Category: Remote Working

Holding Pattern: Combating Time Blindness with a custom daily planner

The curse of meetings

I’ve always hated meetings.

Whether in-person or remote – they always felt like an interruption; A distraction from what I was supposed to be doing. A disruption to productivity. One single 60 minute call could effectively de-rail an entire day.

Over time, I’ve adopted various strategies to limit the number of calls on my calendar, and deliberately batch them to mitigate the heavy cost of context-switching.

Such an aversion to calls can often be seen as laziness, but the truth is that not everybody operates in the same way, and I’ve come to realise that rather than a deficiency, the manner in which my brain perceives time, concentration, and obligations is just a bit different from others. (While not exactly the same, there’s a good article that touches on the idea of the Maker v. Manager schedule).

To some end this has been a blessing. For one thing, I have managed to avoid the trap that many mangers or senior people seem to fall into – with constant, back-to-back meetings attended out of a self-imposed sense of expectation, sucking up all of my available time.

However. Meetings are also unavoidable. And dare I say it, also sometimes beneficial. Especially if you work remotely – as it provides an opportunity to communicate ‘face to face’, rather than asynchronously over text – with all of the associated positives. As a result, I have continued to search and experiment with different ways to hopefully lessen the cognitive burden.

Time Blindness

Something I discovered was that my natural inclination is to fixate on any scheduled calls as the ‘big thing’ for that day, which in my mind then squeezes out the ability to do anything meaningful on either side. A kind of time blindness.

I tried different ways to combat this. For example: Tagging every item on my to do list with an estimated time of completion. The idea being that this would force my brain to realise that there was time to do other tasks, even if it felt there wasn’t. However, nothing really stuck.

The closest I came was with a physical daily planner. By laying out the ‘big things’ I had to do on paper, I could clearly visualise the amount of time left – which was always much more than expected.

As much as I love the tangibility of that… it is also inherently inflexible. Schedules change. Things move around. And you can’t easily change what has been commited to paper. So… I created my own digital version.

The Daily Planner

Holding Pattern is a bespoke daily planner that I created with Claude Co-Work.

It pulls in data from my personal and work calendars via Google oAuth, and allows me to augment these bigger ‘events’ with smaller additional daily ‘tasks’ that aren’t important enough to warrant their own calendar entries.

Similar to my old-school paper planner, the tool allows me to visualise each day in a way that clearly demonstrates how much time there actually is – rather than fixating on the one ‘big’ meeting or call.

Fake data!

Another feature I built-in was the ability to tag, and then check-off or track different events. This produces a list of completed tasks, demonstrating at a glance how much (or little) I have done over any given period, and providing a source for producing bi-weekly personal updates.

I need to do more, clearly.

There are definitely tools out there that do various bits of what this tool does. Calendars, To Do Lists, Planners – but none of them combined all of the features I wanted in a single place – without additional fluff or complexity.

Implementation

The planner took a day or so to build, and is hosted on GitHub Pages, served via a custom subdomain to make it easier to remember.

It relies fairly heavily on Google oAuth – both to connect to my calendars, but also to synchronise the additional ‘task’ and settings data to Google Drive. That, coupled with the bespoke personal nature means that it is unlikely to be much use off the shelf to anybody else. But… perhaps it will help to spark some ideas for folks out there who have similar struggles with scheduling. The project source is available on GitHub, should you want to poke about.

While there are certainly many major questions about the advent of AI technology, I can’t help but be impressed and excited about the potential it provides for individualised solutions like this.

07/05/2026
Sabbatical Reflections from 2019
As I prepare to head off on sabbatical later this year, I realise that while I posted my plans for my first sabatical, I didn’t actually share my reflections publicly on return. Instead, I posted on one of the many internal websites that we have at Automattic. Re-reading it recently, I thought that it was worth pulling this out onto my own blog for posterity. Below is what I wrote up back in June of 2019 for my colleagues, after going back to work (nb. that it has been slightly amended to remove references to a8c specifics).
Hello. I have returned from the sabbatical oasis. In many ways it feels pretty good to come back into fold, as no matter how great the sabbatical is, it still feels strange to be outside of the everyday Automattic community. That said, it is also a bit of a shock to the system; feeling akin to turning on a bright light in a room after you’ve been lying in the dark, so please bear with me over the next week or so while I catch up and readjust. It will take me a bit of time. 🙂

Before I went away, I was pretty disappointed that I would miss RightsCon in particular, as it is always a fairly motivational time. In retrospect I am glad I didn’t go, as it would almost definitely have limited what I got out of the block of time away.

As is customary, here is a recap with some details of what I got up to, as well as some general reflections, and thoughts about what coming back means. I had wondered about whether I should hold off on this until I had been back for a bit, but changed my mind. It is also a bit longer than I anticipated, so you have been warned!

Sabbatical observations

The first week I slept a lot, and felt guilty about it because I wasn’t doing very much, and didn’t want to waste the time. I realised though that my body was clearly just catching up on rest, and winding down to actually shut off properly. It doesn’t just happen instantly.

My life is usually so packed and rushed all the time that being able to just take the space to breathe and not rush things was great.

As part of that, I realised how many commitments I have outside of work, and how much time and energy they take up.

This also helped me realise what exactly I was spending my time on, and reassess things accordingly. In other words, cut down on commitments that were taking up a disproportionate amount of energy and space – as well as to make room for other things that I had been neglecting. I offloaded some responsibilities to other people, and didn’t feel the need to always stay up to date or in control of things as I usually would.

