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Sept. 27, 2021, 6 a.m.
How Jimmy Little Uses OmniFocus

Today, we chat with digital media product manager, Jimmy Little.  Using OmniFocus and contextual computing, Jimmy’s able to navigate to the exact information he needs as quickly as possible.

Show Notes:

Jimmy talks through his system that uses automation to bind multiple products together via deep linking.  Shortcuts and automation combine a central “dashboard” in Obsidian with OmniFocus, Toggl, DEVONthink, and more.

Some other people, places, and things mentioned in this episode:

  • OmniOutliner
  • Kinkless GTD
  • 43 Folders
  • Merlinn Mann
  • Leo Laporte
  • Macbreak Weekly
  • Screen Savers
  • Jira
  • Atlassian
  • Trello
  • Getting Things Done Book
  • Shortcuts
  • Applescript
  • Omni Automation
  • Obsidian
  • Devonthink
  • Keyboard Maestro
  • Streamdeck
  • Toggl
  • David Sparks Contextual Computing
  • Craft
  • Box
  • iPhone Backtap
  • Telegram
  • iMessage
  • Slack
  • JimmyLittle on twitter
  • JimmyLittle Instagram
  • OmniFocus
  • Slack
  • Transcript:

    Andrew J. Mason: You're listening to the Omni Show. Get to know the people in stories behind the Omni Group's award-winning productivity apps for Mac and iOS. My name's Andrew J. Mason. And today we talk to Digital Media Product Manager, Jimmy Little on how he uses OmniFocus.

    Andrew J. Mason: Hey everybody. Welcome to another episode of the Omni show. My name is Andrew J. Mason. And in this episode, we're talking to Digital Media Product Manager, Jimmy Little. Jimmy, thanks so much for joining us and talking to us about your OmniFocus system.

    Jimmy Little: Hey, thanks for having me. This is fun.

    Andrew J. Mason: Well, catch us up. Talk to us about who you are, where you're from and where you find yourself these days.

    Jimmy Little: Well, I'm originally an East Coast guy. I grew up in Virginia and moved to New York right out of college and did my thing there for a while and about, I guess, seven years ago, moved to Southern California to take on my current job. And here we are in Burbank, California.

    Andrew J. Mason: Excellent. And help us wind back the clock. How did you find yourself coming across to OmniFocus or the Omni Group back in the day?

    Jimmy Little: I've always been a computer geek and a productivity nerd from way back in my college days and my early New York career, I was a production manager for a large special event designer. We did huge weddings and parties and stuff, and I was the uber-planner for that, and that got me into OmniPlan, actually, I was a Microsoft project guy before that, and then switched to Mac and got into OmniPlan back in the day. And that led me down the road of found out about OmniOutliner eventually, started Kinkless GTD and then eventually, I guess in, I think it was late 2007-ish, the OmniFocus Beta came out and I started going down that road then. I was a big 43 folders guy back in the day. I literally had the rack on my desk with literally 43 folders in it and listened to a lot of Merlin Mann podcasts. And he was heavily pushing OmniFocus in the early days, so I got into it by way of listening to him in other podcasts and shows.

    Andrew J. Mason: Yes. Me as well, Leo LaPorte and Merlin Mann, the screensavers and MacBreak Weekly.

    Jimmy Little: Yeah. I think I started, what was it? Early 2008, I think OmniFocus first came out?

    Andrew J. Mason: That's right.

    Jimmy Little: And then late 2008, it came out on iPhone and I was in on day one on all of that.

    Andrew J. Mason: That's awesome. And honestly, not super uncommon for folks that we've had on the show before. I believe that kids are using the term OG these days.

    Jimmy Little: OFOG.

    Andrew J. Mason: That's right. Talk to me about the areas of focus that you have, or different spots in your life? How all encompassing is OmniFocus? Or is it just a particular slice of your life?

    Jimmy Little: Depends on what year it is really. I go in and out of what I'm putting in there. Currently, my current setup, when I was a single man, let's go back a few years to back when I was a single man, everything went into OmniFocus, because that was my system, everything was in there. A few years ago I got married, had a kid and now I'm 95% in OmniFocus. And then I have two shared lists in Apple Reminders that I'm in with my wife, just the grocery list in a house to-do list. So I'm almost all in on OmniFocus, definitely all in for all of my personal stuff.

    Jimmy Little: It gets a little more complicated and I have a lot of automations and stuff that take care of things when it comes to work, because we don't obviously deal with OmniFocus at work. We do a lot of JIRA and Atlassian and Trello and that sort of stuff at work. So I keep all of my stuff in OmniFocus from work, but work stuff doesn't technically go into OmniFocus.

