How I Work

How I Work

Thomas McDonald has had his How I Pray series of blog posts in which he asks various people about their prayer life (including one of particular interest to me), modeled on Lifehacker’s How I Work series, in which people describe their work situations and tools and habits. Then, of course, Tom did a How I Work of his own. Jeff Miller[1] of The Curt Jester followed suit and so Tom challenged several others to do the same and I took up the gauntlet. So what follows are my answers to How I Work:[/lead]


South of Boston

Current Gig:

Communications Director for a three-parish collaborative within the Archdiocese of Boston. In my role I manage all the communications platforms of the three parishes, including the bulletin, posters/flyers/programs for events, a weekly radio program with the pastor, web sites, and social media. My role also includes responsibilities for strategic pastoral planning, which involves the writing of a three-year pastoral plan for the collaborative.

One word that best describes how you work:


Current mobile device:

iPhone 6 (64GB); iPad 4 (64GB)

Current computer:

2011 MacBook Pro 15“, 2GHz Intel Core i7 with aftermarket 250GB SSD and 750GB HD replacing the optical drive (personal), 2013 iMac 27”, 3.2GHz Intel Core i5 with 16GB RAM and 1TB HD (work)

What apps/software/tools can’t you live without?


Omnifocus is where it all starts. It’s a project and task management app whose central methodology is built around David Allen’s Getting Things Done book. Everything must go into Omnifocus if it’s to get done. It’s where I offload my brain. I have hooks into Omnifocus from Mail, from the web browser, from my phone, through Siri, even.

Creative Cloud is the new kid among my indispensable apps. As Communications Director, I’m responsible for the weekly bulletin for our parishes and since I’m on a Mac, I can’t use Microsoft Publisher (and I’m grateful for that.) In addition to using inDesign to put together the bulletin each week, I also use Photoshop to create quick graphics for social media and Lightroom to organize all the photos of various parish events. I’ve been using a service called to do some of the great graphic design we’ve had and I can use Creative Cloud to edit and even adapt the designs to other uses, like turning posters into pamphlet covers.

Evernote is my second brain. It’s where everything goes that I will need to find and remember someday and I use it for both personal and work storage. One key way that I use it is that I have a notebook called Parish Bulletin and every time I get something that needs to be in a future bulletin I store it there. I then give it a reminder date of the Tuesday before the Sunday it needs to be in. (I do the bulletin on Tuesdays.) I also precede the title with an acronym for one of the parishes (if it’s parish specific) or ALL, if it’s a general item. Then when it’s time to do the bulletin each week, I just call up everything with a reminder date of the current day. Anything that’s repeating gets a new date when I’m done with it and everything else has its date cleared. This is just one way I’m using Evernote.

All my files live in Dropbox (or nearly all; my archives live on a Transporter). This means not only that all my files are accessible from whatever computer or device I’m using, it also means they are backed up and versioned in the cloud. It’s not my only backup solution, of course, but it’s one of them. I do pay to get 100gb of storage.

I’m a fanatic about passwords. Just ask everyone I work with and live with. I use almost exclusively 20-digit passwords with numbers, letters, and symbols (unless for some reason the site or software requires a less secure password, which drives me crazy.) 1Password lets me have unique, secure passwords for every site and service and I only need to remember the one password (get it?) that unlocks 1Password itself. And since that password unlocks the software on my computer, it means it never has to travel through the Internet where it could be hacked. I also use the Vaults feature to keep separate vaults for personal and work.

I could go on and on about indispensable software and tools, but I’ll stop here.

What’s your workspace setup like?

My office has windows on three walls and so I have my back to the windowless wall, of course. The desk itself is an old wooden affair, probably older than I am. On top of it, I have a height-adjustable work surface that allows me to elevate the computer to work while sitting or standing.

What’s your best time-saving shortcut/life hack?

