Well, we're in India and the other team's in England. It doesn't really make sense for us to fly everybody to a central place. Can you just deliver the courses as a webinar?" And so we did that. We'll do that, too. We're flexible.

Andrew J. Mason: Do you have any recollection as to where maybe you first came across The Omni Group, changing story arcs over to that side of the fence, was there a moment? Was it kind of a slice of time? It just slowly became aware of that software? But where did that start to enter in the picture for you?

Brian Hogan: So it was probably around 2009, 2010. I was doing some documentation work. I had written my first book, and I was doing some preliminary documentation for a work project at the time. I was still a software developer. And I kept seeing these really nice drawings from other people and their stuff. And I, "What are people using these days," because I'm an illustrator user. I had used Freehand when that was a thing. I'm reasonably good with Illustrator, it's just not great for doing the kind of quick stuff that I want to do. And everyone's, "Oh, it's OmniGraffle. You got to check it out." And so I did, and I was hooked. And I don't try to do a lot of customizations, but if you were to pick up one of my books, you probably easily identify all those flow charts, those screen mock-ups, whatever, those are done on OmniGraffle. You can see it's very clear, I'm not trying to go nuts with it. But I found it was really good because it was intuitive. It was very quick for me to be able to put things together, connect the dots, draw the lines. I was impressed with the software.

And then my editor at the time said he was a big fan of OmniFocus. I was skeptical, because I don't do well with to-do lists. I am happy to put things on them and then forget about them. But OmniFocus was the first one that actually stuck for me, so I gave it a try, gave it a demo, and I've been using it I think since version two, the very early days of version two. I've turned several other people onto it. And then for when I was teaching, I discovered the that OmniOutliner makes a great way to organize semesters with a lesson plan for each course. And so I had my lesson plans with my competencies and my learning objectives. Everything was aligned. So when I had to turn in for an observation, someone comes in and... Yeah, when you teach, somebody will eventually come in and watch you teach, like another instructor or whatever. And being able to hand them, "Here's my lesson plan, and here's how each thing that I'm doing aligns to the learning objectives that we're doing for today," that was really valuable. So the multi columns support and OmniOutliner was what allowed me to make that real easy for me to keep track of.

Andrew J. Mason: I'd love to know, talk to me a little bit about any advice that you might have for somebody who is maybe just entering that space, specifically OmniFocus and thinking about to-do lists, task managers. You said, "Hey, honestly, I wasn't originally a huge fan of them," but at some point, the workload just gets to be a little bit more than the brain can take on and you're like, "Okay, I need something for support here." What advice do you give somebody that's maybe in that space but hasn't quite made the leap into a task manager or just the idea of expanding responsibility? You got to do something.

Brian Hogan: One of the things that I gravitated towards OmniFocus about was that it allows me to put aside the things that I don't have to care about right now contextually. In the previous versions, you had contexts. Now everything's just based on tags, but I still use it as though they were context. I know I have a ton of things related to a book that I'm writing, a massive list of things that I need to do for my book that I'm writing. But while I'm working at my day job at Temporal, I don't want to see those, I don't want to be distracted by them, I don't want them staring me in my face saying, "Hey, these are due, these are due. Don't forget about me."

And that's what I think is really valuable is figuring out a way to compartmentalize the tasks that you have because there's going to be tasks that you have for home, tasks that you have for work. Now, I'm actually a big fan of the Eisenhower Matrix doing things in terms of importance and urgency. And so I've set up tags and OmniFocus for urgency and importance so that I can view my OmniFocus list in terms of the Eisenhower Matrix. Oh, these are the things that I got to schedule. These are things I got to do right now because the house is burning down. These are the things I should delegate to other people. And I don't typically have tags for not urgent and not important. I will use that quadrant of the Eisenhower Matrix to say, "I'm not adding this to my list. [inaudible 00:09:10]."

Andrew J. Mason: Yeah, you can throw it right in there.

