THE OMNI SHOW

Andrew J. Mason:
You're 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 hear how Randy J. Hunt uses OmniFocus. Well, welcome everybody to this episode of The Omni Show. My name's Andrew J. Mason, and today we're talking to Randy J. Hunt, which I'm pretty sure having J as a middle initial just makes it an amazing conversation to begin with. Randy's an executive, artist, musician, and writer, and from my experience, heck of a nice guy. He served as head of design at Grab, head of design at Artsy, and VP of Design at Etsy. And, Randy's the author of Product Design for the Web. He's currently chief product officer at morning, a coffee tech company. You can check that out at drinkmorning.com. Randy, thank you so much for joining us today.

Randy J. Hunt:
Hey, thanks for having me.

Andrew J. Mason:
Randy, there's always the propensity from people like me to give a two to three minute soundbite bio that's really largely career based. I have a feeling that you're much more than just the two or three sentences about your career. Can you give us a little bit more of about yourself, your current reality, and where you find yourself?

Randy J. Hunt:
Oh sure. Well, I'm an American designer, that's probably the good two word summary, currently living and working in Singapore. I come from a generally sort of background. Parents were creative and kind of tinkerers and makers, both in hobby, sometimes profession. I was a musician before I got into design, and technology was always around. My dad was an electrical engineer turned software engineer, and so gadgets and gizmos, computers and software tools were always present whenever we were doing other creative stuff. I think that's really just kind of informed how my life works in a way. So as I move through other sort of creative or professional pursuits, tools and technology that both enable them but also manipulating the tools of technology as part of the creative practice has been something really present in my life. Where that channeled itself professionally is I ended up working on both sort of software product design, brand design, experiences in a commercial setting. And for me that's been a lot of multi-sided marketplaces online. I love commerce, I love small businesses, and that's probably been one of the strongest through lines in my professional life, probably 15 plus years now of working on marketplace. Always through a design lens, and always in this kind of blurring of maybe the art and science, and blurring of the brand, the product, the business mechanics. I'm happiest when things are in the messy in between.

Andrew J. Mason:
So really I've made up a rule. I'm not actually sure if it's true 100% or not, but I tell everybody that when you're doing an interview show, "the host gets to have at least one selfish question." And following a little bit of your career track and seeing how you've seen some success with really great organizations, I think I remember you saying at one point something to the effect of, "I feel really lucky in life because what I love to do and what I'm good at happened to be the same thing." For anybody that's out there that either they're really, really good at something but they're not necessarily passionate about it, or they really love to do something but they just haven't found that alignment that awards them in a professional context, can you speak a little bit to how that's worked out for you, or any lessons or ideas that you've been able to draw from that?

Randy J. Hunt:
Oh wow.

Andrew J. Mason:
Sorry.

Randy J. Hunt:
No, this is great. It's an important question because I know it's relevant. I mean, I would have that same question for someone else or something, I'm sure. So I don't position myself as an expert there or something. But why I laugh is because ... Maybe it's hard to articulate. I would say some of the things that seem to somehow have been most effective for me or choices that work have been largely intuitive, which is a very unsatisfying answer. It's not like, "Here's the step 1, 2, 3 I did, or here's this make important question and when I answered it for myself, I flip to the other side and everything crystallized and made sense." I think a lot of what I do is I try to, it's going to sound so corny, one, I try to be genuinely helpful to other people. I believe in a kind of a little bit pay it forward-y karma-y. I have found that when I give generously to others it comes back, or it feels like it comes back. I don't know, I don't measure it, but I feel like the universe returns to me good stuff. So I try to be helpful or give towards things with no expectation of specific return. I feel like that has maybe over time attracted people. And then those people are the bridges to opportunities and things. So the people trust you over time, and then when you have an idea to do something that aligns well with your interests, they're more likely to say yes. That's me reflecting on this; it isn't a calculated choice. Oh, if I'm nice to people for two decades, then one day when I want to pursue my creative passion, somebody will be like, "Yeah, we'll pay you for that song." No, not like that. But rather than maybe over time trying to show up that way consistently has allowed me to have a community that's sizeable enough. I don't mean I have some massive following or anything like that. I just mean enough valuable relationships that when I have different interests, leads, questions, pursuits, I kind of bounce between my crew of people and there's enough to propel things to the next stage or something like that.

