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

March 20, 2023, midnight
The Return of Jimmy Little

Today we’re joined by Jimmy Little, a senior digital product manager.  Jimmy returns to share the latest iteration of his productivity system and how various elements have changed since he last joined us in 2021.

Show Notes:

Andrew and Jimmy discuss how to stay on top of a demanding workload and personal life, powered by OmniFocus and a fresh slew of automations.  If you’re looking for a novel perspective on getting things done, you’re in luck!

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

- OmniFocus
- Jimmy Little on Episode 84
- Leah Ferguson on Episode 99 (First mention of Johnny Decimal)
- Johnny Decimal
- Obsidian
- Cocktails and Coffee
- Joe Buhlig on the Bookworm Podcast
- Jira
- Confluence
- Trello
- Omni Automation
- Shortcuts
- Applescript
- Jimmy on Mastodon


Andrew J. Mason: You are listening to the Omni Show where we connect with the amazing communities surrounding the Omni Group's award-winning products. My name's Andrew J. Mason, and today we have the return of Jimmy Little Sharing how he uses OmniFocus. Well, welcome to another episode of the Omni Show. Hope everybody's doing well. My name's Andrew J. Mason, and today we're talking to senior digital product manager, Jimmy Little. Jimmy was with us on episode 84 talking through his OmniFocus setup and it's been a few years and a couple of things have changed, so we thought we'd have him back on just to chat about what's new. Jimmy, welcome back to the show.

Jimmy Little: Hey, good to be back.

Andrew J. Mason: Last episode, we covered a lot of ground, so let's start from that point. The year was 2021. What's new? What's different? What's been happening in your life since the last two years?

Jimmy Little: Oh, not too terribly much. Still at the same job. Got a little promotion a few months ago, so I'm a senior product manager now, which is super fun. We are currently in our going back to the office mode. We're back four days a week now as of just couple days ago. I've been going back in three or four days a week since November when they opened the building back up. But now it's official company policy, everybody back for four days a week.

Andrew J. Mason: All of the poor introverts and stragglers. I totally understand that.

Jimmy Little: Learning to live in an office again. Yeah. The first couple months I was there was super lonely, let's say. There was not many people there the first couple months and then slowly built up a little bit and then couple days ago, the floodgates opened and every desk is full and there's a line at the microwave at lunchtime and all of the weird office stuff you have to deal with.

Andrew J. Mason: And last we talked, you had a three-year-old. Now, presumably five years old?

Jimmy Little: Yep, he's almost five. We're doing the kindergarten hunt trying to figure out where he is going to transition out of his preschool into kindergarten and dealing with all of that. Trying to wrap it around to this episode, I've got a giant OmniFocus project of all the stuff I'm dealing with, with school hunting and whatnot.

Andrew J. Mason: Such a cool season in time. We're there with one of ours as well. Talk to me about what's new. So last episode was episode 84. It's been almost two years. I remember contextual computing, I remember automation. What's happening with OmniFocus and the surrounding software and how have things shifted over the last year and a half, two years for you?

Jimmy Little: Nothing terribly drastic has changed. I've had my system locked in for a few years now and I'm pretty happy with it. What has changed is, first of all, there's a lot more automation involved. I'm a lot more into Obsidian now than I was last time we talked. I'm on the OmniFocus 4 Beta right now, so some of my little workflows have changed with some of the new features of OmniFocus 4. But in general, my system is still the same. I think I've refined it a little bit. I've started keeping things a little bit more organized using project codes, which we can talk about. Like I said, a lot more Obsidian automations and I got a lot more into perspectives with OmniFocus 4. I used a bunch before in 3 coming up to this. But now with the new perspective bar on the iPhone, the one across the bottom that slides back and forth, that thing has completely changed everything about the way I use OmniFocus on mobile. Version 3 home screen where you have those big blocks and then the list of perspectives at the bottom, I almost never used that. But the way it is now with the sliding perspective bar across the bottom and the hierarchical list of projects, I think they call it the outline or whatever they call it, those two things in 4 have completely changed the way I organize everything.

Andrew J. Mason: Product codes. I remember a recent guest, episode 99, Leah Ferguson, told me about something called Johnny Decimal. Is this what you're talking about and is that how it plays out in your OmniFocus system?

