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Oct. 13, 2020, 10 a.m.
How Allen Pike uses OmniFocus to run Steamclock

Allen Pike runs Steamclock, where he helps design and develop polished apps in beautiful Vancouver, Canada. His work ranges from strategy and product management to coordinating design and development. Previously, he was a Software Engineer at Apple. On weekends, he hosts a podcast about silly facts.

Show Notes:

Allen leverages OmniFocus to capture and prioritize the best ideas when working at SteamClock. His unique blend of perspectives and workflow afford him the feedback he needs to make mission-critical decisions quickly.

Some other people, places, and things mentioned:

  • High Output Management
  • Getting Things done
  • Allen's Inside OmniFocus Article
  • Super Mario Bros 3
  • Super Soaker Water Guns
  • Transcript:

    Andrew J. Mason: Well, I so appreciate that. Because when you're recording remotely, you just never know what you're going to get. Maybe it's the most expensive, amazing sound equipment ever, and maybe it's their internal mic. You don't know.

    Allen Pike: I ran a podcast for a while that was a video game design show. And so people who would work on games would come in. And it would range from people who were audio people who would be calling in from a sound booth, isolated with padding on all the surfaces. And they would have multiple mikes trained on them so they could pick the one that sounded the best. And they wanted to work on the audio files before they sent them to me.

    Allen Pike: All the way through to one guy who worked on a game that was very jokingly bad. And he recorded from his Windows laptop. And I'm pretty sure the laptop was closed, and the microphone was in the laptop, and you hear the fans. I was like, "Are you sure you're recording from another microphone? Because it sounds pretty bad on Skype." He's like, "No, no, no, it's fine."

    Andrew J. Mason: You're listening to the Omni Show. Get to know the people and stories behind the Omni Group's award-winning productivity apps for Mac and iOS. My name's Andrew J. Mason. And today, we talk to Allen Pike on how he utilizes OmniFocus.

    Andrew J. Mason: Welcome, everybody, back to the Omni Show. I'm so excited because today we have Allen Pike, from Steamclock Software, talking to us about how he utilizes OmniFocus to get things done. Allen, thank you so much for joining us today.

    Allen Pike: Hey. Good to be here, Andrew.

    Andrew J. Mason: Absolutely. So Allen, you run Steamclock Software, and this company has been around for a while. Can you give us some history of how things got started for you?

    Allen Pike: Yeah. Steamclock had our 10 year anniversary this year. Which, in a scheme of software companies, is pretty long, especially app development companies. But then we're talking about Omni, which is one of the few companies that puts us to shame in terms of how long Omni's been writing software and selling software, so I guess we're in good company in the decade plus group.

    Allen Pike: But we started 10 years ago, as a lot of software companies do, is just me and my co-founder were working out of his basement and trying to make software that people love. And built up just to one hire at a time. That was 10 years ago, the two of us. And now we've worked our way up to 12 people. And just slow and steady wins the race is the name of our game, so to speak.

    Andrew J. Mason: And so Steamclock creates beautiful apps. Do you have any examples that people might recognize?

    Allen Pike: Yeah. One thing that we launched in the last six months, which was a fun side project for us, was a game which we'd never published before. And so we made this game called Two Spies, which was a passion project that ended up getting more attention than we expected. Got featured by Apple quite a bit. One of their game of the day, features in the app store, and various other things.

    Allen Pike: And so we've had quite a lot of players playing now and there's features that early on we expected that nobody would be playing online, there wouldn't be enough people playing the game to have other opponents. Where it's just like, "Oh yeah, play against someone." But what if no one else is playing? And then we have thousands of downloads a day. We're like, "Well, I'm pretty sure you could find an opponent now." So we're adding features that we didn't expect to do into this side project.

    Allen Pike: So that's one thing that people might've seen. And we have clients that range. A lot of our clients are to other tech companies. And so, over the years we've worked for a variety of larger companies, as well as startups. Pretty commonly, even though we're in Canada, a lot of work we do is Bay Area and New York startups that are gone out of their stage of, "Is this product going to work?"

    Allen Pike: And then they are going into the stage of, "Okay. Well, we have this," especially often web-oriented product that people love. And they're like, "But we really want a good app." Or maybe they have a janky 1.0 app. And they're like, "Okay, it's time to do a really good app." And so we'll often come in and ship a high quality version to our clients. So that's our client side of the business. And then we use the profits from that to build our own stuff that we like to work on and might turn it into a product side of the business.

    Andrew J. Mason: What a cool life path that you've taken. Do you have any insight as to how you got started doing this? Just wake up one day and say, "Hey, we're going to build great apps." Where does that passion start for you?

