THE OMNI SHOW

Marko Anastasov: It ends up being as a pretty manageable sort of to do list, not something that overwhelms me, but it still contains all the information that maybe in the future will be important, but it doesn't get in the way. So I think that's a big advantage of OmniFocus versus pretty much any other task list manager.

Andrew J. Mason: You're listening to The Omni Show where we connect with the amazing community surrounding the Omni Group's award-winning products. My name's Andrew J. Mason, and today we learn how Marko Anastasov uses OmniFocus. Well, hello and welcome everybody to this episode of The Omni Show. My name's Andrew J. Mason, and today we're honored to have Marko Anastasov with us. He's the co-founder of Semaphore and Operately, writer of Signals, where he explores the craft of building better teams and products. Marko has been a longtime OmniFocus user who brings a thoughtful blend of engineering precision to everything he creates. Marko, it's really exciting to have you here with us today. Thank you for joining us.

Marko Anastasov: Thank you very much for having me. I'm very excited to talk about productivity and OmniFocus today.

Andrew J. Mason: Before we dive into that, talk to us a little bit about your backstory. I actually got to hear one other interview and you're originally from Yugoslavia, correct?

Marko Anastasov: That's where I still live, but I'm a co-founder of Semaphore and Operately. Both of those companies are international and remote first, so fortunate to just work with people all over the world and make a little dent are there.

Andrew J. Mason: And that's exciting. Talk to me more about Semaphore and Operately. Talk to me more about what are the companies known for? What do they do? And if you're just level setting somebody on the elevator and they're asking, "Hey, what do you do?" Share a little bit more about what those companies are.

Marko Anastasov: By trade, I'm a software developer, but entrepreneur now for almost 20 years. Semaphore was really born out of what was previously when my co-founder, who I still work with to this day, Darko, we had some kind of failed early web 2.0 startups. Then to actually earn a living, we got into consulting in web development. And it was a period when we were sort of, I would say, owning our craft and growing as really maturing as software developers because we were just straight out of college. As part of that self and continuous improvement process, we came across this practice of continuous integration, which in software development means you're testing everything all the time. Basically, you have some automations that run some scripts that verify that your applications work. So we saw an opportunity basically back in the day, this was around 2011, to build something for that's very easy to set up and runs very quickly in the cloud. So back in those days, making useful services as a SaaS was a pretty big deal. So this was a time where GitHub was already pretty big and there were also great platforms for deployment, but there wasn't something in between. So we chose to do something. That's when my journey as a serious product builder and builder of product companies started because anybody who gets a little bit of traction, I guess learns quickly that it's not just a product, you also need to build a company in parallel.

Andrew J. Mason: Let's switch over a little bit and talk to me more about how you came across the Omni Group or OmniFocus as well.

Marko Anastasov: Well, I've been a Mac user also for many years. And for anybody who's kind of curious, what is some of the top quality software out there for Mac, you inevitably come across OmniFocus in the area of task management. So I've been aware of it for a very long time. And then in times when I found myself getting a little bit overwhelmed and with rudimentary to do lists in plain text files or whatnot, I decided to give OmniFocus a try. So I know there was a tweet that I posted when I maybe installed it for the first time, which was 2018. So I remember that that's the year. It was a time when I had to juggle sort of... I was still making things, but I was also obviously a manager.

Andrew J. Mason: Talk to me a little bit more about maybe your current typical workday and does OmniFocus have a place in that? And if so, just how your regular day might unfold.

Marko Anastasov: My day nowadays usually starts the night before. I like to go to bed with a pretty clear idea of what I'm going to start doing in the morning. So I usually open OmniFocus to get a clear sort of perspective on the whole landscape of things that I'm working on and responsible for. Sometimes I don't, because frankly, maybe there's an ongoing project which is absolutely top of my mind and I know the first next thing is going to be problem or task that I need to tackle. But I do review OmniFocus on most sort of evenings just to make sure that... I don't even do weekly reviews almost anymore because I just go through things pretty quickly on almost a daily basis. What's changed relatively recently is I've never been much of a calendar person. I would just keep my calendars empty and just have meetings and kind of that's it. But recently I did start as a completely different, Operately as a business management, like a company operating system kind of application and there's personal and family life, of course. So my core sort of split in OmniFocus is along the lines of those responsibilities. So I use folders and to separate these and then maybe have one more level of folders for different areas of work in each. But when I know that, okay, next morning I'll be working on Semaphore, and then I just basically click on the work tab on that folder in OmniFocus, and that's all I see. So it's pretty manageable. And so similarly, I've started using a calendar to sort of just keep track of how I spend my days. This is where also partially technical quirks come into play because you usually have multiple Google Workspace accounts, for example, or something. I've started recently using an ocean calendar. I found it pretty lightweight and it can connect very well with multiple Google Workspaces. For compliance reasons, at Semaphore, we've made connecting to Google Workspace a bit more complicated. And so for some reason, macOS has become a little bit buggy in that area, so I no longer can have a reliable connection to that account.

