As many of you know, I’m a pretty avid tracker of my tasks and the things I need to do. I do it mostly because I need to get those things out of my head — where they distract me and keep me from focusing and sometimes are forgotten — and into some kind of trusted system, where I know they’ll be there for me later.

Over and over again in my life, I’ve found that being distracted by things I need to remember, forgetting things I need to do and missing appointments has cost me time, money, relationships and opportunities, and as my life has become more and more full over the years, I’ve had to gradually evolve my systems and practices for doing these things.

Because I’ve written about this many times over the years, I’ll occasionally get a comment or a question from someone who has never ever done such a thing. The idea has only popped into their life recently because they forgot to do something important or missed a meeting or something like that.

How to organize your time and tasks

1. Start with paper

The first place that anyone should start when it comes to organizing your time and tasks is with paper. Paper is freeform. Paper won’t fail if you don’t have your device charged or the power shuts down. Paper is essentially infinite — there’s always another page. It is absolutely perfect for getting started with all of this. Plus, if you try this out and it doesn’t work out for you, you really haven’t invested more than the cost of a few sheets of paper.

Get out a blank sheet of paper. It can be lined or unlined. It can be graph paper. I’d simply suggest that it not have a distracting background or pattern. It’s probably better if it’s in a notebook, but it doesn’t have to be.

Along with it, get out a pen or a pencil, a good one you like and won’t leak all over the page and won’t frustrate you while writing.

2. “Brain dump” onto paper

What do I mean by “brain dump”?

What I mean is that you should just start writing down everything you need to do or remember in the future. Everything. Every task you need to get done. Every appointment you have in the future. All of it. Put an item on each line and write enough information so that it’s easy to recall later what it is that you’re describing.

At first, your stuff will be focused on the next week or two, because those tasks are at the top of your head. You’ll think of the most urgent stuff that needs to be done and appointments that are coming up in the very near future. As that starts to clear out, you’ll start writing down important things that are further out, like your partner’s birthday or a trip you’re taking in a few months. Those things are important to record, too.

You’ll also start to notice that some of the things you write down are pretty big and are actually made up of lots of little pieces. For example, you might write down your partner’s birthday, but then you realize you need to get a gift in the days before that birthday, and perhaps you’re going to plan a special meal for that day. I generally refer to these as “projects.”

For many people, a lot of these tasks will be professional in nature. For most people, I see no problem with intermingling professional and personal to-dos and appointments. That’s what I do. So, include work tasks and upcoming appointments on there, too.

This list will probably get quite long, and that’s OK. It should get long. You want to get all of those tasks and appointments out of your head so that they’re not distracting you or taking up “brain space.” What you’ll come to notice is that a lot of the tasks you write down have a few traits. They often have a date associated with them, either a due date when it has to be done or a specific time when it must be done (like a doctor’s appointment). Some of them will have a location associated with them, like tasks you might have to do in the city.

As your list gets longer, it can start to become useful to find ways to “group” things that have traits in common. At first, the big things you’re probably looking at are due date and appointment date. A really simple way to handle that is to have a highlighting system. A simple way to do that is to go through your list each morning and highlight everything that’s due today. Don’t worry too much about organization at this point. For most people, going further than this with organizational tools isn’t all that helpful, particularly at first.

Personally, I first started keeping track of to-dos in a notebook when I was in high school. I had a separate 80-page notebook at school and I just started listing all assignments and things for extracurricular activities and chores and things like that in there. I’d cross off things as I did them and write in new things when they came up.

After a year or so, I started adding a separate column to the front of each item, where I’d list the time and date when it was due. This helped me to quickly see when I needed to take care of things.

I also started getting in the habit of “finishing out” pages sometimes. If a page was getting mostly crossed out with just a few things left, I’d copy those things all up to the current page and then get that old page entirely crossed off so I didn’t have to look at it any more. Everything I needed to see was always on the most current two or three pages of my notebook.

This system worked for me through college, actually. I kept track of everything in college in a college-ruled or graph ruled notebook using this exact system.

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3. Establish a routine of looking at whatever you’re using frequently

The number one thing that makes having a “to-do list” useful is getting into the habit of looking at it frequently. You’re always adding new things that need to be done, crossing things off that are done, and looking at it to see what you need to take care of next.