    Andrew J. Mason: All right. So I have to use this opportunity to ask a completely selfish question, wasn't in the scripted questions that I sent you, so here we go. We're actually about to have our third kid.

    Jimmy Little: Congratulations.

    Andrew J. Mason: Thank you. So excited about that, but I always love whenever somebody else is in parenting and OmniFocus, or GTD, or task management, love to ask this question. How do you handle tasks or projects as it relates to parenting and children? Any advice or tips or takes in that space?

    Jimmy Little: I'm a big areas of focus guy. I read all the GTD books back in the day and all that. But so I do have, my son's name is Gary, and I do have a Gary folder in OmniFocus where I keep all my Gary projects. Right now, there's only a couple, but I have a Gary to-do list, which it's a someday-maybe list of things we want to do together. We're planning a camping trip, he's three, I'm taking on his first camping trip in a couple of weeks. I'm pretty excited about that. So I have Gary camping trip project in that folder right now.

    Jimmy Little: In the beginning there was a lot of recurring tasks. You've already been through it twice, so you know there are things that have to happen at the same time every day when you have a child. And he was my first, so it's like, "Well, I got to write this down or there's no way I'm going to keep up with all this stuff." So in the beginning there was a couple of recurring projects, or projects with recurring tasks that were just constantly, you have to do this at this time. This is when he gets his medicine. This is what he gets his bottle. This is when he should be going down for a nap, even though he probably won't, but this is when he should have been. All of that stuff was in recurring lists.

    Andrew J. Mason: Okay. So me too. And can I just say for any parents out there that are utilizing OmniFocus, or GTD, or anything like that, there's no shame in writing down brush teeth, when putting it on a recurring project, because you got to, you got to do it. So sleep deprivation, got to do it.

    Jimmy Little: Yeah.

    Andrew J. Mason: Let's switch gears and talk about review. How does reviewing look in your system? Do you do any reviewing at all? I

    Jimmy Little: I do. And it looks completely different when I'm starting a project as to when I'm in the project. I'm a very optimistic reviewer. When I start a project, then real life jumps in, I do get to the review at least every week or 10 days. I know a lot of people like to sit down and do it every Sunday night or whatever and have their routine of doing that, but with a three-year-old in the house and a job and everything, sometimes you don't get a Sunday night to yourself, so you do it on Tuesday morning or whatever. It's fine. You can't be locked into this stuff.

    Jimmy Little: I do set review intervals when I set up a project, some of them are as often as every two or three days for a large work project that's constantly changing, and some of them are once a year, once every 18 months. But when I do sit down to review, I prefer to do my reviews on my iPad. We have a, not a large house, but we have a townhouse, and it's got a small patio on it and we have this hammock chair out there hanging from the ceiling. And that's my favorite thing to do is just grab a cup of coffee and go out to the hammock chair with my iPad, and even if it's in the middle of a work day on a Tuesday afternoon, I leave my home office and I go downstairs and I go out on the patio with my iPad and I do my review out there.

    Andrew J. Mason: Beautiful. I know it's not always possible, but when it is, carving that separate space for review, that's really helpful. How about those people that are just getting started in OmniFocus or task management, do you have any first sets of go-to tips or tricks? Or anything that you would say, here's how I would start if this were me and I was just starting over, here's what I would do?

    Jimmy Little: I think one of the big challenges that when I get people onboarded with OmniFocus is they either, they try to do two things, either they try to move their entire system over all at once, whatever their old system was, which I think that's a bad idea when you're also trying to learn new software if you don't know what you're doing in OmniFocus yet, because OmniFocus is a very complicated piece of software if you allow it to be. And that goes into my second tip in a sec. But trying to learn everything that OmniFocus does while also moving your entire system into OmniFocus, that's probably going to frustrate a lot of people and probably discourage them.

    Jimmy Little: And the second tip would be to start small. Don't move everything at once. Try to move a list or two. Don't dig into the inspector in OmniFocus yet, right? Just put some lists down, create maybe two projects that are single action lists, move everything over from reminders maybe the first time, just say, "Okay, I have these two or three lists that used to be in reminders, now they're an OmniFocus." and run with that for a few weeks, see what happens. Maybe add a tag or two after a few days. "Oh, well these three tasks all have the same context in GTD terms. All of these I can do while I'm in the kitchen. Okay. So I'm going to add a kitchen tag to that."