    Allen Pike: I've always been product-oriented. I didn't really fully realize how much that was true until I was going through some old stuff from when I was a kid. And I had this giant binder of paper that my dad had given us, just these big stacks of bound paper that we could draw on or play with. And there'd be pages and pages and pages of ideas for products.

    Allen Pike: I was seven-years-old and was like, "Here's what the super soakers that we should make." Except I called them water blasters or whatever. I was like, "Oh, here's the 10 different super soakers I would make. And here's 10 video games I would make." And like, "Oh, here's all the cars I would design." I think every kid plays around with that, but I had just pages and pages and pages.

    Allen Pike: And I didn't think of it at the time, it was product design. I thought it was just like, "Yeah, that's what kids do. They draw 45 different cars from 3 different manufacturers that would then be competing in this artificial world." That's just the weird kid that I was.

    Allen Pike: And so, as I got older and got into computers, a really natural thing that I gravitated to was making stuff on them. So that ranges from a variety of things. And obviously software is a pretty good living. So that's where the economic side of it is focused.

    Andrew J. Mason: You brought out a memory for me. I haven't thought of this in literally a decade. When I was in third grade, used to draw out levels to Super Mario Bros. 3 using a graphite pencil and notebook paper during subjects I wasn't paying attention. But just so funny. Before Wii, or Super Mario Maker, or anything like that. That's hilarious.

    Andrew J. Mason: And it's normal. To parents out there, it's normal for your kids to do this kind of stuff because they're gaining skills. We don't think of it as product design. But it's just such a cool concept to know that something like that for you has transferred into such a practical use these days.

    Allen Pike: Yeah. Everything is practice and it can start early. I'm a big believer in the transferability of skills. So the work I did as a teenager, making a bad card game that never went anywhere, and then trying to pitch it to people and people weren't interested. And then I was like, "What am I learning? I'm learning sales and I'm learning product." And it was 1 of 10 abject failures of things I tried to make in high school. But each time, I learned things by failing.

    Andrew J. Mason: That's awesome. So excellent backstory there. Let's fast forward to you've got these skills now in your life and you come across Omni. When did that happen for you?

    Allen Pike: Yeah, I'm pretty sure the first exposure I had to Omni was when I was working at my first software job. Maybe I was just out of high school or just the beginning of university, so many years back now. But my boss there introduced me to OmniGraffle and it was a very Mac-oriented company.

    Allen Pike: And I was trying to plan something, design some system of some kind for a project we were working on. And he was like, "Oh, you need OmniGraffle," and got us a license. And I was like, "Okay, this is what you need to do." And I really enjoyed using it. And so that was my inbound to being aware of Omni.

    Allen Pike: And then as I started to more focusing on the career path of being independent, independent software developer, and wanting to start my own company, I started becoming a lot more interested in, "Well, what other companies are doing that? What other companies have built a durable business around selling software on the Mac and high quality user-focused software?"

    Allen Pike: And so then I started seeing more and more about Omni, just talking and meeting people in that space. And then got really into OmniFocus over the last five years as I grew my previous, more primitive to-do management system. So then, that's been my biggest contact point with Omni in the last five years or so, has been being an OmniFocus user and letting it run my life.

    Andrew J. Mason: Well, yeah, let's actually dive into that. What does the structure of your OmniFocus system look like? Are there any go to, first thing, day-to-day things that you do?

    Allen Pike: There's two big things that fundamentally... I use OmniFocus, obviously. Other people use different tools, and to-do systems, and task management systems to achieve this. But the two core things to me are, A, working on stuff that's important instead of only working on stuff that's urgent, which is a common productivity, getting things done thing. But actually moving that forward, I'm spending a higher percentage of my time on what I've decided is important, longer-term stuff. Rather than just it popped up right now.

    Allen Pike: And the other half is, which is an offshoot of that, but especially in the last six months has been a bigger thing for me that I'm focusing on, is less stress; less anxiety around, "Am I forgetting something? Is there something that I'm supposed to have done and I haven't done? And also, is there something that I'm procrastinating?" And that's bothering me and wearing on me. And so, overall, those are the two pillars, for me at least, is why is it worth going to the effort of setting up and managing a system for deciding what work I do, are those two key things.

    Andrew J. Mason: One of the most interesting things about people setting up systems for work is to see what happens as those systems get disrupted. Do you mind sharing a little bit of what the last few months have looked like for you guys?

