The zen of keeping lists

It was one of those sleepless nights, when my brain turned against me, yelling demands: do this! don’t forget that! Chucking piles of things at me to do, to remember, to forget, adding to the perpetual To-Do list of my life, ruining my hopes of a dreamless night.

I should have gotten my ass out of bed to write it down. But even that gets complicated. My attempt at being organized quickly turns into a jumbled mess of contextless half-sentences written on the back of PG&E bills. So along with the soul crushing, incessant gathering of things to do to simply survive, I had one more thing to add: “Think of system for organizing To Do’s”.

I love list

The way I see it, there are two kinds of people in this world: list people and non-list people. List people get that little endorphin kick from checking the “done” box, fancy themselves doers, know how to prioritize, and are generally pretty type-A. I’m a super-list person. I don’t know any non-list people.

I work for a company that basically sells ways for people to make lists. I have every productivity app on the planet at my disposal. And I have lists in all of them.

But it all recently came to a head. My organizational house of cards crumbled as my list-lines started to blur. I couldn’t find one of my lists when I needed it most. And when I got berated by my disobedient brain, I had nowhere to turn.

I got anxious, I had taken on more than I could chew, my BHAGs (big hairy audacious goals) were too big, and I didn’t know where to start. I was throwing caution to the wind, doing things I’d never written down, things that didn’t boil up to any major goal. I was…. disorganized.

That’s when I had a self-intervention to reassess my list-making strategy. That’s when I decided to take lists seriously. This is my story. Naturally, in a list.

#1 The mighty pie.

My list-making strategy starts with a pie.

Here’s the tldr; on my pie theory: Your time and brain-space is pie-shaped. Finite. It’s simply impossible to give something 100% of your time and attention. And every time you add in new interests, ideas or, quite frankly, people, something else has to give.

I use this visual to remind myself that saying yes to one thing, is saying no to something else. This was a powerful realization. I spent most of my 20s saying yes to every activity and opportunity that came my way. Yolo’ing, if you will. Which was fun, don’t get me wrong. But I can’t say I accomplished much. Without the pie, I wouldn’t have realized I was even making a choice.

The pie is about compromises and prioritization — two fundamental concepts when it comes to list keeping.

Big goals get their own slice

In reality, your pie probably doesn’t look like this. It’s probably more like 50% work, 40% family (especially if you have kids) and 10% sleep. So how do you make time for those BHAGs? You have to carve. Even just writing it down, acknowledging it’s existence, posting a motivational meme on Instagram, gives it validity in your pie-verse. If you don’t create space for it, no one else will.

My BHAG is to publish a novel. Writing a book takes a lot of work and even more brain-space. It required a lot of saying no to things, like trips and nights out with friends (cutting into the Fun slice). But if I didn’t give it a slice, it wouldn’t have made it to my list of lists, and never would have happened.

Your ideal pie

Drawing your ideal pie is tougher than it seems. You’ll find yourself asking big existential questions, like what do you want from this world. You’ll also realize how much space certain things take up without your permission. But this exercise should be empowering — by recognizing what your pie looks like, you can to take back ownership and redesign it the way you want. That’s where lists come into play.

#2 List of lists.

Next, break your big goals down into smaller achievable pieces. There’s a ton of research to support this concept. In fact, a new book just came out about this called Think Small by Owain Service and Rory Gallagher. You can hear a summary about it on the latest Freakonomics episode.

Key takeaway: be specific. That’s why lists are so important. You can’t just carve out random time to work out. You have get specific — Vinyasa class at 12pm.

I started to combine my life and career goals with my mundane, everyday shit, because, just like Hugh Grant says in About a Boy, it’s all just units of time. The difference between me and Hugh, however, is that I’m trying to make those units support The Mighty Pie. It doesn’t make sense for me to silo things like work and family life into separate places. We’re not living in the 1950s when people had a work and a home self. There’s just one pie.

Here’s all the parts that support the bigger slices, (or in agile speak, the epics that support the initiatives of my life):

The point of this exercise is two-fold: 1. to see how much stuff rolls up into the various slices, so I can break it down, prioritize, and execute on a plan 2. show the world my neurosis, while mapping these slices to tools, so I can get some god damn sleep.