Andrew J. Mason: I want to pick up on something you just mentioned too about, was I correct in hearing that you used the calendar in some ways to almost journal how you did spend your time versus how you're actually planning your days moving forward? And if so, has that become instructional for you to see how actually time ended up being allocated?

Marko Anastasov: Yeah, I approach it, I guess, from both sides. So during the evening, on most days, I would flag a couple of things that I wanted to do that are on OmniFocus. I would also just have a block of time in the morning because most days I do deep work up till lunchtime or a bit further. I like the feeling of allocating that, like creating that event in the calendar. It gives me a feeling of being in control. And then as the day unfolds, I just create events for different things. So nowadays, we are actually starting a third thing, which is not yet public. So there's a lot of moving pieces. It sort of keeps me in the check. I've also sometimes look at things from... I invert, look for the negative visualization. For example, on Monday, I would imagine it's Friday and what would be a completely terrible situation to be in? And then I say, maybe on this project, we haven't even designed the first iteration of this new screen maybe that we're working on. And then on Wednesday, you would think, actually, if I don't do something with my schedule, it might actually end up being like that. So that's why I do these things to just have a visual, a bit of feedback that yes, I have these big chunks in the morning. I do succeed in protecting that time. And it's not even maybe protecting my time, it's just being focused myself and not steering away.

Andrew J. Mason: Not a whole lot of people use the avoidance to trigger positive behavior for yourself. Well, I don't want that to happen. So because it's Wednesday and I haven't done anything on it, shoot, if I don't do anything, then yikes, we're going to be in trouble here if I don't kick things into gear real fast. Yeah. And so with this mindset, you've kind of held yourself up by your own bootstrap saying, "You know what? I know that I might sometimes do more to avoid a bad situation than I will to draw myself toward that positive situation." There's something about that that's really interesting to me.

Marko Anastasov: Actually, I think I've found a lot of times you succeed by doing things to avoid failing. So you have to lose yourself in order to find yourself. And I think personal productivity is like that.

Andrew J. Mason: Do you do any tagging or perspectives in OmniFocus or is it just very much a simple task manager and that's the structure that serves you best?

Marko Anastasov: So there was a time when I used all of that, but I don't anymore. I found that I sure like and sympathize with the idea of categorizing everything that you do. When I was stretched too thin the most in my career, I at one point actually bailed on OmniFocus and I started with a Google Sheet and just ended up creating charts and looking at my time and types of activities from different angles. But in such situations, there's no tool in the universe that can really help you. You can only help yourself. There are times when I don't use OmniFocus for two days maybe or three, because I'm just lucky enough to not have too many other things and I can just focus on some creative thing. But then I know there's a place that I trust, a system that I trust that's a true list of all my ongoing commitments. When you look at that, you just have to be honest with yourself like, "Okay, how many things can I possibly move forward effectively?" On the other hand, if you are working in a team and sometimes you actually have to realize it's 50% me, but 50%, maybe we don't have the right skillset in the team and you have to change something in that area. And I use it mainly as folders and projects and I don't use customer perspectives. I started by having just two contexts for maker and manager, but I don't even apply that anymore. It just doesn't work for me, I think, personally, because the moment I start categorizing the little things, then I want to categorize everything and it gets in the way of flow. So I've just over the years learned what is my right measure of categorization and that's it. But I do use what does mean a lot to me are these types of projects or deferring things because it's really helps me clear the view. So for example, I would have everything that I have it related to Operately, but there's a maybe project which is just a placeholder for ideas and it's all kind of on hold or there are things that are kind of sequential. So I use the sequential type of a project or a task with sub items. And so when I focus on that whole area and then I go into that mode where you're viewing only what's available, I have a pretty manageable list of things that are like, and I also sort by importance. So my top priority is the first on the list. It ends up being as a pretty manageable sort of to do list, not something that overwhelms me, but it still contains all the information that maybe in the future will be important, but it doesn't get in the way. So I think that's a big advantage of OmniFocus versus pretty much any other task list manager.