    Allen Pike: The changes over the last six months... Our team was a very in-person type work environment. Not really because the type of work that we do in doing software development, so it totally can be remote. But we happen to have two founders that just really enjoyed in-person, were fairly extroverted people that having a office that's separate from... We love our kids, but it's nice to have like a space. It's like, "Okay, your work is work. And then you come home, and home is home." And so two people who liked that, and then invested in having a nice office, and then hire other people who also have that mentality.

    Allen Pike: And so it's been a bit of a cultural shift moving to remote work change for us, but it hasn't changed the way we're doing our work that much in terms of how we're managing tasks and stuff. The biggest change for me on how I'm using OmniFocus in using my productivity focused tools is that piece of making sure that I am not letting things worry or... Everyone's going to be worried in some degree, but using it as a tool to decrease stress, which is something that is not the number one most obvious thing. When it's like, "Oh, why do I use that task system?"

    Allen Pike: Some people's tasks systems cause them stress. And depending on how you set it up, it's very easy for it to do that. But also using it strategically as a... I keep thinking about this thing, or I keep wishing I had already done this thing, and then setting up the system and using it in a way that makes that stop being on my to-do list. Whether because I did it or I decided I'm not going to do it in that. So that's been a tool I've been using more often.

    Andrew J. Mason: I am familiar with the idea of urgent versus important. Do you have a way to slice or manage the data that you really get to hone in and zoom in on those pieces that really are important? How do you cut through this stuff that, "I shouldn't do this, but I really want to focus in here"? Or maybe your advice to new users about how do you do that?

    Allen Pike: Yeah. The due dates is one of the ways that a lot of people who are new to either OmniFocus or other task management systems, will quickly start to get themselves into a variety of problems around due dates. Where the default way that you will tend to... Or at least the way I default tended to, is I would create a task. And then I would select the due date as when I would like...

    Allen Pike: I like the idea of having been done. This is the thing that I think I have to do. I like the idea of being done in two weeks. And then two weeks come by, and then it's one of the many, many things that have now say claimed that they are overdue. But out of all those things, only three of them are really overdue. And actually, maybe none of those things are the things that are really the most important things.

    Allen Pike: And so, obviously, on an hour to hour basis, you need some system, some perspective. I used to use custom perspectives, a common thing people would use is the "due and flagged". You take all the things that are due soon, and then all the things you put a flag on, and then you make a customer perspective of that and work out of that for what you're working on like hour to hour. I did that for a long time. That works fine, depending on how disciplined you are about your flagging and your due dates.

    Allen Pike: I've been more recently working out of the "today view" in OmniFocus. Which I have a tag where I say, "This is the stuff that I would like to work on today, or yesterday, I thought should be done today," and use that to try and keep a working list of 5 to 10 things that I'm only looking at it in a given time. And then I have customers' perspectives that I used to feed that, which I could talk a little bit more later.

    Allen Pike: But on the question of, "How do you slice through and try to get it focusing in?" Focus is right in the name of the product, OmniFocus. How do you focus in on what's important and not just urgent? Due dates almost are the opposite of that.

    Allen Pike: Due dates are for the urgent things and make sure that it's something that really is urgent, that you really need to renew your driver's license. Otherwise, you're breaking the law to drive anywhere. Then, yeah, make sure that those things have due dates and that they do get done. Maybe actually they belong in your calendar.

    Allen Pike: But in the context of what's important, the thing I find helpful is having zoomed out periodic... I do quarterly. Or I call it seasonal because quarterly is still a two businessy, even though I run a business. But a seasonal check-in, both for my personal... I do personal goals and business goals at separate times. But sit down, and I don't even necessarily need to spend that long about it, but what are the three things that are most important for the next three months?

    Allen Pike: That are like, "I will feel like I've really moved forward in a meaningful way in terms of getting towards a longer-term goal, or improving my quality of life, or finishing something that's important to me. What are the small list of things?" For personally, I only pick three. For work, I pick more than that.

    Allen Pike: And then, in OmniFocus, I use tags to say that these are the actually important things, these are the personal goals, these are the work goals. And then those behave differently in my different perspectives. And I try to make sure that those are getting populated out and not just the all sorts of good ideas or interesting things. Or like, "Yeah, I probably should do that. And now those just fill your inbox and your "today view" without any evaluation as to how important are these things.

    Andrew J. Mason: Well, I do want to share with the audience that there's a fantastic article that you've written for Inside OmniFocus. It's been a few years now, but it was coinciding with the release, I believe, of OmniFocus 3. Does most of what people will find inside of that article ring true still?