Start keeping it on your bedside table and look at it every morning, at the very least. Ideally, you start taking it with you throughout the day, adding things as they come to mind, crossing things off as you do them, and looking at the list for the next thing to do.

What you’ll find is that if you get into the habit of looking at it frequently, it will start to feel like an extension of your brain. Inside your head, you’ll stop trying to remember things to do and upcoming appointments. Instead, you’ll just trust that they’re on paper and you won’t think about them anymore. They won’t pop up in your head to distract you and you won’t find yourself putting in mental effort to remember them. That’s a great thing, and it’s one of the big benefits of moving to an external system for tracking this stuff: it allows you to focus more on whatever you’re doing because you’re expending less brain energy keeping track of all of this stuff.

Paper has a huge advantage over digital tools for simpler, smaller lists. If your current list of to-dos is less than four or five pages, then do it on paper. Why? The act of writing all of this stuff down by hand allows you to think through that task a little bit, and in that process, it will often reveal things like how important this task really is or whether it should be modified or whether you should even be doing it at all. Dropping these things into a digital system is faster, but that speed takes away that contemplation and you’re usually worse off for it.

When I was using this paper system in college, I found myself taking it with me constantly. In the morning, I’d usually pack my backpack based on what was coming up on the list. My usual routine was to go to classes, then fill the gaps between classes at the library, and I’d always start those sessions by looking at my notebook and seeing what I needed to read and study. Those notebooks got beaten into oblivion, with the cover falling off and pages falling out. That system helped get me through college and into my early career.

4. Try a paper calendar

Eventually, as I entered professional life, two things began to happen. One, I began having a lot more appointments. In college, I had a set schedule each semester and my appointments outside of that schedule were relatively few in number, so just writing things on my to-do list with a date beside them was enough. In my early professional years, the number of scheduled appointments and meetings skyrocketed.

So, the next step, if you’re finding yourself with a lot of appointments, is using a paper calendar. There are many paper calendars out there in the world. Personally, I find that simpler ones are better; if they’re overly complicated, you’re probably better off moving to a digital tool. The Clever Fox planner is a wonderful simple planner, but pretty much any simple one that you’d find at an office supply store or even in the office supply section at Target will be fine.

At that point, move everything that must be done at a particular time into that calendar. All of your scheduled meetings and appointments should go in there. I also recommend putting major project due dates in there, but don’t put every task in there or else it will just get overwhelming. Things like birthdays and anniversaries should definitely go in there.

For me, my calendar often spawns stuff for my to-do list. For example, if I’m looking ahead at my calendar and I see a birthday coming up, that means I should add a to-do to my to-do list to get a gift for that person soon. I’ll often add the appointments for each day to my to-do list so that I can mostly just look at my to-do list when I’m on the go.

Again, this all comes back to the routine of checking things frequently. I know that all of my long term scheduled stuff is in my calendar and all of the stuff I need to be doing is on my to-do list, and I know that those things only stay valuable if I dump everything in there so I don’t have to think about it. That system only works if I add stuff frequently (whenever I think of it or become aware of it) and if I check it frequently (so I’m not missing stuff). The calendar needs to become a very regular part of your day, just like the to-do list, or else they’re largely useless.

In my early professional life, I used a paper notebook as a to-do list and a paper calendar, and that handled everything well up through the early days of The Simple Dollar. I’d look at my to-do list and calendar each morning, look at what was coming in my calendar and add relevant to-dos to my to-do list, and then mostly focus on my to-do list throughout the day, adding stuff as it came to mind and crossing things off as I did them, just like before. If something was obviously an appointment, it went in my paper calendar.

For the vast majority of people, a system like this will handle everything they need to keep track of. I only suggest moving to digital tools if these things aren’t handling things for you, because the contemplative advantage of paper – a huge advantage, which I discussed earlier – is lost when you move to digital tools, and you have to come up with ways around it.

5. Use a digital planner when paper is overwhelming

When The Simple Dollar got rolling, I began to realize that the paper to-do list and the paper calendar weren’t cutting it anymore. It was fine when my life consisted of my 9-to-5 job and my marriage and my social life, but when I added in becoming a parent and also the management of The Simple Dollar as it grew from a hobby to a little side gig to basically a small business, I was getting overwhelmed. My calendar looked like a field of chicken scratches and my to-do list was page after page after page after page of things to do. It was becoming unwieldy.