The first week I spent in Tokyo (which was just the second week of the sabbatical itself) was especially good. I was on my own, which I had been a bit apprehensive about, as I don’t really enjoy totally solo travel all that much. As it turned out, it was the perfect way to really begin the sabbatical properly. I would literally spend full days just walking for hours and hours, speaking to nobody, taking in everything. I didn’t have to be anywhere or do anything or look after anybody or answer to anyone. It felt like I had gone on some kind of silent retreat, and it was brilliant. Genuinely relaxed and free.

After three weeks things began to feel weird, as it was about as long as a significant holiday – but I knew I wasn’t going back any time soon. That caused some cognitive dissonance, which wasn’t completely unpleasant.

I realised that it was okay to have days where you don’t do much. You don’t need to be doing things constantly to make the best use of the time. That said…

I found myself breaking into a routine a couple of times – where I would just go to the gym, go to band practice, etc – and I didn’t want that to happen. So… I took the opportunity to say yes to things that I wouldn’t normally ever have time to do, or would put off (see more below).

What I actually got up to

Before I went away, I outlined the things I wanted to do over the three months. It really boiled down to allowing more time for the things that are important to me in life that I never usually get to focus on. Making music, reading, writing, travelling, and seeing friends. I deliberately kept them fairly broad to avoid tying myself into specific things and feeling bad if I didn’t get round to them. As it panned out, there were some things I didn’t get round to as much as I would have liked, but there was always something else that took its place. For example, I didn’t really play much guitar – but I did end up starting a new band and learning bass. I didn’t make much electronic music either, but I did rediscover a love for film photography, and developed a whole bunch. So it is swings and roundabouts. Either way, I felt like I made the most of the time I had as best as I could, which is what’s important.

Some specifics of what I did:

Spent a full month in Tokyo, which was amazing.

Bought a bunch of really nice cameras I had wanted for a long time, and learned lots of things about them.

Shot lots of pictures, mostly on film.

Started developing again, learned a bunch of new things, and processed 50 rolls in total. Also got a new scanner to replace mine… which was over 10 years old!

Shot on motion picture 500T film for the first time successfully (a bit more of a complicated chemical process than regular film).

Flew in a private plane across Scotland. Yes, I got to have a go at piloting, and no, I would not do it again. https://allmyfriendsarejpegs.com/2019/05/23/an-evening-in-the-sky/

Discovered lots of new music, and went to a lot of gigs – including a great multi-venue festival in Tokyo.

As well as continuing with my old band, I started a new one called Hog Wild, and spent a fair bit of time practicing with them, and writing some new tracks. An example here: https://soundcloud.com/hogwildband/matchbreaking-not-a-love-song

Did a few DJ sets, with varying levels of success. Lessons learned include always having a backup audio source, and checking that your laptop charger is actually plugged in properly.

Visited my parents in Canada, and spent the time touring vineyards, drinking cider, and lying in the sun with a book.

Went to the Islay whisky festival. Camped in the rain, and got a very nice exclusive bottle of Laphroaig. https://allmyfriendsarejpegs.com/2019/06/22/islay-whisky-festival-2019/

Posted and worked on a whole load of blogs (13 or thereabouts published)

Made time for some old friends I hadn’t seen in a long time, including a weekend down south. https://allmyfriendsarejpegs.com/2019/05/19/a-long-weekend-down-south/

Drove a friend’s band down to London to play a gig.

Read a whole pile of books (around 16), and enjoyed being able to just read for hours at a time because I enjoyed it again, as opposed to cramming it in for ten minutes before falling asleep at night.

Spent some time doing some legal academic work… including speaking on a panel in Edinburgh which was discussing defamation law reform in Scotland and meeting some friends from Twitter who were in town for a conference. I also finished off my second journal article, which I found out today has been accepted for publication by the European Intellectual Property Review.

In total I spent over half the time away from Glasgow, which I think is pretty good going. There are things I would like to keep up, and things I would like to start doing which I never did, and that’s actually okay. One of the points I had to keep reminding myself of was that the sabbatical isn’t the be all and end all – and not everything needs to be completed. There will be more time off in future!

Coming back

This is the trickiest part. Coming back from three months off is always going to be difficult, not least because of the catch up and changes to routine that are involved. Fears over how or where you will fit in are (apparently) normal, as are questions about whether you’ve fallen behind, and what the future will look like. I am personally very pleased and grateful that I’ve been able to take the time off at this point in my life; to spend it on existing, thinking, and creating. I am also glad to be able to come back to a community of people that I have a lot of respect for.

Over the next week or so I am going to take the time to gradually get back into the swing of things. Clearing out my e-mail inbox and pings will take a wee bit of time, but more importantly, I want to get a feeling for how things have moved on while I’ve been away, where the team is at, and where I can best contribute – including whether or not my role should shift to focus on different areas. I’m looking forward to the challenge.
19/01/2024
Remaining Productive with Things: The Pandemic Edition

Back in March I wrote about how I managed my time using the task manager app, ‘Things’. The gist of that post was that rather than struggling to remember or stay on top of all of the various activities you want to complete (no matter how small) – you chuck them all into Things, and free up the mental energy that would otherwise be expended in tracking them.

