Focused - 19: Nobody Grades You on the Scaffolding

Episode Date: April 18, 2017

Every independent worker will agree that being organized is important. But should you adopt an organizational system? How can these systems help you, and are they worth the investment? Jason and David detail their own personal organization systems and discuss approaches to getting more organized, as well as tools to use to help in the process.

David Sparks and Jason Snell spent their careers working for the establishment. Then one day, they'd had enough. Now, they are independent workers, learning what it takes to succeed in the 21st century. They are free agents. Welcome back to Free Agents, a podcast about being an independent worker in a digital age. I'm David Sparks, and I'm joined by my fellow host, Mr. Jason Snell. Hi, Jason. Hello, David. How are you? Good, good.

You know, a recurring theme on our show is that for an independent worker, time is quite literally money. So what about that? How much about becoming and remaining a free agent involves time management skills? We thought for an episode it would be fun to get serious a little bit about the concepts and tools to help you stay on target. I'm just going to give a little spoiler alert here, a little warning that I think you're going to get mad at me in this episode. I've read the outline. Yeah, yeah. this episode i've read the outline um yeah yeah but i i'm i can't wait to find out about task management and staying on target what will that be like so i hope i hope you can help me help me

through help me understand this because i think i i suspect that i have a i do have a system but it's like the non-system system that's a self-built system. And I'm kind of interested to see how other people adapt other systems as well to keep this. Because we all do need to manage our time and our tasks and fulfill our tasks on our deadlines and things like that. You can't just pretend that you don't have deadlines. That doesn't work. So everybody's got a system one way or another if they're going to be successful. Yeah, and really for an independent worker,

it's super important that you take charge of this because if you can't manage your time properly, you are inevitably going to be polishing off the resume. I mean, so much of this show is about fear of having to polish off the resume. Yeah, yeah, but it's definitely true. I think you're right. I think one of the things that makes it hard for me to understand this concept a little bit is that I've always been a person who, through whatever personal means, has managed my time, but I also understand that there are a lot of people out there, if we just totally

abstract it, an employee who has a manager and the manager tells them what to do. And I can see how you could end up feeling like you don't have to have these skills, that you don't build up these skills because in the end, somebody else is going to tell you i need you to do this today i need you to do this we have this with my my son right now like his teacher and he's a seventh grader so again i think everybody should have these skills but they probably don't his teacher is trying very hard to get him to take uh charge of his own projects and know like he needs to spread out this project and do it over the course of two weeks in order to get it done instead of doing it the night before. And he's

struggling with that. He's 12. It's understandable. But I have seen that in larger organizations where there are people who, for whatever reason, have never really had to take control and responsibility for tasks in a project or just aren't very good at it and they rely on someone else. And if you're an independent worker, you cannot rely on someone else. Your client isn't going to call you up every day and say, how's it going with the project? Here's what I need you to do tomorrow. That's not going to happen. Or if they are, that means they're not going to be your client much longer. No, no. I mean, that's like an outsourcing relationship where they view you as an employee.

And that's not being an independent worker at that point in your attempt. Yeah. So just a little spoiler when I saw in the outline that you really don't have a huge system in your life. I didn't get mad as much as I was a little bit envious because I think one of the takeaways for the show right at the top is your task management system should be as complex as it needs to be, but no more complex. And, um, you as a, as an independent writer, which is a lot of the way you pay for your shoes, it's,

it's a pretty simple list. You know, I mean, like you've got your article you're writing for this publication and that publication, then you've got your own stuff you're doing for your sites. And a lot of that stuff is schedule based. So it makes it really easy. My life is madness. You know, I represent 150 or so different corporations and they all have different filing deadlines in different states, a lot of them. and some of them get into litigation where I've got deadlines at the court, I've got to get things filed. And, you know, my daughter's very involved in her school and we help. So I've got deadlines there. And then I've got things I'm doing at Max Barkey that I need to get taken care of. So suddenly, I can't just have a simple

system, I need to have a complex system. And I, you know, I realized that years ago and took the necessary steps. And that's really, I think, one of the reasons I was able to ultimately to go independent. Not only does it give me the understanding of what's expected of me, but it gave me the, I guess, the professional chops that people trusted me to come along with me. So, it was really important to me to have a good system. And when we talk about systems, I think it's worth saying that there are like systems, capital S systems, and then there are systems. Like, everybody who has to perform tasks has a system, a personal system. Now, it may be like me where it's kind of just grown up around me,

but a lot of people, they struggle to find a system that works for them. And that's when you get into the capital S systems, which is somebody wrote a book, somebody's got a piece of software that says, here's how you do this. And people take those, and sometimes they ape them, sometimes they adapt them. But in the end, I feel like the goal is you need to find a system, lowercase s, system that works for you. And if it does involve copying exactly what you read in a book about this person's productivity system, then great, or this app's way that they want you to do it, then fine. But I would imagine that in most cases people are like yeah i i i do that but i don't do this part of it and that's all about the personal adaptation because in the end

the goal of this is not it's not like exercise where you run in order to be in shape like it's not like that it's more like you do this you you you take what you can from this in order to get a result which is that you're organized. And so, in the end, you will make your system personal. The goal is not to just, I nailed it, I did everything that was in the book, what do I win? The goal is, what can I glean from the system in the book and adapt to what I do in life so that I can be productive? And that's the end result that you need to go for. And I think that that verges onto being both of us know Merlin Mann, you know, there are issues with productivity as and Merlin's talked about this a lot productivity as a as a goal, like productivity systems as a

goal where you can sort of fetishize the productivity system. And it's like, well, this week, I'm doing a new productivity system. system. And this is one of the dangers of all of these systems is you end up spending so much time on the details of the system that you don't get your work done. So that's a big threat as well when you're doing this. The goal here is to find something that you can adapt to work for you, not something that you can win at, right? at right because that you don't the end result is nothing being productive is the only end result you're really trying to go for here yeah i think the point of all this is to check off boxes it's not to say that i have the ideal system i'm holding up air quotes in the on the podcast i mean maybe maybe for, it's like, I want to really nail this system so that I can tell

people I've got the system. But right, that's not the point. The point is, you've got a bunch of boxes that are your tasks that you need to do, and you need to check them off and move them through and move on to the next task and be a productive person. And it doesn't matter how many apps you've got and how many tracking systems you've got. In the end, the, the,

that's like the structure of your work, like a scaffolding, like you're building a statue or a building or something. And there's a scaffolding. And at the end of the project, the scaffolding comes down and you're left with the building or the statue or whatever, right? Nobody graves you grades you on the scaffolding.