So, when should you move to digital tools? I suggest doing so when you find that the paper-based solutions are becoming frustrating and are taking longer and longer to use. For example, if your full list of to-dos only takes up a few pages, you’re better off with paper, but if you are leafing through 10-15 pages of to-dos (a point that I reached), the system is just not working well. You’re starting to waste a sizable amount of time just looking for and retrieving relevant tasks, and it begins to feel like the system is keeping you from getting things done. That’s when it’s time to go digital.

The advantage of digital tools over paper tools is that it’s much easier to enter tasks and appointments and then, later, to sort through and search through those tasks and appointments. Almost every digital tool makes it really easy to enter new tasks and appointments, and then later on it’s easy to search through those things and see them from different angles. It’s easy to just see a list of everything due in three days, for example. Many tools go further with this organization, letting you create projects, add tags to tasks, and so on, which makes entering a new task just a bit trickier but adds a ton of value to sorting and viewing them.

The drawback with digital tools versus paper tools is that digital tools are far less thoughtful on their own than paper tools. When you write down tasks by hand, the process makes you think through what you’re writing, and that often reveals to you whether a task is worth doing or whether something else needs to be done first. The stuff that gets written down by hand is just more thoughtful and truly useful.

My solution to this conundrum is to review, review, review. I spend less time actually entering things into my calendar and to-do list than I used to, but I spend more time simply looking at my to-do list and my calendar than I did back in the paper days. I actually do a small daily review and a much longer weekly review, where I go through everything in my to-do list and calendar and ask myself whether that thing is really the right thing to be doing, whether I actually need to do it, and so on. I also go through every ongoing project and ask myself what the next thing I need to do to keep this thing moving forward is and whether it’s even a project I want to continue.

Without that, my to-do list and calendar would quickly fill with irrelevant junk. If you just use it as a dumping ground without thinking about whether these things are things you want to actually invest time and energy in, the list becomes overwhelming and full of garbage and thus not very useful.

So, if you move to digital tools for your calendar and to-do list, I strongly suggest getting into the habit of thoughtfully reviewing the things that are in your system. I do a daily review, where I look carefully at everything on my calendar and everything that’s due today or tomorrow, and I ask myself if each of those items is really important, whether there’s something I need to prepare, and so on. Once a week, I do a weekly review, where I go through the entire past week and see if I missed anything, and then review everything coming in the next two weeks with the same methodical approach. That weekly review takes at least an hour, but I usually end up eliminating a bunch of junk from my calendar and to-do list.

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So, in the end, I find myself entering more into my to-do list and calendar than I ever did, but each entry takes very little time. I don’t really think about whether I should be doing this thing, I just get it out of my head. It’s during the review each day that I make that distinction about how important that thing is, when it should be done, whether there are earlier steps, and so on.

6. Suggested first steps using digital tools for organizing time and tasks

First of all, I would only really consider moving to digital tools if you have a smartphone. A smartphone is essential for entering things and reviewing things on the go. If you don’t have a smartphone, stick with paper. If you’re finding yourself just completely overwhelmed with paper to-do lists and calendars and you don’t have a smartphone, it’s probably time to think about getting one.

If you have an Apple/iOS device, my recommendation for your first to-do list manager is Reminders. It’s free and it has all of the basic features you need in a digital to-do list manager. You can quickly type in the task, set the due date, and you’re good to go. You can create multiple lists of tasks, so you can group all of the tasks related to an ongoing project together. You can even create location-based tasks – things you need to do at a certain place.

If you have an Android device, my recommendation for your first to-do list manager is Google Keep for Android. It does almost everything that Reminders does. In my experience, I found it was good to create a new note for every task (so I could give it a due date) and only create a checklist within a note if it was something like a grocery list. I’d then just delete notes as I took care of the task.

For a digital calendar, I recommend Google Calendar for both platforms. It just does everything you could want a calendar tool to do, plus you can access it via the Google Calendar website if you’re ever away from your phone and need to look at it. (In fact, I still use Google Calendar sort of — I’ll explain below.)

7. Need more than that?

Why would you ever need more than these tools? I use a different to-do list manager and a few other tools, but why? Let’s dig into that here.

