007: Check-In #2



Justin gives up on Scrum for OmniFocus, abandons his pursuit of a more full reference system, and gives an update on his struggles with margin.


00:00 Hello and welcome to Process. My name is Justin DiRose, owner of the Productivity Guild and today is time for check-in number two. So we’ve had one of these check in episodes already and the thing that we’re doing in these is going over my goals, experiments and some wins and improvements so that you can kind of get a feel for the things that I’m dealing with in my productivity system and on my productivity journey. And maybe you can learn something from it today. First, let’s do some quick hits. Two short little things today. I guested on the Tools They Use podcasts with Francesco D’Alessio. This was a great conversation that we had regarding OmniFocus and Notion and other tools such as Evernote and the things that I use in my workflow day to day and I just, I really enjoyed sitting down with Francesco.

00:47 He’s a really good guy. If you get a chance, go take a listen to this episode. It’s only about 30 minutes long and it’s a good little insight into some different areas of my workflow that I haven’t had a chance to touch on here yet. Additionally, Francesco invited me to share on his YouTube channel, Keep Productive about my OmniFocus setup. So I’ve got about a 25 minute screencast over there detailing the latest of my OmniFocus set up that we’ll talk about today.

01:11 Now on to goals. Okay, so at the beginning of the year I had set two goals to improve my public speaking by attending toastmasters and to start incorporating daily exercise. I’ll touch on some updates on those first and then we’ll discuss my new goals for March and April on improving public speaking with attending toastmasters. I’ll be honest, I dropped this almost within two weeks of setting out to do it because I quickly realized that I needed to focus on other things on a weekly basis, mainly launching this podcast.

01:42 So in essence, the toastmasters goal moved from going to some extra meeting in the week to just making sure that I can get this podcast out the door every single week for you guys. So that’s, that was the sacrifice there that I had to make. It’s okay because I feel like this podcast plus my screen casting is doing in effect what going to toastmasters was doing by just getting me doing more speaking and articulating my thoughts that way. Starting to incorporate daily exercise was an absolute win for me. I’ve completed it. I officially hit 90.7% of days done exercise. So that was a big deal for me because I know exercise has been something that I haven’t really consistently been able to maintain. But even just getting up and doing, you know, 10 situps or 10 pushups or a couple of planks in the morning was really helpful for me to, you know, start feeling good about exercising and just building that daily habit in.

02:36 I would have hit a full hundred percent of the days over the last couple of months, but I ended up getting sick so I ended up dropping those days. So that brought me down to 90.7 but my goal was to hit 90% and I did it. So I’m really stoked about that. Upcoming, I have two more goals that build somewhat upon the goals I had for the first part of the year. So the first one is to go for a walk every that I’m working now at this very moment in time going for a walk is not the easiest thing to do because there’s a lot of days right now where it’s waffling in around minus 10 degrees Fahrenheit outside, which means that you have wind chills that factor in. And so walking outside is not necessarily the most pleasant thing to do at that point. However, I know that as time goes on I really want to make sure that I’m building a daily walk into my routine because it helps me clear my head especially doing development work.

03:27 Additionally it helps me to get outside. I realized that being in nature is really regenerative for me and so I want to make sure that I’m doing that going forward. So that’s why I’m setting this goal for the next few months. And this will probably develop not just into walking but I may throw, especially when it gets nicer, I may throw some runs in there too. Cause I used to be able to run like a 5K length and I kind of let that go for a while so I want to build back up to getting to there and maybe even hitting the 10k mark as well. I think that’d be pretty fun. Additionally, I’m starting to work on a more full fledged course and this course is going to be focused on the note taking software Bear. So I’ve got, my main goal is to have this course semi outlined of where I want to take with it and then I’m going to take a little bit different of approach with it and, and I’ll explain it here.

04:18 So most courses, people outline them and then they script them and they record them and then they launch them all at once. Well I’m going to take a little bit different approach in the sense of I’m going to outline the course, the base ideas that I want to convey. And then what I’m going to do is I’m going to record each of those modules individually over time those modules will be available under the Pro side of the Guild. So one, we can talk about them there and if anybody has any feedback on the modules, it’s like things that they want to see in the course over time they can give it as I’m making it. And two, it gives our Pro members the ability to consume that as we go. I’ve been doing video modules on a weekly basis for the Pro side of the Guild and those have been good, but I was finding that I wanted to do something a little bit more in depth and more focused.