Nobody like the scaffolding doesn't matter. Like the scaffolding doesn't matter. And the scaffolding is your system. Like you couldn't build the building without the scaffolding, but it's not the point. So that's something to keep in mind as we talk about this stuff is in the end, your work is the point, not the system you used to do your work. Yeah. And just to torture that a little further. Let's do it.

I'm really proud of the scaffolding thing. So go for it. If it takes you four hours to put your scaffolding up so you can work two hours and then take four hours to pull it down at the end of the day. You're doing it wrong. You have bad scaffolding. Yeah. I just, lately we're going to do a show on this in the future. I've been really getting serious about bringing outside help and I've accepted that my control freak personality has to let go and I have to get people to help me or I'm going to blow it. So one of the steps I took in this is I've been running timers to see what I'm doing with my day, not just when I'm working on legal work, but everything, when I'm answering email or whatever. And one of the things I've discovered is my task management system does not take me

very much time. It's a complex system, but I've gotten pretty ninja at it to the point where I'm spending about 30 minutes a day kind of managing tasks and I get a huge benefit back from that. So my scaffolding is really great. But that's something you need to be thinking about. great. But that's something you need to be thinking about. I remember when I was in law school, I had a system. My system then was I had tea in the morning and I had a napkin and I would write down three things on the napkin. That was my three-a-day system. And it was great. I didn't have a wife, didn't have a mortgage, didn't have clients in my life. It was a very simple life. You know, and the three-a-day system worked great. And if you are an independent worker and you can Didn't have a wife, didn't have a mortgage, didn't have clients in my life. It was a very simple life. And the three-a-day system worked great.

And if you are an independent worker and you can work off a napkin, God bless you. That's all I'm going to say. Right. And that's, I mean, again, I don't want to be judgmental here because you will be judging me momentarily, all of you. you. But if the napkin works for you, for what you need to do and the way your brain works, then don't be guilted into creating a more complicated system. If you're making all your deadlines and you're not forgetting tasks and it works for you, that's the whole point. So if the napkin works, that's all you need is the napkin. It's as complex as you need. I would imagine given how you described your life now, right? You can't use the napkin. And the reason you don't use the napkin anymore is because you can't.

And so you've moved on. But hey, if you can do it on a napkin in a Field Notes book, in the Reminders app, if you can do everything that you need to do with that, then stop there because you're doing it. That's all you need. But most of us probably need more than that. Yeah. And that's where the curse comes in. And as we record this in 2017, there are some great capitalist systems out there. There's some great software out there to help you track things when i look over the last 20 years of the software available on the mac and and just you know in the development of ios there have been some really impressive you know steps

and strides made for people making this a lot easier than it used to be. I can tell you like 20 years ago, or my dad, there's no way he could have done, I think, a lot of the things I do simply because there was no way for him to keep track of it all. And it would have been quite difficult, I guess I would say. And so we're very fortunate now. So to a certain extent, these task management systems, which kind of have a little bit of a stigma attached to them it's like oh are you this are you that and whatever but but they they are kind of great that they exist and they give you uh superpowers to manage tasks which i think is awesome look um they wouldn't exist if there wasn't a a need for people to feel like they

need to get their their tasks under control right and so some people have said okay i have a system and i imagine most of these evolve as a personal system that that somebody thinks about a lot in order to juggle a lot of tasks and then they codify it and they say here is my system and you can go ahead use my system see if it works for you too and and because there's a thirst for it. There absolutely is a thirst for it, some of which is realistic, I would say, which is people who need organization, and some of which is maybe unrealistic,

people who think that their job will be solved if they can find the perfect system. And that's just human nature. Yep. And that's why the flip side of this is that in addition to being the best things in the world, these systems can be the worst things in the world because they totally get in the way. Yeah. If you fetishize your system and it's, you know, your work becomes the system instead of the work itself, which I mean, not to put too fine a point on it, that happens. Like

you talk to people who get mired in these systems and they lose track of the actual goal of the work and you need to not do that. But that's the danger here. If you spend time on the system and not on your work, that's lost time. That's wasted time. Yeah, and because we cover this on MacPower Users, and I write about it a lot, I hear from people like that every day. And it's sad. Because it's hard to tell them.

Well, you know how I do tell them when they send me that problem? No, tell me. I send them an email. Oh, boy. You know what? That reminds me of one of our sponsors. Yes. It does, doesn't it?