#3 The list-keepers guide to list-keeping tools.

When I had my organization relapse, I had to take a step back from the weeds of Wunderlist and look at all the productivity tools I was using. What I found were redundancies, confusion, and inconsistencies. This made it virtually impossible to be organized, because there was no system.

To organize: to arrange by systematic planning and united effort

Keywords “systematic”, “planning”, “united effort”… me no have-y.

So, letting my true anal retentiveness shine, I made a system. Enjoy.

The Family & Life Maintenance Slice

Wunderlist. Google Docs, Spreadsheets & Calendar.

Wunderlist: This little app is deceivingly amazing. It’s literally a list keeper. You can share lists with people, like your husband for example. And when you finish something, you press that little endorphin-inducing checkbox, making you even more addicted to checking boxes… or maybe that’s just me.

We also share Google Docs & Spreadsheets for bigger stuff. We keep a shared budget, money goals, tax stuff, contracts, all in Google Docs. That’s where we planned our entire wedding and house remodel.

While I’d love to tell you that we are infinitely organized with little folders for every year full of tax stuff, all of our paperwork is digitized, photos are backed up, and we can use the search function to find everything from pink slips to mortgages. We’re not. But life goals, right?

Last, a shared Google Calendar for all our personal commitments, work trips, appointments, etc. If he arranges some dinner, he checks the calendar to see if I’m free and sends me an invite. If it’s not in the Cal, it doesn’t exist.

The Personal Goals Slice

Trello. Google Docs.

Now Confluence, which I gratuitously use at work, doesn’t work for my personal life. So I use Google Docs. And I integrate my documents into my Trello board. And my Trello board has my personal OKRs in it. That’s right, I have personal OKRs. But at work, I do the same thing with Confluence and JIRA (see The Work Slice).

OKRs are “Objectives and Key Results”. An example of a personal OKR: 
Objective: Build Platform 
Key Result: Gain readership, establish expertise in being a list-keeping-crazy person.

I use the columns on my Trello board for my OKRs. Then I break it down into milestones or actions from there.

The Work Slice

JIRA Software. Confluence. Trello.

You can read my articles on the Atlassian blog about productivity to see how I use JIRA and Confluence to manage projects. And now with Trello’s addition to the Atlassian family, a void in my work productivity has been filled that makes me straight up giddy.

I was using Evernote to organize my quarterly OKRs and daily tasks beneath them. With Trello, now I have a list on my board per OKR, so I’m reminded daily of my goals for the quarter. And then I have individual tasks listed beneath them. I do this because I mix personal tasks and goals with work tasks and goals. JIRA is dedicated to my teams work, our sprints and bigger projects. I simply don’t want to muck up our team board with “Write Medium post about lists” because it’s kind of a personal thing.

The Friends & Fun Slice

Doodle. Splitwise. Venmo.

Let’s start with Doodle. First: STOP EMAILING AND TEXTING ME TO FIND A DATE TO MEET UP. Seriously. Just stop it. Send a Doodle, a quick survey to find a time that everyone can meet up. I’m serious. Stop with the text threads, already.

Second, friend trips, nights out, all that jazz, put your expenses into Splitwise and Venmo each other what you owe. I just don’t even know how else you’d do those things.

#4 Tim Ferris says ‘Just say no!’

Let’s say you’ve applied this article to your life. Let’s say you climbed to the top of the pile of shit to do, peered at it through some pretty apps like Wunderlist or Trello. Then what?

This is the hard part, where discipline and deliberate practice come into play. Where you have to make choices between Sunday Funday at Deloris Park or working on your BHAG. Where you have to say no to make time for the stuff you really care about.

In agile, we have sprints. Where you take a few items from a prioritized list and commit to delivering those items in a 2-week time period. In life, the same can apply (but obviously in a less nerdy way).

If you remember nothing else from this melodrama about listing, heed this: Break down the hard stuff into small, achievable, specific pieces where you can check the “done” box. Drag those pieces to the top of the list. Do 1–3 a day. Lather, rinse, repeat.

And finally, sleep.

Read on to see how I tackled my personal OKRs and became my most productive self. >>