In this video, Todd Brown and Robert Peake talk about when it might be time to give your system a good clear-out — or even jump ship to a new tool altogether.

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00:06 Robert Peake: So welcome again, everyone, to another Change Your Game with GTD Podcast. My name’s Robert Peake, and I’m here, as always, with Todd Brown.

00:14 Todd Brown: Hello Robert, hello everyone.

00:16 RP: Hey Todd. So as we were talking just a few minutes before clicking the Go Live button here, we were thinking about a question, actually, from one of Todd’s clients, “When do you know it’s time for a bit of a rethink or retooling of your GTD system?” And again, to remind you, this podcast series, we will be talking about all things GTD. The intention of that is to help you get a little more done with a little less stress, a little more elegantly. So if that sounds interesting, if you’ve had any kind of sense that maybe your system’s getting a bit bogged down, or it’s time for a fresh think, stay tuned, that’s what we’re gonna be talking about now.

01:00 RP: So Todd, you mentioned that you’re actually kind of feeling like you’re nearing that time yourself. What are some of the signs or symptoms that it may be time for more than just a minor tweak, but actually a more significant change to your use of GTD systems?

01:24 TB: Yeah, I think it’s interesting you describe me as being near it. I’m hip-deep in it at the moment.

01:31 RP: Okay, I gotcha. [laughter]

01:32 TB: I’m halfway… I describe it as sort of halfway through the transition. And as I think about why I decided to make the transition, it really… There was both a push and a pull element. So the push element was that I was kind of realising that my system was… That it was dusty in places. That it really didn’t feel like it was serving me very well. I could feel that there was resistance in me for engaging with certain elements of it and that’s always a pretty clear indication to me that change is required. Now, sometimes the change could be within the framework of the tool and the system that you have already, sometimes it just needs a bit of a refresher or a tweak, but this is where the pull element comes in.

02:20 TB: So I was doing a coaching not long ago, with someone who was using a tool which I have quite a lot of experience with, because I’ve coached it quite a bit, and I know it’s something that you use, which is a tool that runs on the Apple platforms called OmniFocus. My system has been, up until now and for many, many, many years, it’s been in Outlook for Windows, but as I was doing this coaching and I was going through the process of helping this guy who had no experience at all using OmniFocus, so he’s brand new to it. And as I was going through it with him, of course, I was then looking at it with new eyes and I was thinking, actually, on the one hand, my system doesn’t feel like it’s serving me particularly well. On the other hand, I’m seeing this… OmniFocus through new eyes, in a sense. And so I decided that it would be worth giving it a go, and so I’ve been at this now for the better part of two weeks.

03:16 TB: As I say, I’m kind of hip-deep in it. And it’s been really interesting, it’s been kind of… I’ve recognised both limitations in my old system and the way that it was structured, but also limitations in the way I was thinking about my system, so it’s… And my best practice. So it’s been a… So far, I’m feeling very positive about it. It is a lot of work, but I’m feeling very positive about it. It’s helped me to get to a much better place and to feel like I’ve got a system that supports me better.

03:52 RP: That’s great, yeah. So just to be clear, transitioning from PC Outlook to OmniFocus. And what are you doing at the moment, in terms of you mentioned it’s been a couple weeks and you feel like you’re halfway. What are the mechanics of that that are working for you to make the shift while, of course, still living your life [chuckle] a la GTD?

04:15 TB: Rewiring the plane while in flight, is kind of what it feels like [chuckle] from time to time. But it’s interesting. What I started with was a… In OmniFocus, so in the new tool, I first set up all the integration that I knew needed to happen. So how is this going to integrate with email, how is it going to integrate with Calendar, how am I gonna have it plugged into all the things that I know it needs to plug into? That was kind of thing one, the basic wiring, if you will. And then there was, and there continues to be, to a certain extent, a period of time where I was using both systems in parallel.

04:57 TB: But increasingly using OmniFocus and tailing off in the use of Outlook. So as a practical example, make sure that all of the date-specific reminders that I have set up in Outlook don’t get neglected as I’m making the transition to OmniFocus. So that’s, as I say, that’s still a bit of a work in progress. The other thing that I have found fascinating, I did some really fundamental… For example, all of my list entries in Outlook were kept in Tasks, as they are for a lot of people who use Outlook. And what I did was I literally printed out all of them, so I had them all on paper, and then I went through them one by one and I said, “Look, is this something… Is this a reminder that I would want to see in my new system?” And I was astounded how much deadwood I found. Things where, two weeks ago, during weekly reviews, I’d be… I’d sort of say, “Yeah, that’s there, and it’s been there for a while”, and I wasn’t making the mindset shift that said, “You know, you’re not really getting much out of that reminder.”