Yeah, we're sponsored today by SaneBox. This episode of The Free Agents is brought to you by SaneBox. Email can be a crushing thing. Just think about it. All that email starts coming in. You wake up in the morning. There's 50 things in your inbox, and you don't know what's important and what's not. Wouldn't it be great if you had a little digital secretary that would sort it out for you? Let's say, hey, this thing from Land's End, that's just an advertisement. You don't need to have that in your inbox. I'll put it in this other thing that you can look at later. Uh, but this thing from your boss or this

thing from your key client, Oh, that is important. I'm going to make sure that stays in your inbox. So the next day, instead of waking up to have 50 things in your inbox, you have two, that's what you get with SaneBox. Um, every person listening to the show has something they don't like about email they receive and SaneBox has a feature to help you. Like I said, it can sort your email for you. And the way they do this is they just look at the sender and the subject line. It's not creepy. They don't read your email. They just look at the subject line and the sender and they get a really good idea about how you deal with this. It's all cloud-based. So no matter what email system you use, whether you're on iCloud or Exchange or Gmail, the system can work for you. No matter what app you want to use,

it works because it's all web-based. And SaneBox takes care of that for you. They have some other tools, though. They have the thing called the Sane Black Hole. So if there's somebody that keeps sending you email and you're just tired of hearing from this person, you drop their email in the black hole, and guess what? You never see another email from that person again. Another thing they use that is super helpful for me as an independent worker is they have this thing where they follow up for you. So if I send an email to Jason that says, hey, we need to plan the next show. And then I blind copy it to oneweekatsamebox.com. You can blind copy it or carbon copy. It doesn't matter. In one week, if Jason doesn't reply to that email,

SaneBox gives me a little reminder. It says, hey, Jason never wrote back. You better call him up or figure out how we're going to do the next show. That's because I have a bad organizational system, David. That's why I didn't get back to you. Yeah, well, see, there you go. But this is a great way. It makes you look super on top of things with your clients,

and it allows you to keep follow-ups out of your task management system because the email does it for you in the background. And that's just the power of SaneBox. I started using them when I was writing a book about email years ago. And as soon as I realized how great they were, I immediately became a believer. I've been a paying subscriber now for years, and I don't know how I'd get through it without SaneBox. It's kind of magical. So you too can get better at email with something like SaneBox. If you'd like to have a little more email organization in your life, we've worked out a deal with SaneBox just for you. Go to SaneBox.com slash free agents today and you get $20 credit on top of the two-week free trial.

$20 credit on top of the two-week free trial. So that's Sanebox, S-A-N-E-B-O-X.com slash freeagents, and you'll really be happy with it. I'm a believer, gang. I think that Sanebox is one of my secret weapons to handle email. So thanks, Sanebox, for sponsoring the show. All right. Is this where I come clean about my system, David? Yeah, I want to know.

Just tell us, Jason. Just lay it out. We did an episode of Upgrade, by the way, that if I can dig out which one it is, I'll put it in the show notes where I told Mike Hurley my system and he was appalled by it. But here it is.

Now, every time I talk to him, he gives me the stick about it. He's like, oh, yeah, put that on your calendar. But this is how my system has evolved. And it was kind of like this when I worked at ID on your calendar. But this is how my system has evolved. And it was kind of like this when I worked at IDG and it is like this now, which is my system is basically the seat of my pants on one level, which is terrifying. It's not a napkin. But what's really true is that I have tools that have grown up around me to manage my tasks. And this is because every

time I've tried to do a task management system, every time I've tried, I've gotten a new app, or I've gotten a book, I am always pulled away by the thought that every minute that I'm investing, and this is true of anything, right? Every minute you invest in learning something new, you're hoping is truly an investment that you will get that minute back. And that's always the gamble whenever you're learning any new system. And this happens like when I taught myself how to do regular expressions, like back in the day, I read a whole book about it. And the question was, is this all this time doing this going to pay off? And the answer is, yeah, it totally paid off like hundredfold in save time, thousandfold perhaps. And when I learned how to use logic to edit

podcasts, I was like, I put it off for more than a year. I had that program and I didn't use it because I thought I don't have time to learn a new program. I just need to get this podcast out. And finally I found the time and I took the time and I learned it. And I'm like five times, 10 times more productive than I was before. So it was worth it. But you never know. And I would look at these task systems and I would think, I don't believe that this thing will make me more productive than I currently am. And that's not necessarily saying that they wouldn't be good systems. It's more that I thought, I think maybe I've created a system that is frictionless enough and works well enough with what I do that it will be hard to beat that. Because I do believe

we all try to cultivate our own systems and maybe they are dysfunctional and maybe you can't use them. But in my case, I feel like I've been functional with it. I don't see a lot of pain points where I think, oh my God, I can't believe I blew that thing or I didn't do that right or I was so inefficient here or I wasted time. Maybe that's not true, but that's my impression. And then I look at these systems and I think, wow, I'm investing a lot of time in apps categorizing things or making lists when I could just be working. So that's always been the trade-off for me. I got a question for you. Yeah.

When's the last time you laid in bed worried about not knowing what you need to be doing? I couldn't tell you. Okay. When's the last time you missed a doing. I couldn't tell you. Okay. When's the last time you missed the deadline? I couldn't tell you. So why do you need a new system? I mean, that's really, you sound, you're making yourself sound like you're being guilty about not having some super fancy system. But honestly, if you can sleep at night and if you're hitting your deadlines, you're good.

I agree with you. But I will say this, a couple things going on here. One is I have friends who have invested lots of time in these systems and are believers in them. And so that makes me intrigued by it, right? Like, oh, am I missing out here? And I try as a professional writer about technology, especially because most of these systems are not on paper.

Some of them are, but there are apps that tie into these systems i i try to be and just as a human being too not just as a tech writer i try to be open to things right i don't want to just because somebody else is doing something and they like it you know it doesn't necessarily mean it's great but if i just shut myself off and go bah that's pointless i'm not gonna bother then i'm sure that's like you you become a closed off person that way. So I want to be open to it that these, these people I know, and I like find value in this. So maybe there's value there, and I should understand it better. So that's part of it. And part of it is this thought, which is about self improvement, which is just because I'm making my deadlines and not worrying

about not knowing what I have to do in the middle of the night doesn't mean that I couldn't be more efficient, that potentially there's something else I could also be doing that I can't find time to do right now if I was better at organizing all the other things that I'm doing. And I think there's truth to that, right? Like, there are moments during the day where I'm sitting here thinking, what should I do next? I'm sitting here thinking, what should I do next? Not like I don't know what I need to do next, but it's those moments where, and this is kind of a hole in my system, where there's nothing I need to do right now. And I get to make a decision about like, well, what should I push forward? What should I do out in the future? Should I take a sidetrack? And so there's some inefficiency in there. It's not 100% efficient system that I've got. So that's the push and pull there. I do think that the reason that I haven't done this is exactly what you described, which is if I feel like everything's working at a pretty efficient clip, why would I change my system? And the only answer I would give is it's worth thinking about if I could be even more efficient if I adopted one of these. But I've never thought that, so I haven't. Yeah, I think a lot of it comes down to workload and just juggling.