Andrew J. Mason:
That's incredible. And thank you, speaking of generous, for that generous answer. That's huge, and hopefully somebody will find some inspiration there out of them. Tell me if you remember years ago, however long it's been, do you remember the first time you came across the Omni Group as a company, or more specifically as one of their software crossed your path and you were introduced to them? Do you have any recollection of when that was?

Randy J. Hunt:
Yeah, well so I have a recollection of maybe the brand and the group that predates for sure when I started using the tools. This may be wrong, you could correct my facts, but I feel like it was probably OS 9 days or something when I first encountered Omni Group. Probably because of OmniGraffle maybe. I was kind of early-ish in my sort of graphic design part of my career, and I think those tools were around or they were at the store where we go buy box to software or something. I just remember the name existing. In the Mac software world, I mean it's still kind of true today even, relative to other things, but back then it felt if you were to walk into the software shop at the local shopping mall or something like that, there was 14 racks of Windows software, half a rack of some stuff for some other oddball Oss, and maybe one rack for Mac OS. So if you're a fan of Apple computers, you kind of knew everything that was on that shelf. Because if you went to that store once a month, my recollection is that OmniGraffle probably was one of those things. So it'd been in my mind for a long time. I started using OmniFocus after I think reading Getting Things Done. This probably would've been for me around 2000. These dates might be wrong, but it might have been 2007, 2008, 2009, somewhere in there. And so I had this interesting relationship with it. So one, I like opinionated software. I love this kind of the software's not trying to do everything for everybody. It's got a particular thing. Actually the software is a reflection of a mindset, and if you have that mindset then the software becomes that extremely powerful tool for you because they're interlinked. I have found just a few times over that when that is true, you feel really supercharged. That kind of the bicycle for the mind promise really comes out. I used OmniFocus maybe once or twice, or sort of tried to. I downloaded some seven or 14 day trial or whatever this might have been back then, and it felt too complicated. I don't know, there's something about it. I felt like I couldn't quite get in the groove of it. It wasn't fitting; behaviors and software weren't intermingled. And then I think it was a third time I tried it and I did this thing I sometimes do, which is rather than using the free trial, I just paid for it. Which I always appreciated too, that Omni felt like it was charging a fair price to me. Which I mean, it was charging more than other people, but to me that always felt reasonable because I was like, this is what I perceived as a small to medium size software company, and I like people to get paid for what they make. I want the thing to be around. I don't need dollar a month software. I'd rather have fewer, better things in my life. So I like that idea in general. I kind of admired and respected it. And I was like, "I'm just going to buy it." Forget the trial, I'm going to buy it and by spending the money, I'm committing myself to it. I want to get the value out of it now, I'm not like demo-moding it. And so I really committed to taking the sort of getting things done methodology, applying it. So I had the mindset, applying it in OmniFocus, which to me the sort of top line feature set was a really strong match to the getting things done methodology. And I just tried to use it every day. I stopped any other way of keeping track of things I wanted to do. By the time I was three or four weeks into that exercise, I just used it almost every day of my life since. It's like, every time there's a new, "Hey, we're releasing an iPad version and you need to pay for it," I was like, "Sure, no big deal." Because that's so ingrained in my life. The value seems so strong when you use something that frequently. It's like, would you question a pair of shoes or if you're wearing the sneakers every day? You just get such daily use value out of it. So yeah, I just started using it. First probably, it was really in a professional context where most of my tasks seem to exist. But quite quickly it expanded to just being all consuming in my life. So I have very long running projects that get reviewed at long intervals that are almost chipping away at life goals. Then I have other things that are like, remember to bring in the extra shoes from outside, a little chore around the house that my wife asked me to help clean up some stuff I didn't want to forget.