For a while, this approach worked really well, but over time I found that I was confronted every day with a huge list of tasks that needed completed, and there wasn’t any kind of tangible satisfaction in completing them, as I knew at midnight the next day’s tasks would appear on cue. Rather than helping to alleviate stress, Things began to contribute to the overwhelming pressure of everyday life, which had come sharply into focus thanks to national COVID lockdowns and varying restrictions. Things I was ment to enjoy (like making music) were reduced to yet another tickbox to be churned through.

What made the above worse was that there were recurring tasks that I wanted to complete, but often failed to find time for. I didn’t want to take them off my daily list, but I didn’t want them to have the same mental load as other tasks.

Taking inspiration from this blog post, I followed Andrea’s lead, and changed the way I approach task management with Things. Rather than having one large daily list of jobs to get through, I now have them separated into their respective categories. The tasks that I definitely want to complete that day come in at the top, under ‘Daily Tasks’, and I try to keep this to a manageable load, so that I can always clear them out. Other things that I want to get done, but don’t necessarily have to get done that specific day are then available for me to work through, based on how I feel/what energy I have that day.

How my Things to do list is organised now.

This new approach has made a huge difference to my relationship with the daily to do list. Rather than feeling like I am endlessly fighting a losing battle to keep ticking off checkboxes, I can now see at a glance exactly what tasks need to be done that day. By keeping those separate, deliberately chosen, and manageable, I no longer feel like the other bits and pieces that I want to do are a chore. If something isn’t in the Daily Tasks list – it can be done another day… and ironically, since adopting this method, I’ve gotten even more done than usual, because I don’t feel the same pressure to complete everything.

Pomodoro

One other thing that I have adopted which is worth mentioning is the Pomodoro technique. The general idea here is that you split up your time into chunks of about 20 minutes, and deliberately focus on a particular task for that period of time, before taking a break and either moving on to something else, or committing to another 20 minute period of focus.

This notion isn’t anything new. I am sure I’m not the only one who sat in maths and thought ‘Okay just get through the next five minutes and then it’ll be another five minutes after that’. Plenty of people have written about this extensively elsewhere… but it’s not an approach that I’ve ever really come to use in any disciplined way. Breaking up my tasks at work was always too difficult, and concentrating for 20 minutes to then have a break and return to the same tasks felt too artificially scheduled for my liking.

However… since I switched up my approach in Things, I’ve had success using the Pomodoro model for my own personal projects – particularly those that I want to get done but struggle to get the motivation to start. For example, I am currently learning Japanese, but sometimes (often) the prospect of firing up the flashcard app for an indeterminate amount of time seems like too much of a chore, and I put it off. Before I know it, I haven’t done it in days.

Now, I sit down and say – okay, I’ll just do it for 20 minutes just now, and then go off and do something else. Knowing that it’s such a short amount of time means I can focus much more than I normally would, and I have been rattling through tasks like never before. This also helps me work out just how much time I actually spend or need to spend on certain activities to complete them, and it can be much less than I expected.

We’ll see how this mutates and modifies as time goes on, but for now… this is the approach.

26/10/2020
Staying Productive with Things

More than productivity

I am a person that needs to have a bunch of different projects going on at any one time. Whether it’s making music, writing blogs, building weird keyboards, or restoring old iPods, if I don’t keep my mind busy, it quickly begins to turn in on itself. At the same time, my work involves managing a variety of disparate projects that can vary from day to day.

All of this has become increasingly difficult to keep track of over the years, and none of the various calendars, diaries or bits of software I tried really helped. However, about six months ago my colleague and friend Bryan convinced me to give an app called ‘Things’ a go, and it has pretty much transformed how I manage my time. As well as becoming far more productive, I have found that I am far less stressed out, and feel more in control. I had never appreciated just how significant the cognitive load of having to juggle so many tasks was, or how much anxiety I had internalised as a result. Now, I no longer worry about forgetting to do something, or lie awake at night unable to sleep while my brain organises the things I have to do the next day.

At the end of the day, Things is just a To Do list app, but it’s an especially pleasant one to use, with a really smart workflow. Rather than wasting what Bryan would call ‘brain cycles’ worrying about er, things, you let Things take care of them. In particular, it wasn’t until I found myself increasingly filled with despair about the unfolding COVID-19 pandemic that I realised just how invaluable Things had become for keeping my mind clear. Rather than allow myself to become consumed with the developing news cycle, I instead chose to rely on Things more, and focus on what I wanted to get done in the following days. While it seems trivial, this helped tremendously. So in this blog I wanted to share a bit about how I make use of Things, and what I’ve learned.

The Basics

Things is a beautifully designed to-do list app from Cultured Code which runs on both Mac and iOS. It doesn’t run on Windows, and (annoyingly) there is no web or Android version (though see this post for my workaround). The current version at the time of writing is Things 3. It is apparently based on the ‘Getting Things Done‘ methodology.

Boiled down, Things essentially just provides a very pleasant way to quickly create and manage tasks – the beauty of it though is the myriad of different ways that you can view and organise these. At its most simple, you have an Inbox where you can dump all sorts of to do items to be organised, and then categorise them into different subject matter areas or projects.

Tasks can be set to only appear on a specific ‘due date’ – presented in the ‘Today’ window. They can also be set to recur upon completion, or at set intervals.

For tasks that absolutely must be completed by a certain date, you can flag them up with a deadline.

Selecting an Area or Project on the left will display only the tasks that are associated with it, if you want to focus on something specifically.