Andrew J. Mason: We almost conflate everything with anything thinking, "Well, if I put anything in there, that means I can accomplish everything." And just because everything's in there doesn't mean you can do everything. It just means here are all your options that show up. And so I so sympathize with, let's keep it as simple as possible. And it's not even honestly as structured as I'd like it to be, but I know myself well enough to know that if I spend more time on the system than working in it, then I'm not going to get the results that I want to get in life. And so kudos to you too. Not right now, you're like, "Yay, I have discipline. That's great." But also this sense like, "Hey, currently I know myself well enough to know that the best thing for me is sometimes just a simple list that helps me focus on the right things."

Marko Anastasov: Yeah, 100%. I think this distinction that you mentioned working in the system versus or in the company or in the company, they lead to completely different outcomes. So when I'm thinking about all these topics, I usually have in mind my 10-year younger self or just somebody kind of approaching these questions for the first time. And I think it's almost like what I could say is it's okay to, when they say focus is the most important and it's like a total cliche now, but it's true and saying no really is important, but it's very hard when you're in the trenches and you're maybe being asked to do stuff or you just think it's the right thing and it is maybe the first time that you're in this sort of cycle. And so you have to burn a little bit, to understand your limits. When I compare when I was feeling most energized at my company versus not, it's when there is one big goal that we're all working on, one big thing, one big initiative, or maybe it's a crisis and it's maybe not so fun on this day, but it's very engaging and towards the end it becomes also very fun. I'm seeing it as a pattern in personal stuff. And I think that's probably, if you look at somebody like Elon Musk, who is obviously the champion of world champion in how many companies he can oversee and work on and so on, what's he doing all the time? He's just recently announced a new company, a software company called it Macro Hard, the enthesis of Microsoft. And what he's doing is opening literally a war front and his motto is like, "We will absolutely fail unless we take drastic action." And so it's his way of putting the whole company in this one big thing that's most important. It doesn't have to be that dramatic or on that scale, of course. But when you know what is the one most important really thing for you, it's not so hard to organize the rest of the things. It's okay that maybe I need to go to notary, but it's okay if I don't go today because I had a really productive thing going for the first five hours of my day. And if you are just approaching everything equally, like every inbox, every little thing that you need to do, you're working in the system versus really making a difference.

Andrew J. Mason: Maybe one final question. What is it in you or what about you there is this desire to be as productive as you possibly can be? I love hearing where this comes from for different people. What would you say it is that shows up in you that says, "You know what? I want to make sure that as I go throughout the course of my life, not that I do as many things as I possibly can do, but that whatever level of potential that I have or whatever level of impact I can make on this world, I really want to make sure that I make it."

Marko Anastasov: I would say it's important to ask yourself this. And to me, the most fulfilling version of myself is when I can realize my ideas at a rate that I get them. Oftentimes it's idealistic, something you can just aspire to. Yeah, I'm personally driven by just first is computer geek. So making stuff is obviously in the digital space, but I'm driven by making stuff. As long as I get to feel that I've exhausted myself in that side of me day in and day out, I'm happy. So it usually means that, and going back to your previous point, maybe the fundamental guardrail is like that there is, maybe it's not even like, okay, try with three goals, but have one, which is like it's non-negotiable that you do your best job at that one thing. And then these second or third are like, okay, let's try, but I cannot guarantee my best level or the fastest execution or fastest turnaround. I also think we've talked about productivity and efficiency, but there's this whole other side where I think, okay, if you work for hours and hours in deep focused mode on something, it's absolutely fine to just lay on the couch for half an hour and do nothing and stare at the ceiling. That's as important. It's absolutely not every single moment of your day should be tracked and recorded. And unless it really helps you, it doesn't help me. It's always like a yin yang situation. You always got to make sure you have that other thing that sort of helps you reset and just start fresh every day.

Andrew J. Mason: Marko, I appreciate you hanging out with us and sharing a bit of your wisdom. You can definitely tell that some of these lessons have been hard won, but if anybody's willing to listen to them, I believe that they'd be better for them. If anybody's interested in staying in your orbit or hearing more about what it is that you're up to, how can they best connect with you?

Marko Anastasov: Follow me on X/Twitter, @markoa, my username, or find me at my website.

Andrew J. Mason: It's awesome. Marko, thank you so much again for hanging out with us. This has been great.

Marko Anastasov: Great. Thank you, Andrew.

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