I have so many little hacks and shortcuts that I’ve incorporated into my daily workflow that I have a hard time pulling out one as best. I’ve recently implemented Brett Terpstra’s “Hyperkey” that allows me to re-purpose the caps lock key on my keyboard to become another command key alongside command, option, and control. I can now easily open the site in the current Chrome tab in Safari and vice versa with one key command which allows me to see how a site looks in different browsers. I use another Hyperkey command to create a new Omnifocus task using the currently selected file in the Finder or email in Using a combination of Apple’s Services menu (under the application menu), Automator, and an automation program like Keyboard Maestro allows you to really go far beyond what is normally possible.

What’s your favorite to-do list manager?

I named it above as one of my indispensable apps, but it is truly Omnifocus. I’ve been using OF since it’s early beta days and have since snapped up its iPhone and iPad versions. The developers have really embraced the idea of giving you a big inbox into which you can offload anything you need to do. One of my favorite features is the integration with Siri on my iPhone. I can be driving home and activate Siri and then, bam, it’s in my OF inbox. Or I’m emailing with a coworker or a vendor and I want to remember to check back with them at a later date. Every OF user gets a super-secret email address and when I put that in the BCC of the email, a copy of the email gets put in my OF inbox. It’s so powerful and versatile, which has been it’s Achilles heel in the past as well. That power has had the side effect of making it difficult for new users to get started. The developers have done a great job in the past year or so in fixing that and I think it’s easier than ever to get started with it.

Besides your phone and computer, what gadget can’t you live without and why?

Besides those two things, I don’t think there’s a gadget I truly couldn’t live without. Certainly my iPad is very useful at both content consumption (e.g. my daily newspaper, Netflix and Amazon Prime movies) and content creation (e.g. mind mapping, project review, meeting notes). I now read almost exclusively on my Kindle Paperwhite instead of carting around paper books. In my car, I use a wireless Bluetooth headset (one ear only) to listen to podcasts on my phone while commuting every day. In the kitchen, I use the Keurig coffee maker daily to make my coffee, except on the weekends when I have a little extra time and use my Aeropress. But as much of a techno geek and gadget guy that I am, I wouldn’t say I couldn’t live without any of them. I think that’s perhaps a good thing.

What everyday thing are you better at than everyone else? What’s your secret?

Over the past few years I have realized that I have the ability to capture a spoken conversation in real-time, not word for word, but in its essentials, by typing it as it happens. I learned this skill while working behind the scenes on The Good Catholic Life radio program (which is no more, sadly). One of my duties included typing up a daily transcript of the show which was good enough that we had several deaf “listeners” who enjoyed the program through them.

A related but different skill is the ability to type out something while having a completely different conversation with someone at the same time. If I’m in the middle of writing something and a person comes into the room and starts talking, I can continue to write while looking at the person and engaging in conversation. I have no idea how or why I’ve attained these skills, but there they are.

What do you listen to while you work?

Most often, nothing. Our office is pretty quiet and even when I have the windows open (thank God, I once again work in a place where the windows open), I hear mainly the wind. I have tried listening to podcasts, but I either pay too close attention to them and stop working or pay too much attention to work and stop listening. This is especially true of technical podcasts, like Mac Geek Gab or Mac Power Users. More conversational podcasts like those from the SQPN network are much easier to multitask to, but even then I try to keep those for my commute. If I’m listening to music, I have a smart playlist in iTunes called “Lost Hits”, which is all my songs rated five stars that I have not listened to in the past 20 days. Given that I have over 12,000 songs in iTunes and I’m pretty rigorous about rating my music, that playlist can keep me listening for hours. But since it will necessarily only play the very best songs, I also have a playlist called “Lost Near-Hits”, which includes the 4-star songs as well.

What are you currently reading?

I’m on a Crusades kick lately so I’m currently reading The Crusades, Christianity, and Islam by Jonathan Riley-Smith, who is one of the foremost scholars of the Crusades. I’ve just started it, so I don’t have much to say about it yet. I recently finished a middling Star Trek novel called Paths of Disharmony and then John Scalzi’s Lost Colony before that, part of his Old Man’s War series. Other books I’ve recently read were Sherry Weddell’s Forming Intentional Disciples and The Sugar Season by Douglas Whynott, about the maple syrup industry, which is quite timely and relevant and was good.

