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Dec. 26, 2022, 6 a.m.
How Andy Bliss Uses OmniFocus

Today, Andy Bliss joins us to share his insights on using OmniFocus to supercharge work as a performing artist and musician's coach. With a background in both the arts and technology, Andy knows a thing or two about the intersection between creativity and efficiency.

Show Notes:

Join Andy and Andrew as they navigate the challenges of "infinite" capture using software (and how to batch your days to prevent decision fatigue). They'll also delve into the distinction between Projects and Maintenance, and how a system like OmniFocus can help when your schedule is jam-packed. It’s a fantastic discussion on maximizing productivity and efficiency.

Some other people, places, and things mentioned:


Andrew J. Mason: You are listening to the Omni Show where we connect with the amazing community surrounding the Omni Groups award-winning products. My name's Andrew J. Mason, and today we hear how Andy Bliss uses OmniFocus. Welcome everybody to this episode of the Omni Show. My name's Andrew J. Mason, and today we're talking to Andy Bliss. He's a performing artist and musicians coach, and he's exploring the intersection of creativity, technology, and intentionality. Andy, thank you so much for joining us today.

Andy Bliss: Oh, you bet. I'm thrilled to be here. Thanks for the invitation.

Andrew J. Mason: Well, first up, tell us a little bit more about yourself, Andy.

Andy Bliss: Definitely, yeah. I'm a drummer and a percussionist, and I make my living as a music professor at the University of Tennessee. I'm the director of percussion studies there, so spent a lot of my days teaching classes and running rehearsals, but I also direct a nonprofit called Nief Norf, which is a contemporary music organization. We have a really large two-week summer festival that I direct and we have an ensemble that does performing and just generally a lot of coaching of career building and entrepreneurial type things for musicians. So yeah, I've really enjoyed doing this work for quite a while. I've been playing music for as long as I can remember. And when I'm not doing that, I'm also an amateur Lego builder and collector, which is a hobby that has taken over more of my life than I anticipated. So lots of creativity happening on a daily basis.

Andrew J. Mason: Tell me more about how did you first come across the Omni Group, or even specifically, OmniFocus? Is there a certain memory you have in your head or just kind of it's always been there for you?

Andy Bliss: Yeah, OmniFocus, so I think I look back at my email knowing that we were going to talk today and I found an email received from 2010, which sent me on a rabbit hole, when did OmniFocus launch? And I think it was like 2008. So I've definitely been with OmniFocus for a long time. One of my closest friends and I were deep into the Getting Things Done book in graduate school in late undergrad, and so I think that was around 06 and I have to imagine I found OmniFocus as an extension of that. She and I used OmniFocus to get ourselves through grad school and it kind of became part of my work life identity I suppose, that then bridged into other areas in my life. And then down the road, after I got my full-time job here at University of Tennessee, I found myself on a holiday break and I found Tim Stringer and the Learn OmniFocus website, and I remember spending an entire winter reworking my setup.

There were so many great resources and Tim's teaching and coaching is so calming and relaxing. He is an incredible enthusiast of the program, but obviously the discipline around everything with the software. And I'd be remiss not to mention David Sparks. I'm a proud subscriber of his MacSparky Labs. And he and I got to catch up at Macstock a couple years ago. Actually Tim and I did as well. He and I spent a lot of time together attending sessions. So just the community around all of this has been great. I use OmniFocus the most, but I have dabbled with OmniGraffle and OmniOutliner at different times. So definitely an icon that have been in my doc for as long as I can remember.

Andrew J. Mason: I'd love to call out maybe two things there. The first is just the sense of community and maybe it's the larger Macintosh ecosystem, Apple products, but just this sense in which there's a group of people helping each other, which is really, really cool there with the Mac products. And then the second is it's really... I think you're maybe the fourth or fifth person that we've talked to who utilized this combo of getting things done and OmniFocus when it first came out to just be rocket fuel to get through their grad school. Tell everybody about what segments of your life, if it can be divided into segments. What areas do you manage in OmniFocus? What does that look like for you?