    Allen Pike: Yeah. I wrote that article a couple of years ago when OmniFocus 3 was first coming out. And so, some of the article talks about the transition, which is not as relevant now that everyone's probably all upgraded. I tried to structure that article not as a, "Here is the one perfect system that I think everybody should use," because everyone's needs are so different, especially depending on how many tasks a day are you doing.

    Allen Pike: Are you working on one consistent thing? Or one thing you'll see as somebody moves out of being an individual contributor on a team into more of a management or organization operations role, as you start dealing with more and more different tasks that are very different each other. And so your needs and the complexity of your keeping track of how to stay organized become more and more.

    Allen Pike: And that's why I think a lot of people who are help run businesses tend towards a tool like OmniFocus that has a lot of flexibility that you can configure if you want to start simple. And that's what I think it did. It still is relatively true in the article, is describing basically some of the most useful tools in that toolbox in terms of organizing and things you can experiment with. Because I wrote it in a time where I had a system where I was quite happy with it.

    Allen Pike: And then I was like, "Oh yeah, thanks for the invitation. I could write an OmniFocus blog post." And as I'm writing it, I'm researching the tools, I realized like, "Oh, actually, I really should be using this." And, "No, actually, this is maybe not a good way." And like, "Oh, this one folder is just a mess." And then I ended up destroying my entire system, pulling it all apart, and I started experimenting. And then it ended up being an ode to experimentation.

    Andrew J. Mason: Do you ever find that happening where you're dating a lot of different systems or styles of doing something and then you just never really quite settle on one? And it's just this constant state of flux where you're like, "What do I do?"

    Allen Pike: It's something you have to do from time to time. And I think people maybe rightfully learn that you don't want to be constantly working on in the meta of it's very easy to procrastinate by just tinkering with your tools instead of actually getting things done. But every once in a while, for me, that's probably every two to four years, is looking at what are the endemic problems in the system either every few years or when you notice that something isn't working.

    Allen Pike: An infamous thing that I mention in the article, and keeps happening to me, it happens to most people who use tools for managing their to-do's from time to time, is what I call a "due bomb" which is basically a whole bunch of things you can do in a pretty short period where you may or may not be as focused on checking things off and maybe you're distracted or whatever.

    Allen Pike: And then suddenly you go into your OmniFocus and there's 27 things that are due today, and they're red. All things would have been due. And you're like, "There's no way any human could accomplish this many things in one day." And some of these are important, some of them aren't. And so you're trying to avoid that. So anytime you see that, then it's like, "Okay. You can do a reset," and be like, "Okay, what is actually important? And then how am I driving this whole system to serve me instead of the other way around?"

    Andrew J. Mason: That's a really great point, too, about being aware of the form versus function and not just operating within your system, but also thinking about how to best approach it. Because when you just see all this stuff presented to you, you're like, "Okay, I got to do it all."

    Allen Pike: Yeah. And the first time you look at it, you might be like motivated. "Okay. Okay. I know. I'll try and do some stuff." But the thing that it starts to track towards then really screws you up, is that then you started dreading looking at it, or a procrastinated looking at it, or you stop keeping it as organized because you're like, "There's so much stuff in here. I'm just going to do the urgent stuff." Someone's like, "Hey, when is that report coming?" You're like, "Oh yeah, right. I'll do that right now." Or you're in a meeting, and someone's like, "I thought you were going to do this thing." "I'll do it right after the meeting."

    Allen Pike: Once that's happening, once you're doing things based on someone having bugged you for the thing, then you're no longer being driven by your high-minded goals of, "What is important to me or what I actually think I should be doing?" You're instead being just interrupt, urgent, see-driven, which happens sometimes in emergencies. But that tends to be the second order effect from, "I have so many things that claim they're due. How do I pick the next one?"

    Andrew J. Mason: I've been guilty of that. Where you just over capture and over capture, and don't look at where it's actually headed to your inbox in your system. It's almost like, "I ate too much at Thanksgiving, but if I don't look at the scale, then I won't know what the numbers are."

    Allen Pike: Yeah. Well, and that's what happened. It's been a long time for me now, but I've gone through phases where I stopped regularly launching or looking at my to-do system. And sometimes that can be a relief, take a break from it, if it has gotten bad or toxic in some way or another, if you've let it get gnarly. But then, it leads itself to that kind of mentality, yeah.

    Andrew J. Mason: So do you mind me asking, how do you decide day-to-day? Are there specific tags or perspectives that you use?

    Allen Pike: Yeah. Like I was saying, I used to use this "due and flagged" one, or a variant of that. And I think a lot of people, at least some point, do a, "What should I be working on today?" But I've gone to just using a tag. And then what I have in my other custom perspectives that I have are for feeding that tag.

