Joshua Williamson

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The System That Served Me for Years: A Quick Guide

From never brushing my teeth to losing over 100lbs, graduating college early, and trying my hand at a handful of startups, take a peek inside the system that I shaped over those years.

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Intro

First, why even do this? Well, this is the system I started with and what laid the foundation for years of my life. I went from literally never brushing my teeth to being able to do virtually anything I set my mind to, because of this system.

The idea here is to build off of each section. Ultimately, you'll be building your system one piece at a time, using whatever you can, moving forward when you feel comfortable. It took me years to get from start to finish. I'm hoping I can save you time by handing you a nice path forward.

You'll have to start at ground level. I believe clearing your table and having room to breathe is key to deciding what the heck you want to do with your life. It's kind of like Maslow's Hierarchy of needs. It's hard to imagine fulfillment with a python around your neck.

I designed this to be somewhat inclusive, not too wordy (as best as I could) and revisitable. I suggest you come back and keep reviewing here.

Contents

Recommended Reading

My system is ultimately based on reading Getting Things Done, all the way back in 2018. That first read significantly changed how I go about my life, but it's been building for years and years. To keep it brief, here's how I'd boil down reading and why. These are generally shorter reads with high impact. I don't want you to drown in books. Read more if you want or must, but if I could only hand someone five books, these would be the five.

  1. Getting Things Done - David Allen: The "bible" for how I operate productivity wise. I reread this every year.
  2. The 4-Hour Workweek - Tim Ferriss: The biggest takeaways are the automation bits. Also, I can't help but admit, I need more fear setting in my life, and the working out problems backwards, the first principles style thinking, is gold. Another yearly reread.
  3. Atomic Habits - James Clear: The crux of this is, small things add up, and you'll be surprised.
  4. Useful Not True - Derek Sivers: A left field pick that really makes you question things on a fundamental level. Once you've laid the ground work for working through your day, I think you should inspect how you interact with the world and think about life.
  5. Die with Zero - Bill Perkins: It was really hard to cut this list down, but I think this is a top read. Once we're on life direction thinking, this is the easiest book to make a big impact.

Todoist

This is the ultimate home for tasks, and it's the foundation of any habit building. It admittedly was my bread and butter. I was a top 1% Todoist user until they stopped releasing yearly reviews. The idea of Todoist is to be your sort of, operation center. The ultimate workflow here involves operating from the Today view, filters, and a weekly review for maintenance. If you only implement one thing, this would likely give you the biggest bang for your buck.

We should discuss a little "task philosophy" first. The goal of this system is to:

  1. Make you okay with what you aren't doing
  2. Give you peace of mind (not constantly stressed about remembering things)
  3. Give you a general work flow to get more done when you decide to act
  4. Give you access to the things you have to do when you're in the relevant context

With that in mind, let's go.

First, go make an account at Todoist. After you have started, you'll land on an empty page of sorts. Now, this is a somewhat lengthy process, but I can assure you, it only gets easier from here. You have to fill the Todoist up. This is what we'll call capture mode. Before you go further, know I'll rely on premium features. Personally, this has been worth it for me. I didn't want you to get hours in and be gated by premium.

In practice, you capture and sort all the time. Since you're getting started, you need a dedicated capture phase here. Now, just start typing things that are on your mind. Don't worry, as we'll sort this out later. No project is too big or too small.

Some ideas to get you started, think of:

  • Things you've started but not completed
  • Things you need to start soon
  • Commitments/promises (think, I have a dinner next Friday or this thing is due at work on Thursday)
  • People you need to contact (email, phone, in person, etc.)
  • Things you need to read or review
  • Admin tasks to handle (finances, doctors, etc.)
  • Travel you want to do
  • Things you're waiting on from others
  • Media you want to consume
  • Tasks or items related to your hobbies
  • Errands you need to run
  • Habits you want to keep

We'll need to discuss, the 2 minute rule. Ideally, if you can see something through to completion in 2 minutes or less, you should just do it now and save yourself the administrative overhead. For now, leave all of that here and just know it's a future suggestion for capturing but not during this initial capture phase. We don't want you running around in circles right now.

Now that you've gotten your tasks out of your head, take a breather and a break. This likely took an hour or more if you did it thoroughly. Even if you missed some things, some progress is better than none, and you'll get to full capture with more practice.

