032: The Quest for Simplicity



Justin got out of his normal routine, and now he’s evaluating just how complex his own productivity systems are for what he really needs them to do. It’s a journey of simplicity, an simplicity is hard.


Make Time Book


00:00 Hello and welcome to Process, a podcast by Effective Remote Work. My name is Justin DiRose and today we’re talking about the quest for simplicity. Before we begin, be sure to support our podcast and get access to member exclusive bonus content by joining our Patreon campaign at effectiveremotework.com/patreon.

00:19 This last weekend marked the end of our annual company meetup where everyone who works for the company from all over the world gathers together in one single place to socialize and build cohesiveness as a team. What often comes with this is removing ourselves from our normal environments. We’re not sitting at our desk, we’re not working remotely. We’re all together in the same place in a usually a brand new place for most of us. And as this time continued on for me over the course of the week, I began to realize a few things about my life, one in particular about productivity, and that productivity is often super complex.

00:59 What I mean by that is we generally have these huge systems to help us do these things that are actually fairly simple in nature. So for example, sending an email becomes, well, I’ve got to move it over to OmniFocus to create a task out of it and try to batch those up – and while that does make us more efficient at doing it longterm, sometimes the whole process of getting the emails in there and having to process them later and make sure they’re all categorized correctly so that when I’m ready to batch my emails at another point in time that I can do that effectively. Now, that’s not maybe the best example I guess of complexity in a productivity system, but we do have all of these systems in place that help us manage our notes, and articles we want to read, and things that we’ve want to remember, and ideas, and tasks, and communications, and all of that.

01:56 And when you put it all together, it can be really complex to handle it. I know for me, when I try to solve problems in these systems, I tend to make a mountain out of a molehill and that usually leads me to falling off the wagon quite often with my systems. I make them too complex. I make them too in depth. I make them too challenging to work with because I haven’t fully taken the time to dive in and simplify them. Now, I’m part way through the book Make Time by Jake Knapp and John Zeratsky. And the thing that stands out to me about their set of tools that they outlined in the book is the simplicity of them. Now, granted looking at it on the surface, none of it is groundbreaking or complex, but when you combine all these small tactics and tools together, they become a powerful set of simple ideas that can help us move forward to do the things that we’re actually interested in doing in our lives.

02:50 I also know that many of us productivity people are tinkerers or hackers. We like to make stuff. We like to roll our own things. We like to make our own systems and stuff and frankly that’s how productivity should be. No system that somebody else makes will be perfect for us as individuals. But that also means that when we’re making our own systems that we need to go through a journey of discovery to get there. And that often means making a lot of mistakes or blowing things up and starting over, making things too complex that we don’t even want to touch them. And when we think about productivity systems in that regard, we have to remember that building them as a creative endeavor and the best creative things are simple. Think about it. Coldplay is largely successful because of their simple but catchy melodies. Jony Ive is as a successful designer because of the simplicity of his designs. It might be easy to think that, Oh, simplicity is very easy to attain, but in fact it’s actually very difficult and it requires a lot of experimentation, exploration, learning, and ultimately refinement. It takes a lot of time to whittle out what’s on unessential, to bring a system or a creation to be what it’s essentially to be – the most simple but beautiful iteration that it is.

04:19 David Allen talks about how our system should be as simple as they can be, but no simpler and the opposite of that is true. They should be as complex as they need to be, but no more complex. But to hit that sweet spot takes constant refinement. It takes a lot of time. It takes a lot of refactoring, if you will, which is a programming term, which means to make improvements to code. On the broader picture of productivity and systems and stuff. I think one area that burns me out in productivity is this mindset of always striving for more. I personally am, I’m done driving forward to goals and ideals. I don’t want to do that anymore. It’s just a bunch of shoulds. Other people saying, Hey, you should do this. You should do this, you should do this, you should do this. You should have your system this way. You should focus on habits. You should focus on goals. You should focus on the longterm. You should focus on the short term. You should pick three most important tasks for the day.