If you have tasks that you want to get to, but they aren’t time specific, you can throw them in the ‘Anytime’ bucket… and for ideas that you want to explore at some point, they can be filed away under ‘Someday’ for when you get time. You can also tag any task to further organise them to whatever level of detail you want.

There are a bunch of other features as well which I won’t go into in any depth just now – such as the Logbook which keeps track of all of your completed tasks, the calendar integration so you see what appointments you have on any particular day, and the ‘Upcoming’ view which provides a longer term perspective of what’s on the horizon.

How I use Things: Workflow, Tips & Tricks

Everybody will use Things slightly differently, and I borrowed a lot of my approach from my sensei Bryan. However, here’s some of what I’ve found works:

Add everything – no matter how small – I literally add everything I need to remember to do as a task into Things. Whether that’s remembering to wash the dishes, or to chop carrots for dinner, I offload everything onto there so that I don’t need to think about it. At first this can seem pretty ridiculous, or like you are outsourcing your faculties to an app, but it frees up your mind to focus on other things that are more important. This also means that you have a mixture of things you enjoy as well as specific obligations – which helps to avoid dreading opening the app in the first place.

Make use of shortcuts – There are a bunch of useful shortcuts, the most important of which lets you very quickly add in To Do list items to your inbox while you are browsing the web, to be categorised later. Learn these, as the less friction you have in adding tasks or managing them, the easier and more natural it becomes – and the more you can focus on what you are doing at the time.

Only add things to your daily pile that you can actually achieve – It took me a while to realise that I would add all sorts of tasks to my daily list that I wanted to do, but which realistically I would never be able to get done. That ended up pretty demoralising, as I saw the same To Do items rolling over day after day, unchecked. Now, I only add things that I either have to get done, or which I have a reasonable shot at completing, and it has been far more effective.

Organise your tasks for the following day – Every night I look over the tasks I have for the next day, and organise them roughly by when I want to complete them, and ask myself what seems reasonable to do in one day. If it seems like there’s too much, I punt it to the following day. This ritual helps me organise my thoughts and get to sleep faster.

Set smaller goals, and be judicious with repeating tasks – It can be tempting to set a goal like ‘I will do one hour of Japanese study every day!’ and to add it in as a repeating task that appears on your list on the stroke of midnight. However, I found that this was actually counter-productive, as I began to just ignore these broad repeating tasks. Instead, I would manually set much more specific, one off tasks, like ‘Do 2 lessons on DuoLingo’ – which made them far easier to complete.

Use tags creatively – There are all sorts of cool ways you can make use of tags. For a practical example… I save lots of news articles to Pocket, but never actually get around to reading them. The same applies to YouTube videos. Now what I do is chuck them into Things, and tag them with the time they will take to complete – ’10m’ for example. Then, whenever I have a spare ten minutes and I’m not sure what to do – I can dip in and quickly find something to fill that time.

Separate out evening tasks – There’s no point having stuff you have to do after dinner wrapped up in the same list as everything else, and Things lets you specifically ring-fence tasks for the evening within a specific day. Make use of this!

Projects are useful! – I didn’t really utilise the Projects feature for ages, relying instead on individual tasks within Areas, but then I realised you could put Projects under Areas. Game changer. Now I use Projects a lot to manage groups of different tasks that add up to a larger goal, which is really useful.

Summary

…and that’s it. At first I didn’t really get what the big deal with Things was, and thought some of the practices were a bit bizarre and redundant, but I genuinely think that organising things in this way has made a huge difference to both my productivity, sense of achievement, and overall zen. It ain’t cheap, and they need to hurry up and just make an Android app already damnit, but I’m not sure what I would do without it at this point.

26/03/2020
Looking back at how to listen: A year of music
I’ve been using Last.fm – the tracking service to catalogue the music you listen to – since 2004. Since then, I have ‘scrobbled’ about 1,600 different artists, and just over 43,500 tracks.

To be honest, I don’t check in on Last.fm very often, preferring to let it just carry on doing its thing in the background – looking in every once in a while to see how things are getting on. I tend to have periods where I don’t listen to a whole lot of music, and there’s some useful information in there to help spot when that’s happening and do something about it. I can always look back and dig out some of the bands I haven’t listened to in ages, and try and rekindle some of the associated excitement again. I’m not a very good passive music listener… preferring to be more involved when I do.

A couple of months ago I realised that my music habits over the past couple of years have slipped pretty dramatically – going from 5,952 scrobbles in 2013, to 2,671 in 2014, and 2362 in 2015. The figure for this year is slightly higher than it would have been had I not realised and made a conscious effort to listen to more.