    Jimmy Little: But a lot of times I see people that I encouraged to start using OmniFocus, they'll go online, they'll go to YouTube and watch all these OmniFocus pro videos, and these people have 200 nested tags and they'll try to set this system up like this person they saw on YouTube and then they end up just wasting a bunch of time. And then they start putting their stuff in the list and they realize, "Oh wait, none of these tasks fit these contexts that YouTube guy has." So they've just wasted a day and a half setting up the system that is never going to work for them and never was going to work for them.

    Andrew J. Mason: Yeah. If you've listened to this podcast for about a year, you probably get the impression that I am a recovering crazy maker, visionary, and that would not necessarily be an inaccurate estimation. Watch an hour long YouTube video, get inspired, try to re-change everything in your system and then realize, "Oh man, I've just wasted a bunch of time."

    Jimmy Little: One of the other things that I want to point out that, I just went through this a few weeks ago with somebody, and it's not for really beginners of OmniFocus, but people who are into it, like that semi-pro user of OmniFocus that knows what they're doing, they know how the tool works and they're into it and they're ready to go, is they don't get the distinction between when a project needs direction and when a project needs details and they will overthink, they take that David Allen, "everything with more than one task is a project" to heart. And for me that just doesn't work. I'm looking at my inbox now. I have two things in my inbox, to get the phone number from the new dentist from my wife and to make a dentist appointment. Right?

    Jimmy Little: In true GTD world, I would have made a project and put those two tasks in there. And I'm like, "But I'm not going to make a project for two tasks. They can just sit in my inbox and I'll check them off when they're done." Some people need that structure. And some people need that flow in their brain. For me, I can look at two tasks in the inbox and say, "Oh, those are related. I'll do those tomorrow." Throw a due date on them, throw a flag on them, throw my focus tag on it, whatever it is. And they'll show up where I need them to, I don't have to go through the whole process of making a project and setting all that up.

    Andrew J. Mason: I can totally understand that. Sometimes when life moves so fast and furious, you throw a bunch of things into the inbox and then you're like, "Okay, these three have to do with the dentist." That's one of the reasons I love infinite nesting inside of OmniFocus, because you can just say, okay, even in the inbox, dentist, heading, subheading, phone number, next action item, a couple of things to do. Boom, boom, boom. You don't have to set up a full fledged project to get it knocked out. It does sound like you've got a lot on your plate. Is there anything that you do to automate or routinize parts of your system?

    Jimmy Little: Oh, my gosh. I have a lot of automation. Where do we start? Let's see. Well, first of all, everybody can do the most basic of automations. Right? A repeating task is an automation. A defer date is an automation. Hey, keep this out of my face until the computer says it should be in my face. These are automations anybody can do without any other tools. Automations don't have to be complicated. Mine are complicated though. So I do a lot of stuff with shortcuts on my iOS devices. I do a lot of stuff with Apple Script on my Mac. I do a little bit of Omni automation. I don't do any of it myself. I'm not a script or I'm not a programmer, but I can read it a bit. So if I download something somebody else has done, I can usually tweak it a little bit to fit what I need it to do.

    Jimmy Little: But I do have some Omni automations installed. I have the date controls automation, which puts a bunch of buttons in your toolbar for, defer a week, defer a day, two plus one week or whatever. That's great. I've tried the Kanban plugin, didn't really catch with me. We do a lot of stuff at work on Trello. So I'm used to the Kanban, and in JIRA, the Kanban kind of view. And I tried doing that in OmniFocus for my personal stuff, and that didn't really catch on with me, so I'll probably get rid of that one soon.

    Jimmy Little: But besides the Omni automation stuff, I do a lot of stuff with Keyboard Maestro. I have a stream deck every like every productivity nerd in 2021 who's been stuck in his house for a year and a half. So when I'm in OmniFocus on my Mac, my stream deck just turns purple and there's a bunch of buttons on there to jump between projects or contexts, nothing super complicated as far as the stream deck goes.

    Jimmy Little: Keyboard Maestro. I have, what I call my Omni open palette, which I love. I use it a thousand times a day. For people who don't use Keyboard Maestro, it's an app where you can put together these complex macros and keyboard shortcuts and tie them to actual keyboard shortcuts or mouse movements and stuff. But they have this concept of a conflict pallet where if you assign a keyboard shortcut to more than one macro in Keyboard Maestro, you get a pallet that pops up when you hit that keyboard shortcut. So all of my OmniFocus macros have the same keyboard shortcut. So when I hit control option command O, I get a pop up that has just a list of all the macros. And the way Keyboard Maestro does it, you just keep typing and it'll highlight letters and the different entries and the list gets shorter and shorter until something happens.