Last night, yesterday, I had a bunch of calls at the end of the day from various clients. And one part of my job is I don't know when people are going to call me with a bunch of problems. Even I have the best system in the world. It has to account for interruption. And then we had family stuff and I went to bed and I didn't capture the day. If, if you know what I mean, I didn't write down all the kind of results and things I'd promised to do as a result of that flurry of calls that came at the end of the day. And I was laying in bed at midnight looking at the ceiling, you know, and, and I knew it took me a minute to realize how come I'm not sleeping. Oh, my brain is like in the background, trying to remember everything that happened. So

tomorrow morning I can get everything written down and not blow it. And so, you know, ultimately what I ended up doing at 1230 is getting out of bed, going and turning on the computer and getting all that stuff written down. Then I slept fine. Um slept fine. So I need a system. And I think that's part of his fear. You know, when you get a job where, you know, you've got to really take care of things and you can't miss anything, then you get, you know, more intense systems. And I just, like I said at the beginning, it's as complex as you need, but no more complex. So where do we stand right now with task management systems? Like when I grew up, they were always called to-do lists. And I don't really like that word, to-do, because I feel like it's not serious enough, if that makes sense.

I mean, this is serious business. I want to stay independent, and to-do sounds silly to me. So I call them tasks. I don't know. Isn't that silly? I don't know. I don't know. I mean, I can see the difference there.

I mean, there are high test productivity things like to do list, right? That is a it's all a play on that. But you're right. I, I sort of view a to do list as being way more casual. And that's like, you know, I need to mow the lawn this weekend, which is not quite the same. And maybe that's just a I in my mind, I've separated that kind of concept. That's I get a. Tasks sounds very serious, very businesslike. I'm not messing around. You need to concern these days collaboration. Task list collaboration is a thing.

When this all started, we were all writing things down on pieces of paper, and collaboration wasn't an option. But now it is. If you're working with a group of people, having a shared list can make a lot of sense. So I think if you feel like you need something more serious, you've got to think, am I looking for something as a solo solution, like something just for me, or something that needs to be a collaboration? Because in general, my experience is the solo tools are more powerful, but the collaboration tools bring collaboration, which is something everybody loves. collaboration, which is something everybody loves. There's a whole bunch of new kind of science behind task management where people are, it used to be you looked at things in terms of priority. You know, it was it, you made a list, one, two, three, you put something at the top and you just did them in order. And now there's all these different vectors that people have. I mean, they look at projects, they look at priorities, they even look at context, you know, where do

you get something done? A contextual-based task system is one that allows you to be very flexible. We had a, I use one, I use GTD, which we're going to talk about in a minute. And we had a thing at the office back when I was going to the office where the internet went down and everybody lost their minds. I mean, just completely went nuts. You know, internet's down, I can't get any work done. And they all stood around talking about how they can't work. I just went in my task system and I switched to phone calls. Everything that I had that's related to a phone call. I made like 15 calls and got a bunch of work done. And then the internet went back up and I went back to work on

other stuff. So that's nice. But you've got to think about how complex do you want this to be? I think the line you always should be walking with this stuff is don't get into something that's way deeper than you need it to be because that, that is where the quicksand lies for us nerds. And that's why I did so much arm waving of like, watch out, watch out, danger, danger. When, when we started is that I do think that, that a lot of, think that a lot of people, especially who are nerdier, get into the process and then they sink into the quicksand. But that being said, most of these systems, even GTD, are not that difficult and they're all pretty flexible. You don't have to turn it into a huge thing.

You can implement these things on a pretty low scale if that's what you want. So I don't know. I feel like you make a good point that even though everything's working for you, you could maybe be working better with a more complex system. But like I said, if you're getting everything done, I don't feel like it's something you need to, you know, go into with both feet. It's something you should maybe be curious about more than something you should be willing to just change everything over. Yeah. And that's sort of where I am in my process, is I'm always trying to be aware of other tools that are out there that might help me in some area or other. And I have adopted some of those, like for the nonprofit board that I'm on,

we're using Trello now. And that is a about a specific process that I mean, like literally needs to move from left to right. And, you know, you start on the left, and you move it step by step until it reaches the right and having a visual or, you know, internet organizer for all of us to use has been great. And that's a case where I've adopted a new tool that people have told me about that helps us all stay on track. So, being aware and open is important, I think, all the time. Yeah, it's funny. I'm using Trello, too.

Just, you know, as I told you, I'm starting to hire people. I wanted to collaborate. I have a solo system I use for my tasks, but I wanted to have a way just to kind of keep generally on track with the people that I'm bringing on to help me out. And I looked at all the options and Trello is what I used to, because it's a great little collaboration tool. It's not super heavy to get into. So people can use it without a lot of bandwidth and it's a great solution. So I'm glad you're using it. Yeah. So we should talk in a little more detail about how you're managing your tasks and projects. But before we do that, maybe time for a second sponsor, you think?