I think there’s a few reasons for the dip:
- Moving House – I always preferred listening to music through my amp + speakers combo than whilst wearing headphones. In my previous (shared) flat, the audio setup was used purely for those purposes whilst I was hanging out in my room. Now, it’s used as my main output – connected up to the TV. Because of that, it gets used far less for music, and I listen to a lot less as a result.
- Travelling – The past couple of years I’ve been travelling a lot. I have too much music to store on my phone, so rely on Spotify – but that tends to rule out listening to things whilst abroad with no data connection. I also don’t generally really like using my phone for music. I also discovered that the in-built music system wasn’t registering all the scrobbles that it should be…
- Work – Two years ago I went from working in an office where I would listen to music constantly during the day to working from home. Whilst this was great, it meant that I didn’t always need to block out what was going on around me, and ended up listening to music less as a result. In addition, if I needed some background noise, I would tend to opt for the TV.
- Not being involved – I used to be in a band, write for a music zine, and a whole lot more. I’d naturally come across music I loved and get excited about it. I don’t really do this at all anymore.
Now that I’ve worked this out, I’m going to actively make an effort to listen to more music. Here’s some of the things that should help make a difference:
- New bluetooth speaker – I always thought that bluetooth speakers sucked, and generally they do. After trying out a JBL Charge 2 though, and hearing how great the bass response was, I got one. It’s portable, and means that we can listen to music whilst travelling easier – or whilst in different rooms without headphones.
- New headphones – I got a pair of open backed Beyerdynamic headphones that have ultra soft ear cups on them. Coupled with a cheap FiiO mini amplifier, they sound incredible – and I can wear them for hours at a time. Listening to music on them is a pleasure, and means I find myself doing so far more often whilst working at home; concentrating better as well.
- Going to the gym – I stopped going to the gym when I moved flat, as there wasn’t a decently priced one nearby. One has opened up across the road, and I’ve started to go pretty frequently. The music they play in there is utter gash, so that means an hour of music 3 or 4 times a week that I wouldn’t have listened to before. I’m using Vox on iOS currently to make sure that it gets scrobbled properly.
- Finding new music – The times I’ve listened to loads of music in the past has always been when I’ve gotten passionate about it and explored different artists to get excited about. When I can’t think of what to listen to, I tend to not bother. This year I’m going to make more of an effort to explore related songs on Last.FM and become more involved than I have been for a while.
All the grizzly details of what I’m listening to can be found on my Last.FM profile here.
05/01/2016
One Year at Automattic

Today marks one year on since I officially started working at Automattic, and it’s something of a tradition for Automatticians (or a12s as we affectionately refer to each other) to write up an anniversary post. I say ‘officially’, as technically it’s been well over a year. Each employee goes through a trial period as a contractor first, which was then extended further in my case by the relatively long notice period required in the UK. For the purposes of this commemorative post though, we’ll just go with it being a year.

Initially I wasn’t sure I would write anything at all. Why should anybody else care about my work anniversary? The more I thought about it though, the more I realised just how much had changed in the past 12 months, and how crazy it was that I even got the job in the first place. As more than one wise colleague told me back when I was hired: the first 6 months are a bit like ‘walking on air’, and it isn’t till you’ve been around for a bit longer that you settle into things properly. It makes sense to pause and take stock, rather than continue to let things hurtle by.

A lot has happened in the past year.

The most visible thing (and annoying to everybody else who knows me probably) has been the amount of travel that I’ve been able to do. This is partly for work, and partly because of work; a result of the flexible schedules that we are incredibly lucky to enjoy.

I’ve been to San Francisco: the spiritual home for a lot of the online platforms we use today. The trip was both to meet colleagues, and also to check out the unbelievably cool WordPress.com HQ in person. I hadn’t seen my fiancee Grace in over a year, and Ingrid suggested I fly via Denver so we could be reunited for a week or so beforehand. Where else would do something like that?

I’ve also spent time in Hawaii with the forums squad…

Drank rum and swam with turtles in Barbados

Explored temples and had rooftop BBQs in Mexico

Met up with friends in LA, drank whisky and headed to the beach during a 9 hour layover

Was reunited with the city of Chicago for a tech conference

Got the chance to live in Greece for a bit

and visit my family in Amsterdam

As well as that, I got to spend time showing Grace Scotland. This included discovering parts that even I hadn’t been to before… like Islay, the home of whisky.

Fife…

Edinburgh…

Oban, Iona, and Staffa

And we spent a lot of time south of the border in England as well… going away with friends to cottages in the Lake District to eat cheese and drink wine.

or to take last minute trips to Liverpool to sort out the whole fankle that is the UK immigration process.

I even had the chance to play host in my home city of Glasgow, combining work with pleasure (though the two seem hard to distinguish nowadays).

Whilst the travel itself is amazing (and trust me, I know how lucky I am), it’s really the freedom that makes it possible in the first place that’s the most liberating part.

Without having to worry about budgeting my annual leave throughout the year, I can take time to go and visit friends or family – no matter where they are in the world. I can visit places that I would never have wanted to sacrifice my time off for before, because now I can always chuck my laptop in my bag and find a pub with WiFi to work from. This is especially true when it comes to discovering and re-discovering parts of my own country.

Then there’s personal life. I got engaged to a beautiful American girl almost two years ago, and it’s been a long and difficult process to finally get to be together. As you might imagine, moving away from her homeland to a strange place was difficult enough, but it would have been 100 times worse if we weren’t able to spend the amount of time together that we have, thanks to working remotely. We’ve been in the best possible position that we could have hoped for, thanks to getting a job with Automattic.

It’s not just the ‘where’ though, but the when as well.

Rather than meet the challenge of a small company spread out across the globe with more tightly controlled appointments, the opposite is true. There are no restrictions on the times I work at all, with the exception of a weekly team chat for an hour at a time… and even that’s up for negotiation.

My own schedule is… almost non-existent. Rather than squashing my time into a set frame five days a week, I spread out my hours and adapt to what feels right. Instead of forcing myself to sleep at 4am and having to get up three hours later to get ready to catch a bus, I wake when it feels natural. The removal of the pressure to be somewhere at a certain time (not to mention being presentable) has meant that for the first time in my life I actually sleep about 8 hours a night, rather than the 4 I always used to.