06:07 TB: So I found that the volume in my system has gone down significantly, which feels, again, like my new system is just much more nimble and much more able to support me in helpful ways. So it’s not game over, and those are some early reports, but that’s been my journey so far. I’m curious, as we’re talking about it, is it something that you’ve done? In your history, have you… I know you’ve been on OmniFocus for quite a while, haven’t you? Have you used that?

06:39 RP: I have, yeah. Been on OmniFocus for a while of late but, as you know, I was CTO of the David Allen Company for a number of years and, as a result, part of my responsibilities was to try out different tools as they came out, see what they were like, see how GTD-compatible and friendly they were. So there was a period of time in my life where I was transitioning something like every six months. And the thing about a new tool is, you can kind of simulate a bit and get a feel for what the basic features are and read up on it and so forth, but you don’t really know what you’re in for until you live in it, right? ‘Til you absolutely try and live your life using this new tool. And when I say tool, I mean primarily List Manager. The complete system involves good calendar, good capture, a lot of these other components, but the fundamental element, the kind of game changer, which is keeping lists of projects and next actions in context, that was a tool that I was changing to support that part of GTD pretty frequently.

07:48 RP: And like you, I found that actually, it was a great clear out opportunity to take them, and like you, print them out. Very few of these tools had nice integration options, where you could just export and import and you’re on the new tool happily. But also, it’s a really interesting and useful exercise if you’ve been doing GTD for a while and you find that you’re maybe going numb or a bit snow blind to some of these items that actually, as you say, aren’t serving you as a continual reminder. And I certainly found that, so I would print everything out. I also found opportunities to rephrase things, things where maybe I’d been getting a little less sharp with my language to self about what the successful outcome really looked like, or what the most bite-sized, simple, next action looked like on all of those. So that transcribing process was incredibly useful, actually, as you said. Almost cathartic [chuckle] to go in and really scrutinise, is this something I want in the new system?

09:00 RP: One thing, though, I think it’s useful to warn about is Shiny New Tool Syndrome, particularly for people that are newer to GTD, still getting to grips with all of the best practices. I think there can be a tendency to assume the right… Find the right tool and all else will follow, and in my experiences with coaching lots and lots of people, actually using a tool and finding the best practices and approaches is a lot more effective in the early days than tool hopping, which is something I sometimes see, where people go, “Oh, well that wasn’t quite it, so what about this?” And, “If I only had the perfect integration and the perfect automation of this, that, the other, then it would really be great.” When, in fact, it’s actually more about, really sharpen up that project list, get the weekly review going as a habit, build out some higher horizons, etcetera, etcetera, where you get the most payoff as a fairly new practitioner. I don’t know, what do you think? What are… Are there any signs that you’re maybe getting into tool hopping or Shiny New Tool Syndrome versus recognising, yeah, it really is time for a shake up, and that could include a new tool or a new component to my whole GTD system?

10:18 TB: Yeah, yeah. I think… It’s funny, if you’d asked me this question 20 years ago when I was a big-time early adopter, if it was cool and new, I wanted it, and I’ll figure out later whether it’s at all useful or how I’m gonna integrate it into how I work. So that was 20 years ago, that was very much the case. These days, not so much. I’ve had my Outlook system for a long time, for many, many, many years, and so it’s really… It doesn’t feel to me like I’m a promiscuous organiser, or a tool hopper, if you will. It feels to me like this was a good time to be making the switch. And there’s some subtle things in it for me as well. One of the things… Again, I don’t wanna get into a huge amount of technical detail, but in the new system, what I’m using is Outlook for Mac. So I’ve got that as my calendar and my email. And OmniFocus as my list home. And what’s quite interesting about that is that, I found that because OmniFocus runs on basically all the Apple platforms, so iOS and the Mac operating system, what that means is that I can actually clarify and organise regardless of which tool I have in front of me, which is not really the case if you’re using… In my old system, it wasn’t really possible for me to process on the fly with all the devices that I have. So that’s quite interesting and that, so far, is feeling like that’s reducing some friction.

11:54 TB: I think the other thing that’s quite interesting for me is that the… There’s this kind of sense that it’s… I’m much more protective, in a way, of my attention in this new system. I guess it’s really sort of the point… Refinement of the point I made earlier. Stuff is only going in there if I’m really sure it’s gonna serve me. So I’m being more… Yeah, more ruthless about, does this really go in, or is this something that really is… It’s very likely, if it goes in, just to gather dust over time. I’m trying to be very, very careful about that.

12:32 RP: That makes sense.

