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:
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.
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.
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.
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 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.
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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.
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
Calendar: Google Calendar via Fantastical (iOS, Mac)
Important reminders: Due (iOS)
Email: Gmail + G suite
Jack of many daily trades: Airtable (Spreadsheet meets database meets my kind of thing)
Project and Focus area list (paired with Omnifocus)
“Comms” shortcut (personal email, work email, slack)
“Do” shortcut (Omnifocus shortcuts)
Information Sharing: Slack, iMessage
Shared Family Lists: iOS Reminders
Exercise: Apple watch workouts and / or Fitbit Coach
High learning (personal development / high learning)
Leisure (History, Biography, Fiction)
Journal: paper and pen
Habits I keep up almost every week (I slip sometimes):
Review “living” document
Tools to support the weekly habits and other reflection
Trackers: Google Sheets
Reflection docs: Ulysses (iOS + Mac)
Craig’s “living” document
Backlog boards: Trello (Planned move to airtable)
GTD “Mindsweep” checklist: Bear (iOS, Mac)
Habits I schedule every 3ish months:
Tools to support seasonal habits:
Ulysses (Mac, iPadOS)
Reflection private GitHub repository
Habits for once a year, for me typically around the new calendar year
Tools to support yearly habits:
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.
A brief list of the things that have most influenced what I do:
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