Jimmy Little: Yes, and yes. I do use Johnny Decimal in my Obsidian, which is everybody uses it differently, but I use it to break up the big organizational parts of my life. I'm looking now, I have 00 as meta and 10 is my atomic notes and 20 are my evergreen notes. And down to 50 is my sort of personal section and 50.02 is my project section and that's where all of my projects live. The way I do it, I think I learned this from, I want to say Joe Buhlig from Bookworm Podcast, think it was on his website, but I was doing this before in my own little way. And then I read a post that he made a few years ago and it solidified that what I was doing was a good idea and he gave me from reading that blog post that I got a lot of ways to do it a little bit better. So I adopted that system. And essentially what it does is it's like a two letter code for your area responsibility or part of your life. So I have home. I think I have home vehicle, family, personal, there's a few. And then the year, so now '23 and then a number. So I end up with a code that's like... Actually I put the year first, 23HB03. 2023, that's my hobbies code, HB. And then 03 is the third project I've created this year. What that does for me at least is it saves a lot of the crosslinking I used to do with things because now I have this sort of unique code for the project in OmniFocus, the folder in Obsidian and the document in Obsidian, and that kind of links everything together for me with searches and stuff. I still crosslink, but now I don't have to crosslink every single document. If I have a lot for a project, they just kind of live in that folder with that code and then I can just find them through search super easy. That automation is a little crazy. It's far more complicated than it needs to be because I'm me, and I'll share it. I'll put a link in all of these that I'm talking about. I've written up on my website at some point or another, so just go there.

Andrew J. Mason: Okay. So over the passage of time, these number codes, there's sort of a muscle memory factor there where you're just think, okay, 23HBO, that refers to this section of my life and it's fewer keystrokes, so it's easier for me to get to it.

Jimmy Little: Yeah, that's sort of the concept behind Johnny Decimal too, is you start to remember the number more than the code. I am not to that point yet at all. I still have to look in my file list and the side to see what all the decimals are, but the project codes really do help me group things in my mind. If I know I'm looking for something, I can type in 23CE and know what that is and then get a list of all of my projects that are going on from that.

Andrew J. Mason: Well, we're headed kind of toward Obsidian. Let's keep going in that direction. How has Obsidian shifted for you in the last year and a half, two years?

Jimmy Little: So for Obsidian, for me, I keep two vaults, one work vault, one personal vault. The work one is the most important one. For me, I take all of my meeting notes in there. I keep a lot of project notes in there. And then my personal vault is like any other vault you'd see on YouTube of just a bunch of little notes and my project files and stuff like that. But for work, I've started going single screen in meetings just to focus a little better. I used to always have a Zoom window open and my OmniFocus document and my notes document and all this other stuff. And now when I need to be on a video call, that's still there, but now everything is done within Obsidian. I'm using a couple of their plugins, which aren't really important, but there's a to-do plugin that basically makes a task list at the bottom of every document. So what I do with that is as I'm taking notes on a meeting, I'll pop down to the bottom if there's anything that I need to follow up on or any kind of task that I need to add to my project. Then at the end of the meeting, I have another automation, a shortcuts automation. It will go into that Obsidian document, get the project name from the top metadata of the document, which because I use project codes, the project name in the Obsidian document always matches the project name in OmniFocus. And then so it'll keep that as a variable and it'll go down to the bottom and it'll find everything with a checkbox next to it and copy that over to the correct OmniFocus project automatically and then go back into Obsidian and check all those things off automatically. So I don't use task lists like a task list in Obsidian. I don't think that's the right tool for that. I know a lot of people do and that's great. I don't particularly like doing it that way. If I have to do something, it goes into OmniFocus. So I set up this automation and all it does is it moves the tasks into OmniFocus and then marks them done in Obsidian. And that way, for me, a task being done in Obsidian means it's out of Obsidian now. It's in the correct place, and that might be moving a document to the file system or adding something to my OmniFocus system or whatever it is. It just means you don't have to deal with it in this text file anymore. Now go deal with it in the real tools.

Andrew J. Mason: So something I was curious about is that OmniFocus, how does that play out in the corporate environment for you? You were remote and then became hybrid four days a week. How does that shift things in your workflow as you try to use it?

