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Business and work Useful stuff

Cross-platform or best platform?

What is better? A cross-platform productivity system or the best productivity system, even if it is only available on one platform? I was thinking about this some more after I published my previous post this morning.

A productivity system for autonomous adults

The answer mostly hinges on whether you can be reasonably assured that you will be able to use the device/operating system of your choice going forward or whether you need to cater for an environment where you could find yourself working on whatever your employer gives you?

My employer, like many companies, issues Windows-based laptops to its staff. I have been a Mac user for about a decade and I use a number of apps that are only available on the Mac. That said, much of how I work on my Mac is also possible on other operating systems. I write in plain text using MultiMarkdown and I can do that on just about any device and OS. We use Google Drive for internal document sharing and that is available from any modern desktop browser and most smart devices.

One of the reasons I really love MultiMarkdown is because it is truly cross-platform and it doesn’t matter what you are using to write, it will work because it uses the most basic format: plain text. I’m going through a phase right now where I wish I could just do everything in plain text files and easy to migrate and sync files. I want to explore some sort of alternative to Evernote. Evernote is my primary reference repository for my stuff. I have a lot of data in there and I am a bit concerned that Evernote might go away one day and I won’t have an independent and similar system I could switch to.

So the question which has guided many of my productivity system choices has been whether to focus on a cross-platform system or on the best system available to me?

  1. A cross-platform productivity system would be something like Asana, Trello or even a plain text file with some customised syntax to reflect tasks and actions on tasks (I had a pretty interesting system running in Atom for a while).
  2. The best productivity system available to me at the moment is OmniFocus but its value is entirely dependent on me being able to use a Mac and iOS devices day to day. I’m using my MacBook Air for work at the moment but that is primarily because I returned my underpowered, office issued laptop and it hasn’t been replaced yet. This works well enough but if my MacBook Air were to decide to take a vacation on me, I’d have to switch to something else and my efforts to set up an effective productivity system using OmniFocus would be rendered useless.

At the moment I am leaning more towards using the best system available over cross-platform, primarily because nothing else is as good, intuitive and effective as OmniFocus on my Mac and iOS devices. I’ve discovered that “good enough” isn’t always good enough and carries a fair amount of aggravation with it.

The underlying question still remains, though.

Image credit: Pexels

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Business and work Mindsets Useful stuff

A productivity system for autonomous adults

I once lost about a day and a half exploring a new productivity system to help me be more productive. That lost time is one of my favourite life experience ironies. Part of the reason I wound up spending so much time obsessing about a new productivity system is that I am more than a little OCD about that sort of thing.

I don’t remember emerging from that “process” with a coherent system but it remains a personal reminder not to let myself become distracted by the search for something new for the sake of finding something new. Instead, I focus on simplifying my processes and my toolkit with a preference for the stuff that I know works for me. When it comes to tasks, I prefer OmniFocus because I have it on all my devices and because I paid far too much money to just ditch it.

The catch, though, is that it doesn’t tie into anything I could use to collaborate with my team at work. Over time my work tasks have split from my personal tasks because different managers have wanted us to manage projects using different tools which became additional layers on top of my OmniFocus system and another layer of complexity to manage.

When I diverted off the productivity cliff

In my quest for something I could use to tie in with my colleagues, I stopped using OmniFocus as my “everything” productivity app and OmniFocus became my poorly maintained personal task manager and a procession of other tools became my work options. In retrospect, that was probably when things started falling apart.

I used OmniFocus exclusively before I started my current job because I worked for myself and I could focus on being productive, not finding ways to adapt to whichever project management system my managers wanted at that point in time. I’ve tried a few services:

  • Asana, which I really dislike for reasons I can’t quite identify (and some I can);
  • Spreadsheets, which are terrible for managing ongoing tasks and, when I think about using them for this purpose, can make me physically ill;
  • Basecamp, which is a terrific project management service and the only reason it became problematic is because there was no meaningful integration for me with OmniFocus so it required a work/other split to minimise duplication;
  • Pen and paper, which isn’t dynamic and too easy to forget about and ignore because my brain knows it isn’t reliable for me; and
  • Trello, which is my current choice at work and works fairly well except, as I write this, I just think it is another layer of distraction I should ditch and return to OmniFocus.