Brian Hogan: Keeping track of the stuff is one part, but also making sure that it doesn't overwhelm you and distract you. I think that's one of the beautiful things about OmniFocus is that it does have the ability for you to create these custom perspectives and filter out the things that you don't need to see right now so that you don't become overwhelmed by all the things that we have to do in our lives.

Andrew J. Mason: A question I feel emerging here that wasn't necessarily on our list, but I'd love to hear your slice, your take on it because it sounds like something that you would be uniquely positioned to answer. Having all of this experience, teaching people in multiple environments, and you're not just teaching people information, but you're also showing them, guiding them how to learn, and it's not necessarily even an Omni question, honestly, this is just the selfish one for me, but how do you best suggest somebody go about, let me work this through a little bit, but go about learning? Do you get a sense in which there is a best way or a most helpful, most useful way for somebody to go about taking in new information, especially when the floodgates are open, you've got to cram this stuff in, especially knowledge and facts and stuff? Do you lean into learning styles? Do you lean into amounts of information? Is there something about the way that you teach that you're like, "Man, if everybody could get this, it would help accelerate their progress so much faster"?

Brian Hogan: Wow, I could spend a whole podcast on just that question. I'm going to throw the grenade here, and you can search this on Google. There's plenty of articles. The idea of learning styles is a myth, and it's actually a dangerous myth that tends to hold people back because they will convince themselves that they can only learn one way. It's especially dangerous for adult learners. They'll convince themselves, "I can only learn through video," and then when there's not a video available for something, they will just select themselves out of the learning process. "Oh, I can't learn that." It's like a self-fulfilling prophecy. So we do have learning preferences. I prefer video or I prefer reading, but we know when it comes to learning styles, there's no evidence of any studies that are conclusive that suggest that those are actually a real thing.

What does work, especially for adult learners, is starting with the end in mind and working backwards. So you've probably taken a college class at one point where you sat through 16 weeks of lecture, and then you had a final exam, and then somebody goes, "God, those questions, we never learned about that. We never learned. They never said that in class." We've all had that experience, and what that is an identification of a misaligned curriculum. What you're supposed to do, at least in my opinion, when it comes to anything that is a skill, anything you're trying to do that you're developing a skill and you're gaining the knowledge through skill is you think about what are the outcomes I want someone to have at the end? What are the things I want them to be able to do? In performance-based learning, the style that I subscribe to, it's called a competency. These are the things that you should be able to do. They're specifically measurable, they're observable, and you'd be able to do this. I want to do this right on the fly, but if you're doing a course on OmniFocus, one of the competencies is you will be able to build a custom perspective.

Andrew J. Mason: Very specific, yeah.

Brian Hogan: Yeah, very specific, but you'll be able to build a custom perspective so that you can sort your tasks by a very specific project. In doing so, if you think about, "Okay, well, what are all the things that go into that?" Well, you got to know how to create a task or several. You need to be able to attach the projects to them, attach certain tags to them. So those are three or four different things that lead up to that competency. Then I think, "How will I evaluate you? How will I know that you can do that?" So I'll develop some kind of exercise, some exercise that will let me know that, "Okay, I want you to build me a customer perspective that does this, this, this, and this," and there's the performance checklist of all that.

Once I have that, now I have the roadmap of what I need to teach you. I have the entire roadmap because what I'm doing is I'm literally teaching to the test. People are like, "Well, you're teaching the test." No, that's the intention. My goal as an instructor is to help you get 100% on that test. I'm to provide you the tools and the roadmap, because this is an adult learner. This is not a kid, this is an adult learner, and we have to remember that adults have many other things in their world. And the things that they care about is why should I care about this, what will it do for me that I couldn't do before, how will doing this and engaging in this activity make me better at what I'm currently doing, because I've got to pay bills, I've got to do all these other things.