12:35 TB: I’m just curious what… And again, we don’t wanna make this… In some ways, it’s an unfortunate coincidence that both you and I are using OmniFocus. This is not a tool advertisement, this podcast. And I’m sure that someone that’s been on OmniFocus for a long time, who’s making the transition to another tool, again, just because… What they’re doing is having a fundamental rethink of what’s important, how is it structured, how will I use it? I’m sure that would be equally as positive for somebody else. There’s no such thing as a perfect system, or as a completely friction-free system, those don’t exist. You can get a great system, you can get a very, very good system, but perfect is not on offer, at least in my experience. And so it’s just a matter of coming up with a system which works best for you, and again, I think that just the act of transitioning, somehow, requires the kind of thinking that we’re talking about and that you were mentioning earlier, and that, just in and of itself, is a big benefit.

13:38 RP: Yeah. No, no, I absolutely agree. I think one of the things you touched on, which is, do you have what you need with you in all the contexts and places, right? You were mentioning that not all the devices supported having the lists in front of you, and so you found yourself with dead time, dead air, in a sense. I think that’s one really good sign that, yeah, you may need a more supportive tool rather than you’re just going on to the next shiny thing. One thing for me that’s an indicator that it’s time for a shake up is, we have this idea of, are your lists attracting you into doing or are they kind of repelling you with a sense of, “Ugh, my lists.” And that’s not necessarily an indication that it’s time for a new tool, but it is definitely an indication that it’s time for a shake up, whether or not moving to another tool facilitates that shake up or not. It is, to me, one of the things I look for in terms of, “Do I really have only sharp, clear, good next actions that I care about on those action lists, or am I going in each day and scrolling through a bunch of stuff that I’ve really gone numb to, to pick off the few things that I do care about?”

14:52 RP: So to me, that’s one of the big keys. And I think people who tend to be in this for the long game and tend to reap continual benefits from GTD, not that everyone can’t, but those who really stick it have some kind of internal barometer about friction, and some kind of meta-awareness, thinking about how they work rather than just totally being at the effect of it all the time. And they care, right? We care about whether something is easy and self-evident, whether we’re able to set that up for our future selves, that we can have that experience of doing, of succeeding, of winning, of ticking things off throughout the day. We like that, we want that, and if the tool is getting in the way, or just the sheer accumulation of stuff that no longer is truly sharp and relevant is getting in the way, those, to me, are really the fundamental flashing lights that say, “Yeah, it’s time for a shake up.” And yeah, as you say, there’s no perfect tool, right? Until the cybernetic implants arrive [laughter] there’s no… It’s not the saving grace, it’s not the answer in itself, but it can be a way to facilitate a shake up, and it can be useful if there are some fundamental limitations that you notice about not having what you need when you are wherever you are.

16:21 TB: Yeah, I’m completely with you about the mobile limitation. Just to be clear, in my old system I did have mobile access to my lists, that was okay. So I had… And those of you out there who are using Outlook systems, you’re probably aware that the tasks in Outlook sync to various reminders, apps and things. So that I did have. But what wasn’t working was being able to clarify and organise on the move without my laptop, that was not so possible.

16:51 TB: But as you’re talking about it I’m just reflecting on one of the… It’s a small change but it feels like a really important change, which was that I’ve made in my contexts list in the new world. Okay, so in the old world I had a list called laptop offline and laptop online. It was for those things that can only be done if I’m connected to the internet and those things that don’t require an internet connection. And that, for a long time, felt like a helpful way to break things down. And what I’ve replaced that with in the new system is again two lists, but one is called At Keyboard. Okay? So I have a proper keyboard in front of me like on a laptop. And the other one is called At Thumbs. [chuckle] And that really spoke to me as, “Okay, well this is gonna be a small screen kind of a thing that I would be happy doing on a mobile device, on my mobile device.” So again, and without having gone through the system switch, I probably wouldn’t have come up with that in quite the same way, I wouldn’t have been motivated to go through that thinking and make that kind of change in quite the same way. So it seems to, for me anyway, it seems to have elicited both thinking that about the macro thinking about my system and how I use it, but also some micro stuff, as well.

18:17 RP: That’s very cool, and I just know in OmniFocus you can nest those contexts so that you could see… For example, at keyword, you can also see all the thumb stuff. You could do it with two thumbs, you can do at a full keyboard. And even if it doesn’t nest you can highlight both of those categories. Anything that’s just a little bit of online research or browsing can go into the thumbs. But you can see that as well as all the I’ve got to type a lengthy draft thing when you’re at the keyboard. I love it, I think that’s a really great thing for the 21st century, in particular, to divvy it out that way. That’s very cool. For me, I just… I get a little twitchy if I’m not… If I don’t have a Unix command line in front of me. And they just don’t have those on the iOS devices, so my laptop goes with me everywhere. But yes, I think increasingly, sp many people are wanting to use the mobile devices to just kick back on the iPad for a little bit but still be productive in that context. Great tip. I think that’s incredibly useful. And again, if the tool doesn’t support you getting what you need, where you are, and when you need it, maybe time to re-think the tool.