05:06 And so if this is the approach that I’m going to try to take going forward here is make a course by outlining it and then releasing the videos individually. And then once the course is all ready to go, I’ll package it up and then sell it individually for people who don’t necessarily want a recurring membership to view it, though you do get full access to all the courses that we’re doing on the pro side of the guild by having that Pro membership so that, that’ll be an interesting kind of quasi experiment but goal for the next couple of months. I know I probably won’t have the course entirely done in two months, but I’m definitely looking at trying to get at least partially done by the end of April.

05:40 On to experiments. Last time I had talked a little bit about how I’ve been experimenting with Scrum and Omnifocus and how I’m been really trying to figure out my reference system.

05:51 Well, both of my experiments this time are almost the exact opposite of what I was trying to do. Well, let’s get into that. My focus with OmniFocus now is trying to make task management be more like a second brain. Prior, you know, what I was trying with Scrum, I was literally trying to use OmniFocus for everything, dump it in there, try to make sure that I could remember everything that I needed, make sure that I’m trying to keep on top of all the things all the time and I realized very quickly that that was not working for me. So I dropped it. I did a little bit of research and I, I’ve been reflecting on things like Kourosh Dini’s channels of work philosophy when it comes to task management, it’s basically that you can have a limited number of like big projects that you’re working on.

06:35 And then there’s these other buckets of work that you’re doing throughout the day or throughout the week. So things like stuff you need to consider or think about, stuff that you need to communicate to people on, things that you like is the one thing that I am doing is things that I want to do for play. So things that I just want to dink around with or do for fun, that’ll get a special bucket inside of OmniFocus. Because ultimately what I was finding is OmniFocus wasn’t telling me what was most important to me. It was just telling me everything. And I know that when I do task management, I tend to know at the beginning of the day the most important things for me to do. And oftentimes OmniFocus was getting in conflict with that because I’d have 10 flagged items that I wanted to do that week or wanted to do that day.

07:20 And I wasn’t actually doing them because the important stuff was actually getting done. And so I’ve just completely scrapped that idea. And combining the channels of work philosophy from Kourosh, I basically have pared OmniFocus down to just being the things that I’m actively working on so that I can get a big picture view of, okay, well these are the projects that are in play. And so anything that’s active inside of OmniFocus for me is something that I’m actively moving toward. And anything that’s inactive is something that is, I’m, what I’m considered upcoming. And upcoming is different from some day, maybe because these are items that I have directly committed to doing, but they’re just not active yet. And so my upcoming lists, my upcoming folder is actually very sparse at the moment. There’s maybe six items in there altogether. Uh, but as we go forward and as I, as I add more to the system, that’ll build up a little bit.

08:11 But I’m trying to keep it really, really small at this point because I get overwhelmed with all the things that I want to do. And so instead I’m not keeping those someday/maybe items that are, you know, maybe six months down the road or longer inside of OmniFOcus. I’ve actually got some tags inside of Bear that I’m using to hold notes that are my quote unquote someday maybe items I’ve been finding. This is a lot healthier for me. And so then when I’m planning my day, I’m actually either using the TaskPaper App on my Mac and just noting down the six or 10 tasks that I want to do during that day or I’m using paper. And frankly my head is so much more clear now. I have a lot more clarity as to what I’m doing in this moment and I don’t have all this extra cruft that’s hanging around emotionally and mentally that’s slowing me down.

08:57 So this is something that I’m experimenting with so far. It’s been a smashing success for me. I know the challenge that I’ve had with changing systems and mindsets toward it has been, is this sustainable longterm? And so that’s something yet to be seen with this. I’ll be completely honest with you, but the way that I’m feeling about it right now, as long as I stay on top of the system and I don’t put too much into it, I think I’ll be totally fine. As I mentioned previously in the last check in episode, we talked about my reference system and I’ve pulled a 180 on this and basically said I’m not going to worry about it. So one of the things that I struggle with sometimes is keeping worrying about keeping everything in the right spot, but I’ve realized like I have reference materials that I need just about everywhere that I need to put them though my bookmarks, I have one change I have made is that I’ve started using Pinboard and so I, I have an archival account there and so my bookmarks go into Pinboard.