As I see it, the thing about productivity systems and work projects involving teams is that you really have two choices if you want to remain productive[1]:

Option 1 – the team system

Use a system that everyone uses and that works well, generally, for everyone. When I had a small team back in the day, I was looking at Basecamp or Podio (I think). I gave my candidate attorney the two options to look at and she picked Basecamp because it made sense to her. We went with that and it worked well for us. I only stopped using it when my team moved on and maintaining it for one person didn’t make sense.

The key thing with a team-based system is that the directive to use it must come from management even though the choice of what to use should only be made with the team’s input (after all, they need to use it and stick to it and no-one will stick with a system that doesn’t work for them).

Option 2 – The “autonomous adults” system

I was chatting to Don Packett a while ago and I asked him what Missing Link uses to keep projects going effectively. I was expecting him to give me the name of some slightly fringe productivity app (if you know Missing Link, you’ll understand why I wasn’t expecting them to be using Ye Olde Corporate Standard Fare). He surprised me with a really smart and appropriate answer (I wasn’t surprised that it was smart, just because it wasn’t what I was expecting). He told me that they –

aggressively push for ‘autonomous adults’ who can set their own timelines and deadlines and get their shit done in the right fashion.

I love that. As soon as I read that, I realised that a system imposed on a team can, more often than not, reflect an attitude by management that the team does not comprise “autonomous adults” who can be trusted to get their stuff done “in the right fashion”. Instead, people are treated as if they lack the capacity to do what they need to do and be productive.

Update (2016-03-09): Don messaged me and clarified that Missing Link uses dapulse to co-ordinate their autonomous adults, which makes a lot of sense.

This attitude comes through in how they are told which steps to take to complete tasks and when to do them. A better approach is giving them a set of priorities (or, even better, involved in the decision-making process about the upcoming priorities) and left to figure out how to meet them effectively and on time. That doesn’t mean people don’t make mistakes or miss deadlines. Being an “autonomous adult” means being able to make those mistakes, taking responsibility for them and then fixing them without being told that making mistakes somehow deprives you of your right to be a grown-up at work.

My point is …

What prompted to start this little verbal foray into productivity systems was a post by Shawn Blanc titled “A System That Works (for You)” which begins with this truism:

Everyone wants a time management system that works. One they can stick with. One that’s not a pain in the butt.

He goes on to explain what such a system looks like:

  1. It empowers you to do the things you want and need to do.
  2. It aligns with your personality.

What I have learned is that a system that doesn’t have these two qualities very much becomes an obstruction to just getting stuff done. I am also constantly reminded that the key thing is to find a system that just make sense to you and works for you. A system that requires constant tweaking and reconfiguration is, literally, counterproductive. I have reached a point where I can feel just how wrong the system is when I started using it.

A good productivity system should have something that makes it easier to use, enjoyable even. As Blanc noted:

The reason I use a pen and paper is because I enjoy it. The analog aspect adds a bit of joy, which, in and of itself, is enough grease for the skids to keep me on track with using my system.

I definitely find that a productivity system that isn’t aesthetically pleasing to me is problematic because appealing design is a great introduction to a system for me. It is “grease for the skids” to help ease the transition to a new thing and how I can use it.

Most of all, a good productivity system should support you and, as Blanc puts it, empower you “to do the things you want and need to do”. Adding more friction to your workflows is an effective way to dissuade you from using a system and becoming less productive overall[2].

Postscript: I have written a follow-up about a related issue so consider reading “Cross-platform or best platform?” too.

Cross-platform or best platform?

Image credit: Pexels


  1. Being “productive”, to me, means getting stuff done and not spending more than the absolutely minimum time required to maintain your system. If you spend too much time just keeping your system afloat, so much so that it cuts into the time you need to actually get your stuff done, change your system. It isn’t working.  
  2. Of course, now that I am thinking about it more, I am tempted to move all my tasks back to OmniFocus. The challenge with these sorts of moves is that each time you reconfigure your productivity workflow, you take more time away from the time you have to get stuff done so it has to count.  
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Applications Business and work Tutorials Writing

How Instapaper could be an even better research tool

Instapaper has become so much more than a reading app to me. It has become a fantastic research tool too. As good as it is, it could be better (or, at least, it could do one thing better). Bear with me, I’ll explain.