Andy Bliss: Yeah, in the beginning, like I said, it was work stuff and then it didn't take long to where it was really everything, like everything. I tried to run my whole life out of... I'm a big fan of the pillars approach to life or the roles and getting a sort of identity around your areas of focus and areas of responsibility and then building your structure from there has been really helpful. And so I've used it heavily for checklist. When I was a young dad, my first kid was three or so. My wife was commuting two nights a week out of state, and so I was kind of running solo dad a lot at night and I remember I had it. At the time, we had a toddler, a dog, three aging cats, and that was a lot to manage after a full day of work. It's hard work.

And so I had a checklist that I would open in OmniFocus each night on my iPad as I did the order of operations between feeding everybody and thawing food and taking out the garbage and getting the windows shades closed and bathing the kid, and I had it down to hourly blocks that would help my 5:00 to 8:00 PM run smoothly. So I would use it for things like that. But then I would also... I've used OmniFocus for large project management. I think there's a couple of features that I wanted to highlight I suppose, that are some of my favorites. The repeating tasks is definitely a thing that I think OmniFocus does better than anything I've come across. That comes up in a lot of areas of my life. I want to be a thoughtful brother or son. And the ability to go, I really wish I would remember to make this phone call specifically at this time, and it can really help you be the best version of yourself in that way.

The URL recall that you can use to place into different other parts of your life is definitely something I've used, especially for projects if you're doing some writing and you want to refer to the list. And some other things that we can talk about, but really has worked its way into all parts of my life. I mean, I can't think of many other platforms that I've identified with as much as OmniFocus. That purple icon just resonates with me at this point. There's a lot of delight that goes into using the software for me, and I think that's an area of life that's not to be underestimated.

Andrew J. Mason: Absolutely. The delight factor isn't necessarily always quantifiable. You can't see it on an Excel spreadsheet as far as how much more productive it makes you, but you can tell. What would you give as a first piece of advice for somebody that is in that space where there's too much in their head, or maybe the idea of using a task manager's intimidating to them or they just haven't used one before. What would you say is a good first step for somebody?

Andy Bliss: Yeah, I mean, a lot of my students fall into this. They're blooming professionals, especially graduate students. They're experiencing professional and student life overlapping for the first time. As an undergrad, your job is to be a student, usually. Not always. Some students have different scenarios, but graduate students are often on maybe a TA where they have job responsibilities, and this is the first time they've had to juggle learning with accountability in a non-student situation. And this is where sometimes a task management approach comes up in our mentoring. So I've already mentioned the areas of responsibilities. I think just taking a moment to outline those things and really getting clear on who you want to be holistically and how to... It's a classic GTD thing where you do a review in an area of your life has no tasks, and that can be a big red flag.

Maybe I need to be pouring a little more momentum into that area to keep some balance, and that can be really illuminating. But for me, the thing I've struggled with the most I think, is that a calendar is a finite area and a task management system is infinite. I know this as truth, but it's very, very difficult and you can load up OmniFocus or any task management system with as many things as you possibly want. But I guess my advice would be I've really been thinking about energy and time as budgets. The way we think about money, we don't talk about them the same way. And they are finite. Every micro decision we make in a day drains our energy. We only have certain blocks of time in any given day. And so for me, my mental health is best when my calendar and my tasks lists have been reviewed before I wake up because then I have a realistic sense of what I'm going to get done that day.

And it's possible for me to feel like I win. It's not possible to feel like you win if you're only working out of the task manager because there's no way you're going to get to the bottom. Even in six months, you'll probably still not get to the bottom of everything that's in there. And so I guess that would be my advice is to just manage how much you're putting in there. I could talk a lot about someday maybe lists and text ideas, recipes, notes. That was a major problem for me for a long time was what do I do with all these text items? I've recently found a bit of a solution there, but for a long time OmniFocus, I tried to use it for that, and I actually don't think that that's the best case scenario for some of those ideas.

Andrew J. Mason: I know for some people, OmniFocus can be one piece of a much larger puzzle. Do you mind going into what have you ultimately settled on as kind of a workflow that works for you?