Let's sort these into areas. These should somewhat jump out at you as you're perusing through these categories. My areas are:

  • Responsibilities
  • Work
  • Hobbies/Interests
  • Self Improvement
  • House
  • Relationships

Ultimately, all of my tasks could go there. I ended up giving my wife her own section outside of Relationships. To reflect these, I suggest you make new projects (Todoist's term) and color code them. I would have the overarching areas there, then, I would have subareas under each. I'll take Responsibilities as an approach.

Responsibilities:

  • Responsibilities
  • Responsibilities Someday/Maybe
  • Responsibilities Icebox (the Icebox is where tasks you're wanting to do but waiting on others go)

If you need to further subdivide the areas, feel free. It's especially difficult when Todoist limits you at 300 tasks per project (area).

Next, we will develop tags. These are important for your day to day actioning. Tags should be context based, although you can get a little more detailed with that. Here's some ideas for tags:

  • @computer - Things I can only do at a computer
  • @digital - Things I can do on a computer or on my phone
  • @home - Things I can only do when I'm home
  • @errand - Things I can only do when I'm outside the home
  • @next - The most important tag of all, your next action for a given project
  • @waiting - This shows you're waiting on someone else, usually attached to a specific next action. It's like extra coverage.
  • @work - Not mine, but it's something you can do when you're at the office only
  • @quick - A task that'll take 15 minutes or less to close out

Now, for each of the items you've laid out, we're going to have to clarify a few things.

  1. What's the end goal of this? With that in mind, we can then shape everything around this. Most people's systems fail because of two reasons, lack of clarity or priority. Getting really clear on what you're after is key. (putting Mom down doesn't mean much but Call Mom to catch up on life does)
  2. Are you responsible for it? If not, you should put a task to follow up as a subtask, and then icebox it.
  3. Is this something you want to do within the next year (or some other predefined timeframe)? If not, it should go into your Someday/Maybe list for that area.
  4. If you are responsible, what's the next action? This is the most important question you can ask. (Remember: Sometimes you just don't have information. Research XYZ is a common action of mine. Use it!)
  5. Next, work through what all the actions you can foresee to reach the final desired goal of the project.
  6. As you go through adding the actions, tag them with the appropriate tag (@next, @computer, @errand, etc.). Remember, a project should only have one next action (you can only do one thing).

Repeat the above process for everything in your inbox. Take as many breaks as you need.

THE DATE IS SACRED - A point worth repeating. This is the second reason people's task systems tend to fail, priority. When items have a date, that doesn't mean that's a desire to do it that day. The date is sacred. You only put dates on things that need done THAT DAY. Habits also take this by your cadence (everyday, every Wednesday, etc.). This will be extremely important when it comes time to operate out of your system.

Now, here's where the fun begins, operation!

To put it simply, operate out of the Today view. This should be your go to. Ideally, you're covering anything and everything due that day before you move on. Sometimes, you can't do something (like nightly routines or schedules) or just don't have the capacity or context to do it. Given that, you would then move to your filters.

Filter suggestions:

  • @next & !@waiting - The easiest, simplest one. If you don't have many projects, operating from the next filter is perfectly fine. This excludes things you're "waiting for"
  • @next & @CONTEXT - This is helpful when you're at any given context and want to check what you can do. I'd do this for every context filter.
  • @waiting - This is useful in your weekly review, to see if you let any waiting items lapse

Speaking of, upkeep is extremely important to not let these systems fall. It requires a few things from you:

  1. When you have something to do cross your mind, get it into your system as quick as you can. An example: You go to the garage, realize you just took the last AA batteries, you write it on your list.
  2. Weekly you should
    • Empty your head: Write down everything much like a mini version of the big capture from before
    • Upkeep your next actions: See if any next actions went stale or are done
    • Review your Someday/Maybe list: Ask if there are any items you'd now like to action on. Move them to the projects list.
    • Review your Projects list: Ask what the next action for every project is, and see if any newly arrived actions to take to see it to completion

Finally, iterate. Your first solution will not be your forever solution. It's okay to make changes as you see fit.

Sheets

These next few sections are much shorter as we've already laid the bulk of the work out for ourselves. This is one level higher than the previous. Todoist has you get ready to action on the day to day and keep your commitments. Our sheets setup will help you review more and determine how you want to spend your time. This allowed me to really nail down where my time went and further focus what I do in my next actions.

The template is fairly simple. I kept a timesheet for every day that I programmatically copied and sorted in my Google Drive. For this, all you'll need is a Google account.