Andrew J. Mason:
It's so interesting you say that, because I think we all, whenever we're on this kind of a journey, realize that you don't need it until you do. And when life's responsibilities start to expand or there's just more to keep track of than you can consciously keep in your head at any given time and things start falling out the backside of your head, you realize you need something. Tell me more about what areas of focus you might have that are tracked in OmniFocus. Is it just one slice of your life, or is it the entire gamut?

Randy J. Hunt:
Yeah. Yeah. It's funny, I almost use it... So I view them all as tasks. They all have kind of an action to do. But some of them, maybe for other people, might almost feel like a bookmark you'd keep or something like that, or some kind of reminder. So for example, one of the tags I use, I create tags for people in my life and when I have an idea of a good gift for that person, I tag it to them. So I have a gifts project and then they're tagged to people. Basically the action is to buy the gift or to give the gift. But sometimes they're on a long arc. It might come up, it becomes irrelevant two years later. They've got a birthday coming up or they just accomplished something or just thinking of them that you want to do something. You're like, "I knew I thought of something cool for that friend." But to me they're all action oriented. I don't look at those frequently. They're more like ones I go seek out. So they're not showing up in my review queue at a frequent interval. I have many projects that are work and professional related. I often create in parallel for myself in the professional context the same information, architecture, and nomenclature as I would like at a job or something. So let's say I was leading a big software company out here in Southeast Asia for a while. Then we would use an OKR process to manage priorities and stuff inside the company. I would create a folder and create projects that matched each one of those OKRs in OmniFocus so that I can organize my own actions in that same way for that professional context. But then now I'm not in that context, I'm not using that same thing. So I kind of adapt some sets of it so I could match between OmniFocus, which to me feels just like an extension of my brain, and the more shared way of organizing activities that's happening in a group of people.

Andrew J. Mason:
Yeah. What would you say to that person that is just getting started, either with OmniFocus or something as broad as task management? How do you advise somebody if they need any go-to first tips or tricks? What's your go-to advice for somebody that's just kind of getting their head around, "I need something more"?

Randy J. Hunt:
One is to just put everything in one place. When I describe how I use that sometimes it can sound funny, because it might literally be buy socks. Like, do you really need to put that in the same thing that's reminding you to clean up the notes for a coaching conversation for a member on your team? You're like, "Do these things belong in the same thing?" And for me, "Yes, that's kind of the point." Everything in one place. The other, which I suppose is the next step or something, is just to stick with it. I think that I've gotten more value out of it the longer I've used it. Putting everything in one place and sticking with the program is where the value reveals itself, at least in my own experience. Now that I've got all the to-do's in one place, ta-da, now I get everything done in my life. Definitely not. There's way too many things on that list. There's stuff I'd snooze forever and things I end up just deleting and never doing. But sticking with the program is really powerful. And so then maybe what is the program? For me I review things. I look at my inbox every morning. But I also look at my inbox whenever I kind of have some downtime and I feel like doing that. So it might be in the day, I know that I maybe added some things, but on a commute or something I'll just pop up and categorize my inbox quickly so I keep that clear. And then I sit down and do the reviews whenever reviews tell me I need to do reviews. And then I basically keep OmniFocus open all the time on my laptop or something. It's kind of my personal operating system in a way, so I'm always referring to it. I'm constantly adding and checking out of it, or checking things off, adding things to it. I think that was really helpful, too. I live with the list. It's not like I make the list and then I've written everything down, and tomorrow I'll come back and go over my tasks.

Andrew J. Mason:
This is really surprising to me. I've had the honor of interviewing a lot of people about how they use productivity and you're one of the few that I've talked with that said, "The one I started with is the one I've stuck with." Even I've fallen victim to the shiny new feature syndrome where some software will come out and it promises to change everything. The downside I don't see is however much of your life that's invested in the other software, there's a chunk of your brain missing from 2012 to 2013 because it's all in there and I haven't migrated it over.