    Allen Pike: So I try to have this "today" tag, which is just a small number. And constantly trying to train myself to not overstuff things into claiming I'm going to do them today. It's like, "Really, what am I going to actually do today or tomorrow?" And then I'll use the "today" tag for that. And there's a keyboard shortcut for toggling things.

    Allen Pike: And then I have custom perspectives that will feed when it's like, "Okay, I'm starting to get a little bit low on stuff that I, that I have for today or for tomorrow. When there's three things left or whatever, I'll go into..." One of the perspectives I have, I have one that's called "office next", but really I should rename "work next" because the office is no longer a concept.

    Allen Pike: But the "work next" perspective is my projects, which are roughly sorted by priority, and then things that are flagged in those projects, and then I think there's maybe a little bit more [inaudible 00:19:51] than that. And then anything that's in any of the projects that I flagged with that this is a goal. So even if it's not something I flagged, it's effectively flagging the whole project.

    Allen Pike: It's like, "This is the important projects. And then here's all the other stuff that I flagged for one reason or another," is ideally something that's not necessarily needs to happen this week." But any of the stuff that's flagged, I've evaluated it as, "I think this is actually something worth prioritizing 'soon'." And then I pull things out of those. And then when I review, I try to clean those up. I use those perspectives.

    Allen Pike: And then I have a home equivalent. Where it's like, "Okay, what should I do today at home? I've checked off most of my stuff that I flagged as 'today', and then I can switch into that." And then it's like, "Past Allen thought that these might be some good things to consider." And then it's a larger list I wouldn't work out of because it has 40 things in it, but it's good nominees.

    Andrew J. Mason: That reminds me of... David Allen does this bit where he talks about widgets to crank. You have a preselected or buffet of items that you can do when you're in a certain context or feel a certain way. I love that you precede that with these perspectives that lead into saying, "Okay, once you're done, the stuff that really needs to be done, here's this menu of items that you can choose from."

    Allen Pike: Yeah. And the thing about widgets ,and getting it set up so that you can just "dumbly" do the tasks is something that I figured out how to relearn, because no one wants to spend more time than is... You don't want to accessibly be grooming your backlog all the time and tweaking the exact wording of things.

    Allen Pike: But I recently got a little bit to a laissez-faire about letting the naming of the issues be things like "fix the fan". And it's like, "Fix is a pretty vague verb, Allen. What exactly do you mean by fix?" And that sat there for quite a while. Until it's like, "Okay, Google fan parts." And then that happened.

    Allen Pike: And then it's like, "Well, why don't I just do that right now?" And I do it, and then now I'm on the path to actually getting it. But then, making sure that it gets named in a way that dumb me can do it instead of high-minded having coffee and reviewing my task list now.

    Andrew J. Mason: Let's say somebody has their system set up, at least preliminarily. And what advice or tactics do you have for somebody who's just getting things going, and you're like, "Hey, have you considered this?" Because a lot of us do tend toward the urgency, the due dates. And then you open up OmniFocus and you're confronted with a sea of red.

    Allen Pike: Yeah. The "due bombs". Yeah, there's a few things that I tend to suggest because I'm often encouraging people. I don't mass say every human being needs OmniFocus. I often actually encourage someone to learn a bit about the relationship they have with their work, and what work they want to be doing, and how to prioritize it by working in a simpler system.

    Allen Pike: Whether it's even just like the default Apple reminders, note, or something, or even paper so that you could get a little bit... You're not new to task management. And then, also using like the "pro" task management tool at the same time. But once you are getting into something like OmniFocus, then making sure that you are trying to at least have meaningful due dates if there is a due date.

    Allen Pike: And then if it doesn't have a meaningful due date, but you do really want to get it done soon, then try to come up with some system of either flagging them, or projects, or tags where they get done soon, and you can decide to do them soon, but that you don't create this like, "Okay, past me is constantly saying, 'Picking due dates for every single item.'" And then we're always a little more optimistic at that stage. So that's one good starter tip.

    Allen Pike: Another thing, even more broadly, is trying to keep it pretty simple. OmniFocus has lots of features that you can dig into as you go. But starting with just the basics of, "Okay, I'm going to capture stuff in the inbox. And then I'm going to clean them up by putting them into projects without even needing projects within projects or a lot of sub folders."

    Allen Pike: But 5 to 10 projects, you put this stuff in the projects, and then you have some system, whether you flag items or you make a tag and call it "today" or whatever you decided where you're going to work on today, and then try to get a system rolling with that. Where you are getting things done and you're keeping track of stuff without necessarily immediately being like, "I'm going to create 100 custom perspectives," is going to feed me exactly...