  1. Go to Drive
  2. Create a Time Management folder
  3. Create a templates folder
  4. Create a folder for the given year
  5. Within the year folder create this or all months remaining
  6. Within the templates folder create a sheets file named something like timesheet_template

The Template:

  1. A column of time stamps in whatever granularity you want (I like 15 minutes).
  2. A category column - optional (mine are like Work, Free Time, Sleep, Personal Care, Responsibilities, Friends, Family, Commute, Wife)
  3. A notes column, to detail what you've done
  4. On the right, a sort of summary section - Again optional but very handy
  5. In the summary section, you're going to want to use a SUMIF where the list is a list of all of your categories and then the cell with the SUMIF formula is beside it to enumerate, summing over the range of your category column from step 2.

Now, I kept 7 of these copies, that way it made moving them out for every week easier.

Once you've done that, copy the appropriate amount for the remaining week into your main Time Management folder. This is where you'd go to get the latest logs.

Now, everyday, just simply do your best to log where your time went. Like any skill, it gets easier and easier, and like the Todoist adoption, you'll know what tweaks you need to make as you go on.

As for the weekly review, I had a section similar to the summary section but summed over several rows. At the end of a given week, I would paste in my data. Simply do this alongside your weekly review of Todoist. If you're interested in these templates, give me a shout via the contact page, and I'll send them over or try to help you out.

Obsidian

Obsidian is the final frontier. This is where my daily notes, weekly sprints, and monthly sprints lived, as well as the entirety of my second brain. For these purposes, we'll just go over Obsidian and the first three uses. You should arrive here much like before, once you're comfortable with the previous level (or just aren't interested in it in this case). I'm not going to give you as much instruction here. I will just recount what I have done for you to draw inspiration from.

Setup is extremely easy. Personally, I did SyncThing to sync and the like, but if you're tech averse, just buy Obsidian pro for their syncing capability. Otherwise, you can probably solve it yourself. I won't belabor that point.

The big thing you get from Obsidian is a way to edit these files called markdown files. Think of them as just sheets of fancy notebook paper that last nearly forever (since they're digital files). Templates is also the other big gain here, but in a way, the world is your oyster.

First, the Daily Note. This is the bulk of the benefit. There is a templates plugin. I suggest you setup the daily note to have the date as the name, filed away in some folder with your daily notes. It's that simple. Ideally you can go back and forth between days. Now, you simply write what you want to write in these. It's almost all iteration from the beginning here. If you notice constantly needing or wanting to write something down, use "#" or "##" of any number, making a heading for it, and put that into your template. I had work, personal, health (carried me through anorexia recovery).

Second, we're going to shift to monthly, which is a little weird. Now, not to get too detailed, but I divided my life into 9 areas, identical to the ones you see on my home page. Mine are:

  • Relationships
  • Hobbies
  • Business
  • Fitness/Health
  • Life Direction
  • Productivity
  • Lodge
  • Responsibilities
  • Learning

I then asked myself what would I do for the next 4 weeks in these various areas. You can go a step further and prioritize them down to 2 or 3 to work on in a given month. Then, I laid out what I'd like to do in those areas, made those projects (tasks) in Todoist, put them through the Todoist pipeline, and TADA!

Finally, weekly sprints are similar to monthly sprints, with their own templates and the like. I pulled down what I could conceivably do that week, in my review, into the weekly sprints. This kept me moving forward towards bigger goals but having a manageable workload.

I also used this as a second brain. In short, everything got written down here that I could. I would write on interests, agendas with people, hobbies, anything. I'm going to leave you to imagine how to use this other than what I detailed above.

Beyond

AI integration is probably the biggest thing I've ever done, and it's well outside the scope of this already lengthy post. I've actually recently just made my own "Operating System" that smooths out the edges of the above solutions and keeps them in one nifty place for me. This means I have since left Todoist, Sheets, and Obsidian behind. That is DEFINITELY well out of the scope of this blog post though. I used this system for years and could easily and gladly go back. It was for a tiny margin and fun that I built out my current system (which still doesn't measure up in some ways). Anyway, I hope you enjoyed, and if you have any questions, please send them my way.

I would be remiss if I didn't mention I do coaching for this very thing. If you're interested, send me an email, and I'll put you on the waitlist. I'm hoping to open up two more slots in the next couple of months. If you're reading this and you see Consulting or Coaching in the navigation at the top of the page, that's where you'd go. Otherwise just hit the summon me button on the home page.

Josh

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