The to-do list manager I currently use is Omnifocus. I started using it when I was first transitioning to managing The Simple Dollar as a small business rather than just a hobby because the tasks were simply overwhelming and, at the time, there weren’t a lot of robust task managers available. By the time there were a lot of other options available, I had just become very used to Omnifocus and there’s no compelling reason to switch. I would not recommend it to most people today — or even to myself today if I were starting over. It is complex — sometimes almost needlessly so. There is a massive learning curve to using it well. I like to compare it to using an espresso maker with tons of knobs and other things when, for almost everyone, a Keurig or a simple drip coffee pot or a cold brew pot in the fridge makes plenty good coffee and it’s much easier. I stick with it because I put in the time to climb that learning curve a long time ago when that was the best option, but I don’t really recommend it to most people today. There are a lot of great options that offer more options than Reminders and Google Keep without the complexity of Omnifocus (Todoist and Things come to mind, both of which I dabbled with but couldn’t quite convince myself to move to fully).

I still use Google Calendar as my calendar tool, but I usually enter new things using Fantastical. Fantastical talks to Google Calendar and enables you to enter appointments, along with their dates and times and a lot of other information, by typing in something that approximates normal English, but it’s just quirky enough that you kind of have to learn how to talk to it to get a lot of value out of it. Again, there’s a learning curve involved (not a super steep one), and unless you’re entering tons of appointments, that learning curve probably isn’t worth it compared to just using Google Calendar directly.

I use Evernote for note-taking. What do I mean by note-taking? I mean things like interesting articles, book summaries, notes I take from lectures, ideas for future articles for The Simple Dollar, outlines for potential book ideas and plans for trips — all kinds of stuff. Basically, if it’s a piece of information I think I will want to refer to later that isn’t really something that specifically needs to be done or an appointment, it winds up in Evernote. Whenever I want to see if I have information on a particular topic that I found earlier, like an earlier Simple Dollar article or something I found two years ago and want to save, I just search Evernote. I have literally thousands of notes in Evernote. If that sounds like a really useful thing to you, use Evernote. If it doesn’t sound all that useful, then don’t bother.

One final thing that I really feel like I should talk about here is time tracking. Time tracking means that you’re keeping track of how you spend your time, much like how you’d write down each expense you make when you’re trying to track where your money went when building a budget. I wrote about time tracking in detail several months ago. In short, I use an app called Timery on my phone. Within that app, there are a bunch of separate timers for different things I do in a typical day — writing, reading and research. I just tap it once to start a timer, then tap it again to stop that timer. It keeps track of that data so I can look at it later on, reviewing how I used time over the course of a week or a month or a year.

I do it for two big reasons. One, it forces me to be intentional about how I’m using my time. If I start a timer for “writing,” then I know that I should be focused on writing until I stop that timer. If I’m starting to get distracted from that, I stop the timer and recognize that I’m switching to doing something else. Second, it has forced me to become really honest about my time use, which has had a ton of benefits in my life. I decided right at the start that I wasn’t going to “lie” to this tool and that it was going to reflect, to the best of my ability, how I was using time, and that sometimes means that I have to admit that I waste more time than I like on completely unimportant and rather unfulfilling things, like browsing social media or playing a mindless game. The reports generated by the tool are interesting, but they’re not incredibly useful other than perhaps recognizing what times of the day I work best and other patterns like that.

I honestly started with the time tracking as a 30-day challenge to try to understand how much time I was wasting and I found that it was something that really clicked with me, so I kept it around and use it most of the time. I don’t use it when I’m on vacation or visiting family for holidays, but for largely “normal” weekdays and weekend days, I’m usually tracking things.

Again, if it seems interesting, try it. If it doesn’t seem like it would be useful to you, skip it.

8. If you do one thing, start with paper

Dump the things you need to do and remember out of your head and onto a sheet of paper or onto a page in a notebook – multiple sheets if needed. As new things come to mind, add them. As you take care of things, cross them out. Only move to other things if you find value in that basic system but are finding specific problems with it, like too many tasks to manage or a large number of appointments.

In the end, that’s really what I’m doing with the systems I use now – they’re just more complicated versions of that system, and the more complex tools help me deal with having a lot of tasks and information to deal with.

Start with paper, though. Everything else follows from that.

Good luck.

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