    Jimmy Little: So I have that set to control option command O. And then if I just immediately hit O again, that goes to the quick entry inbox. So I just click, click, done, an entry. I can also hit the first letter of a lot of projects or folders that I have set up for different areas of my life that I access several times a day. That one saves me a ton of time. Otherwise, I'm command tatting into OmniFocus and then hitting command O to get to the quick open, so it saves me a few keystrokes here and there a hundred times a day. So that's totally worth it.

    Jimmy Little: My big shortcut, okay, this is the one that saves me a ton of time for work. I'll throw this one in there. I have a shortcut that I can run it on my iPad and it will create an OmniFocus project, get the link for the OmniFocus project, it'll create a group in my DEVONthink, and get the link to that group. It'll create a new project through Toggles API for my time tracker. And it'll create a markdown document in my Obsidian because I'm a productivity nerd in 2021, so I have to use Obsidian too, that's the rule. It ends up spitting out this Obsidian document that has all of the data I need for the project, and then it has these back links to my OmniFocus projects, to my DEVONthink group, and to my Toggle project. I have all these links in this one markdown document that I can jump around.

    Jimmy Little: I'm really, really big into working in contexts. David Sparks has started calling it contextual computing and I stole that from him. I was doing that thing for years, but I didn't really have a name for it and then I think last year he named it contextual computing, so that's what I do now, that's what I call it. But I have these interlinked documents between Obsidian and OmniFocus and DEVONthink, and whatever websites or GRL links for work or Confluence links for work, those are the systems we use at work. So all of those get into one place and this Obsidian document is my homepage for that. And my OmniFocus project links to that Obsidian document. So when I open my OmniFocus project, I click a link, it opens that Obsidian document and everything I need is there. And those are also of course in stream deck buttons.

    Andrew J. Mason: If you don't mind going even further down the abyss of nerdiness, I've got to know, because I think that our audience will appreciate this. Where do you specifically use Obsidian versus DEVONthink? It sounds like Obsidian is more for project support then?

    Jimmy Little: We have pretty strict rules at work about where we can keep documents and that sort of thing. But for all of my personal OmniFocus tasks for work, I keep in OmniFocus, but those are just links to JIRAs or links to our official work task management systems, because I'm technically not allowed to keep any of that stuff in my personal system. And that's where I came across Obsidian, because I tried Notion, I tried Craft. I tried all these online note-taking things, but none of them would pass security review for my company. Obsidian, if you choose to not use the Obsidian sync service, which I opted out of, Obsidian is just a bunch of local markdown files. I keep them in our work cloud storage. We use Box for work. So I keep them in a Box folder, so they're available everywhere, they sync through Box, they don't sync through Obsidian service, but I do have my notes synced on to all of my devices through official channels.

    Jimmy Little: But that's what led me down the Obsidian road. And the reason I use Obsidian and DEVONthink is, DEVONthink, a lot like OmniFocus, you can just click on any item in DEVONthink and say, give me the link. So those links go back as markdown links into my Obsidian documents to whatever PDF's, keynote presentations, whatever it is. DEVONthink is my file system for work.

    Andrew J. Mason: Thank you for breaking that down. I'm a visual thinker. So it sounds like OmniFocus is the physical task centers. DEVONthink is the actual files that are involved in it. And then Obsidian is the spider web that holds everything together.

    Jimmy Little: Exactly. Yeah. Then you say the spider web with Obsidian, they have that big graph view that everybody loves to show off their huge graphs. I never use that. That's always off for me. I don't care how my notes are interlinked. I do a lot of back links, but I don't really care how all of those links tie together. I just like being able to link between things when I'm looking at a document, if I need to jump to a project, or to something else, or to start a timer in Toggle, I can just click a link in that document and all that happens in other places, I'm not jumping around all the time.

    Andrew J. Mason: Well, my next question was going to be whether or not there was anything unique in your system. I feel like you've already answered at least a slice of that. Is there anything else about your system that people would find unique?

    Jimmy Little: Sure. There's a couple of things, I think that I do differently that a lot of other people don't. The OmniFocus official inbox is very, very temporary for me. Inboxes in general in OmniFocus are not, but I told you earlier, I have all these different folders for areas of my life, areas of responsibility, whatever people want to call them. So I have a personal inbox and a work inbox and a list inbox. So each of my big folder sections, I have a specific inbox for. If I can help it things don't go into the main OmniFocus inbox, they go into of these areas of responsibilities inboxes.