So we got to set them up with a good successful path forward. And you can apply this to anything that results in a skill, because along the way of developing the skill, you will develop the knowledge that you need to it. If I ask you, "How do you patch a wall in your house?" What's the outcome? The outcome is you need to be able to make a smooth patch with the right texture and all that kind of stuff, all things you got to learn along the way. The outcome, you're going to assess yourself because you're going to look at the wall and go, "Well, I did a good job." So then you got to learn all the things backwards from what that new... And so you develop that skill and that knowledge.

Andrew J. Mason: I know it's meta, but I mean as people are listening, I can just picture them saying like, "Oh gosh, this sounds a whole heck of a lot like project management." This is really good project management thinking, as well. There's a corollary there where you think about, "Okay, is this a sequential project? What are the steps that need to happen in order for us to get to the outcome that we need? Is this a parallel? Can they happen in tandem?" There's a lot of these questions that I don't think we ask ourselves by default. And even you were talking about in teaching during courses and lectures and stuff, it doesn't happen by accident or automatically. But the good news is, and tell me if this is true in teaching as well, I feel like you don't have to waste that thinking. That's what routines, that's what automation and templating is for, is where you do the hard work of burning the calories in your brain one time, and after you've done it's there and you don't have to do that ever again, and you can crank the widgets again. Speak a little bit to me about is there a role for automation in teaching or even in your life as you're executing on the day-to-day stuff that you need to do. How does that show up for you?

Brian Hogan: Automation for teaching, a lot of that, like I said, with OmniOutliner, actually just having my lesson plans in a template. Here's the lesson plan of the template. I'm not thinking about what I got to put together. I got to have it... And you'll find that when you're teaching if you teach in a traditional environment, there is some lesson plan template that college asks you to use or something like that. I got to do a report every Wednesday morning for my job. I'm not putting that task in OmniFocus every week. It's a recurring task. That's another thing I like about OmniFocus is I can put the recurring task in there. When I check it off, it appears for next week. It appears on my to-do list, and I see it on Monday. "Oh, looking at my week in advance, this is what I got to... Oh, remember, do that thing."

Now, I know I got to do it. I know I have to do that task, but having the automation in there with a reminder puts it front and center. And as it gets closer, the other reminders will show, "Hey, you got to remember to do this Tuesday night." "Hey, remember, this is the thing you got to do." If you remind yourself too much, you'll turn off their reminders and you get annoyed. So you have to find that sweet spot of what works. And so for me, I have a reminder that goes off one minute before each meeting. It's not enough for me to forget about it, but it's not also not enough time for me to start something else and then miss the meeting.

Andrew J. Mason: That's really smart. So it's like you will pay attention to this right now and be rewarded for that behavior or it's gone.

Brian Hogan: Yep.

Andrew J. Mason: Something that's so obvious about project management, and laying things out, and templating inside of the business place, inside of your workplace, it's so obvious. Aha, of course I need to do that. Who wouldn't do that? That makes sense to me. But why is it when it comes into our personal world, we're surprised that Christmas is coming again this year. What do you think that is inside of human behavior that causes us to be surprised that something's predictable?

Brian Hogan: All I have is a guess, but work is hard for a lot of people, and it takes up most of your mental space. And even if you have a job where you can just put work down at the end of the day, you're still probably thinking about an interaction you had or something like that. And we're working more than ever now. There's so many things going on and who sets up a Trello board or a Jira board for their personal life? It just feels like too much work. It feels like work.

Andrew J. Mason: They're out there, Brian. I promise you.

Brian Hogan: I know they are, I know they are. I absolutely know they are, but it's not the average person doing that, because when you make personal life feel like work, yeah, I don't want to do that. I'll remember that. I'll remember that I got to do that thing. I'll remember that. That's my fear. That's my feeling is that we're just so busy. Minding the family calendar is a chore of its own, so you're just going to get caught off guard by these kinds of things because your mind is focused on that immediate. What's the immediate thing I got to do?

Andrew J. Mason: And by the way, if you are out there and we just pegged you, we're glad you're here. It's okay. We're not judging you. It's okay.

Brian Hogan: I don't think it's a bad thing. I just don't know if there's that many people that do it.