    Allen Pike: I have this Rube Goldberg conveyor belts of tasks coming in and out, and hiding and showing, and stuff. Because there's a certain amount of maintenance for any given thing, and there's a vast universe of things that you can try. And then some of them are really, really worth it. But that's dependent on your workflow.

    Allen Pike: You're almost designing a thing based on your psychology to exploit/feed your own psychological strengths and weaknesses. And that's something that you have to do iteratively and not just sit down for design 100 custom perspectives at first. There's a whole bunch of little flags, and options, and things you can do. And you can play with them, but try to keep it pretty simple at first would be my first.

    Andrew J. Mason: Okay. So keep it simple, but make it in a way that makes sense for you?

    Allen Pike: Yeah. And the way you configure it is then molding how you... You're hopefully molding your future behavior. But also, you hopefully have the introspection that you're an expert in yourself. And so, the things that make sense for different people, like I'm saying don't use due dates... And I'm pretty sure Mike Hurley is an extreme OmniFocus user and he lives out of it. And at least, at one point, he was talking about how he may not always use OmniFocus, but another tool like OmniFocus.

    Allen Pike: But he was talking all about how he plans out for the week of the due dates of every single thing he was going to do that week, and everything has a date. I was just like, "That just wouldn't work for me, or at least not today me." But that's cool, too. And so every single advice somebody has about, other than probably to start simple, we just filtered through. Like, "What are the things you're good at in productivity? And what are your weaknesses?" The customizable tool means you can adapt it so that it suits what you're good at and what you're bad at.

    Andrew J. Mason: We mentioned just knowing yourself, and the way that your life works, and being able to see certain patterns that show up that you can recognize. Do you do any of the scripting or the Omni automation stuff in order to speed up that process for yourself? How does that work for you?

    Allen Pike: I used to do a lot of scripting and automation. I was a programmer by background. And so the way that our minds work is, "There's a problem and I want to solve that problem, and the software doesn't solve it for me on its own." And then it's like, "I'm going to write some software that will solve this problem."

    Allen Pike: And over the years, I've become a little bit more shy to it in terms of having a bad experience where I write something as a script, not specific to Omni apps, but just in general. That I'll write a script, and then I'm humming along, and that script is for my workflow. And then the script breaks because an operating system changes. One time was like I renamed my... Or I got a new computer and then the computer had a... the name had a space in it.

    Allen Pike: And then one of my scripts couldn't deal with the space in the computer name. And then I was like, "Oh, I really should fix that script." But in the meantime, I don't. And then problems accumulate or whatever. And so I have developed a philosophy specifically around my workflow of trying to make it not fragile. And so trying to make it so that it's hard for it to break and that the passage of time is unlikely to make it. So suddenly I end up in one of these "due bombs", or something like that.

    Allen Pike: And so I'm a little more cautious about scripting and that kind of stuff than I think most programmers are, but I think I would encourage people. The reason why I still think it's something worth investing in, I always at least keep on my radar of things to consider, is that it really fits into the philosophy of, "Can you do a small amount of work now to have a big impact over the long-term?" So I think it's fundamentally a force for good, but I just maybe have been burned a couple of times by dumb scripts that I wrote and then broke my own future self.

    Allen Pike: I think scripting is particularly valuable for people who have a lot of versions of the same type of task. Let's say you are somebody who works on commercials and you do 10 commercials a month, or something like that. And for each one, here's the 15 things that needs done. And then templates, and scripts, and things that you're doing a lot of similar work.

    Allen Pike: Whereas, the type of work that I do is varied from task to task to a point that's to a fault. Where like, "Okay, I'm doing graphic design, and then I'm coding, and then I'm reviewing interview candidates, and then I'm doing accounting." And then every five minutes, I feel like I'm in a totally different place. I rarely have tasks or projects that are similar to one another. So I feel like my scripting, it's a little bit harder to find big wins when the tasks are really varied like that.

    Andrew J. Mason: That is so interesting to me because I've talked to so many people who are less versed in terms of scripting knowledge, and how to structure code, and think programmatically, and those sorts of things. And yet, here we have somebody who's probably on the forefront of scripting because the company that you run, saying, "I don't think templating is necessarily the way to go for me."

    Allen Pike: And I think a lot of it just comes about the work that I'm doing. I think if one day I ended up going back and being a solo developer, and working on lots of the same tasks across a day, I think my mind would go much more back to that, "How do I automate these things?" Also, I'm in this very privileged position where I have employees who can do things. And so it's like, "Oh, we need this report."