Randy J. Hunt:
Yeah, yeah, totally. I've had that experience a few times where I get the shiny tool thing. Of course, my approach, I like everything in one place is I was kind of double tracking it in a way, which is just super tedious and not a good use of anyone's time. But what I found was that, again, because it's about this opinionated or opinionated enough. For sure, to me, OmniFocus feels opinionated. But it's also very flexible. You can use parts of it anyway. I mean, you can use tags however you want. They're tags, right? It's very kind of a morphous thing. But what I found is that other things I tried were less opinionated, or I had to do effort again to kind of make it the same as OmniFocus. Like, how would I use this the same way? Like, the way of using it was working so well for me, but the fact that this other tool that popped up which maybe had a feature that was appealing in the moment or something, all I was trying to do was just use OmniFocus basically. The behaviors were the same and I'm like, "Why change? It's just silly. Why have another tool?"

Andrew J. Mason:
Randy, tell me how you use perspectives. OmniFocus offers the ability to slice data however you want to in a way that makes sense to you. So if it's tags, or date based, or show me only the information that's in these folders, you can kind of create these shortcuts to data that makes sense in a way that you like to look at it. Do you do any of that?

Randy J. Hunt:
I have in the past. What were they even? I think the only custom thing I use right now, or I don't even know if I made it custom or it's one of the existing ones but that's not by default exposed in the UI, is I often go back to the recently changed one because I use it so frequently. Sometimes there might have been a note in it that I forgot about and in some context I wanted to refer to it. Or also sometimes I might accidentally close, I accidentally check something off. I'm constantly using the tool that there's things like that I might have mistapped or got distracted on my laptop or something. So having that one really handy, I can be like, "Oh, that was that." Because it might be like, "Hey, send so-and-so this link to this article" might be a task I have for myself. And then I send it and then I'm like, "Oh, someone else would also like that." I realize an hour from now, "Where was that link again?" So I can go back to the recently changed ones and I can find it easily.

Andrew J. Mason:
I really love this story arc that I'm hearing emerge from your use case, Randy, where it's disciplined use of the tool is actually what ensures that you have success with the tool. So it's one of those things where just because can is available doesn't mean it should, and so you figured out what you should use. It's not necessarily every feature, but the features are there that you need. It makes me feel like I already know the answer to the next question, but I'm going to ask it anyway. Do you do any automation? And that can be as complex as JavaScript or plugins, or as simple as a repeating task.

Randy J. Hunt:
Yes, so I do. Okay. I do repeating tasks. The most common ones are for people I want to talk to in my life. So I have these reminders to call, email, message people. At certain intervals that pops up in the day, reminds me to reach out and say hi or check in with them, see how they're doing. I also use, not automation, but I basically have these template projects I use for things that happen inconsistently, but that happened multiple times, but not in regular intervals. So example, I have a template project that's all for packing for a trip and it's a list of all the stuff I need to make sure I got my adapters or I got enough pairs of socks. The first thing is to check the weather and count the number of days. So I've got all the tasks in a bucket and it totally lowers my stress and anxiety anytime there's a trip. I just open up the project. I usually do it on my iPad actually, so I open up the project, I'm focused only on that. I kind of carry it around my bedroom or house and it's really easy to tap that while I grabbing my stuff. I use the feature where I email in, so I email to my sort of Omni address stuff for my email. I use that very frequently. And then I also use the feature in iOS where it basically sucks in from the OS Reminders app. Because sometimes I'll dictate to Siri a thing, like, "Remind me to do this," or something, and that ends up in my inbox in OmniFocus. I love using that. I like to work while I walk a lot or something, I like long walks and stuff, and so sometimes it's just easier to dictate a thing than type it in. I use that fairly frequently.

Andrew J. Mason:
Randy, I feel like you're the anti-power user power user, where you're seeing a lot of success with what you're doing, but you don't have OmniFocus hooked into Fantastical, hooked into Agendas and it spits out something into Obsidian.