Yeah, because I'm going to take a little while. All right. Yes, I won't, but you can go first. This episode brought to you by FreshBooks as well. When you're racing against the clock to wrap up those three projects and you've got your system in place, you're prepping for a meeting later in the afternoon, you're trying to tackle a mountain of paperwork. This is what it is like to be a free agent. Our friends at FreshBooks believe the rewards are worth it, just as we do. They build tools to make challenges easier for all of us. So you talk about tools to make your life easier as a free agent. This is a great example. With the growth of the

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There's a 30-day unrestricted free trial available to listeners of free agents. What you need to do is go to freshbooks.com slash free agents and enter free agents in the how did you hear about us section so they know that you came from this show. Thank you to Fresh Books for supporting this show and all of Relay FM. See, time saver. There it is. Timely. That's getting help. I agree. All right, David, tell me what you do. I? Time saver. There it is. Timely. That's getting help. I agree. All right, David, tell me what you do. I want to hear it. It's not that complex, really. I went through, I started with a napkin in law school and then it started getting gradually, it quickly became apparent to me that would not work anymore.

When I first started practicing law, I was super nervous all the time. I remember the first couple of years of my life just laying and looking in bed because people bring these problems to you that you need to solve for them. Sometimes it's the biggest problem in their lives. And you just lay and you make your best call during the day. And then at night you go and you look at the ceiling and say, I hope I made the right call. And you eventually learn to cope with that. But then at the same time, you learn, I want to get better at making sure that I don't make mistakes. And what are the ways to do that? And task management is one of the ways.

So I went through all these systems. I went through, eventually I settled on a paper system. And this is like in the mid-90s, which was the Franklin Covey method, which was these books and paper, and you'd write down the things, and you'd have a whole priority system you would get into. And then I would copy things over that I didn't get done to the next day. It was very complex, but it allowed me to stay on top of things. allowed me to stay on top of things. Then years later, as I was getting increasingly nerdy, a lot of my developer friends started, you know,

getting into this thing called getting things done or GTD. And I thought it was a cult, you know, because everybody that got into it was super into it. And I'm like, I don't need something like that in my life. And eventually I went ahead and read the book and realized that, oh yeah, I'm joining. So it works really good for me because it's a system that uses project context and priority. Like I was talking about earlier, it gives me multiple ways to manage my tasks. And because I have essentially two careers, I'm a lawyer and I'm also a guy who writes books and videos and stuff about technology.

So I've got all these different masters in my life I've got to serve, and I have to make sure that I have everything in place. And that really helps me. And as the kids grow up, you get increasingly involved with schools and social groups and that. So I went ahead and did that. For years, I kind of rolled my own. I had an OmniOutliner-based based system for years and then omni group eventually made omni focus which is an app that they've been developing now i don't know how many years probably five or six years maybe longer i've lost track but but that one landed on me just like it's just the perfect solution for me for the way i happen to use gtd which isn't fully Canon, but it's close enough. It's a great software tool.

The thing I like about my OmniFocus system is that it's very fast for me to not only manage things, but also to check up on things. They have like a review process built in. So every client comes up for review every X number of months. So I can just kind of audit what's going on to make sure everybody's happy and getting what they need. They have a very powerful automation system built into it. Like if someone calls me and says, I want to build a new corporation, I run a template and I have like 20 tasks, auto-populate everything from confirming the name to checking with the accountant to filing the necessary documents with the state and preparing this and everything down to the very you know last piece of following up to make sure they got everything they needed in the mail

all that just happens you see that that is the when i describe what i'm doing this this is the thing that that if i was doing work that every time I said yes to a particular kind of work, I knew what form it would take. And I generally don't do this. Like, that's, that's the truth of it. But maybe like, back when I was a features editor at Macworld, back in the old days, you know, every edit, every feature you do has a bunch of steps, and you know what the steps are, and you need to go through all the steps. And even then, you know, it's not as complex as something like what you're describing. But that's where I see real value in these tools is, is is automation and templating that just templating alone,

the idea that every time I do task A, I do it in this order. You know, when the project starts here or when the project ends here, you can figure out what all the dates are, where everything is due, make them all like that is perfect. Like I, I, if, if I needed to do that, uh, because that's the sort of thing where people used to have like a piece of paper that said, here's how this works. And then you'd go to your calendar and you'd start writing in like one after another and, you know, and you don't need to do that. You've got a system that you just say, I'm doing task X and it needs to be done by this. And boom, 15 different milestones appear. Yeah. And I'm a big believer in checklists. And this is in essence, a check, a checklist that comes up every time. I do the same thing for podcasts i mean this show um started out

as a as a template project and you know everything from confirming the time to record to creating the outline now after we finish recording i'll have tasks that show up in terms of um publishing a link to it and you know maybe putting it on twitter whatever i've got on that template it just kind of tells me what to do. And that's why I always like the idea. I think David Allen's the one who first used the term cranking widgets. I love the idea of having a system that if it's working efficiently, you spend most of your time cranking the widgets,

producing the content, doing the work, and not thinking about, oh my goodness, what am I missing right now? Right, exactly. Anyway, so that's what I do. So I use OmniFocus to largely run. goodness what am i missing right now right exactly um anyway so that's what i do is i so i use um omni focus to to largely run i've looked at other systems and because i write about this stuff i've played with a bunch of other apps and web services and every time the the new hotness comes out i set up a test account and use it for a couple projects just to see how it goes and and they just never

really draw me because omni focus which is really a solo system more than a collaboration system but it is a super powerful solo system and then to the extent i need to collaborate i'd go to outside applications and and that kind of depends like some of my legal clients are very tech savvy i represent a lot of it and developer types and they love to work in Slack. So Slack becomes a place where we keep track of information. And increasingly, I'm bringing those folks into Trello if I need to collaborate with them on anything. But usually, when people hire me, they don't want to be included on the task list.

