So to start out, this is my current set of tools and processes to try and stay organised in my life. I have WAY too many balls to juggle with, and there are occasions when a ball gets dropped, so I thought I’d share what I do, and why, and see whether there’s anything useful folks can throw in my direction to help me drop things less.

What do I need to juggle?

As an Engineering Manager for a cross-functional team, in a start-up where the future is always changing, and where many systems are integrated with systems owned by other teams I find myself needing to juggle:

  • Leading a cross-functional engineering team
    • Career growth and engagement for all my folks
    • Company, People and Project OKRs and performance
  • A bazillion parallel, cross-team projects and initiatives
  • Being involved in any/all questions and issues with the product
  • A working week 80% in meetings and needing to trace things between meetings
  • Prioritisation and scheduling of work items
  • Ideation and driving of team initiatives to collaborate, communicate and work more efficiently
  • Research of new tooling, processes, ideas

In addition to the “day job” I am a homeowner, father and husband, and with that comes a metric tonne of additional projects, plans, responsibilities and things that need tackling when I’m not at the keyboard.

Task Management

The entire window of Things3 project and task management software, software by Cultured Code.

I’ve used a lot(!) of task management tools in the past, and a few different processes too, but right now I’m using the GTD (Getting Things Done) method of task organisation, using @culturedcode Things3 app on MacOS, iOS and my Apple watch.

I have several Areas (groups of projects based on different responsibilities):

  1. Ada Health (the day job)
  2. Career
  3. Personal
  4. Someday

Within Areas I have specific Projects (Goal-based outcomes that are supported by specific Tasks):

  1. Ada Health
    1. TEMPLATE (a default template to duplicate for new Ada projects as they arise)
    2. Me
    3. Mobile Team
    4. Project 1 (name redacted)
    5. Project 2 (name redacted)
    6. etc
  2. Career
    1. General
    2. Personal Book of Positivity
    3. Leadership
    4. Reading
    5. Mental Health
    6. Blogging
    7. Speaking
    8. Writing
    9. etc
  3. Personal
    1. Family
    2. Garden
    3. Home
    4. General
    5. Finance
    6. Hobbies
    7. Errands
    8. etc

Within each Project I have relevant Headers for the type of project it is, and under the Headers all the Tasks live. An example might be:

An example Project in the software Things3 project and task management software by Cultured Code.

  • Ada Health
    • Mobile Team
      • [To Do]
        • Discussion on tracking DORA Metrics
        • Share talk on Progress over Perfection
        • Remind team to schedule company party dates
      • [In Progress]
        • Schedule Threat Modelling for Project 1

The great thing about Things3 as a tool is that the different timeframes are filtered automatically, so “Today” shows me a great view with all of the Projects that have a task scheduled for Today and then the specific talk within the Project.

Prioritisation

The Tags dialogue of Things3 project and task management software, software by Cultured Code. Tags shown are the Eat a Frog and Eisenhower Matrix task management methods.

To help with Prioritisation, I use several methods:

  1. If the task has an absolute Deadline (must be done by…) I assign it that date and I assign a When date (would like to do this on…) to give myself time to complete it
  2. I use the Eisenhower Matrix as nested Tags to help prioritise unscheduled tasks
  3. I add an “Eat That Frog” tag for the horrible tasks

Notes

For Notes (e.g. Meetings) I used @RoamResearch for ages with its automatic Backlinks functionality and that worked great, but the monthly cost was a turn-off.

Recently I started to trial @obsdmd which is similar, but stores everything as flat .md files which makes for far better formatting than a bazillion nested line items, but it’s less useful in terms of backlinking and being able to see all times that a specific link was used. For example, if I want to click on the “Team - Mobile” link, Roam shows all times I used the link and the content of the page it was linked on, which gives me context. Obsidian not so much (that I can see).

I’ve also started to experiment with using Things3 itself for notes on specific one-off tasks, for example this blog post is a Things3 task I have in my Career (area) > Blogging (project) > Drafts (heading) > How to Juggle (and drop only a few balls!) (task) and I’m editing the blog post directly as markdown in the task Notes area, ready to copy and paste to my blog.

TL;DR

I have a reasonably dialled-in way to keep track of a manic life, but it’s not quite perfect as I’d love to have everything in a single place.

What do you do to keep track of a manic life and stop dropping one of the many balls you’re juggling?