Randy J. Hunt:
Yeah. Yeah. Yeah.

Andrew J. Mason:
I guess I just hear a lot of calms surrounding it, where it's disciplined but it's moving forward.

Randy J. Hunt:
I used to do lots of things like that, not only with OmniFocus, but other things. Maybe I've felt the pain enough over a couple of decades of those systems become fragile. That's been my experience. There's three things linking together, and then that middle thing goes from being a free service to a paid server, so that middle thing changes the integration. But I'm not trying to spend my time integrating tools, right? You're like, "Oh, I got to spend a Saturday morning to solve this a different way, or now it's in Zapier," or whatever it might be. I've kind of lived through some of those things. It's the same, I don't know if you were involved in the WordPress community back in the day or something. You're like, "Oh, great, this plugin will solve that problem." And then you're like, "Oh, I've got 14 interrelated plugins, and then one of them doesn't support the new PHP," and you're like, "Well, there goes a week." So I just prefer to keep the stuff as simple as possible, and then only integrate when the pain threshold's too high. But I used to be different. It used to be quite fun. I'd be like, "Oh, I can puzzle all this stuff together." I don't feel the need for most things now. That's true of OmniFocus, but it's true of lots of parts of my life.

Andrew J. Mason:
Randy, is there anything in your journey that you have experienced that could be instructional for somebody who maybe isn't quite where you are yet? It doesn't necessarily have to be a failure, but had I had the opportunity to do that over again, I probably wouldn't have done it this way.

Randy J. Hunt:
Yeah, it does bridge pretty well. I think I went down a path at some point of trying really hard to get something like the task list and Basecamp to sync over to my OmniFocus or something like that, at a time when I was working in a professional environment that we were using Basecamp to be the primary project management tool. But I came back to things like that a few times, and I think that ultimately not really necessary, at least for my purposes. The other is, I think, trying to find a way to make OmniFocus more than a one person experience. There've been a couple times where I've bumped into that. I'd be like, "You know what'd be great is I could just share this task with my wife." I've come around to just feel that I think of it as an extension of my brains, and so it's personal in that way. That makes it really powerful and I have that mental model of it. It also has the limitations that come along with that, which I just accept. Meaning someone can't add other things into my brain. It's not shared. It's an extension of me, and that's fine. I manage the threshold between it and other stuff, and that's okay with me.

Andrew J. Mason:
I think that's a really honestly good way to look at that, where it's this mental model of a second brain. You're able to externalize your thought from a privacy standpoint, and just from a free flowing, freedom of thought standpoint where you're able to get the information in there that you need to without worrying about anything. The flip side of that's really funny too. David Allen used to always have this anecdote where he wasn't sure how something got into his inbox. He didn't remember having that thought or anybody put that there, and then over time, he found out that it was his wife, Catherine, starting to seed some ideas that he needed to have or needed to act on. It was her subtle way of nudging him.

Randy J. Hunt:
Yeah, yeah, sure. The other thing I think is maybe it's not about the software, but it is like the sort of behavior. While I put everything in it, in a way, it's worked much better for me and I've observed myself and others have a challenge. And I don't do this, which is to treat it more like a low. I think it can get tripped up by being, even though I put everything in it, I don't mean to add all the tasks. If I did something else that never made it in, it doesn't need to be a record of everything I've done. I guess that's the thing. If you treat it as a record of what you've done, at least for me, you're just too backward looking. It's like I use it as a tool to shape how I spend my time now, not as a record of how I've spent my time in the past or something.

Andrew J. Mason:
Randy, this has been a really great conversation. Really honored to have you as a guest on our show. If any of you are interested in connecting with Randy or his world or what he is up to, you can head to RandyJHunt.com. Randy, this has been an absolute honor. Thank you so much for joining us.

Randy J. Hunt:
Hey, likewise. A lot of fun. Thank you.

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