They hire me to just get the ball into the end zone. They don't care how it happens. They just want it in the end zone. So I don't need to do a lot of task collaboration. When I talk to some of my friends in the tech side of my life who like run websites, like you run a website and you have Dan Morin and other people helping you out.

I don't know what you guys do to keep track of who's doing what, but, but OmniFocus isn't really great for that because it's not a collaboration tool. So it just depends. But I'm increasingly finding myself going to Trello for collaboration type work, which I find very useful. And the thing I like about it is I can bring anybody in on a Trello and they can figure it out whether they're geeky or not.

Right. And so that really solves that problem for me. And then all the background stuff, they don't really see what I'm doing. They don't get my full list of things I'm doing because they don't really need it. They get into the pieces they need going to Trello. Yeah, they just get some cards that they need to move around. Yeah, yeah. And I really, I can't understate the success of templating in this stuff.

I would say that more of my tasks are created by templates than not, which is a good way to do it. With a system like this, though, you've got to maintain it. And one of the things I would recommend if you're going to go the software route and get serious about this stuff is plan on dedicating a little bit of time at the beginning and the end of each day to make sure that you keep the garden pruned. Because if you don't, then it becomes useless to you. It was just a big list that you don't manage. It doesn't matter. I mean, that is literally what has happened to me every time that I've tried to use any sort of task management system is that it comes time for me to put in the time to manage it, to prune it, to, you know, make sure that it's in the right

position. And that's that moment where for me, I just go, yeah, I just like, like, again, because I'm sitting there thinking, am I going to take time now to, to be productive in things that don't actually advance my work? And I know they do. I know they do. But this is the trade off. And this is the mindset you have to go in is if you're going to go in here, you have to go in on the whole thing or it will just come apart. There's no point. There's no point in doing this halfway, I feel like, because then you're not organized and then you're really just throwing things into a bin and wasting your time because you need to do the maintenance too. Yeah, I feel like for you, as your business evolves, you may need to upgrade at some point.

It's true. In fact, I was just thinking, we do the Six Colors newsletter, which is monthly. And right now it's simple enough that I don't worry about it too much. I can keep track of that in my head. And I know this is the moment where Mike Hurley would just be appalled.

Like what, you keep track of it in your head? It's like, well, yeah, there's like three pieces to it. And I, I ping the people who contribute to it in the middle of the month. And I say, um, I made a new doc. Here it is. I don't need to have a thing that says, uh, you know, make a new doc and then email Dan and then email Stephen Hackett and then write your column and then write another article and then paste in their articles and then go to MailChimp and send it out. Like I don't need need that. But I will say, if it got much more complicated, I would, right? At some point, tasks get complicated enough that you can't hold it all in your head. You'll miss a step, right? So, and that's the point where, like, again, I don't need a to-do

list somewhere that says, turn on the heater, turn on the light, turn on the computer, open the door in the morning. Like, get your tea. I don't need those lists because those are simple enough things. They're patterns. It's fine. But above a certain level, there are tasks that get complex enough that you need that kind of automation. So I agree with you. I feel like I've got a few things that are on the verge of needing some sort of templating. I was trying to hold on to some stuff. And if I forget about it, people who pay me money are going to be very disappointed.

And so I had to get up and write it down. And as soon as I offloaded it, I got it out of my brain and put it into a system I trust. Then it was like, okay, go to sleep. You're fine. And it just depends on how deep you go down that road. A couple other things about this is I would recommend, and we're getting to Mac Power Users territory, or I even did a multi-hour video on OmniFocus if you're really interested.

But be careful about when you get a system about overdoing it. I was just at a conference, and somebody showed me their system, and they had 43 items that were overdue. And I'm like, that doesn't make any sense. If you have 43 overdue items, you don't have any overdue items. You're overdoing it. Make it honest, like Jason was saying earlier, and stick with it and you'll be happy. What about you? Oh, boy. So, a lot of my work is cyclical. And so, this is what Mike gives me a hard time about is I use my calendar as a planning system. And apparently, you know, apparently, other people don't do that. Apparently, people use calendars for appointments, but a lot of my appointments are for my work.

So I put due dates on my calendar as all day events. I put a time that I need to work on something as a calendar event. And an example is like, I write a column for Mac world every week and I turn it in. I try to turn it in the same day because as an editor, you like to know, I'm going to get that column from Jason on Wednesday or whatever. So I have, uh, I have an item in my calendar as a weekly event that basically on Tuesday afternoon from two to five or one to three or something like that, uh, write my macro column. And I have a lot of that because I have a lot of podcasts where, you know, we record like we're doing right now during a block. It's not sort of an amorphous, you need to do this today.

It's like, you're going to do that from 9 to 11. So, I've got all those things in my calendar. So, I've got a lot of stuff that just repeats every other week, every week, and I just keep them on the calendar. And I think that's fine if you've got one or two. If you've got seven or eight, it's a problem. Well, think about it this way, though. In some ways, it's a different, and I'm not endorsing this for anyone else, but just to explain myself, in some ways, it's not that different if you sit at your desk in the morning

and you look at your list and say, here's my next task. Or if you sit down at your desk and you look at your calendar and it says, right now, I should be doing this. They're not that different. They're not that different. And for me, it helps to say same time every week, I'm going to write that column. And it doesn't always, it doesn't always work. I'm out, I'm doing something else. And I will move that appointment with myself to a different time. But it's very clear, like this needs to be done. And I'm going to block out time to do it where I'm not going to have it. Now that part of this is it's a habit for me from and a defense mechanism

from when I was managing a group of 50 plus people, which is I had a lot of meetings. And the only way I could get work done outside of the meetings, and this is that is a telling statement, if there ever was one about me keeping score in a different way where the I didn't consider the meetings getting the work done I considered outside of the meetings getting the work done but anyway I would make these appointments with myself where it's like I'm going to write my column now and I had to do it that way because otherwise somebody would send me a meeting invite and I would, my day would fill up with meetings and I would have no opportunity to do the writing I needed to do or the editing or whatever. Yeah. It's funny how meetings, even important meetings feel like an intrusion.