Andrew J. Mason: No, no, no. Talk to me about the overall context that your software finds itself in terms of OmniFocus, in terms of OmniOutliner, more so I think than Graffle. But what's the flow of information look like? Are there any corollary programs that flow into them? How does the data get pulled out of it? Does it just land there? When you're checking things off, does the data go anywhere after that?

Brian Hogan: For the most part, nothing comes out of it. OmniFocus is where tasks go to get finished, but things flow into it from a lot of different places. I absolutely love the fact that I can just forward an email to my inbox. That is the thing I probably use the most. There's busy people and productive people. You've probably heard, [inaudible 00:19:11], "Oh, I'm so busy, I'm so busy," and there's productive people. And I know people, you get addicted to Slack messages and you have to answer the Slack message. You get an email and you have to answer the email. If you look at the most productive people in your life, you can't get a meeting with them today.

Andrew J. Mason: That's right.

Brian Hogan: They're going to schedule it into the future. They're going to schedule all things. And if you look, because it's not like they're not doing real work, they're doing things that they're accountable for. They can't just be interrupted. They cannot allow themselves to be interrupted. And I think we can't allow ourselves to be interrupted. We can't react to the Slack bells or every notification that comes in. And so one of the things that I do that I picked up from watching the most productive people in my life is that I have triage time for my email and my to-do list. So throughout the day, stuff gets put into the OmniFocus inbox. And then during triage time during the day, I will go through it, "Oh, for this project." I'll tag it and move it out of the inbox. I don't do that throughout the day. I don't try to tag and project and do all that stuff, because OmniFocus is a great quick add interface, but it's still not of the moment.

If I'm talking to someone, and my boss is rattling off a bunch of stuff he needs me to do, I can't be trying to click all the boxes and whatnot and do that. I got to get it written down. So I'll actually just write down on a thing. And one of the things that I've discovered is there's this fantastic app for Mac called Drafts. It's a tool that I use. I write everything in there that it's not code. My ideas start from there. I will move things from Drafts to Obsidian, or I am a software editor, so I use a terminal-based text editor called Vim. But I start my ideas in Drafts because I can do them anywhere. And one of the things that Drafts has is a community plug-in that lets me take a list of items in Drafts and send them to my OmniFocus inbox.

So as my boss is rattling off things that I need to do, I can just pull each one on its own line. When the meeting's over, select all, boom into OmniFocus inbox. And that's a fantastic way of making stuff work like that. I do have the keyboard shortcut for the quick add. I have a stream deck here on my desk. I don't do streaming very often, but I do use it for automations, and so I have buttons. I have a button to bring up a screenshot tool, and a button to bring up my OmniFocus window, and a button to bring up the OmniFocus quick add because it's easier for me to just push the tactile button than it's to remember the keyboard shortcut. It's like OmniFocus becomes the place where I catch the things I have to do and then get them off my list.

Andrew J. Mason: I love the intentionality around separating the collection of the work and the doing of the work. I think for a lot of people, that just kind of mushes together, and it becomes this amorphous thing that you try to untangle. There's just spaghetti there that I have to undo. And when you have the intentionality of separating those two items out and you say, "Okay, at any time during the day I'm going to remain in flow, remain in state, take the items in, that's fine, but I'm still working on the thing that I need to work on and not be distracted by the bells, the whistles from all the notifications," and saying, "Okay, now there's an intentional time that I'm actually going to work on. What am I doing here? What is it that I'm trying to accomplish?" For some reason, just even that little nuance-y, tiny level of intentionality I think puts the ownership, the responsibility back in our court and gives us that sense of, "I'm doing what I can control." Maybe I do have a triage style of job where it is latest and loudest all the time, and there's not a whole lot I can do about it, but having that just little slice of intentionality there I think goes a long way in giving us the feeling of control over an ownership of our own lives. That's a really cool thing.