    Allen Pike: It's more likely that our operations manager or our producer is going to create the report than I created the same report every week, or something like that. I always have to try to be a little careful when I talk about advice about how I do my work. And I try not to use my team as minions, but there is a bit of that. That can happen, too. When there's a repetitive task, it's like less likely that the manager is doing that task than the team members, for better or for worse.

    Andrew J. Mason: But it does make sense. Every single problem in that space, a lot of them are different. And so should be treated with equal attention that warrants that. So that makes sense to me. I'm curious though, are there any speed bumps or roadblocks that you've run into that you think might be instructional for people?

    Allen Pike: Yeah. As the team grows, one thing, we're hiring smart people, if we're doing our job right. Which I think we are. So we're hiring smart people, and they're learning, and we're training people. And people are getting not just smarter, but wiser as they learn more about software development.

    Allen Pike: And so, over the years, and especially in the last couple of years, the rate and frequency that really good ideas come up has been going up and up where people have just great suggestions. You're having a one on one, and somebody is like, "Oh, why don't we do this?" Or, "This would be a good idea. We should have documentation for that, or we should do this thing."

    Allen Pike: And more and more, I'm like, "Yeah, that is. We should do that." And so adding things to my OmniFocus, adding things to in my inbox of things that I should do. And then before I started to become wise to this, it would be such a good idea, I would out of my OmniFocus and then tag it with "today". I'm like, "I'm going to do that today because that's such a good idea."

    Allen Pike: But the more smart people you have, the more good ideas you have. And then pretty soon we're producing more than one full day worth of good ideas of stuff to do per day of work, let alone the work that we're supposed to be doing that actually makes money, as opposed to all the meta ways to improve the business.

    Allen Pike: And so, that's a great problem to have, but that's been the recent thing I struggle with across the team, is then an idea comes into me and the default is like, "Hey, person with the most..." As a manager, I have the most context across the whole company. "What about this idea?"

    Allen Pike: And then, for me, then learning how to, A, sometimes in the moment set expectations, like reasonable expectations. Like, "Yeah, that's a good idea. Maybe we'll have to think about it. Let's come back to that because it's not really that high impact compared to some of the other ideas that we're working on." Or, B, "Put it in my inbox."

    Allen Pike: But then when I'm reviewing stuff, have the discipline to not say, "I'm going to work on this right now." Because using some of those things, talking about, "Is it important, or is it just urgent, or is it just interesting, or whatever," and using different reviews and stuff like that, and having different approaches to come to terms with my backlog of stuff that...

    Allen Pike: Unless something changes, which I guess life will always change, but for the time being, my backlog of good ideas of stuff that we should eventually do is going to continue to grow faster than the list of things that we're doing, and how to be okay with that. And then still use that as an asset so that we're doing the best things.

    Allen Pike: And one of the ideas that you'll read in management and leadership books is trying to do the high leverage tasks. Like the ones where if I put in two hours into this, then 20 or 200 hours of good will come out it, by either future me or other people on the team. Instead of the thing that's mechanical, "If I spend two hours, then it will be like two hours better," if that makes sense.

    Andrew J. Mason: I so appreciate the classiness with which you approached that. Because I haven't myself gotten to a place where somebody comes up to me and says, "Hey, here's a great idea," and it is a great idea. But I know, just in the back of my mind, "This is not going to happen." And for me to look at them just straight in the face and be like, "That's an amazing idea. We're never going to do that."

    Allen Pike: I'm Canadian. I can't just get just say that point blank. And often they're good ideas, right?

    Andrew J. Mason: 100%. They are. And I actually love the idea of capturing it into the inbox to use it as something to marinate on the idea itself and just email it back to yourself in the future, use the deferred date and just say, "Okay, is this something I really am interested in implementing?"

    Allen Pike: Yeah. And one thing that's really powerful with any time you're trying to go through a set of things and figure out, "What are the things that matter," are looking at them all together. And so sometimes it can be like, "Here's a good way..." Like someone has an idea of how to increase revenue or whatever our goals are for the app, increase retention or whatever it is, that we want.

    Allen Pike: And so, on itself as a inbox item, it might look like a great idea. And it might sound like a great idea in the meeting, but then when you put it in the list of my 23 things that we were looking at ways to increase retention, it was like, "There's no way this is top 10," once you see it in the context of other stuff like it. So that's another way you can use it to find a...

    Allen Pike: And then you can go into like, "Wow, that seems really great. I'm not sure when it will be in our top five biggest ways to solve that problem. But I totally agree with you. That if we put in that time, we would get more than that time amount of benefit out of it. So let's put it on the list."