05:27 These are a lot of tools, but there’s so many people out there to just push on and say like, Hey, this is the way you have to do things, or this is the way you should do things. This is the right way to do things, but in reality, productivity and building a system, a simple system is a journey of self discovery. I do ultimately want to invest in what matters to me, my relationships, my family, my learning, my personal growth, but I don’t want it to be mechanical, and productivity frankly can sometimes be so mechanical, but these things that matter to me in life are very organic and sometimes you can’t account for them. Sometimes you can’t build time in your schedule enough for them. Sometimes these organic things come up in life that you want to explore, but you can’t structure it. You can’t just say, I’m going to put this thing into a project and I’m just going to figure it out all up front or try to figure it out as it go and then somehow structure it so you can explore it. There’s a little bit that can happen in that regard. Don’t get me wrong, but for me, I’m so done personally just trying to structure stuff when in reality I am in search of a productivity system that helps me feel restful, one that helps me stay focused on what matters to me every day. One that helps me to be flexible enough to explore and create and one that helps me to reflect, learn, and ultimately grow.

07:13 Yes, Getting Things Done can help me with this. Yes, the bullet journal can help me with this. Yes, a lot of the tools that I have in my tool belt already for productivity can help me with this and there’s nothing wrong with any of those things. What I’m ultimately talking about here though is adjusting a mindset. That productivity is not about achievement, that productivity is about being on point. It’s about being human. It’s about being people, taking care of other people, taking care of ourselves, learning and growing and yeah, being effective at our work, but also being effective at our lives. Being effective at our relationships, at our family. It’s a tough thing to go down this path because it takes so much time and investment to do it and to do it well. But when it comes down to it, when I tried to blow things up and make them too complex, I have a really hard time sticking with it. I found this out by trying to bring everything back into OmniFocus. I love OmniFocus. It’s a fantastic tool, but when I try to use it to put all of my projects and stuff in it, I ultimately feel constrained by it because it feels like too much to manage and it’s too boxed in and so I need to explore what that looks like in my workflow.

08:53 Ultimately, as I’ve been reflecting on this over the last few days, there are really five spaces of a system that I am in search of developing and making simple. First a space to collect, think on, and process raw ideas and materials. These are quotes that I read in books, ideas that I have, random stuff that comes to mind that’s not really like an actionable thing or something that I’m even going to work on right now, but I need a place to collect those so that I can come back to them later and integrate them into my system where they belong. Second, I need a space to connect ideas.

09:39 I’ve been finding that having a notebook is really helpful for processing ideas out, but it’s not really that great for connecting thoughts that I’ve had in the past. And so this is where something like the Zettelkasten comes to mind where the whole point is to put processed information into it and thoughts that I have that are a little bit more fleshed out so that over time it can grow and become a knowledge base so to say of connected information where I can not only see connections that I’ve made previously but make new connections to thoughts and ideas that I’ve had previously and recorded in there.

10:19 Third, a space to hash out projects and to work on them. Well, frankly, I have a hard time having my projects and my single action lists in the same place because to me they’re completely different things. Taking out the trash on a Thursday night is not the same as me finishing developing a plugin for work. They’re two completely different things in my head and so I’ve got to figure that out. So that also means that number four is I need a space to keep track of essential tasks that aren’t projects. And then lastly, I’m looking for a space to view and manage longer timescales. I’ve been using Notion for this right now, but I want a system that can last me the rest of my life, one where even generations to follow can discover my meanderings and learnings to learn from themselves. And maybe a tool like Notion might not be around that long.

11:18 Evernote might not be around that long. Heck, I suppose even text files might not be around that long, but I guess we’ll have to see. We don’t really know yet. At least they’ve been around this far. Ultimately what I’m saying is that I might be a little bit idealistic here and what I’m looking for, but I really just want a simple system that can help me be more effective at exploring my own life and contemplating what I’m finding and what I’m learning. So as I mentioned, Zettelkasten for an idea space to connect ideas. Maybe I’ll use paper to process ideas and maybe I’ll use Evernote or Discourse or text files to handle some of these other things. Maybe I’ll continue using Notion. May be I’ll try to figure out how to do stuff on paper better. I don’t really know. Maybe I’ll keep it all in OmniFocus still.

12:08 These are all just musings that I’m having right now because I really haven’t made decisions on what this looks like, but what I do know that for myself as I, I want to commit to a journey of life that’s full of exploration, full of learning. To be able to integrate that knowledge, to be able to share that with my kids, to be able to share that with the people that are around me, to be able to be a benefit to them. That’s ultimately what’s important to me. I’m going to explore things that are interesting to me. I want to explore the world around me and I want to engage this creative side of myself a little bit more. Cause when I systematize things and I try to stay too rigid to that, I feel like it limits my creativity. Other people might not have that experience, but for me, having a loose system that’s more of a rhythm than a routine really helps me out.