Andy Bliss: Yeah, I'd love to. I remember a couple of years ago I was out mowing my lawn and I mentioned Tim's stuff with Learn OmniFocus. I was way into some of the Mac Power Users podcast and buying a new app all the time. And I had found Fantastical and TextExpander and MindNode and Slack and the SetApp group, which is incredible, everything they offer there and Day One and Ulysses and I was finding myself to be really passionate about all these apps. And I remember thinking, I wish I could draw up an HQ headquarters map of how my system functions because sometimes I'd find myself putting things in the "wrong place" as I trained myself to keep it as simple as possible. And then as you know, I also have a similar parallel set of apps for audio and video like Logic and Sibelius for... And even Lego has a couple apps that I go to when I'm in that context of life.

So it can be a lot. In the last few years, there's been this big shift in PKM, personal knowledge management systems, and I feel like that's been a really important step for a lot of people. Myself included. I tried Roam Research for a little while, but I eventually found Notion, which maybe some of the listeners are familiar with, and it's really, really been helpful for me in a lot of different ways. It solved that text problem that I was referring to in that I could open up different databases and different dashboards for different areas of my life and keep those kinds of things in one place, which then allowed OmniFocus to sort of live its best life as a task management system. And even certain checklists, I know OmniFocus can do it and do it well, but I would end up setting the visibility wrong and then I'd finish the checklist. And then when I'd want to go back, it wouldn't be there.

Or they would all be there, but they'd be checked off. And it's like, no, this is not how this is supposed to work. And you end up spending 20 minutes like fiddling. You want to be out of the fiddling mode and into the working mode as much as possible. So I found a lot of use in my system with Fantastical. I mentioned the calendar, the importance of managing time and then Notion has been a really great dashboard place for me to pull a lot of these tools together. So that then when I am trying to decide what to do, I can really be focused on the task list with some of the Omni Group's software.

Andrew J. Mason: That sounds like a really good workflow, and hopefully that inspires some people to get some ideas if they haven't kind of set one up for themselves already in a way that works for them. What about the OmniFocus slice? Do you have any custom perspectives that you slice or dice the data in a way that makes sense to you the most?

Andy Bliss: Yeah, I've got a couple things there. I think perspectives is maybe the most important part of learning how to use OmniFocus because it can hold so much information. It can be really addictive to add a ton of metadata and all of the contexts, an energy level and a vehicle and in what room I'm in and am I leaving the room or am I coming into the room? And you can really go crazy with the tags, but sometimes that just becomes a distraction. And of course the more tasks you add, it just becomes really unwieldy. And so I have a few perspectives. I definitely have one for all of the pillars of my life that I mentioned. So I'll have a home and house one, or I'll have a couple of the major areas of work might be like team management and administration. Or one for finance, whether that's budget overview or fundraising or grant writing.

I've kind of got all that in an area of work. I've got a kind of community recruiting CRM, I guess side of work life, definitely one for some creative projects that I'm in and then things I'm trying to put out into the world. So I have those. And one pro tip I guess that I'll add is even that list of perspectives can get really unwieldy. And so a while ago I added about five or 10 perspectives that have nothing in them except a dotted line as the title. And what that does is it basically creates an empty perspective that shows up as a line. And then I drag that line around in my perspective's dropdown menu in OmniFocus, which allows me to, if you have 15 or 20 perspectives, you can put a line between the different ones, which I found to be really, really helpful because I have my perspectives organized of course.

And after you add about 10 of them, they start to get kind of messy. And so I'm a big fan of customizing your space and using emojis and visual things to make it feel delightful and make it visually clear. And then of course, the GTD context stuff, as I said, you can add a million tags, but I think the two I use the most are low energy. Like you said, end of the day I've got 90 minutes and I'm gassed. It's like, what can I just get done? So when I have energy tomorrow, I don't really need tags for high energy. It's pretty clear usually what I do when I do that. But when I have low energy, it's like I can pay that bill or I can just get some of this low end stuff off. And then also phone calls. The older I get, the more my short 10 minute commute home and to work is a really important time where I can check in with a family member or make a quick work thing and just knock something out so that tomorrow maybe I'm slightly ahead of the ball in terms of getting something done.