Jimmy Little: Well, it's tough because I work on some things in digital streaming media that are what the company considers confidential, new shows that haven't come out yet, things like that. I deal with metadata. I'm a taxonomy ontology guy. I don't deal with video files or any of that, but I have a lot of the metadata for these videos, episode titles, new show titles, descriptions, that sort of thing, things that could be considered spoilers for upcoming episodes or whatever. We're pretty strict about what can and can't leave the company computer and can't be put into non-company systems. So a lot of stuff that I deal with at work is in our Jira board. We use Jira for Project [inaudible 00:09:10] or Confluence or Trello. We have a bunch of internal versions of these big tools that we use that doesn't leave the company ecosystem. And for stuff like that, I still do a lot of stuff in OmniFocus for myself. And again, that's where these project codes come in because I can link things together that way by creating a project in OmniFocus for myself. And these are things that I have to do personally that nobody else really needs to deal with. Anything that other people need to deal with, that stays in the company tool. We'll make a ticket in Jira and let that flow through the system or whatever. But if it's something that I need to do or if it's something that I need to do as a product manager, I have to write requirements all the time. So one of the first things that comes up for something new in Jira is like, here's the epic, which is what they call groupings of tasks and stuff in Jira. Here's the epic. First task is get the product requirements and that's assigned to me. So I will create a project in OmniFocus for that, link it back to that Jira task obviously, and then everything that I need to do to complete writing those requirements I will keep track of in OmniFocus because nobody else needs to know what my hundred steps are to do that. That doesn't matter. And then whenever I'm done with that project in OmniFocus, I know I can jump back into Jira and move it to the next step, close it out, whatever the workflow needs to be.

Andrew J. Mason: That's really funny. I really think about the flip side of the work scenario where to your coworkers, you're probably just this really efficient black box that results spit out of, so it doesn't necessarily matter how that happens. Who cares how it happens? So from their perspective, it's just like, hey, this person produces results. I remember last time we talked about your review process and how it was more of a fluid thing. There wasn't this one and done review that happens in a formal manner, but just this rolling thing that happens continuously over time.

Jimmy Little: Well, from a work perspective, I do that Monday morning. I have no surprise to anyone I'm sure who's ever read anything that I've written, but it's a bunch of shortcuts. So I have a recurring project in OmniFocus that's seven steps, and each one of those steps is like run this shortcut basically. But because of Omni automation, there's an Omni automation that... I'm not good at JavaScript, by the way. I didn't write any of these Omni automations. They're all stuff I found on the website or things at Sal Soghoian and helped out with in the forums. One very simple one that I use all the time is I have it mapped to Command U for URL, which it's an omni automation that'll just go into the notes of the task and find a URL and open it. It's super simple. And what I've done is I've put the URL to the shortcut that I need to run in each one of those tasks. So now Monday morning, I sit down, I say, okay, run week note shortcut is the first one. So I just hit Command U and then it runs the shortcut in the background and then I see dash shortcut creates some documents in my Obsidian vault for the week like some summary pages and that kind of stuff. Automatically creates those documents for me and then I see them show up in Obsidian. Then I just check off the box. My weekly planning has gotten exponentially faster since I've started systematizing it into using OmniFocus to run a shortcut that creates it in Obsidian. It's pretty amazing and it's just one keystroke to finish this task. Like I said, I have seven things that do. Most of them just run a shortcut to add things to my calendar or create documents in Obsidian or whatever it is.

Andrew J. Mason: Jimmy, talk to the person that's not a coder like you say you are, but they don't feel like they necessarily have the skillset needed to build out a really good automation. I feel like this next level has emerged for you. I remember last time we talked about automation and how it was helping you out. I feel like there's another level that's emerged for you now where there's been automation groups, almost like Lego blocks that build on each other and it's a new perspective I haven't necessarily seen before. Talk to that person that hasn't built automations stacked on automations.

Jimmy Little: Yeah, and that's actually a pretty good analogy of how I actually do it. When I build an automation, I'm not a coder at all. The last coding I was proficient at was like HTML 2 and the mid 90s. I don't code [inaudible 00:13:16]. But I feel like I understand how the flow of something should work and that's why something like shortcuts or even Apple Scripts to an extent, which is pretty readable. I couldn't write Apple Script, but when I get Apple scripts from other people, I can read them and understand them and things like that that allow you to use these building blocks. And shortcuts, I mean that whole thing is just building blocks. I have five or six OmniFocus specific shortcuts that are just add whatever the shortcut gets to this project in OmniFocus. And by saving those as different shortcuts, that means I can run them from just an ask for input, whatever. I type something in, and then the next step is run add to my work inbox shortcut. And that'll take whatever I typed in and just add it to my work inbox and I don't have to choose from that list or I don't have to have five separate shortcuts for my five different projects. I can have one shortcut and let me choose which project I want to go, and then that will open a different shortcut that's kind of hard coded to each project as a function, if you will, in computer science terms.