09:49 Anything that I want to save on the Internet goes there. And then my notes go into Bear. I’ve got a file cabinet folder that handles all of my paperless paperwork that’s sinked up through iCloud and it’s been working just fine for me. And so of course there’s the little tidbits of things like, hey, there’s this piece of paper that’s got some cool information on it and we want to save that. So where does that go? I’m still trying to figure that out a little bit and I’m probably land on something like Evernote because at this moment in time I do value having the ability to search text for those types of things. You know, OCR documents inside of them. And Bear doesn’t do that at this moment. But I, I’m experimenting and I kind of discovered something and I’ll have to check it out, but I wonder if you OCR document before you put it into Evernote if it’ll still search inside of it.

10:35 And so that’s something that I’m going to try and see so we can maybe talk about that later if you’re interested in and finding out what happens with that. But I’m also realizing that I need to be okay with having some stuff analog and some stuff digital and not having to worry about making it crossover. I’ve always been a fan of nice notebooks and writing, you know, I’m a songwriter and so I love just getting into paper and messing with that, but I’ve always wanted to have it everywhere. I want to have it in my notebook and I want to have it in my computer and you can’t get it to sync up that way. So that’s ultimately a challenge. But I am realizing I just need to back off of that and not worry about it so much and just make sure that when I’m going through my notes at the end of the day that I’m putting important stuff into the digital system so that it doesn’t get forgotten.

11:20 And if I’m just processing out ideas and things, they’re just going to stay in my notebook. If there’s something I’m going to act on actively, then sure I’ll move it into my system somewhere. Or if it’s something that I absolutely need to save for future reviewing, sure, I’ll take a picture of it and put it in something in my system. But as of right now, I need to just back off a little bit from trying to have the perfect system where paper and a digital stuff is all sinked up.

11:45 So I may have mentioned this in the past, but one of my favorite tools that I’ve grabbed out of agile results or getting results the way as the name of the book is reflecting and choosing three wins and three things that need to be improved. The way that JD Meier talks about it is doing this at the end of every week.

12:02 Well I’m, I’m not committing to do that every week, but these check and episodes I feel like are a good place to do that. And so I want to hit on my wins and improvements for the last few weeks since we did the last check in episode. Win number one: I hit my exercise goal. This is a huge deal. I mentioned previously that it’s been a little difficult for me to keep that habit and so just being able to daily get that habit in has been a big win in my book. Number two, scaling back what’s in my task manager and leveraging other parts of my system. We just talked about that in depth, but that one has been the biggest alleviator of stress for me. And number three, being intentional with margin. I mentioned a couple episodes ago that that’s been something I’ve been struggling with and trying to figure out. And frankly I feel like I’ve been getting somewhere with this and a lot of it has been due to mindset, not necessarily needing to put time in my more time in my schedule.

12:53 It’s really looking at my schedule and saying I’m totally in control of this. I realized I was thinking about my day and in my life in a reactive state basically where I had to be on all the time to respond to things and do things and you know, be this task master type deal where I’m just working and getting stuff done and pushing forward and all of that. But I realized that like, no, I’m in control of my day and so I’m backing off intentionally and I’m not worrying about it as much. And frankly not worrying about it as much as helping me to have more margin but still get more work done. It’s really quite interesting how that works. But I have to say that it’s been a big win for me.

13:31 Now, that’s not to say that margin hasn’t been without its challenges. So for my improvement, number one, I’m still trying to sort out how to make sure I’m getting what I need and my family needs. Cause there’s always a balance there that needs to be found. Making sure that you’re getting enough time with your kids, making sure that I’m getting enough time with my wife, making sure we’re having enough family time together. It’s just being intentional with what I’m putting in my calendar and intentional with what we’re doing as a family. Because the time we do have is, you know, we don’t have major blocks of free time where we can just do whatever at this point. So we just have to be intentional with it. Number two, I could get more granular with my time tracking for non essential work tasks. So things like admin work that I’m doing, billing, uh, you know, spending time catching up on the Guild.

14:22 Improvement number three, I need to make sure that I’m continuing to give appropriate space to my brain to actually think through problems and projects that I am taking on. This goes back to Chris Bailey’s idea of scatter focus in the book Hyperfocus and this is one of my favorite ideas from a productivity book that I’ve read and for those of you who don’t know, what that is is basically letting your brain relax and not focus on any one thing at any given time, but really just engaging the thoughts and basically letting your brain connect ideas, connect dots to different things. That’s what happens when we sleep often and we can be intentional to do that throughout our day.