Andrew J. Mason: It's so funny because who happens to be passionate about productivity for people that you talk to. Not too many that I know in my immediate circle of friends are like, ah, I found out a new productivity tip and that just made my day today. But for people that are, what makes you passionate about productivity?

Andy Bliss: Yeah, I think it's that I'm passionate about workflows and intentionality and systems thinking because it helps me. First of all, it helps me improve my mental health. I feel like more calm when I'm in control and when my system is working. And when I'm not, it's really easy to get overwhelmed. It allows me to be the most present with the people I care about. Of course, my family, my wife and kids, but also my students and my collaborators. When we are in that space, I want to be in that moment and completely focused. And having a system on the backend that helps me ensure that I've captured and am in control of my responsibilities helps with that. And then it also allows me to ship my best work creatively. A lot of what I do, there's a lot of logistics involved in being a percussionist.

It's not as simple as get your clarinet out of the case and start making sound. A lot of what we do, we have to collect the instruments and find a place to set them up, and then we can't get this instrument where it needs to be. It's too far away, or there's like a mounting problem or this piece uses a click track or has various technology and you can really spin your wheels if you don't make the checklist. And then inevitably as you make the list, you will reorganize the checklist to you immediately see a clearer path through. And as I've gotten older, I have a family and a full-time job plus this nonprofit that I'm involved in, and it's a lot to keep track of. And so having a system like this and then switching the contexts through the system allows me to be in the moment and toggle those switches on and off as I go through my week.

Andrew J. Mason: You mentioned templating earlier. Do you do anything as simple as repeating tasks or as complex as JavaScript or coding in the name of automation? Where does that sit in your system?

Andy Bliss: Yeah, it's something I'm always reaching for that I don't always have time for. I have a stream deck XL staring at me here on my desk that's gone sorely underused, not because it's not powerful, but I just can't find the time to get off the carousel long enough to kind of really, really make it work for me. But yeah, I use text expander every day. I try to batch my days to avoid decision fatigue. I think that's a form of automation that's really important.

Notion has been huge for the templating side of thing, which automates a lot of you want that perfect checklist that's going to take you through a repeating project. For me, as a professional musician, we often play concerts, right? That's a pretty straightforward thing. There is a chapter of that project after the concert that almost always gets dropped. The follow up, maybe you want to post some photos to your website, maybe you want to reach back out to a collaborator or an audience member and say thank you, or set up a time to explore future things.

Maybe there's some bookkeeping and finance things. Maybe things come up at the actual event and there's like a shutdown and reflection chapter that if I'm making a checklist is going to be there. But if I'm not, it tends to not show up. And so automation is great for me because it forces me to go, no, no, no, it's not quite time to run off to that next thing yet. Let's finish this correctly.

And automation has helped me with that a lot. I also use Airtable a bit. Some of the forms I find to be best in class in the way you can get information from others. And I think lately the focus mode on the iPhone that just came out with the new operating system is something that really has piqued my interest. I really love the idea of shifting context, kind of like the volume where they film the Mandalorian. It's like the whole room can just change. And I just love the idea of hitting a button and all of a sudden all my apps that I need and my screens are there and my do not disturb is turned on. And boom, I'm fully in this mode because I find that friction is kind of what can be the difference on a day-to-day basis between getting to something and not.

Andrew J. Mason: Is there anything that you tried on your productivity journey that maybe you wouldn't classify it as a failure? People know that I love to ask this question because I want to save anybody the misstep if they don't have to do it themselves. But you look back a mile or two from your journey and you say I thought this was something that was going to make my life better. It didn't. And if it were up to me, I'd say go ahead and skip that part.

