For the launch of my new blog design, I am doing a series of posts on workflows. The first will be about my personal, everyday workflow, the way I use tools to try to get things done. The second will be about my writing workflow. The third is about my digital audio workflow, both recording and listening.
This is going to be a massive nerd-fest, so if you are not in the mood for a long read about personal productivity software, stop now. I’ve benefitted from the many bloggers who have shared their tips and techniques for dealing with the onslaught of modern digital work. I’ve learned some stuff by trial and error, and hopefully, if you choose to read on, you’ll find one or two interesting things in the posts that follow.
So, what is a workflow? My definition is the combination of tools and processes that I use to accomplish a task. The human-machine (software & hardware) interaction that helps me get work done. Given the amount of time we all spend interacting with software on computing devices of various kinds, and the productivity pressures of modern life, it’s worth being a little thoughtful about your workflow.
One of the greatest myths of the computer revolution is that a device or a piece of software represents a “solution.” Most of the tools in my computing arsenal require a lot of time and effort before they blend seamlessly into a flow and help me get things done. Often, new hardware or software starts off as a problem and only becomes a solution after a steep learning curve and hard work. The workflows in these posts represent solutions that work for me.
Two caveats. First, these are my opinions; sometimes I’ve tried competing products and rejected them, sometimes I have just settled on the first thing I’ve tried. These aren’t necessarily the best choices. They are simply my choices. Your mileage may vary. A lot. Second, I am an unapologetic Mac user. I own a couple of awesome Alienware X51 PCs that I use to play games, but I don’t work on them beyond some web apps in the Chrome browser. Most of the tools in these workflow posts are highly Mac and iOS specific. I’m sure someone out there will know better, cheaper alternatives to many of these products on the PC. Or Ubuntu. Whatever.
I have to get this out of the way up front: I hate email. Well, not email itself, which is pretty great, but rather email clients. Unfortunately, my everyday workflow is dominated by email, so I spend a lot of time either in the Mac Mail client (which I use to aggregate my email accounts), or a Gmail or Exchange web client. I used to use Outlook/Entourage, which I found slow and buggy. I tried Sparrow, which worked fine for Gmail — nothing special, but simple and efficient — but not for my Exchange mail (the company behind Sparrow was recently acquired by Google).
My email workflow is inefficient and error prone, but I haven’t found any better way to do it over the last 20 years. Any time I’ve tried to develop automation to help me process my in-box, I’ve ended up with errors or lost email messages. I depend so much on reliable, timely email that I end up laboriously, constantly going through my in-box by hand, sorting, deleting and prioritizing. Ugh. Maybe I haven’t figured out the deep ninja tricks to make an email client work for me, but I’ve really struggled to develop a sensible workflow around my in-box. My only golden rule is to respond immediately to anything that’s susceptible to a quick resolution. The longer something sits in my in-box, the more error prone my workflow gets.
Because my overflowing in-box is a poor proxy for a task list, I tend to work from my in-box out to various other tools which I use to track tasks and projects. I’ll discuss task management later, but I have come to rely on the great Clip-o-Tron 3000 plugin for OmniFocus. This is a great little plugin — you launch it from the Services menu in Mail on a highlighted email message and it creates a task in your OmniFocus in-box with the text of the email as the task’s note. Great for getting email into a more manageable form.
I use the Mac Calendar as well. It works fine with Exchange and with Google’s Calendar, and I get a lot of shared calendars from people and organizations through Google. I tend to use Calendar for appointments and due-date specific tasks, while I use OmniFocus for my “next action” stuff.
Given the continued primacy of files in my workflow, the most important tool I use is Dropbox (disclosure: Benchmark is an investor). I absolutely adore Dropbox. If you don’t know what it is, stop reading this and go get it. I’ll wait. I no longer use the Documents folder on my Mac; instead I default file storage to my $99 a year 100Gb Dropbox account.
The great thing about Dropbox is how seamlessly it integrates into my computing environment. Because my Dropbox folder exists as a folder on my computer, it is available off-line and can be manipulated just like any normal file system folder. I always have access to all my files on all my devices. It also does a good job syncing settings for some of my software. It’s a hard disk in the cloud for my mobile devices. I don’t view it as a backup strategy, but it certainly gives me peace of mind that my files are synced and replicated in multiple locations. Essential.
I am also a big believer in basic file formats, because basic file formats give me the flexibility to avoid software lock-in, future-proof my work, and also use single-purpose tools on files to accomplish specific results. I try not to use apps that don’t have native support for either plain text, OPML, PDF, Markdown or some other broadly adopted format. A great thing about the Mac is the ability to print to PDF from any application. The combination of these basic file formats and Dropbox is fantastic, as it allows me the independence to use, for example, a new text editor that comes out on the iPad with all my existing files, no conversion or translation necessary.
One of the most useful workflow tools for file management on the Mac is Hazel. This simple program runs in the background as a system preferences panel and does one thing incredibly well: it applies rules to folders, like smart folders on steroids. This sounds kind of arcane, but in practice it’s magic. For example, I have a rule that watches my Downloads folder and moves any .dmg files to an “apps” folder on Dropbox at the end of the week. I have another one that looks for local Garageband projects and moves them to a Shared Music folder on a server. I have another one that cleans up my Desktop folder, and another that cleans up my Trash. Very cool.
Despite all this, I don’t love using folders as the main organizational scheme for files. I am currently playing with the academic research tool Papers to organize and keep track of board meeting presentations, pitch decks, and other company information. It feels very academic and designed to solve a publication/citation problem, but it gets rave reviews so I am seeing if I can adapt it to my needs.