    Jimmy Little: Well, when I'm at my desk, I just type it in, so it's easy, but when I'm on mobile, I actually have another shortcut that I built. It's a menu and basically the options in the menu are, add to personal inbox, add to work in box, add to Gary inbox, whatever it is. I have four or five inboxes right now. And I've tied that to the, if you use an iPhone, there's an accessibility feature called back tap you can us, so I've assigned that menu shortcut to the back tap gesture, the triple back tap gesture. So wherever I am in the phone, whether I'm on a home screen at a different app, whatever, I can triple tap the back of the phone and I get this menu that pops down and I can pick which inbox, and then I get a text input field and then type something in and it goes away. And I know that's in my personal inbox and OmniFocus, or my work inbox and OmniFocus. I didn't have to open OmniFocus. I didn't have to copy and paste anything. I don't have to do anything. It just goes where I need it

    Andrew J. Mason: That's really cool. That actually provides a level of clarity when you have multiple inboxes, because if you know that home has a certain cadence work has a certain cadence and you know that they're moving in a certain space, you'll know which one probably needs more of your attention, and so you can just pay attention to the one without having to go through or rehash all the other pieces of the inbox to get to what matters in that space.

    Jimmy Little: Yeah. That's relatively new for me. Ever since I worked for my company, since I guess 2014 is when I started, I worked in an office until March 2020 when everybody else went home. And that's when I started these different inboxes, because everyone talks about home-life balance and everything but for the last year, there is no real home-life balance. Everything is home and life all the time, and work, and kids, and other responsibilities and hobbies. I know this isn't video, but we're on video. This has been by background Zoom for a year and a half. This is it.

    Andrew J. Mason: People can't see it, but there's a bit of a mess behind me in the background too.

    Jimmy Little: This is how everyone knows me. Right? And we've had a couple of reorgs at work and I'm on teams of people that I have never met in person. So not having that separation between work and life in real life, getting that separation in my systems, has really clarified a lot of things for me over the last year and allowed me to keep track of things better.

    Andrew J. Mason: I appreciate how well thought out that is though, because I have a buddy that talks about how it never was supposed to be work-life balance as much as it was work-life integration. And since things are integrated, you're always a dad, you're always a husband, you're always a worker, then you're able to separate them out at least at the software level.

    Jimmy Little: Mm-hmm (affirmative). Even on my desk here, I technically have a work-home separation. I have two different computers, my work laptop, and I have a Mac mini, but they're hooked up to the same monitor. I just flip the input on the monitor for work and then flip back to the other one for home, so I'm still looking at the same thing. There's no separation.

    Andrew J. Mason: I actually have gone through this journey from the inception of OmniFocus. Have you had any, what you would consider to be mistakes that other people might instructional just so they don't make the same missteps?

    Jimmy Little: I think we've hit on some of this stuff, but they're all mistakes that I've made or choices that I've made that I found out later were not the best choices. Things like trying to get everything into one system even if it doesn't fit. That is something that I tried for a long time to get everything into a single system. OmniFocus, whatever it is, whether it's a task management system, or a note taking system, or communications, never going to get my mom to switch to telegram, right? My communications are always going to be on iMessage, and Slack, and SMS, and Facebook Messenger, whatever it is. I'm not on Facebook, but a lot of people are. Whatever it is, you can't expect everyone else to move into your system, so you have to be more flexible with how your systems work so that you can integrate with the world around you.

    Jimmy Little: I learned that with OmniFocus personally, when I started this job and not everything was in OmniFocus anymore, and I started having to integrate with the work systems, but I didn't want to completely work in their systems. I wanted to work in OmniFocus and I tried so hard to make the work system fit my OmniFocus system for six months. And it was just a bunch of wasted time. I built a ton of automations that I didn't need when I'm like, "You know what? Maybe I just go over to JIRA and look at the JIRA board." And that's what I have to do today.

    Andrew J. Mason: That's a really good point. Sometimes it's not worth automating, just do the thing. Jimmy, if folks are interested in catching up with you or connecting with you and what you're doing, how can they do that?

    Jimmy Little: Well, I'm all over Twitter, if you can handle political and tech news snark. I'm just at Jimmy Little on witter, then Instagram and all the social things, but Twitter and Instagram is where I hang out mostly. I got a website at, which is my personal blog and whatever I do goes up on there. The tagline is, internet ramblings fueled by adult beverages, and that's basically what it is. It's not often updated, but it's there if you want to go check it out, all the links to all of my social stuff is there as well. And for the people who are listening to this show, I'm in OmniFocus, Slack all time. Feel free to DM me, say hi, send an emoji wave.

    Andrew J. Mason: Jimmy, thank you so much for spending time with us. This has been awesome.

    Jimmy Little: Sure. Thank you.

    Andrew J. Mason: Hey, and thank all of you for listening today too. As always, you can drop us a line at the Omni Show on Twitter. We'd love to hear from you there. You can also find out everything that's happening with the Omni Group at