My travel broadly falls into three categories:

  • <1 day trips. Meetings / study / shopping / eating
  • Whole day trips. Work.
  • 1+ day trips. Visiting my family. Vacations. Business trips.

I use a different bag for each purpose.

Small trips - Cambridge Satchel Company

I bought a Cambridge Satchel Co. Classical Satchel in the summer to replace a cheap shoulder bag which I'd been carrying since the early '00s, and was beginning to look like it'd been run over by a tank. I've loved the understated styling of the Cambridge Satchel Co. brand for years. It's smart and elegant; and I like that it transcends any social occasion. I could take it to a hipster cafe or a gig, but it doesn't look out of place at a pinstriped meeting either. 

The leather is thick and a little inflexible although I expect it'll become more supple with age. Yet the bag is also relatively lightweight. I chose the 13-inch model. It's big enough for books, even my laptop in a pinch, but small enough that it forces me to be thoughtful about what I carry with me. This encourages me to empty it when I get home; processing any items I've collected throughout the day.

The satchel's discretion, plus the fact that it's not easy to open, makes me feel that I'll be less of a target for pickpockets, especially if I wear the bag across my body rather than dangling off a shoulder.

My one gripe is the strap. It's too thin and can dig into my shoulder, even through a thick coat and jumper when the bag is fully loaded. This can be addressed by buying a strap cushion which the bag a lot easier on your shoulder. It would be nice if Cambridge Satchel Co. would something like this with their bags but for a product I expect I'll be using for a decade, buying one myself is a relatively minor inconvenience.

Whole day trips

Trips which  necessitate a change of clothes (like commuting to a day job with a dress code), or day-long expeditions, involve carrying more stuff. I prefer a backpack to a shoulder bag for anything this weighty. 

The Berghaus Twentyfourseven 25L backpack is tough, discrete and inexpensive. As with the satchel, it works just as well when I wear shorts and a t-shirt as when I wear a suit. Most important, I find that it's comfortable with generously wide and soft straps.

>1 day trips

The inscrutably-named [Samsonite Base Hits 55cm Upright]( is the most effective roller bag I've tried. It feels tough, lightweight and perfectly sufficient for a week's travel (although I travel light). As with my other bags, discretion is the better part of valour. The wheels are relatively quiet even on rough pavements and the handle mechanism feels extremely robust.


The real trick to the way I organize my bags is that I keep a "pod" containing my entire suite of mobile tools. The ThisIsGround Mod has been a revelation. It's costly, but it's also something I expect to outlive me. The mod when closed has a clamshell form with a handle on one side and the kind of zipper that I'd normally expect to find on a parachute bag.

The inside front has loops for pens / stylii, and pockets for business cards, a smartphone or cables. The inside back has a large pocket for a tablet; and I manage to squeeze in my tablet's keyboard cover as well. The real trick is the insert. You can order your mod with one or more magnetically-attached inserts which are designed for different uses. I picked the Writer insert because I needed loops for extra pens, and a pocket for a pencil, eraser and sharpener. There's enough space behind the insert for a notebook as well.

The Mod has forced me to decide what I need to carry around with me at all times. Once that choice has been made, it's easy to transplant the Mod between the larger bags as needed; guaranteeing that I've always got my essentials with me.


I think that those who are aware of mind maps and outlines (I explore the differences in some detail in The Productivity Habits) tend to use one or the other. I like to use both together, but for different and very specific purposes. Mind maps, being visually clear, are great for the speedy capture and analysis of information. For complex projects, like writing a long paper or a book, a plan for a multi-phase project, or deconstructing / synthesizing an argument, a tool which offers more detailed control of structure is essential. 

While mind maps allow you to represent a cascade of information on a two dimensional plane, an outline represents the same cascade in the manner of an indented list which you would read top-down. Because of this, outlines sit somewhere halfway between a mind map and a block of text.

This is useful because it makes it easy to add lots of information to a node on an outline. A node on a mind map shouldn't really contain more than a short sentence, but an outline makes it easy to expand this, even up to a full paragraph. Even so, a branches can be collapsed, moved around, and the whole document restructured just like a mind map, allowing you to fine-tune the structure.