15:02 And I’ve been finding that if I can just give myself even a half an hour to sit down with my notebook in front of me without an agenda and just start writing down the things that are coming to mind, I realize that I’m connecting a lot of different ideas and actually getting some really good ones through that process and I don’t have to work for it at all, which is the crazy, amazing thing, but I’ve been realizing that I need to spend more time doing that because it gives me space to be able to actually think through and see the path forward for myself.

15:32 That’s all for this time. If you want to join in on the discussion for this episode or if you want to connect with others who are in the process of becoming better on their productivity journey, head on over to the Productivity Guild at productivityguild.com. Or if you want to support this podcast and get access to video modules, productivity courses, and more, consider signing up for a Pro membership at the Productivity Guild for just $10 a month. Lastly, if you like this show, rate us on iTunes or recommend us on Overcast. My name is Justin DiRose, and join me next time on Process.


Here’s the YouTube video featuring Justin’s current OF3 workflow…

Most of our workflows for our task manager stays the same. Every once in a while (perhaps once a quarter or whenever major changes happen in your lives), it’s a good idea to adjust our projects/checklists/tasks setup to reflect the new situation.

That’s the awesome part about just starting something. We won’t know how something fits into our lives until we actually try it. Then we can pivot to a slightly different direction and get to a goal that way. Oftentimes there is more than one path to take to reach a destination.

Oh man, I’m such a lazy person. I just recently got back into exercise after getting a scare. I had a family emergency with someone close to me heading to the emergency room. Then I attended two funerals for a couple of old high school classmates. I also did my annual physical and saw my blood pressure shoot up into the danger zone. So I guess I’ll be joining Justin in watching my health much more carefully. One of the things I’ve needed to do is to get the tools necessary to make exercising easier to perform and to track. I’ve never been a watch-wearing person but I think I’ll make an exception and look forward to getting an Apple Watch. I’ve already downloaded the Streaks Workout app as well as catch up on what other people are doing with their Apple Watches. Getting the tools to make a goal easier to do is helpful.

Looking forward to seeing the Guild’s new courses! if anyone else has any ideas of something that you’d like to explore, the Guild is all ears!

Better to have tried than to never have tried at all. OmniFocus is flexible but sometimes we need a different tool to get what we want. I love OmniFocus but I also use Trello’s card view for certain projects. I also use the Agenda app to keep track of project progress. I tried to keep track of my projects’ progress in OmniFocus but I realized I needed a complementary tool for that. I can keep track of task completions but I also needed a progress report. I use Agenda to take notes and record any victories and obstacles that may have occurred during the project. I suspect I could use Bear as a note taker and keep of track of my projects’ progress that way.

I’ve always had a tough time juggling my admin tasks (routine or single one-off tasks) and my Big Rock projects. I attempted to do that with this post:

TL;DR: I set all of my projects to On Hold status. Then I turn on only a small handful of projects by setting the project status to Active. When I visit my Big Rocks perspective, I see my “active” channels or current Big Rock (active) projects.

If anybody has a different way of creating channels of work ala Kourosh Dini, I’d love to explore it with you.

+1 on this idea! I thought I was being cool and wanted everything in digital. But I can’t neglect all those years of school where I relied on pen and paper a lot. Analog does have its place in our world. It’s just a matter of figuring out the balance.

Agile Results will have to be something that can be explored in the Guild! :wink:

Yep, It can’t be all about work. I think I’m still trying to struggle with this myself. How about you guys?

Thanks for a great podcast episode! :heart:


Did you get the Apple Watch in the end? I too recently had a scare, and have tried to kick start my daily exercise habit, whether that’s cardio, resistance, or yoga… Having people to compete against also helped drive me to work out harder than I would ordinarily have done… That had a huge impact on motivation, which is most of the battle really…


Yes, I did buy one. I didn’t care about the Apple Watch until the HealthKit ecosystem started developing.

My own health scare came about earlier this year and I was certainly motivated to trying out the Apple Watch to track my habits.

Being able to capture and measure my progress has been a great way to keep me on my game. I have a draft in Ulysses exploring my personal thoughts about the Apple Watch. I’ll have to polish it soon enough! :wink:

I’m a lousy record keeper and having the Apple Watch and iPhone to record things like my blood pressure, heart rate, weight, and other miscellaneous health data has been helpful.