I do nearly all my reading on a Kindle these days. For whatever reason, paper books have lost their allure for me. I just can’t seem to finish one in a reasonable amount of time. I don’t know whether it’s because I have to carry around the book or because the actual experience is different. And it has to be the Kindle, not the Kindle app on my iPhone or iPad. The iPhone is too small and the iPad is too heavy. The Kindle is just right and with the backlight set low, I can read in bed with the light off so as not to wake up the toddler.

What has changed over the years since you started and what do you do differently?

When I first started with Catholic World News back in 1996, I was working from home over a dial-up modem on a PowerBook 520c. There were no content management systems so all our news was emailed out every day to our subscribers through my email app and our web site was a series of HTML files I put together. I had no domain of my own for email, I just had an email address through my Internet service provider. Twenty years later, I’m no longer working from home on a daily basis, but I can essentially work from anywhere as I can connect to the Internet anywhere. My computer’s screen is as large as a large TV was back in 1996. I have a mobile computer in my pocket, a tablet computer on my desk, a portable computer in my bag, all synced automatically through the cloud. Frankly, I’m not sure I could have done this job twenty years ago with the technology of the time, not to the level of professionalism and innovation I work toward.

Over the years, I got a DSL line, then cable broadband. I started a web site under my AOL screen name, then bought my own domain. I started a web server in my home office running over the cable broadband then moved to actual offsite hosting for my blog, moving from static HTML files to a rudimentary CMS then to pMachine to Expression Engine and now to WordPress. I’ve edited an online news service and a print magazine, ran social media for an archdiocese, and produced a daily radio show. Each change was made possible through technological advancements that lowered the barrier to entry, but it also ushered in a new era in which doing these things on a shoestring budget with a small staff was possible.

  1. It’s interesting to see that despite our very different jobs, how many tools Jeff and I share in common: Dropbox, Markdown, Marked, TexExpander, Drafts, Brett Terpstra’s Hyperkey, Alfred. I don’t list them all above, but I use each of these every day.  ↩

Image Credit

  • HowIWork_Desk: Own photo
  • Very impressive! WIth your new job, as communications director, is the job according to a specific description or are you developing it more on your own as it evolves? I’m just curious, as the collaboratives are new in the Archdiocese and I’m wondering how your role came to be. 🙂

    • The role of communications director in the collaboratives is indeed new and it came about through some conversations between me, the pastor who I knew beforehand, the director of pastoral planning for the archdiocese, and the director of financial services. The pastor and I were discussing a different role when this idea came up. There’s no written job description yet as we figure out what it can do, but it makes sense to have one. After all, what is the Church, but a giant organism of communion to communicate the Gospel. Thus we see my role as straddling both the administrative and pastoral spheres, and being primarily pastoral and evangelistic.

  • Dom,

    Yet it is interesting our shared tools for different uses. Although some of it is not entirely coincidental. When I first got a Mac in 2007 I raided your Mac related Twitter follows. Which of course led me to their blogs and then podcasts.

    I find it interesting that I had not mentioned 1Password in my own post. It must be that it has become so integral that I don’t even reflect on how much I use it. Other password management systems have much improved, but still 1Password is the gold platform for both continued improvement and their commitment across OS and platforms.

  • Love the setup; you’ve inspired much of my workflow over the years, from OmniFocus to Markdown to Hazel Anf Evernote.

    Hope you did t pay for the Scalzi books, though:

    Check out John C Wright if you like sci-fi; Hugo nominee this year and a recent convert if I understand correctly!

    • Thanks for the heads up about Scalzi, Josh. I won’t be reading anything else from him. I know about John C. Wright and several other Catholic scifi authors.

  • […] been three years since I first did a “How I Work” blog post (at the prompting of Tom McDonald) and since then I moved to a different full-time job and then to […]