Organising A Disorganised Mind

Actionable tips for bringing order to chaos

A few years ago Anthony Bourdain, rock-star chef turned travel documentarian, passed away. I’ve recently been watching some of his shows and a particular quote struck a chord with me:

“I understand there’s a guy inside me who wants to lay in bed, smoke weed all day, and watch cartoons and old movies. My whole life is a series of stratagems to avoid, and outwit, that guy”

The vices are different, but you betcha I can identify with the feeling behind them — the desire to procrastinate on what you know you need to do is innately tempestuous in a world of instant gratification. Those that have worked with me, at least over the past couple of years, would probably be surprised to hear that. I project, at least I think I do, that I have my shit together and my life organised.

Beneath the surface, a delicate network of systems and processes keep chaos in order and life in balance. If one were to be removed, the house of cards inevitably fall. I’d wager that many others feel the same. In the days of productivity theatre many project that they’re born hustlers when they’d rather be kicking back with their mates, and it’s systems that help them achieve.

Here are the stratagems that I’ve found to be working for me, so far, that might help you too.

Conduct a Weekly Review

The first thing I do on a Monday morning, without fail, is conduct a weekly review. It’s sacrosanct. In this time I clean up my Inbox, Calendar, Evernote, and Google Drive before reviewing how I’m tracking to goals and finally set out my tasks for the week. It usually takes me about an hour, but I find it’s a worthwhile investment to start the week with a clean slate and a clear plan for the week that pays dividends throughout.

Tiago Forte details a solid process here.

Set Priorities and Goals — Quarterly

Each quarter, I’ll set personal OKRs on software called Weekdone. If you need a primer on OKRs, here’s a good start. They’re not for everyone, but a system so you know what your goals and priorities are for the medium-term is critical.

Looking upwards, these should align with the wider business strategy and you should be able to see a clear connection between how achieving your goals will contribute to the wider business. Looking downwards, they should feed into your weekly and daily plans. I find a quarterly cadence works for me, so I set them with my manager quarterly, review them weekly as part of the Weekly Review, and they form the framework for my Task Management process.

Task Management — Weekly & Day to Day

I marvel at folk who can keep their todo list in their head or on scraps of paper. For me, I prefer to use a digital tool to help juggle multiple projects across teams with competing deadlines. I use Asana simply due to habit, but it’s really a matter of personal preference.

Each quarter, I’ll set up a new Weekly Planner project with different sections based on my quarterly OKRs. This becomes the command centre for my weekly planning. I’ll list tasks that help achieve each OKR under the relevant section. Then, at the start of each week as part of my Weekly Review, I’ll go through the list and assign myself any tasks that I want to complete that week.

Each day generally has a theme for me — Mondays are for Team and Product, Tuesdays are for New Business etc — depending on what my OKRs are for the quarter. This helps me stay in the right frame of mind for the type of tasks I’ll do on each of these days.

So now I have themed days and a list of tasks. I timebox each task, estimating how long it will take to complete, and schedule them based on the priority or theme.

Track Time

This is a new one that I’ve been trailing during the pandemic.

Working from home, I found myself getting frustrated at the end of the day, not knowing where the time had gone. Following a recommendation from a friend I’ve been using an app called Clockify to track my time, categorised against different tags and projects. It’s helped to ensure I’m spending time on projects and areas that matter.

A second order effect has been that it’s made me more accountable for my time. Interestingly, the average person only spends 3 hours productively in a standard working day. I find I’m leaking less time away with distractive tasks or messing about because I only log time whilst focusing on a task, and it’s a little embarrassing if your productive hours don’t stack up at the end of the day.

I also hate the fact that I like that this motivates me, because now I’m a slave to a tiny little clock that’s keeping me on task. I feel like I’m working in an oppressive warehouse environment where I’m penalised for taking bathroom breaks. I’ve imposed oppression, invaded privacy and enacted corporate overreach on myself. Weird.

Remove All Possibility Of Distractions

The most powerful change in this list is also the most simple. It may seem drastic, but turning off as many notifications as possible prevents context switching (jumping from task to task), helps sustain focus and perform deep work. One study even finds that we spend only 3 minutes on average on a task before switching to another. Turn off Email, Slack, Social Media, Teams notifications on your computer, set your phone to ‘Do Not Disturb’ and focus on the task at hand. I then either set time aside to go through these or quickly triage between meetings/calls.