Brian Hogan: It's about having the confidence that I didn't forget about something, because there's a lot of stuff that is going to come in, especially in certain roles where there's just a lot of information coming from different places and you've got a person on my team needs me to look into this, my boss wants to look at that, oh, the customer success team has an issue here. I got to deal with that. And yes, we're going to put those in our Jira board, but I still have to follow up, and I don't want to track five or six different systems. So a link to the Jira item might end up in my to-do list so I can remember to go back and look at it later. It's the confidence that I have that I have captured the things that I have to do. Yes, the workload is going to be overwhelming. It's always going to be overwhelming. Capturing it gives you the confidence. You don't even have to sort it yet, just get into the point. And we talked about this earlier, what kind of advice would I give people. Just get into the act of capturing the things you have to do. If you're going to try to improve the way that you eat, one of the first things that someone will do is they'll say, "Make a food journal," because they want you to start actually getting in the habit of writing down all the things. Same thing with a to-do list. You're not going to be successful with to-do lists if you're not in the habit of adding things to the list. So that intentionality of just adding things to the list will help you gain that confidence that you need to say, "I know I have a lot of stuff to do, but at least I know about all of them. They're all here. They're not in my brain taking a brain space. I have offloaded them to secondary storage," basically.

Andrew J. Mason: I love that because it's not necessarily any less overwhelming or depressing, but at least you know what the game is at this point because you're looking at the jar, and it's full of tasks, and these are the things I got to do, but at least I know exactly what they are. I love the statement about systems. Everybody has a system. You might not necessarily know what it is, but it's happening whether or not you're aware of it. Talk to me, Brian, about any advice you might have to a younger version of yourself that, "Hey, I thought this was a great idea when I was doing it, when I was rocking through my system, and working on just how my workflow goes and trying to figure out the best way to get things done. I thought this was a good idea, but looking back, maybe not so much." Don't necessarily call it a failure. Don't necessarily call it wasted effort or energy, but there's something there about that. If you're going through it yourself, just skip that slice because for me, I thought it was a good idea at the time, not necessarily.

Brian Hogan: Earlier in my career, I would rely too much on my memory. The idea of getting things out of my brain and onto paper or onto a list, I relied too much on that. And it worked for a while, but as you progress in your career, you get more responsibilities, which means more things that are going to consume your memory space. And if you're not tracking it, somebody else is. Someone's going to come and ask you, "Hey, remember that thing," and you can only get by so long with having somebody else nudge you before they start having questions about your capabilities and your competence. If I go back in time, I think that's the thing I try to get by myself really hard is you get things out of your brain earlier, become more accountable to yourself, become more accountable to others by getting things out of your brain and onto some kind of secondary place. And then, I'm a big fan of Eisenhower Matrix, but get into something that gives you a decision matrix or some kind of a decision process that you can follow so that you could determine what the priorities of things are, because what's important to me is not the same thing that's important to my boss. And understanding what urgent and important means in your context, that's going to be different from me. But having a system that you can follow for yourself that helps you identify those things, I wish I would've learned at a much earlier. I think I would've had a much easier time with certain kinds of projects in my past.

Andrew J. Mason: I so super appreciate the time that you've spent with us. I really feel like just being in-moment, in-state, the fact that you've been able to give us that time speaks to what you were talking about earlier, the ability to separate out the latest and loudest to be able to actually, "Hey, I've got a real person in front of me. We're actually having a real conversation." How can folks connect with you, what you're up to, and just find out more about you, and communicate with you if you'd like that?

Brian Hogan: Yeah, I'm on whatever it's called these days, X or Twitter. I'm B as in Brian, P as in Patrick, Hogan, H-O-G-A-N, so BPHogan. I'm also on Mastodon and Bluesky with the same handle. And you can find me on LinkedIn, and I have a website, I did really good with the branding here. We got the same username for everything. And I would love to talk with people, love to learn more about how other people are handling their productivity challenges. So yeah, please reach out. Let's have a conversation.

Andrew J. Mason: That's awesome. Brian, I so appreciate this. Thanks so much for joining us today.

Brian Hogan: You bet.

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