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@wilsonng how have things been going (esp. concerning health) with the Apple Watch one year down the track? I find the gamification of challenges does help me get out more, the standing goals are good too. I have AutoSleep installed, which has definitely given me good insights in to sleeping, I‘m getting enough Z‘s now. Diet is next on The list, probably my habit focus for June.

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The Apple Watch has made checking my measurable easier. Yes, I’m still trying to maintain consistent streaks for the 3 Apple Activity Rings. I don’t always hit them but I’m more confident that I’m more consistent with achieving them now.

Having the timer on my watch helps with Pomodoros has been a blessing. I don’t have to reach for my iPhone all the time.

I do check my Autosleep statistics but remind myself that I shouldn’t get too anxious if I don’t get enough sleep the night before. I’ll find a way to catch up or at least learn that I can’t push myself as hard today.

Most notifications are turned off so I don’t get the constant distraction from emails and messages.

I installed the Streak app on my Apple Watch to make it easier to check off certain habits that I’ve been trying to establish. The trick is to not have too many habits. Focus on a few first to get a steady rhythm and add 1 more in the next month. Or change out one habit for another habit.

The main thing I’ve learned about my Apple Watch is to have just enough faces for myself.

I created one face for sleeping. The only widgets I have on that screen is the time, auto sleep, and auto wake.

I have an exercise face which includes Carrot Fit, my heart rate, and activity rings and a timer to countdown a 30 minute workout.

Another face is for weather with the temperature, weather, and UV index. I use this mostly for outdoor exercise. I check the weather at the moment and the next couple of hours to see if I can do an outdoor run or lawn mowing when it’s not too sunny or the summer rain isn’t pouring like crazy.

I have a “timer” face with the stopwatch, timer, alarm, and next appointment widgets. I use this at work a lot. I might try a new task and am not sure how long it would take. I start the stopwatch app and start the new task. I can record how long it takes to do a new task. I record it in my BuJo and then track it again when I need to do the task. This helps me find an estimated duration that I can enter into OmniFocus. I do try to gamify this by treating to beat my previous personal best by 1-5 minutes. The better I get at a task, the faster I can finish it.

I have the timer app to countdown Pomodoros of 15-30 minutes for a lot of my routine tasks. I don’t want to linger. I might also countdown my time spent my customer inboxes for Facebook, Instagram, and email. I try to spend a 30 minute time block clearing out customer requests in those inboxes before saying I’ve had enough and need to work on something. If I don’t do this, I’ll never get the rest of my work done and spend too much time in Facebook, Instagram, and email.

My other “work” face includes the Due app to nag me when a Due app item pops up. This same face holds my Streaks app to make it easier to mark a streak task as complete. I have the Drafts app here to easily do voice capture and transcribe something into the Drafts app.

Overall, I try to keep as few faces as needed and organize them by activity…

  • Exercise
  • Sleep
  • Work
  • Outside weather
  • Calendar (timer, stopwatch, alarm, appointments)

Keeping the Apple Watch as simple as possible and avoiding any unnecessary notifications has been a key element in my enjoyment of my Apple Watch. All the newsfeed apps, emails, sports scores are disabled on my watch. I do have a weather app that dings me of major weather changes like flooding, nearby fires but that’s about it. My calendar appointments are enabled to notify me on my Apple Watch as well. The Due app’s notifications have helped me keep my streaks alive.

Have you found different ways that the Apple Watch can fit in your life? It would be interesting to see if there are any changes to your life…


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Thanks for the reply, very interesting. I do appreciate my little wrist computer (S4 cellular) to remind me to get up every hour, track workouts, sleep, timers etc. And the weather - important as a nice-weather cyclist kinda guy :slight_smile:

I‘ve played around trying to use different watch faces, but I still find it a „hassle“ to have to swap faces, so I keep the necessary stuff on the Infographic modular, and search for everything else.

Has the watch changed my life for the better? I would argue yes. The standing up as mentioned before, knowing the UV on sunny days (I‘m very fair skinned), taking the odd phone call…listening to podcasts/music while out and about without my phone, wouldn‘t want to miss it anymore. Has a firm place as a „main device“ in my upgrade plan alongside my iPhone and iPad - looking to upgrade one of them every year, making me use them for three years each then replacing.

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