13:07 I love new experiences and sometimes getting out of the norm is one of the best things that you can do to solve problems. To look at the world and in a fresh light or even have fresh eyes on the very same things that you look at every single day. It’s ultimately a journey to build a system like this and like I said, I might be a little too idealistic to get to where I want to go, but I have an idea. I just want my tools to help me be more restful and intentional about the things that I am pursuing in life versus making me feel like I have too much to do at a given time to even feel like I can be okay. That’s really what I want. I just want to, I want everything to be okay in life where I’m not overwhelmed by the things that I’ve chosen to put on my plate. I need to be better at saying, no, I need to be better at getting cruft out of my system, but ultimately some of that is by design. The way that I’ve made it, that it’s easy to add things. It’s easy to put things in there and it’s easy for things to just sit there for ages. I’ve gotten better about this over the last few years, but ultimately the choice is mine to be able to make it as simple as I need it to be.

14:31 Well, that’s all for this time. If you want to join in on the discussion for this episode, head on over to the Effective Remote Work Community at community.effectiveremotework.com. Be sure to join our Patreon at effectiveremotework.com/patreon to get access to our exclusive members-only content. If Twitter’s your thing, you can find me at @justindirose, and the podcast and community @effectiveremote. 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.

1 Like

Some great thoughts there @justindirose, and timely for me as well. I love simple and effective thi gs, but all to often tend to (over)complicate things. Maybe that’s me, maybe a human trait.

Anyway, thanks for the episode!


Trying to have ALL your life goals and tasks in a single tool is deceptively a simple approach. At least for me.

I love a task manager for maintenance and repetitive routines: Either single action lists or routines for which we can follow templates or procedures, like packing or weekly shopping, or reviewing your financial assets. It works just fine and makes this chores simpler for me.

I can even stretch a task manager it to do a weekly review and keep a a project list (real projects are unique, complex things, not sequential routines), just beause I already use it for the above.

But I have been unsuccessful trying to manage projects, personal or professional as a series of tasks. I feel I have to do it elsewhere and then try to push it in the task manager to attain the theoretical simplicity of having all in a single place.

That doesn’t work for me. I’d rather have specific tools for specific needs than trying to have a one size fits all method for disparate things.

As an illustration: I still carry an ipod to listen to music instead of putting it in my smartphone. It allows me to focus on music, saves me phone battery, interruptions and distractions induced by my ‘one size fits all’ phone gadget.

I’ve always preferred separate HIFI devices to an integrated stereo system. I like specific apps rather than complex software…

Simplicity may be in the eye of the beholder

This is the exact point I’m trying to make in the episode – there are things that are simple, and then there are things that are on the surface simple, but really are complex.

I’m finding for myself that the case you exactly describe is true for me too. I see projects as requiring a vastly different approach than tasks, which is why I now have all my tasks in a Bullet Journal, and my projects in Notion. It’s simpler for me to work that way.

I think you’re right here.

@rosemary extensively uses OmniFocus, but the system she’s built is simple for her.
@wilsonng uses OmniFocus as a task database, and plans/works his day on paper.

While there are principles we can all apply to building our simple systems, one person’s system is not going to be simple to another because we all think and work differently. Hence why we have to go on this creative journey of discovery to build our own simple systems.


One way to simplify is to learn automation. @Rosemary and others love to use tools such as Hazel to organize their downloaded documents or IFTTT.com to create actions that act upon triggers. There’s also Siri Shortcuts, Keyboard Maestro, and Drafts to automate repetitive tasks such as creating repeating projects or commonly used workflows.

My personal favorite is to have Keyboard Maestro automatically move OmniFocus to the left side of my screen and Fantastical on the right side of my screen just by hitting a keyboard shortcut.

Learning these automation tools looks intimidating and sounds not-so-simple. Take baby steps and automate one workflow at a time. Over time, I had a small group of Keyboard Maestro macros that I routinely use. It cuts down on time and it makes my workflow feel “simple.”

I used my BuJo to simplify my daily work. It’s so much easier to look at my BuJo with my list of tasks and projects instead of wading back into OmniFocus.

One part of simplicity for me was to identify the routines I work on daily or weekly and have checklists to go through each workflow. I have a daily review checklist, weekly review checklist, a monthly review checklist, as well as other checklists. I can offload the checklists off my brain and on to paper or an outline.

Most of my work is based on routines. Identifying those routines and find ways to reduce the steps down to a minimum helps.

Keep your system as simple as it needs to be and no more.

I’ve seen my checklists and automation tools make my life feel more simple.