My outlining weapon of choice is OmniOutliner. From the same developer as OmniFocus, my task manager of choice, I've benefited from the same level of reliability and customer service that would be expected from a relatively expensive suite of software. It's currently available for Mac and iPad, and will shortly be shipping for iPhone as well. I find the software to be clean, logically-laid out, and capable of producing attractive results which is important for a form of information which lends itself to presenting complex concepts and plans. 

I do find synchronization to be a challenge as OmniOutliner doesn't yet support any of the most common syncing services. However, I rarely use outlines to capture information so ubiquity is less important than outlines, and according to Omni Group's 2015 plans this will not be a constraint for much longer.

Mind Maps

I have a small set of criteria which I use to choose amongst the mind map tools available right now.

Low friction

Entering information must be fast, as must the process of reorganizing it. I'm prepared to sacrifice high-end features in order to achieve this.


Since this is a tool which is used to capture information, it must be available on as many of my personal devices as possible, sharing information between them, preferably automatically.


It's rare for a mind map to be the final form that a piece of information will take. Rather, I use them to capture and process information before using a different tool to turn them info the finished article. For me, that usually means text or diagrams. As such, it's important to be able to take information out of the mind map, either as a plain text outline or a standard outline file format such as OPML. The ability to export as an image or PDF is also useful for those occasions where I want to take advantage of the efficiency of a mind map to share information with others.

MindNode by IdeasOnCanvas matches these criteria very nicely. A close second is iThoughts, although I find that while the latter is more powerful, it's not quite as intuitive and synchronization isn't quite as seamless as MindNode.

Task Manager

The job I'm asking my task manager to do is probably the most important of any of my software choices. In essense, it houses my second brain.

I've been using OmniFocus several times a day, on various devices, since 2009. It's probably the most sophisticated task management tool that exists, and I would happily pay triple what Omni Group charged. Here's why:


Many task managers allow you to form your own system for working with tasks. I feel that this is intellectually-lazy. It creates a mess of due dates, priorities, inconsistent folders, and tags that don't mean anything. I'm attracted to tools which are built around a process or a philosophy. OmniFocus employs David Allen's Getting Things Done method, a method which has informed so much of my own. This prescriptive approach is opinionated, brave, and highly effective. 


The Omni Group have shipped versions of OmniFocus for Mac, iPad and iPhone. This means that my task system is ubiquitous, whether taking notes, studying in depth or in a pocket. This is important because it makes it easy to capture and review tasks, but more important than that, easy to habitualize the capture and review of tasks.


I also really like the fact that OmniFocus makes it relatively simple to build custom perspectives, giving you a particular view of your data. I have perspectives for all of my likely situations, displaying available tasks deferred to the contexts which constitute those situations. This means that if I tap the "Study" perspective, I see all tasks which are appropriate to that situation. I'm working on a paper describing this process in more detail. I also recommend Kourosh Dini's excellent book, Creating Flow with OmniFocus.


Where OmniFocus really shines is its ability to conduct a review of captured tasks and projects. It's easy enough to capture information, but that's useless unless you have an easy system to review the right information at the right time. Reviewing the actions in a particular situation is made easy with perspectives, and freshly-captured tasks can be seen using the Inbox view. However, to conduct a regular review of projects, there is a dedicated Review mode built into the iPad and Mac version of OmniFocus; and coming soon to the iPhone. This makes it quite easy to go through every outstanding project, check that it has at least one available or deferred task, then say whether the project is current, paused, done, or to be dropped.

I've yet to see any task manager implement this mode as effectively as OmniFocus has; yet it is essential for keeping your system maintained and up to date.

The company

I have a lot of respect for The Omni Group as a company; and that is important for the vendor of such an important tool. I've found them to be very conservative when it comes to features that could compromise the stability and security of data, and their post-sales support has been consistently excellent. They are more expensive; but this is a situation where a high price is a good thing, because it inclines them to look after me as a customer. 


There are lots of task managers on the market, but the only other tool which I think is worth considering is Todoist. Unlike OmniFocus, Todoist supports many more platforms, including Windows, Android, and has a native web version. While not quite as a focused as OmniFocus it is reassuringly expensive which gives me confidence about the intentions of the company behind it.


