“The System” I Use to Try to Run My Life Better

My “system”1 is the label I use for the tools, documents, and habits that I rely on to help me live closer to the life I want to be living.

I've built this system over time to clearly understand and live up to what I am committed to.

I use it as a framework for my day to day, as well as to help me know when I should not commit to something new or when to clearly renegotiate what others expect from me when things change.

This is a longer post than I usually write, here's a table of contents to jump to different sections:

Edison Bulb

Background

All of this is for me personally. I do my best not to impose any of it on anyone else. But, I try to set clear boundaries and design everything so that it fits well with the “systems” of everyone around me, whether it’s my coworkers, my family, or society as a whole.

I leverage these things every day, every week, every “season”, and every year.

Day to day, the system is my “external brain” helping me with however much mental energy I have remaining at the moment and while I’m in different stages of auto pilot.

I make time for a series of regular check ins to review both the contents and the structure of the system and then adjust based on what’s working, what’s not, and what’s changed.

I use my system everywhere. I try to set it up so that I have all of the tools needed available on my phone and on whatever devices I’m using.

But, I also try to maintain the core of it in a way that can be followed with pen and paper if I choose to be more disconnected.

The Why

I maintain all of this because I want to live my life in the most intentional way I can.

For better and worse, I want to do more than I will ever be able to do. It’s how I’m built. And, like many people I’m a way more ambitious planner than a “doer” even though I get a lot done.

I don’t want to let myself down or make commitments I won’t be able to live up to.

I want to live a life full of great days— have a fulfilling family life and career, plus get to explore as many of the interests and joys of learning, exploration, community, and service as I can.

In order to be more effective at that I need to be thoughtful in a way that powers the intentionality I try to practice.

The challenge

I do sometimes struggle with the magnitude of information I’m trying to keep and organize. There’s always a danger of making this type of system unmanageable or that the work of managing it starts to crowd out the work it's meant to support.

I have to be mindful to not let things get too out of balance and that I’m spending more time making progress on the things I care about vs. tinkering with organizing the system itself.

The upside

It’s a humbling but very empowering thing to have a written down record of what I want to do, what I’m doing, what I’ve done, and a habit that forces contending with what I can realistically focus on.

I genuinely believe I’ve made more progress on the things that matter to me in every phase of my life, and have spent less time obsessing about the things I’m not getting done since I started making a serious effort at this.

I think some people feel like you have to choose between being a slave to a system like this vs. trying to "just be." I think that's a false choice, and that when it's properly balanced, the system is what helps me to "just be" and trust that I'm not forgetting something vs. getting lost in anxiety and frustration.

I could be fooling myself and wasting a bunch of time and energy, but it doesn’t feel that way. Your mileage may vary, but hopefully something I do can be remixed or swiped to benefit you.

My System

My goal is to write more in detail over time about how I leverage each of these pieces in more detail to share what I’ve learned, as well as explain my thinking as I add, change, and remove various pieces over time.

If there's something in here you want to know more about, reach out.

If you want to get updates as I write more in detail about these things, join my mailing list.

Daily (Working days)

Habits

If I keep all of these habits on a work day it’s a 13 out of 10 perfect day - I’ve probably been averaging around 6-8 out of 10 depending on what else is happening in life or with the job. But something usually slips and I try again the next day.

  • Morning track sleep in “rise and shine” tracker + time sleeping in past 6am
  • Deep working time in the mornings (personal work early morning, then pivot to the day job)
  • Mindfulness block between personal and job deep working time
  • Tread-desk working for about an hour
  • Try to get a high intensity exercise or cross training in during lunch time block
  • Audiobooks / high learning podcasts on commute in to the office
  • Meetings / collaboration in the afternoons
  • Shallow work / email in between meetings and collaboration
  • Lower energy / fun podcasts or music on the commute home
  • Medium energy tasks around the house or exercise / stretching if missed earlier
  • GTD style processing task inbox and “two minute rule” tasks
  • (Experimenting) “Done with work” ritual
  • (Experimenting) Journaling - short what happened that day, gratitude
  • Dinner with the family
  • Chores and cleanup
  • Low energy tasks + relaxation until bedtime
  • Daily questions
  • Leisure reading
  • Sleep (hopefully early enough to get 7+ hours)

Tools

Tools I use pretty much every day:

  • Primary task manager: Omnifocus (iOS, Mac)

    • Capture “inbox” items - thoughts, ideas, todos, and reminders as they come up

      • Omnifocus iOS and Mac inbox capture
      • “maildrop” email address into Omnifocus inbox
      • iOS reminders synced with Omnifocus inbox
      • Alexa to do list synced with Omnifocus via IFTTT
    • Routine ‘checklist’ tasks with recurring due dates
    • Less critical reminders with soft due dates
    • Store detailed tasks for projects
    • Tags to filter specific tasks for certain times / places

  • Calendar: Google Calendar via Fantastical (iOS, Mac)

    • Work calendar
    • Personal event calendar
    • Family shared calendar
    • “Planned time” calendar for time blocking

  • Important reminders: Due (iOS)

    • “Nag” repeating reminders for things that need to get done
    • Routine nudging reminders for when I get jogged out of “auto pilot”

  • Email: Gmail + G suite

    • Apple mail app for non work email (iOS)
    • Gmail app to keep work email separate on off hours
    • Gmail web app for all email on Mac

  • Jack of many daily trades: Airtable (Spreadsheet meets database meets my kind of thing)

    • “The One Thing” for family, work, side or hobby projects, etc.