Andrew J. Mason: Up until this exact point, I've been thinking about automation as this long complex journey from start to finish that you fill out and if something's wrong, then you edit the journey, the entire journey from start to finish and create a new one. I haven't been thinking about individual pieces that stack on top of each other, individual automations like custom Lego bricks or... I have to to continue that analogy. This is kind of blowing my mind a little bit.

Jimmy Little: That's how I started. Actually, my last project that I set up in OmniFocus about a week ago was a project to clean up my shortcuts because I had like 600 shortcuts because I would do that. I would build them all out, oh, this one's slightly different. I want this one to resize the image to 800 instead of 600. So I copy the shortcut and just change one thing instead of using it as components that it should be used as. I've wrote a shortcut to clean up my shortcut. So it went through all my shortcuts and listed them all out and then created... Let me look at my OmniFocus here. Yeah, it's my shortcut to clean up project. I am actually two weeks into it now. I have 442 to go. But what the shortcut did is it took an entire list of shortcuts, 500 and something, whatever it was, broke it up into chunks of 15 and then used OmniFocus's import as task paper shortcuts action to import each one of those groups of 15 as a main task with 15 sub-tasks, and iterate through the dates and set a deferred eight for each batch. So now my next batch I'll be doing on Saturday and then the Saturday after that, the Saturday after that, and in 15 or 20 batches I'll have gone through all of my shortcut to clean them up.

Andrew J. Mason: I don't know why, but I have the sense that you and Sal Soghoian would get along very well.

Jimmy Little: While I'm talking about that, saying that I was deferring these to the next month and everything, I want to talk about deferred because every couple of years I go on this vision quest, this journey through other task management systems and I always end up back at OmniFocus. Every time it's because of defer dates. Defer dates are super powerful for people like me especially. I can't remember anything. I write everything down or I will lose it in my head somewhere. And I think a lot of people are like that. But the problem with using a system without defer dates is you just end up with a giant list of stuff all the time. Like this, it defers each batch of shortcuts clean up. Even though there's 442 tasks in this project, I'm only going to see the next 15 on Saturday when it's time to look at him. I don't have to look at the big list of stuff, right? For long-term planning, I keep all like, order mom's birthday gifts, send mom's birthday gift. I have tasks like that in a project and I don't need to see that in November if her birthday's in April. So being able to defer things... My latest deferred task, I have a perspective that's just all of my tasks with deferred dates into the deferred date order. My longest deferred task is in June of 2032. No, I'm sorry that's wrong, 2036. 2036, I have a task to update my will a couple of months before my son turns 18. I'm not going to remember that and I don't need to see that task for the next 14 years, but I know in 14 years that task is going to pop up when it's time.

Andrew J. Mason: Jimmy, here's a question for you that I only get to ask returning guests, and that is how do you advise somebody over having flexibility in your system? You don't seem surprised by the yearly journey to the pilgrimage out to other task managers just to see what's new and different. You don't seem surprised by what defer dates do to your system. How do you handle that flexibility needed to grow over the long term?