This is an area where you want to spend money. You'd buy yourself the best pacemaker if you could; by the same logic you should buy yourself the best task manager. I depend on OmniFocus. It works best when you buy into the process that it's built to support; unlike other task managers it won't work for you if you go against the grain. That said, if you're trying to implement the habits I described in The Productivity Habits, or similar systems, OmniFocus will serve you very well.

Info Dump

In The Productivity Habits, I wrote about the need to create an "info dump" into which you can archive complete information. This includes work you have finished yourself, notes, documents, articles, even emails. 

The interesting thing about archived information is that it's neither alive; like your current projects, nor dead; like the stuff you've deleted. It's unconscious. It has no immediately usefulness, but lots of potential usefulness. 

This means that the way live information is dealt with doesn't strictly apply. An example is filetypes on your computer. Knowing whether a particular file is a text document, a spreadsheet, a PDF or an image is very important when you're actually working on it. But it's meaningless in an archive.

A good archiving tool must be able to store multiple types of information together, and treat them equally.


DEVONthink Pro Office is my preferred choice. It's the most sophisticated and powerful knowledge manager that I've tested. I generally prefer simple tools, so why the exception in this case?

DEVONthink is, in my ways, the epitome of the ideal info dump. You can drag pretty much any kind of file into the app and it will make sense of it. Everything from Microsoft Office files to PDFs, web links, text notes, and more. The Pro Office version, which I use, has the ability to archive emails from Apple Mail using sophisticated date filters. This is invaluable to me. I have a repeating task set every six months to archive my email into DEVONthink before I delete it from the mail server. Additionally, the DEVONthink Pro Office integrates nicely with Fujitsu's excellent ScanSnap series of scanners. I don't have much use for this personally, but for anyone who deals with reams of paper, the ability to archive that information into accurage, searchable PDFs will save a lot of time. 

DEVONthink Pro Office also integrates a powerful OCR feature. This can digitize the text in scans and images, turning them into searchable files. This is incredibly useful if you're in the habit of screenshotting or photographing images with text.

While it's very easy to get stuff into DEVONthink it's also quite easy to organize it. Folders can be nested inside folders, making it easy to replicate your Importance Tree structure in DEVONthink. Tagging is especially useful for people who need to finely organize data in a very large project, although I don't make much use of that feature myself.

Asides from capturing data, the most important role of a knowledge manager is that of retrieval. Even if it was easy to capture information, the tool would be useless if it was difficult to find the right piece of information. DEVONthink's "Find" function is reasonable, although I rely on the more powerful "Search" function under the Tools menu. This makes it easy to find tune the search and to deploy DEVONthink's secret weapon: the "See Also & Classify" function. When you select an item in your DEVONthink database and enable See Also & Classify, you will see a dossier of items which relate to whatever you've selected. This can include any file type. It's a game-changer.

Local data

The other thing that draws me to DEVONthink is that it stores my data locally, on my computer, without relying on a cloud service. The information contained in my DEVONthink database is incredibly personal; including complete work, thoughts for future projects, and an archive of my communications. Keeping this data secure and safe is very important and, frankly, I don't quite trust services like Evernote to do a good job at keeping my information from prying eyes. DEVONthink data, by contrast, is not transferred to any third party. The fact that it's data is local means that a comprehensive backup strategy is likely to include your DEVONthink data.

This strength is also a limitation. I would like to see DEVONthink offer the ability to encrypt the database before hosting it on Amazon S3, Google Drive, Microsoft OneDrive and the like. This would combine pre-internet encryption and modern sync capabilities. Synchronization, while possible, is a pain right now. As such I think it's a tool for people who use a laptop as their only computer. Their mobile app, while perfectly usable, is also very limited. I would like to see an mobile version of DEVONthink which, at the least, features the See Also & Classify function.

DEVONthink maintains DEVONthink Personal, Pro and Pro Office. I think that this is confusing and unnecessary. The best version of DEVONthink for anyone who deals with information in a serious way is Pro Office. At less than $150, it's very reasonably priced considering the problems it's capable of solving.

These issues aside, it remains the most powerful knowledge manager tool available and I recommend it to anyone who would like to use a powerful, secure tool for archiving their data. If you'd prefer to sacrifice power and security for the sake of better ease of use, and the benefits of having your data everywhere, Evernote is an excellent alternative.