    Andrew J. Mason: Allen, something I really have grown to appreciate over the course of our conversation is this idea that you not only utilize OmniFocus, but there seems to be a really logical, just helpful thinking approach that you use when coming in contact with the system. Do you have any, and even outside of Omni, but just any overall or general suggestions for how to help people think in that logical way that helps them produce, leverage the best results? Even in the course of this episode, that statement about two hours of investment being 200 hours worth of a result as a potential factor in decision making for how you do stuff, do you have anything that just falls along that line? Even a book, or talk, or anything like that?

    Allen Pike: Yeah. I've been trying in the last six months when you're talking about things have changed to be reading more, have more frequent reading, and a wider variety of books, as opposed to just over, over my go to's of the things that I enjoy, like reading more and more things about design and things like that. And so, I broadened out a little bit into books that I would have previously been pretty skeptical of, like businessy books and things like that.

    Allen Pike: So for the idea of this high leverage task, which it might be... So the most famous, you're talking about the show about OmniFocus. The Getting Things Done book, obviously, is the most famous, stereotypical, "Okay. You're going to read only one book about how do you maybe get value out of OmniFocus than the getting things done book is going to be your default."

    Allen Pike: And probably, most people who care enough about OmniFocus to be like, "I want to read some books to be more effective at getting my work done," would have read that. But the one I read recently where that idea of high leverage came to me is called High Output Management. And it was written by a guy who had run Intel for many years. It's probably about 20-years-old. So it has some, what I would now consider, old fashioned ideas. And I don't agree with everything in the book.

    Andrew J. Mason: Like synergy.

    Allen Pike: Yeah. Optimizing synergy and things like... The way that he talks about people, it doesn't really align with my philosophy in terms of just how do you... He literally says, "How do you exploit people's strengths, and your earlier employees strengths?" It's like, "You're literally just talking about exploiting your employees." Just like, "You said the quiet part out loud, man. You could at least pretend that you don't see them as they're changeable cogs."

    Allen Pike: And obviously their section's talking about how valuable talent is in public. So not to universally say, "Do everything in this book," but there's some really good ideas if you're in a leadership position and you're trying to figure out, "There's so much stuff I could be doing. How do I do the stuff that makes the most impact on my team and my organization?" Then that was one I read recently that had some good ideas that I've been working and picking the good ones out of that.

    Andrew J. Mason: Very cool. This has been an awesome interview. Thank you so much for your time. I do want to ask one more question, just to throw out the net catch all. Do you have any final words of wisdom? Or, "If I could get the whole world to know this about OmniFocus, or the way to get people engaged in a proper way, or something that I think would be the most helpful," what would that be for you?

    Allen Pike: I think that the things that I have the deepest emotional connection to, in this game of OmniFocus and getting work done, would be the two ones that we talked about. Like avoiding due bombs and fake urgency. And the flip of that, which is finding systems that let you spend time on what you've deemed important.

    Allen Pike: And that's not a novel thing. Most things to talk about productivity and how you want to organize your life will at least touch on this idea of the important things that are not urgent versus urgent things that are not important. But I think that's something that is worth everybody continually reminding ourselves about.

    Allen Pike: And also, not just doing the, "Yeah. Yeah, I know about that. But things are urgent and I get sucked into interruptions, and there's emails and I need to do the emails." But thinking about what systems do you have about how you pick what you're going to work on, and when you're going to work on things, and are those systems helping you spend time on the things that are important?

    Allen Pike: In that, in a year, will they matter, basically? And then continually trying to refine them so that you're still doing that. Because it's easy to say, "Hey, I know I have these goals," and then let it slide.

    Andrew J. Mason: Allen, I know that people are going to love this episode because it's just very practical. And I just appreciate the opening up your system, just that we can see the inner workings of everything that's happening here. Do you have a way that people can keep in touch with you if they want to continue that conversation?

    Allen Pike: Yeah, for sure. I write once a month on, my creatively named website. Allen, A-L-L-E-N, Pike. And I tweet, for better or for worse. Sometimes I maybe regret that being a common way that I share stuff in the world, but other times it brings delight. So people on Twitter, you can check me out @apike.

    Andrew J. Mason: Perfect. Thanks, Allen.

    Allen Pike: Thank you.

    Andrew J. Mason: Thank all of you, too, for listening and being a part of this episode. We're so grateful to be able to share the story of how people get things done with Omni software and products. I just am so grateful to get to share this time with you guys. If you find this episode helpful and want to help us out, absolutely leave a review or rating on iTunes. If you want to keep up with us and what we're up to check out the Omni Group at or head to @theomnishow on Twitter.