One of the consequences is that weekends are becoming less defined as time goes on. It’s common to not just forget what day it is, but also to lose connection with the feeling that that day should have. There’s no downer on a Monday, or excitement on a Friday, for example. Going back to work isn’t a chore, and Monday isn’t even really the start of a week any longer. Working when you are most productive means you might work 13 hours on a Thursday, 4 on a Friday, 5 on a Saturday, and 7 on a Sunday, so the whole structure of life begins to lose the meaning that it was previously infused with.

This doesn’t work for everybody, but it does for me.

For the past year, it’s felt like I’ve really lived, rather than just living to work.

Then there’s the actual work itself.

Every day I work with software that both myself and a large chunk of the web rely on for our websites. My team in particular fight to defend freedom of speech; protecting our users from censorship, and highlighting when companies try and abuse their position on the web. It’s something I’m very proud to be a part of.

To top it all off, I can count some incredibly smart and hard-working people both as co-workers and friends.

Something that has really hit home over the past year is that if you want to achieve something, you’re the one who has to make it happen. More than a platitude: you can’t sit around and expect things to drop into your lap, or put decisions off until you are 100% ready; you have to just go for it.

Here’s to many more years. If you’re like minded, there’s all sorts of cool open positions with Automattic here.

25/11/2014
How Alfred Changed (Ruined?) My Life

From day one when I started working at Automattic, there was a strong focus put on different tools and apps that would help out with our daily tasks. Everybody is a power user, with their own tips and tricks, which means there are plenty of different things to explore.

One of the tools that was used by a few people, and championed by my pal Bryan is Alfred (If you don’t use a Mac, sorry, you may as well stop reading now). At first I was suspicious. I installed the app, but was never all that convinced. It didn’t fit neatly into my existing workflows, and it felt more like a hinderance than a help. In the past couple of months though, Alfred has become indispensable… so much so that I find myself lost when I use other people’s Macs.

Note: Some of the functionality I am describing requires the PowerPack, which currently costs £17, but you can try out the core features for free. The PowerPack has definitely been worth it for me, but bear that in mind.

What is Alfred?

There are plenty of other articles online to explain exactly what Alfred is, so I’ll be brief.

Alfred is the ultimate quick controller tool for your Mac. It’s like TextExpander, OSX Spotlight, Clipboard manager, and multi-search toolbar all rolled into one… but even better than that.

You start by assigning a hotkey to bring up the Alfred search box. It looks something like this:

I experimented with a bunch of different key combinations until I settled on ⌘+K. This might seem like a weird choice, but it felt like the best option given the way my hands naturally sit on the keyboard.

This unassuming search box has the power to become the command centre for your whole Mac.

Web Searches

How many times do you search Google, Facebook, IMDB, Wikipedia, or anywhere else a day?

To borrow Bryan’s advice: Whenever you search a website, consider adding it as a custom search in Alfred.

This is what the screen looks like:

I have a whole pile of custom searches, but most of them are for work, so I’ve only shown those that will be common for most folk.

Setting these up is pretty straightforward, so I won’t go into details – instructions can be found on the Alfred site itself. What’s important is how it works. Say I want to search IMDB for a particular movie. I would call up the Alfred box with my hotkey, and then type IMDB, followed by the movie title. Like so:

Hit enter and I get taken straight to the search results, rather than having to go to imdb.com first. The same sort of setup can be used for almost any site that has search.

Snippets

One of the features I use most often is the ‘Snippets’ feature. This has two main functions: a clipboard manager, and a storage for commonly used pieces of text that you don’t want to have to type out over and over again. You can access this through the main Alfred box, but of course you can assign a specific hotkey if you use it frequently. For me, that’s ⌘+O.

If you are familiar with tools like TextExpander, you’ll find the concept familiar: you input all of your predefined texts into Alfred, and then you can recall them at will through the use of a short phrase. I used to use TE and really liked it, so was hesitant to move over to Alfred’s way of doing things. It seemed counter-intuitive to press a key combination to bring up a window and then type in the keyword for my predef, rather than just typing in the predef directly.

Whilst it takes a bit of getting used to, where Alfred really wins is its fuzzy search matching for predefs. Whilst before I would have to remember the exact phrase, in Alfred it will show you all of the similar responses. This means you can have far more variations than you could remember, and find them easily through the use of a common word. When dealing with DMCA takedown notices, I use the word DMCA in the title. Start typing one, and the list narrows down to the relevant ones. Combine this with the clipboard history (which you can set the retention duration for, or disable altogether), and you have everything you need for working in support at your fingertips.

What’s even cooler is that Alfred will remember the selections you make most frequently, and float them to the top of the list, which is a major time saver. This is something that applies for all of the app’s actions, and is difficult to explain just how helpful it is without trying it for yourself.

Workflows

Workflows are one of the more sophisticated parts of Alfred. Here, you can create complicated recipes that do all sorts of things (or use ones already created by other people).

Here are some examples of the sort of Workflows I have set up:

Launch Alfred Preferences – I am constantly modifying or updating the snippets I use in Alfred. As a result, I’ve set up a hotkey (⌘+;) to bring up the preferences panel. You can download this here.

Connect to VPN – I have a number of VPN services that I use to connect to different countries for testing and anonymity purposes. Rather than have to manually connect up to these through the Mac task bar, I have it set up so I can hit one key combination to connect to London, one to connect to the USA, one to Romania, and so on.