As a bonus, my team knows how I work and that if they have something urgent (and few communications are truly urgent) they should ring me twice to break the ‘Do Not Disturb’ and know that if they do, I’ll drop everything to help.

Collate Content For Reading Later

The internet is a bottomless pit of content. Your attention is a scarce resource and businesses monetise your attention for their profit. Every headline you see and newsletter you receive is optimised to claim a slice of your limited attention. With this endless stream of information and interruptions it’s easy to end up context switching and losing focus to read an article that’s dropped in your inbox.

I use a combination of Pocket, a read-it-later app/extension, and Unroll.me, a service that rolls up all of your newsletters into one daily email rather than having your inbox peppered with enticing content throughout the day. Think of it as gorging at an all you can eat buffet with servers constantly approaching your table with gluttonous treats. It’s easy to say yes to if the option is right in front of you. Remove that tempation.

This is not to say that all content should be ignored, rather that it’s beneficial to have a system in place that encourages you to be selective with the content you consume and when you consume it.

Maintain Inbox ‘Close To’ Zero

There are two types of people in this world — inbox zero, and inbox 5,000. I’m firmly in the camp of the former, but that doesn’t mean I spend my days swatting away emails as they come in. I’m a simple man, so I have a simple system. When I open my inbox, usually 2–3 times per day, I do one of three things:

• Reply Now: if I can reply within two minutes and want to, I do it there and then.
• Reply Later: if it’s an email that requires any thought beyond that 2 minutes, I forward it to my task list (Asana) to be scheduled as part of general task management. I then slot it in based on it’s priority versus any other task in there.
• Reply Never: I have a pretty good sense of whether I want to respond to an email or not. If I don’t, I simply archive and forget about it. Nothing more, nothing less.

Know Thyself

Know when you work best, and build your schedule around this.

Life might get in the way, particularly if you’re working across timezones or have family commitments, but having a sense of when you do your best work allows you to protect this time for your most challenging tasks.

This also requires organisations to support flexible working and trust their teams to be the best arbiter of their own productivity and performance. It’s worthy of a whole topic itself, but this principle can be applied to building a team of complementary skillsets and drivers so that each person’s projects and tasks give them energy rather than drain their energy.

Ringfence time for curiosity

I’ve found that setting time aside to simply think is beneficial.

I’ll have a key prevailing problem in mind that I want to work on during the week, be it work or personal, and consciously carve out time to think on it and hopefully solve it. Throughout the week I’ll take notes if I have any particularly illuminating thoughts that would help me solve the problem.

Come the weekend I’ll either grab a coffee, or preferably a beer, and allow my mind to play with the problem. Sometimes a solution comes to me, sometimes it doesn’t, but going through the process is never fruitless — it usually clarifies my own thoughts or gives me a base to work from and seek help from others far smarter than me.

That being said, sometimes you’ll start pulling at a thread and feel like you’re unravelling a ball of string. If that happens, do everything you can to keep pulling at thread to see where it leads. Don’t stop if your mind is flowing.

Ideas are fleeting — if you have a random one whilst out running it’s best to stop immediately and write it down. Conversely, if you’ve hit a wall just park it and come back later.

Final Thoughts

This may seem like a time-consuming network of different tools and processes just to keep me from spiralling out of control, but it’s what works from me. They’ve all become habits now and take no time at all to complete, and any time is an investment in getting stuff done and being happier.

It may sound like I keep myself in a straitjacket in order to get things done, but it’s what works for me and I ensure I build room for free thinking, learning, and innovation into my planning. These processes actually free up time to dedicate to these important areas. It’s systems, not goals, that lead to best outcomes.

If you don’t manage the constraints on your time, the constraints will manage you.

PS: Part of the reason I’m beginning to write and publish is to get feedback on ideas, expand my thinking, improve my writing, and even meet new people. Well, that and to avoid losing 40 dollars (below). I’d love to hear your thoughts on this topic and my virtual door is always open! You can find me on Twitter or email me.

https://twitter.com/ChrisJCastle/status/1258487916042637314

Quite honestly, I’m not sure where this writing experiment will go, but if you want to follow along drop your email here and I’ll let you know when I’m sharing ideas again.