Andy Bliss: That's a great question. I think I have a couple thoughts about that. One would be just stay in reality. OmniFocus is not reality. It's a database. And I've alluded to this already, but it can be really easy to get in there and it's so beautiful and it can feel really great to have that system perfectly in order. But I have found myself reaching for this perfection where every task or project I have coming up for the next five years is in there and it's maybe not five years, but a while, is fully mapped out. And everything is... It's like the mise en place. Everything is right where it's supposed to be. And for someone with my type of personality that can actually be paralyzing where it's like, we got it just right, and I almost don't want to do anything now because if that makes sense, we can become perfectionists about our systems.

But when I look at the most creative people, it's kind of like the difference between the Instagram desk versus a film studio. We all love the beautiful cinematic desk shots or setup shots, but I don't really know many people who are getting great work done who aren't in a little bit of a mess. When you go in a film studio, there's cables everywhere because the cameras and the lights are plugged in and the mics are on and everything is running because they're doing work.

And this is the same in a kitchen, and this is the same in an art studio. You're not going to get much painting done if you don't get your hands dirty. So I think that would be my advice is just to keep a healthy relationship between the doing and the planning. That balance is so critical and it's not one or the other, but we just have to constantly be looking at both sides. And some of the times in my life where I've been the most productive, things have been a little bit crazy because I'm deep into the work and we need the system to do only enough to get us through the job and nothing more.

Andrew J. Mason: That's really good advice. And I actually want to add this question in too. Is there anything that we haven't talked about that you're like, man, if given the chance, I would love to speak to this.

Andy Bliss: I just have maybe a couple thoughts about projects versus maintenance these days that I wouldn't mind chatting about a little bit. I was actually just talking to my team about this, this semester. The older I'm getting, I'm 41. I've got a 10 and a five year old. I really love my job and I'm super, super fortunate to do what I do every day. And then when I go home, I have this creative hobby that I'm invested in and I'm spending time with my kids. And I've been thinking a lot as I get to this phase of life about where projects fit into that. Because I feel like you reach a point in life where you've spoken for all of your time. You've kind of got standing commitments that require maintenance and energy. There might be new projects at your job that kind of come with the season.

As a university professor, I have classes and those classes come to a stop and then they begin again. So there's like the relaunching of that whole climb and that whole sequence. But as I'm getting older, I'm just finding that there's less and less time for other things because generally speaking, the bandwidth is a bit filled. And so in the old days, I used to try to fill OmniFocus with everything in my life. And I would go in there and I would do that. And in the last couple years, I've been noticing myself actually trying to empty it. And I really just try to save it for the big rocks of things that I'm attacking that month or that quarter, because increasingly the things I'm doing on a daily basis or a monthly basis even are maintenance related or they're like the equivalent of habits and routines. This is a thing that I need to do once a week. This is a thing I need to do every morning. This is a thing I need to do at the end of every month to keep these processes flowing.

And you get to a point where it's like there's no thing to add. So if you want to add anything more, you're going to have... Something else is going to have to go. And it's our job then to optimize the things we're engaged in and make sure that they're fulfilling us creatively and maybe financially and we're fulfilling our days with things that we really, really love to do. But that's a corner I've been turning personally lately that has had my mind in terms of this relationship between projects and what is a project and what is just a habit and a routine, which used to be like brush your teeth and now it's like run the financials for my nonprofit is a habit and a routine. It's got a lot of different moving parts, but at the end of the day, there's certain grants I need to apply for every year, and there's certain classes I teach every fourth semester. And it's kind of crazy how the scale elevates that way.

Andrew J. Mason: Andy, this has been an awesome conversation and thank you so much for sharing your wisdom. I really feel like there's people out there that are benefiting from that. How can folks get in touch with you if they're interested?

Andy Bliss: Oh, yeah, sure. I've got a website at and they can sign up for my newsletter there, which I'm kind of trying to get moving. I have the best of intentions, but sometimes life gets in the way. I'm also on Instagram, AndyBliss4. And then if they want to learn more about our nonprofit, the website is That's N-I-E-F-N-O-R-F. And then my Lego side of life is Bliss Brick Studios, and I'm on Instagram and YouTube for that.

Andrew J. Mason: Andy, this has been awesome. Thank you for joining us.

Andy Bliss: Oh, absolutely. Thank you so much.

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