Shorten URL with bit.ly – By typing in ‘bit into the Alfred box, I can paste a URL and have it automatically shortened using the bit.ly service. What’s even cooler is that this works with your custom shorteners. In my case, it shortens using http://allmy.fr – which I own.

Control PopClip – PopClip is an awesome wee tool for the Mac that another colleague and friend Mark introduced me to. It pops up a whole host of configurable actions you can take on text when you select it. I wasn’t a big fan at first, as it was popping up at inappropriate times, but it did have a lot of potential to be really useful. I created a workflow to toggle PopClip on or off using a keyword, or to bring up the menu with a hotkey when you want it. You can download that here.

Check if a site is down – To check if a website is down globally, or if it’s just me experiencing problems, I type ‘down’, followed by the URL. Alfred checks with http://downforeveryone.com/, and displays the result.

Add a task or appointment to Things or Fantastical – Quickly add a new task or appointment to the Things task manager, or the Fantastical calendar app, rather than fire up the apps themselves.

Open apps with a hotkey or short phrase – e.g. typing ‘sn’ into the Alfred box to open Simplenote. (More detail on the hotkey part in a section below)

Search for and play songs from Spotify – Self explanatory. (#)

Randomise your MAC address – for when you need a new MAC address to bypass time restrictions on the WiFi in hotels/airports/cafes.

IP Address Check – Quickly check your internal and public facing IP addresses. I use this to confirm if I’m properly connected to a VPN or proxy.

Show Workflow Commands – Remembering these workflows is hard. This workflow creates an on-screen list of all the commands with details of what they do. Very handy!

There is a whole pile of different examples over on Packal.org, so that’s a good place to start if you are looking for inspiration.

1Password Integration

If you aren’t using a password manager yet, stop reading and go install one. Seriously. You remember a master password, and these applications both generate strong passwords as well as storing and filling them in on websites automatically.

I used to swear by LastPass, and was perfectly happy with it thank you very much. Then I discovered that Alfred integrates with 1Password.

As well as being able to trigger the 1Password application with a hotkey or phrase, I can search for stored logins from the Alfred box, hit Enter, and get taken straight to the website and automatically logged in.

This means you need to spend a bit of time tidying up your stored URLs to ensure that they are correctly set to the login page rather than the signup page, but it’s worth it. I’ve now completely switched over to 1Password as a result.

Hotkey Trickery

One of the more complicated tricks (in terms of setup) I’ve found with Alfred relates to the use of Hotkeys.

Hotkeys are awesome things. They let you fire up apps, or specific workflows without having to search for anything in the Alfred box. The problem is, a lot of the key combinations that are available are already used up by system commands in OSX.

A guy called Daniel Setzermann has come up with a novel solution to this. It essentially involves installing a couple of tools to re-map your Caps Lock key to the unusual key combination CMD + ALT + CTRL + SHIFT – aka the ‘Hyper Key’. This kills the use of your Caps Lock key, but really… when do you ever actually use that anyway? Never. That’s when. At least, you shouldn’t be. If you need to change text to all caps, you can always get a workflow to do that for you.

This takes a wee bit of time to set up, and even I was hesitant to go through the steps, but stick with it; it’s well worth the initial effort.

The beauty of this is that you can now set up really great hotkeys like CAPS + S to launch Spotify, or CAPS + C to launch Chrome, etc. Here’s an idea of what my workflow for this currently looks like, though I’m still adjusting it to find what combos stick best in my memory:

Daniel explains how to set this up really well on his site over here. (Scroll down a wee bit till you find the relevant bit)

But… this sounds awesome. Why has it ruined your life?

It is awesome. At first, I was reluctant. Changing habits and your engrained workflows is difficult, and I didn’t really get how Alfred would be all that useful at all, even despite the explanations of some really smart people.

Having stuck at it though, I don’t think I could live without Alfred (ok, maybe a slight exaggeration). Alfred is like the gateway drug to productivity.

One of the results of using Alfred more is that I’ve finally reduced the size of my dock, and hidden it completely (until I mouseover). I no longer need to launch things from the dock, and I can quickly see what’s open by Command Tabbing, so I’ve opened up a whole extra bit of screen real estate that I was previously chained to.

Whenever I use somebody else’s Mac, it’s a nightmare. It feels unbelievably clunky and old. I’ve switched from a personal approach based heavily on clicking and moving the mouse about to one that is primarily hotkey based. I haven’t even really scratched the surface of what’s possible in this post… and I’m still discovering new things every day. Alfred lets me launch things quickly and smoothly, to concentrate on what I’m actually meant to be doing. No more trying to remember where that particular network admin page is located… Alfred knows.

Alfred knows.

07/10/2014
Why Barbados? The Importance of Remote Worker Meetups

One of the defining things about working at Automattic for a lot of people is the meetups. We fairly regularly meet up in different parts of the world to get to know colleagues, work on projects, etc. The location can be anywhere from Cardiff to Hawaii, and one of the latest trips I went on saw us travel to Barbados. This naturally has led to a whole host of questions, not least the staff of the hotel who bemusedly asked: “you came to work on the BEACH?”

Below I respond to the usual queries that people have, which will hopefully mean they make a bit more sense.

Why do you need to meet up anyway? I thought you’re meant to work on the Internet

Working at ‘home’ (or on a train, at your friend’s house, a coffee shop, the pub, in a hotel, on a boat…), and the flexibility that it brings is amazing. The autonomy that we have allowing us to work our own hours, wherever we want, means that we can set up your schedule to fit your life, rather than the other way around. I personally work better in a number of shorter periods of time spread out across the whole day, so that’s usually what I do.