I am a big believer in the to do list. I’ve read David Allen’s Getting Things Done and, while I’m not religious about it, I have internalized a lot of the GTD methodology. Being a venture capitalist, and formerly a CEO, my day is usually filled with lots of small, discrete, and often disparate tasks. The core of my daily workflow is managing and processing lists of things I have to do, usually by myself: research, writing, phone calls, introductions, investment decisions, board meeting follow-up, etc.
One problem I’ve always had with strict GTD is that the old contexts for work never really matched my workflow. Like many modern workers, I have a lot less formal separation between home and work, desktop and mobile, than GTD contemplates. If you use the GTD methods but have experienced this same problem, read Sven Fechner’s “A Fresh Take on Contexts.” Worked for me.
I’ve tried pretty much every To Do list program out there. I’ve tried using outliners and text editors. I’ve tried using paper. My requirements for a task management tool are pretty simple. It has to be fast, accessible, and available on multiple devices (with good sync).
After a lot of trial and error, I’ve settled on two tools for my task management: OmniFocus and Asana (disclosure: Benchmark is an investor). I use OmniFocus for my individual, daily brain-dump task management, and Asana for managing tasks on team-based projects.
OmniFocus is a pretty canonical implementation of the GTD methodology, but that isn’t why I adopted it. I like the speed, the UI (particularly the keyboard shortcuts and mobile apps), and the sync. It is deeply integrated with the Mac OS and iOS, so it plays nice with many other apps in my workflow. I spend a ton of time in this app every day, and it would be the most difficult piece of my workflow to replace.
I use Asana mainly for collaborative tasks performed with teams, where it really excels. I am extremely excited by the promise of Asana, particularly the openness of the platform and the ability for the fundamental data architecture to solve so many different collaborative task management problems, from bug tracking to planning a kid’s birthday party.
The thing that’s particularly great about Asana for teams is how it can aggregate a lot of a project’s history and data and even decision flow in a single interface, taking tons of email out of my in-box and creating a historical record of the project. If I was running a startup again, I’d organize around Asana and Dropbox and Google Docs from the get go. It would probably cut company email traffic down by 50%.
I love Asana’s slick web client. I wish they had an equally slick native mobile experience and I know they are working hard on it. If I could use contexts on my personal projects in Asana, and if it was as deeply integrated with other apps as OmniFocus, I could imagine doing all my task management in Asana.
I use Evernote to keep track of all the little bits of information that I amass in my daily life. I probably only use a fraction of its capabilities, but it works to organize little bits and pieces of digital clutter, despite its wonky interface and unnecessary complexity. It’s highly searchable and works well on mobile devices. I used to store my browser bookmarks in the cloud on Delicious until it went away, and I moved all my Delicious bookmarks into Evernote where they coexist with everything else I store in there. It’s the best “digital shoebox” that I’ve used, but I think it’s ripe to be disrupted by an innovator with better design sensibilities.
I use Instapaper as a cache for longer articles that I want to save to read on airplanes. Very simple and very powerful, great on mobile devices. I love how it puts these articles into a standard format, so it feels like I’m reading a personalized magazine or newspaper rather than a collection of saved web sites. It’s a worthy companion to Twitter, if, like I do, you use Twitter as a firehose of information, a next-gen socially-curated RSS news feed. Integrates really well with the Kindle, too. I wish there was a video version where I could cache things to watch off-line with a personalized, consistent interface.
I do a lot of work in what’s historically been known as the Office Suite of software applications. I do a lot of writing, I do a lot of business modeling and other math in spreadsheets, and I do a lot of presentations.
The looming end of Microsoft Office as the dominant productivity software for business is a joyous thing for me. The old canard that Office was necessary for file format compatibility is fast disappearing. While I have Office installed on my machine, I rarely use it. I never use Word for text editing (I’ll talk about that more in the Writing Workflow post), and I prefer Apple’s Keynote for presentations, having abandoned Powerpoint long ago, so all that’s really left is the spreadsheet, and there I’ve largely replaced Excel with Google Docs. I love the ability to share that’s inherent in the Google suite, and I like the web integration (the ability to look up stock prices into cells through Google Finance, for example). I wish it was a little faster, though. It’s good for the kind of spreadsheet work I do, but it is not really suited to big, complex, inter-linked spreadsheets.
This is a subject for a separate post, but given the current state of identity (and security) on the internet, a password management tool is no longer an option but rather a necessity. In the past, these have been marketed as convenience tools (“automatically log on to websites!”) but their ability to generate strong passwords that I don’t have to explicitly remember is now the higher valued use for me. I’ve used two that I really like. 1Password has tons of features, decent mobile clients, but no native sync (I use Dropbox to sync it, but it’s a hack). In my experience, it has pretty buggy integration with browsers. Lately, I’ve found myself using LastPass more for my web identities, and 1Password as a more general identity vault. LastPass has a good 1Password import, and it’s not a lot of overhead to run both, so that’s what I do.
For me, Chrome plays an important role in my identity management, because I can use Chrome Apps to get access to my Gmail and Google Docs as well as third party sites that integrate with my Google identity, On my game PCs I do all my work through Chrome; I don’t own any client software other than games and anti-virus. Amazon and Apple are my go-to commercial identities (and Valve/Steam and Xbox Live for games); I have credit cards on file and one click commerce enabled. Amazon Prime may be the best (and most dangerous) commercial innovation in the history of the internet.
Identity management is both more of a challenge and more promising on mobile where apps dominate. A lot of the best apps, like Uber, manage my identity and credit card info in a way that makes their service incredibly seamless. It is interesting that Facebook Connect plays a greater role in my identity management on mobile than on the web, because it’s more of a pain to create new secure credentials on the phone or tablet. I’ve also just upgraded to iOS 6, and am looking forward to seeing how the new Passbook evolves.
So, that’s a pretty exhaustive look at my everyday workflow. Next, writing …