Right. Right. And you could argue that was my job, was the meetings because I was a manager. I was a senior manager. I had lots of meetings, but it didn't feel like that. So I have carried that with me, which is I'm making these appointments with myself. And fortunately, a lot of what I do is not, I'm taking on a project that has 15 steps and it's going to have an arbitrary end date. And I have to figure out what to do to get it there. A lot of what I do is the same every week or the same every month or the same every two weeks it's on cycles. And so for me, that means I can get away with using a calendar for a lot of this stuff because I know for the, so when we do free agents, we record these sometimes two at a time. We release them every other week. And I have an

all day event that repeats every other week that says post free agents. And that's it. That's all it does. And I know on that Tuesday, I look at my calendar and go, oh, I need to post free agents and that's it. That's all it does. And I know on that Tuesday, I look at my calendar and go, oh, I need to post free agents today. And that since, since posting free agents is a, a task that only takes an hour or two because I edit the episode that morning and then post it. I don't edit them in advance. I do it right then and I post them. That's enough for me. I don't even have a block on that day that says, do it now. I just say that day it needs to go out and I make the time. And I realize that that is in many ways really unconventional, but because so much of my work is like that, because so much of my work is deadline oriented,

I've gotten used to putting the deadlines on the calendar and then just looking at it. Now you could ask, as Mike asked, what if you've got a project that takes five days to do? You can't just put it on the calendar because if you don't look at that event until the day before, you can't complete the event. And it's like, yeah, that's true. But most of what I do is not that kind of thing. Is any of the stuff you do that kind of thing? Really? The book that I wrote the last couple of years, I did updates to and initially wrote a book

for tidbits. That's a good example of a long-term project. And for something like that, we had an agreed set of deadlines for that. And that was totally separate. I didn't have a thing that said finish the book. And then like, you look for, you know, no, I didn't do it that way. But most of my work week to week, day to day, absolutely is cyclical. It's not, it's a rare different project that comes in that changes that I have to build a different structure

for. But that's me, right? And your workload is very different than mine in that way. So that's why the system has evolved for me is because it's kind of all I need for most tasks. I should say that it's not my only organizational system. I do actually use Apple's reminders app i have a special list in there called story list which is where i collect all of the stories that i want to write story ideas basically and that's not a to-do list per se it's a data collection point uh reminder to myself of uh this idea that i had because a lot of times then i will forget story ideas and then i'll think what was i thinking so i just put them in reminders and I use that. But again, that's not a, that's not a specific task. Instead, I will put a blob on my calendar that says,

write a six colors piece today. Um, that, that is recurring. So like on Wednesday, I think Wednesday morning, I've got a blob that says, write a six colors piece. And that's just, or Wednesday afternoon, I guess, cause I do a podcast in the morning and that's just sits there. And that's a prompt for me to say, oh, I should be writing a six colors piece right now. So I'm scheduling my time. And then in this case, I get to pick from the bin of story ideas or come up with a different one and write that. But in that case, the list serves as a way to get it out of your head. So you don't have to try and remember. Yeah. And that's true. I mean, the reality is that usually my brain serves as the way to get it out of my head because these story ideas flit through.

You know, I have a list for like science fiction novel ideas as well and short story ideas because those flit through my head every now and then. I think, oh, that's a pretty good idea. And I write it down because I will never, I can't tell you how many times I've thought, whether it's about a piece of fiction or it's about a story for Six Colors or Macworld or something like that. Oh, that's a really great idea, and I don't write it down, and I cannot remember it later, because they just, they come and go. I think it was Field Notes that had the slogan, I'm not writing it down to remember it later,

I'm writing it down to remember it now, something like that. I forget. Yeah, no, I'm not writing down to remember it now, I'm writing it down to remember it later. The idea that the act of committing something to a note actually fixes it in your mind. And that's true, too, that the act of writing it down makes it more likely that you will remember it later. For me, it's both. I need to remember it all of those times. I need to remember it when I'm looking for a story to write. And I'm like, what am I going to write about? Nothing's going on. And then I look at the list and I'm like, oh yeah, that's a good idea. And I'll write that story. So that's, I mean, that's kind of it. I, I do for, for things that are complex chain of tasks, I generally will construct a document. It's often a Google doc, or it could be a spreadsheet that says like, here are the things that I need to accomplish with dates. I will do that. That's something that if I was using something like OmniFocus, obviously I would do it in the app.

But since I don't use a tool like that, a lot of times it ends up being document-based where I have my, like for the book, I had my chapter list and deadlines and all of that in a Google Doc. And that was my reference point about what chapter was I going to work on next? What things did I need to go back to? That was how I did it. You can even do that in a spreadsheet as well. Yeah, absolutely. So it's one or the other. And it depends. I mean, I have for my, some of my podcasts where planning is a big deal, like I haven't even talked about, like The Incomparable is a good example where I have to plan those in advance. There's a big panel.

So only certain people are on specific episodes. And we got a lot of topic ideas. And every week, there has to be an episode. I can't miss a week. If I travel, it doesn't matter. I can't miss a week. It's a weekly podcast. I've been doing it for almost six years. Every week there's an episode. That requires planning. I have a spreadsheet. That's the answer. I have a spreadsheet. Clockwise, the same way. I have a spreadsheet. And with clockwise, we have to book two new guests every week. So all the guest planning goes in the spreadsheet. With Incomparable, it's topics. I am usually thinking as much as 20 weeks out, maybe even 30 weeks out in terms of topics. Sometimes it's just the rest of the year. And they keep moving around and new ones come in and I slide them around. And I'm always keeping an eye for when can I schedule it? And will I always have an episode to release every Saturday? Because that's important. Like you can't, oh, well,

two next week, but none this week doesn't work. I need to release an episode every weekend. So I have a spreadsheet for that. You know, you're talking about calendar-based task management. I do a bit of that. And the way I use that is, sometimes I'll have a project that for, you know, because of interruptions, and just other press isn't getting done, and it's weighing on me, you know, everybody has that feeling like, well, I really wish I had done the Jones project, you know, and it's not done yet. And when I start feeling that kind of stress, I will make an appointment. I will block time sometime in the next several days.