19:32 TB: Yeah, I think that’s another interesting one, that all of a sudden these devices like my iPad that I’ve had for a long time, all of a sudden it becomes a tool which can in some sort of way be used much more actively in my new system than it was in the old one. In the old one… Don’t get me wrong, it was a way… It was a place where I could get access to my lists, I could, of course, read email, look at my calendar, all that kind of stuff. But it wasn’t really a… I really literally got to the point where I was starting to call it my distraction machine. It was where I was looking at the news websites or the news apps and I was looking at everything but productive stuff. And all of a sudden now because the software also runs on the iPad and synchronises of course up in the cloud with everything else. If I’m at my iPad I have all of the functionality that I would have on the other platforms and that’s, again, very cool. It means that the… Sometimes I think about the fact that one of the hazards we have or one of the risks that we have in all the technology that’s around us is the distraction is only a mouse click away or a finger swipe away. Distraction is there all the time. And this sort of reverses that for me. I have the sense that… Yeah, but productivity is also only a mouse click or a finger swipe away in this new system, and that feels like a… Like you say, as a positive change as well.

21:11 RP: Yeah. Well, you wanna have those options, right? Depending on how you’re feeling, where you’re at, how you’re doing. The little moments of potential productivity that we can snatch away when we are in a good state but we just happen to be in an airport lounge or a few minutes as another client’s running late or whatever. Those little moments aggregated together can make a big difference. So if your tool isn’t supporting you using really all of your available time as appropriate. That doesn’t mean work every hour of every second. Sometimes the most appropriate thing is, close your eyes for five minutes, take a breath, get ready for what’s next. But if you are in a resourceful state, can you use… Can you use five minutes? Can you make good use of five minutes? If not, again, you may need a bit of a shake-up in the tool. Or more probably you may need a bit of a shake-up in terms of how you’re doing lists and that may precipitate a re-look at the tool. Any burning thoughts, Todd, in terms of… I think we’re getting close to time here. In terms of either identifying or supporting a bit of a shake-up in your systems and how to make that work given as you said, it’s a little bit of a rewiring the plane-in-flight kind of situation.

22:35 TB: I think the first thing I’d consider is if you are feeling resistance to your system, to engaging with your system, try to localise that as far as you possibly can. Does that seem to be a thing about a lack of mobile connectivity? Does that seem to be a thing about… I’ve got the wrong context, I can’t… When I’m in a given state or with a given tool I can’t very quickly see the right kinds of reminders in front of me. So I’d, as a starting place, assume that your existing system, the core of your system might be okay, it’s just not maybe structured quite the right way.

23:14 TB: And then, if you come to the conclusion that, “Well yeah, but I really kind of fancy a whole new… A whole new me, a whole new GTD me”, then what the heck. You know? Start over. Start over, pick a tool that you think sounds good to you. Go back to paper for a while. Go to anything that will encourage you to do the fundamental thinking about, “Hey, what’s in here? Where are the clean edges in my system? How do I prefer to work?” Those kinds of questions. They’re obviously really important and really fundamental. And changing a system will force you to make those really. How about you? What would be your advice for the audience?

23:58 RP: Well to me the changing of a system in some ways can be a bit like an enormous weekly review, right? That’s a great framework for me for walking through the process and making sure the new system is complete and is gonna serve me in subsequent reviews. Also in the weekly review can be a really good barometer for how is the system doing in terms of serving me or not. If you come away from the weekly review going, “Wow, I got through it.” It’s a very different experience than coming away from the weekly review going, “The system has got me, this is great. It’s on it, it’s working. I’m ready to go for the coming week.” So to me that’s a potentially big indicator of whether or not it may be time for a shake up, is how are you doing with the weekly reviews, do you get that sense of, “Yes, the system is helping me.” Or is it more of a, feel like you’re pushing a rock uphill kind of a thing.


24:53 RP: So those are things, I think, to look out for, for sure. And to help you make the switch. I just mentioned, as always, we do this for a living. We support individuals in finding the ideal systems for them, accounting for everything that they do. So if you are… If this does peak your interest, you’re looking for your next level game, do get in touch with us about one-to-one coaching. So, again, thanks for being with us, and as always if you have thoughts, questions, concerns, anything that you’d like us to address in future sessions, we love hearing from you. So [email protected], [email protected] is the best, easiest way to get in touch with us. And until then, go be productive, scrutinise those systems, make sure they’re really working optimally for you. And from me, from Todd, we’ll see you next time. Bye for now.

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