Jimmy Little: I think I have three answers to this. Number one, remember, projects are free, right? You can create a project whenever you want. If it's more than a couple of tasks and you want to keep it separate, put it in a project, you can complete the project, you can drop the project, you can delete the project later, it doesn't matter. But I think being able to keep those things grouped together helps keep you from getting overwhelmed by your system. And having one list or project that has 300 things in it, my shortcuts cleanup project notwithstanding, is not the best way to do things, I think. So keep things separated. It's easier to filter and see what you need to do at what time. The second thing is when you're setting up a project, think about the review frequency. One of the best things about OmniFocus other than deferred dates is the review process. And that's something else that no other app gets right in my opinion. To be able to say, "Okay, I'm going to look at this project and see if it's still meeting my needs every X days, every X weeks," whatever it is, and being able to set that review frequency is something that you should really consider. You don't need to look at every project every week, which is I think the default. I don't remember what the default is cause I don't use default review frequencies for anything. I have some like my work inbox. I review that every day and then I have a financial health project that's mainly just questions like, "Hey, are you still using this app you're subscribed to?" With a defer date for 360 days after I started the yearly subscription, to remind me to look at this. Am I still using this? Is it a worthwhile subscription? That one, I look at that one every six months. That review is set to six months. And then schedule your reviews. You can schedule and tell OmniFocus what day do you want to be reminded to review this? And I have them broken up across all seven days of the week, so I don't have to ever sit down for an hour and do my weekly review. Every day, I'll see two or three projects on that badge in the review and the sidebar, and I'll look through them real quick, mark them is reviewed and then move on. I know a lot of people like to, and I used to do this, grab your iPad and go out on the patio with a cup of coffee and spend an hour looking at your weekly review. I don't do that anymore. I do two or three at a time while I'm sipping on a cup of coffee and watching a YouTube video to break a work or whatever.

Andrew J. Mason: I love that. And the third one?

Jimmy Little: What was the third one? I said I had three things. Oh yeah. Learn how repeating tasks work and learn how to nest repeating tasks properly. This is something that took me a long time to wrap my head around and once I did, it's super powerful, but it does get confusing sometimes if you have a recurring project with a repeat date and inside that is a task with a repeat date. And some of them are set to repeat from completion and some of them are set to repeat from the assign date. Figure out how that works because once you do, it completely changes everything the way you use it.

Andrew J. Mason: Very cool, specific slice there. Do you happen to have an example of that as it's in motion?

Jimmy Little: Sure. I'm actually figuring it out this week. I told you earlier, we're going back to the office and it's starting to get busy now that we're going back three or four days a week, but we work in what they call a hoteling office. We don't have assigned desks. We can just go online, pick our desk for the week and then move around as we wish. I don't want to move around. I like where my desk is. So part of my weekly planning is to jump on this website where I have to book my desk and book my desk for the next week, but the next week doesn't become available in the software until Wednesday. So most of my weekly planning happens on Monday morning. And then I have one task in my weekly planning that has to happen on Wednesday morning. So because of that, I had to take the repeat off of the weekly planning project and then put individual due dates on each task and then set the repeats for those. Because if I had the project repeating weekly and the task inside it repeating weekly, then every time I click the task off, the project would show back up because it would be ready to repeat because all the tasks will [inaudible 00:21:57].

Andrew J. Mason: Totally unrelated but am interested. Is that release on Wednesday, is that the mad dash for concert tickets? As soon as the countdown hits zero, everybody just goes for the window seat?

Jimmy Little: Not yet, but I think it's going to be that way coming up. Just the first of this month, we started going back, so it's going to be interesting. We're kind of hoping that once everybody shakes out, they'll start assigning desks to people or maybe just learning, because you can see where everybody's sitting in the software. There's a floor plan and you pick your desk and all that. It's pretty well done software, but I kind of am getting to the point where I can look at it and be like, "Okay, this person always sits here so I know where to find them, and nobody else is going to book that desk." And hopefully that'll all shake out naturally. We'll see.

Andrew J. Mason: Jimmy, as usual, such a great conversation. Love having you on as a guest. Any final words of wisdom that we didn't get to share here?

Jimmy Little: One thing that I've learned, especially over the last couple years since we talked last is that I like using the right tool for the right job. And I have learned that sometimes your task manager is not the right tool. You don't have to put everything in there. I used to keep all kinds of basic lists in OmniFocus and I found that cluttered up the way that I was trying to get my work done. So I've moved a lot of those lists out. Same thing going as we were talking about Obsidian earlier and how I don't do my task management in there because that's not the right tool for the job. It's okay to have lots of tools in your tool belt, right? There is no one everything app, and I don't think you should try to make any one app an everything. Do what that app is designed for and do it well. And then I don't need a list of the YouTube videos I want to watch in omni focused that lives in a different app that is specifically designed to hold YouTube links. And it's great. And it works well.

Andrew J. Mason: That's perfect. And then if folks are interested in catching up with you, remind us where we can find you.

Jimmy Little: Yeah, well my blog is still at And I am like most of the nerds in my life, I am off of Twitter completely now. Don't look for me there. I am on Mastodon at

Andrew J. Mason: That's great. Jimmy, thanks so much for joining us.

Jimmy Little: Thanks.

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