    • Project and Focus area list (paired with Omnifocus)

      • Active projects
      • Ongoing - Focus area
      • “Incubating” projects
      • Ongoing - Longer term
      • Someday / Maybe
    • Meal Tracker
    • Exercise Tracker
    • Book Tracker

  • Automation: iOS Shortcuts + integromat

    • “Comms” shortcut (personal email, work email, slack)

      • (Planned) Time / action / location driven list selections

    • “Do” shortcut (Omnifocus shortcuts)

      • (Planned) Time / action / location list selections
    • Sleep tracker + sleep journal entry + integromat into google sheet
    • Daily questions entry + integromat into google sheet
    • “The one things” pop up
    • Random focus album
    • Home ETA
    • (nixed) “Mind like water” calendar aware shortcut (slack, email, Omnifocus)

  • Time tracking: Toggl + Timery (iOS)

    • Set up to track granularly to each type of project / routine task
    • (Planned) Changing to track broad categories of different types of time buckets with descriptions and tags to roll up
    • Auto starting “Sleeping in” timer via integromat
    • Driving time tracker


  • Information Sharing: Slack, iMessage

    • Work Group Chat
    • Professional Groups
    • Personal website and other automation / notifications
    • Social Groups

  • Shared Family Lists: iOS Reminders

    • Groceries
    • Warehouse Club
    • General

  • Exercise: Apple watch workouts and / or Fitbit Coach

    • workouts for walking / running
    • Fitbit coach for cross training

  • Mindfulness: Calm (iOS)

  • Books: Audible + Overcast (iOS) + Kindle

    • High learning (personal development / high learning)

      • Converted audible audiobooks via [Tuneskit](https://www.tuneskit.com/audio-converter/) to use in Overcast with smart speed
      • Kindle app on iOS for skimming / highlighting / highly visual books (usually checked out from library via libby app)

    • Leisure (History, Biography, Fiction)

      • [Kindle paperwhite](https://amzn.to/39otG1Y)


  • Music: Apple Music

  • Journal: paper and pen

    • Working on building / incorporating journaling as a habit
    • Gifted Moleskine
    • Studio Neat Mark One

Weekly

Habits

Habits I keep up almost every week (I slip sometimes):

  • “Weekly” Review

    • Make sure task inbox is fully processed
    • Organize / prioritize new projects
    • Review active projects

    • Review “living” document

    • Review 3 year vision
    • Review other reflection documents
    • (Every 2 - 4 weeks) Full project list / status review
    • (every 2 - 4 weeks) Fill out complete “mindsweep” checklist from GTD

  • Weekly Planning

    • Decide on / record “the one thing” entries for the week
    • Time block planned time calendar - deep work, exercise, etc
    • Look ahead on the calendar 4 weeks to be reminded of what's coming up and whether we need a weekend "off"

    • “Board time”

      • Write up daily schedule for the week on the whiteboard together
      • Plan meals

  • Budget Time

    • Reconcile all expenses with budget
    • Review together where we are vs. budget + what’s coming up expense wise

Tools

Tools to support the weekly habits and other reflection

  • Weekly whiteboard

    • Backed by google family calendar

  • Trackers: Google Sheets

    • Daily questions tracker
    • 1-10 “craziness” level expected vs. actual weekly tracker and mini journal entries

  • Reflection docs: Ulysses (iOS + Mac)

    • Craig’s “living” document

      • GTD horizons
      • Seasonal goals
      • Yearly themes

  • Backlog boards: Trello (Planned move to airtable)

    • house projects
    • website posts


  • GTD “Mindsweep” checklist: Bear (iOS, Mac)

    • (Planned) move to Omnifocus project template

Seasonally

Habits

Habits I schedule every 3ish months:

  • Seasonal Review

    • roughly 3 or 4 times a year
    • Review seasonal “where do you want to be” objectives on family, work, health, side projects and hobbies.
    • write down how I did
    • write out what I’m going to do as a result
    • Reflect on whether yearly themes, 3 year vision still apply

  • Seasonal Planning

    • Update / create new seasonal objectives and goals
    • 3-4 month calendar look ahead

Tools

Tools to support seasonal habits:

  • Ulysses (Mac, iPadOS)

    • Full focus markdown editing of “living” document, other reflection documents

    • Reflection private GitHub repository

      • Revision history for reflection documents

Yearly

Habits

Habits for once a year, for me typically around the new calendar year

  • Greek tradition of living how you want the rest of the year to go on new years day

  • Yearly review

    • review and write out what happened each month by looking at pictures, calendar
    • reflection ritual journal process
    • review / reflect on core values and if anything has evolved
    • read previous letters to the future

  • Yearly Planning

    • clarify and write down new yearly themes
    • clarify and update 3 year vision

  • Write new letter(s) to the following year for yourself and family

Tools

Tools to support yearly habits:

History

I started trying to go beyond assorted “to do” lists for my personal life around late 2014 when I bought Omnifocus after having heard about different aspects of Getting Things Done, mostly from listening to podcasts featuring Merlin Mann.

I’ve had a long love affair with Trello dating back to its earliest days thanks to following Joel Spolsky’s blog, but I never could quite get it to fit all the types of information and commitments I was trying to manage. I did try to make it work as the only tool for everything for a startup product team at Haven. It got messy.

In 2015 between jobs, I finally read David Allen’s book cover to cover and made a full honest go at implementing the full GTD system. While I don’t follow it completely to the letter now, that couple of weeks of trying to stick to it fully is still the core of most of this. Complete with many items living on my “Someday, maybe” list.

I’ve also adapted various other tools and approaches with all their warts and annoyances over time to try to make it more perfect for me. I hope someday I’ll get to the point where I’m not changing something significant very often.

Influences and inspiration

A brief list of the things that have most influenced what I do:

(This post contains affiliate links.)

  1. Ohhhh, the system.

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Published February 18, 2020.