I'll look at my calendar and say, okay, Wednesday afternoon, I don't have anything going on. I'm just going to take two hours and do nothing but worry about the Jones Project and work on that then. And that's a way I use a calendar in conjunction with a task management system, but I don't use it as the system. It's weird.

It works for me. You can see why. You can see why. In fact, I would even argue that not only my history with meetings, but the nature of my work led me to this point. Yeah. And it all makes sense to me. I mean, I don't really feel that upset as Mike did with your system. really feel that upset as Mike did with your system. I feel like maybe as I think your business is going to grow and at some point you may have to consider going a little deeper, but the warnings,

you know, the signals are there when you need to do that. When things feel like they're falling through the cracks, when you feel like you're not really on top of things is when you need to start really looking serious. I don't really, we don't have the answer for you. If you're listening to the show and you're having no problems, then you probably should stick with what you're doing. If you are worried about it, look into a system. I would suggest that GTD is a very good system on almost any business, especially as a solo person, to give you a, especially as a solo person, you know, to give you a basis to find things. I've bought probably 15 copies of the book over the years to give to friends when they, when they call me and tell me that they're suffering and they don't know what to do. And, and sometimes it takes and sometimes it doesn't.

Did we say it? It's getting things done by David Allen is the, is the book on GTD. Yes. Do you need to, do you need to have the book to, to use a tool that's based on the concepts? I think the book really helps. And they did an updated edition of the book. It's not super tech-friendly if you're nerdy. But, I mean, once you start using it, you can get it going. If you're on a Mac, I would recommend OmniFocus, frankly, because they worked with the David Allen Company, and they've got a lot of the great tools in there.

But, you know, full disclosure, they've sponsored me and other things I've done in the past. So take it for what you will. I think that if you're collaborating with a lot of people, there's some really great cloud tools showing up that are worth checking out. Todoist was mentioned. There's a bunch of them. And just take a look at some of the cloud stuff. Trello, I think, think is i'm really happy with trello yeah it's not it's not for everything but that's good it's good at what it uh it's good

at what it's good for and and nothing else i think and i like that about it that it is if you want an all-purpose system trello is not going to do it i think but if you want a place that everybody can look at a shared sort of stack of cards and and and make notes on them and move them along and i just i really love the visual nature of it of moving things from left to right if you've got any process like that where you have to see where things are in the process and how close they are to coming out the end of the pipe and like i said we do that for our my non-profit boards recruitment system is a trello board and the idea there is new potential recruits start on the left. And we built a process that we're supposed to have about like, who talks to them when,

and when do they get voted on the board and all of that. And it was all kind of like hard for people to follow until we put it in a Trello board. And now like the names start on the left, and then you just move them through. And you know what the next step is, and the next step is listed, and then the last step, they're on the board. It's great. Yeah, yeah. So a bit of parting wisdom on all this, keep it simple but not too simple. I mean, you can see even Jason's system has got nuance to it. I mean, the way you're using the calendar, and you've got other pieces,

and now you've got lists for long projects. So I can see that you're kind of developing your own thing, and it seems to be working for you. I think a lot of people make the mistake with this, and this is something that I hear about all the time, is you get one of these systems, whether it's something you cook up yourself or something you read in a book, and you start to feel empowered by it, because you can be more productive if you get serious about this stuff. And that leads to the second level problem of taking on more than you can chew. You know, you just suddenly you've got this great system.

And I get emails all the time from people saying, well, you know, my problem is now I have 10,000 tasks to track. I'm like, well, your problem is that you're not being a big boy and big girl about turning things down. You never would have been able to track 10,000 tasks in your head, but because you have a computer that can do that doesn't mean that you can actually physically do that many things. I think a lot of people fall in the trap of saying, my productivity system is so productive, I can be more productive. And basically, they just fill the void with more work. So instead of doing 15 projects and feeling overwhelmed, they're doing 30 projects and feeling overwhelmed. Maybe you should just be doing 20 projects and having time to go to the park with your kids.

So be careful about that because that's the second level trap you fall into with this stuff. You start to feel empowered by it and you take on too much. Yep. I agree. I mean, listen to David, everybody. He has more of a system than I do. He can tell you more about it. But yeah, I think the parting wisdom for me is very much the same. The point of the system is to help you get your work done.

Don't ever lose sight of that. That in the end, your work and your productivity is the important part, not doing a system and find one that works for you and take that capital S system that somebody put in a book and turn it into a lowercase S system that is applied to your life and works for you. And if it's not exactly what is in the book or what your friends are doing, if it works for you, that's all that matters. Amen. All right. Well, thanks to everybody for listening to this edition of Free Agents. I feel like we'll probably talk about this subject more in the future. There's so much to talk about, but that's a good overview of the whys and wherefores of task management systems. You can reach us,

tweet at us at Free Agentsfm on Twitter. You can go to our free agents group on Facebook, facebook.com slash groups slash freeagentsgroup. And of course, you can email us. There's a contact link in the show notes page at relay.fm slash freeagents. Now, Jason and I don't have the only ideas about a good task management system, and we're getting ready to do a feedback episode. So if you've got some thoughts on it or questions let us know we'll get it in yeah use any of those means to contact us and let us know your suggestions and we'll put that in the feedback show which should be happening in about a month bye everybody Thank you.