Communicating online, and working remotely is something that a lot of us have gotten used to from a young age. For me, it was spending time on IRC and forums when I should have been out drinking in the park, or whatever else Glaswegian teenagers are meant to be up to. As a result, it feels natural to develop friendships online. However, even for hardcore Internet geeks, meeting in person is important. Some of my oldest friends are those that I originally met online. The key distinction between them and others who I eventually lost contact with is that we ended up hanging out in real life too. Digital bonds can be strong and effective, but to really understand someone you need to spend some time together in person.

No matter how adept you are at online communication, the quirks of text-based speak (as opposed to voice, rather than mobile shorthand) mean that you can often be at risk of taking certain things that are said the wrong way, or not quite getting the intended meaning. I think sometimes people who are so used to communicating via digital mediums end up forgetting to inject their words with semantic meaning, so it can wind up even more difficult to read into.

The bottom line is: it’s important to meet people in person, especially if you are working with them daily. You get to know individual traits and idiosyncrasies, so that you understand how they come across online better. It means you have a better connection for when they next need to ping you to ask for help with something on Skype, and it’s not just an avatar staring back at you. This gives a whole different, and positive frame of reference, which makes working together a whole lot better (and more productive). The coolest thing for me is that moment when I can hear a person’s voice in my head whilst reading what they’ve typed out – that’s when you know it’s working.

You’re just away on a jolly!

On meetups, we always have defined projects that we will spend time on – ones that are easier to co-ordinate in person. That said, the point is not just about completing tasks. Infact, arguably the most important thing is getting to spend time with colleagues that you never usually get the chance to see, as I’ve explained above. It’s the longer term benefits from this that have the bigger impact than the short term gains from project work. If it was at anywhere else, it would probably fall under the aims of the dreaded, mandatory ‘company retreat’, with words like ‘team building’ and ‘co-worker bonding’ getting banded about. That’s pretty much exactly what the point is, except this time it’s done right. We actually want to spend time together, because we never get the chance to.

On top of that, I always used to wonder why businesses would spend so much money flying their sales people out to places like Australia and Chicago, to require them to return after just a day or two. To me, surely it made more sense to make the most of the expenditure on those flights in terms of personal development. If people are exposed to the cultures and places they visit, and able to enjoy them more, then they arguably become more happy in their jobs, and their knowledge about how to work with them grows. To me, it makes perfect sense to spend time in different places – your workforce becomes smarter, and more culturally aware – something which is an invaluable asset when working with customers from all over the globe.

So why don’t you work together all the time then?

Firstly, working together all of the time simply isn’t possible for a distributed company like Automattic. Employees live all over the world, where they choose, and so to bring everybody to one (or even multiple) places in a permanent fashion doesn’t make practical or financial sense. This isn’t even to mention the fact that doing so would go firmly against the independent culture that is so deeply ingrained in everything that we do.

Secondly, whilst seeing each other is awesome at meetups, it’s a fallacy to assume that it would be better to do that all the time. I love meeting up with other people, but I work far better when I’m in my wee cupboard office at home (or in bed, to be fair). At the end of a meetup I’m usually knackered, as it’s a pretty intense period of time to spend being social constantly when you’re not necessarily a naturally extroverted person.

Working remotely and meeting up every so often gives the best of both worlds: the independence and freedom to work where, when, and how works best for you, but also at the same time getting the chance to develop deeper bonds with people. Spending short bursts in person actually helps groups become closer, rather than elongated periods where they have to be.

Why do you need to go to Barbados though?! Can’t you go somewhere less exotic?

This is probably the one that most perplexes people. The fact that we met up in Barbados might seem ridiculous on the face of it, because of the distance from where I am, the weather, rum cocktails… everything. However, it makes more sense than might appear on the surface, for some of the following reasons:

1. Distance. Anywhere we pick will be far away from somebody. On our Barbados meetup, the majority of people were from North and South America, which meant that Barbados was actually one of the most central locations we could have found. Ironically, I had less flight connections going here than I would have flying to many cities in the USA, and the travel time was about the same as that to Chicago. I know where I’d rather be going, given the option.

2. Red tape. Bringing together a bunch of people from different countries means you need to think about visas, and border clearance. Whilst I’ve had a hard time at the American border a couple of times, that’s nothing compared to the hassle that some of our crew would have had to endure. (ever seen a Sri Lankan passport?) Barbados meant that all of our passports were accepted without a visa being required, and getting through customs was a breeze.

3. Language and Currency. In Barbados, everybody speaks English, and the currency is legally tied to the US Dollar at a ratio of 2:1. That means that people could use their own currency or credit cards, and there was no hassles when we were trying to organise things with the hotels or restaurants (not due to a language barrier anyway). Whilst you might want to avoid precisely those things when going on holiday yourself, they make life a whole lot easier for a week long meetup.

4. Cost. The price for the hotel, food, and everything else can wind up being a whole lot cheaper than you’ll find in either the US or the UK. The only thing to contend with then is travel costs, but these actually worked out comparable as well, given the location of Barbados, and the frequency of the flights.

The question really is – why on earth not go to Barbados? The food is good, the weather is great, the people are friendly, the beach is right next to the hotel…

Unless, of course, you have to have a terrible time for it to be considered work.

29/05/2014