As you may know, Instapaper introduced highlighting and commenting (or Notes) some time back. If you are using the “free” service you are limited to just 5 notes a month but if you become a Premium user for a mere $29.99 for a year (or $2.99 for a month), you have all the awesomeness that is Instapaper available to you.

My work involves a fair amount of writing. I typically write around 3,000 to 4,000 words a week in the form of blog posts for my employer’s blog. I also write guest posts for industry websites now and then and edit blog posts that my colleagues have written. My writing tool is Byword and I am a big fan. Reaching the point where I write those articles usually means doing a fair amount of research. That involves finding useful materials, saving them to Instapaper where possible and later going through my saved items in Instapaper to review them more closely.

Comments and highlights in Instapaper

At that point I use the highlighting and commenting tools a lot to pick out phrases and ideas that I want to incorporate into my articles. I created IFTTT recipes (here and here) that take highlights and comments and add them to running Evernote notes for each article.

The results are nicely laid out Evernote notes with all my highlighted texts and comments. It’s a useful way to aggregate all those highlights and comments in a central reference that I can go back to when it is time to write my article.

Comments from Instapaper collated in an Evernote note

Instapaper has a Notes tab which has a list of all your highlights and comments but I haven’t used that. I’ve been using Evernote for years so it seemed like a good idea to just send my highlights and comments there rather than use the Instapaper option.

Instapaper’s Notes view

I was home sick for a few days last week and my idea of rest was to research and start writing a mini-thesis about ad blocking and different perspectives on it and solutions for the challenges it creates. At one point I was highlighting and commenting so much I received a rate limiting warning from IFTTT telling me that I was about to hit an hourly limit on items sent to Evernote (I didn’t know such a limit even existed).

At the end of my research phase I had a dozen or two Evernote notes with dozens of items in each which I thought would be useful in my article. What hit me is how relatively unproductive this workflow is where I have a lot of material to review after the initial research. Making all those notes and highlights practically useful requires me to go through my Evernote notes and manually extract all of those items into some sort of outline of my article. My favourite outliner is OmniOutliner but any OPML-based outliner would work just about as well.

Usually I don’t use an outliner too because my articles aren’t generally as complex as this ad blocking piece. In this case, an outliner became essential. I was working on my outline and I realised that as terrific Instapaper is as a research tool, being able to automatically export all those highlights and notes into an outline that I could manipulate afterwards would be far more effective than flat Evernote notes.

The benefit of an outliner is that I can drag lines around and re-order the outline pretty easily. I could possibly even create an initial draft of the article in the outliner and finish it off in Byword or another word processor. It would really depend on how I structured my outline and how much of the article I’d want to write in it. In this case, I still did my writing in Byword but I split my screen and placed my outline on one side of my screen as a reference and wrote in the Byword window.

My split screen OmniOutliner-Byword perspective

An alternative to this option is to just use Scrivener which is an excellent writing app. I started my article in Scrivener because it has an outlier function and the capacity to collect research materials in the app itself but I switched back to my Byword/OmniOutliner combo option – I just felt this strong need to stick with plain text in a simpler writing window.

Because my outline was more of a secondary outline after I finished my initial research, I still had to go back to Evernote to find individual quotes and arguments and combine material from both sources into my article. If I had been able to automatically send highlights and comments straight into an outliner, it would have placed all my reference materials into one outline from the start and made it a lot easier to structure that data for reference when I started writing.

So, my wish list for 2016 (I’m putting this out into the ether in case it is possible to make this a reality) is for some option to automatically export highlights and comments into coherent outlines just as I can create a similar workflow for Evernote. One possible solution is to create an integration with Dave Winer’s Fargo.io outliner. It should be something simple and create an OPML file that you can manipulate later to create the basis of an article or similar document.

Image credit: Writing by Unsplash, released under a CC0 dedication