How I Work, January 2021 Edition

Way back in February 2014, I was interviewed as part of LifeHacker’s “How I Work” series. Nearly 7 years have passed since that interview. A lot has changed, both in the tools I use, and the way I think about productivity, so I thought it was about time I brought that interview up to date. Here, then, is how I work in January 2021.

The basics

Apps, software and tools I can’t live without

To say that I can’t live without any of these tools is a bit extreme. Indeed, if there has been a significant change in my overall productivity philosophy over the last seven years, it has been toward simplicity. In 2021, I am trying, as much as practical to get the most from the tools that come with the systems I use, adding additional tools only where absolutely necessary. With that said, here’s a glimpse of my infrastructure.


Apple’s iCloud forms the foundation of my infrastructure. I recently merged our various Apple services into the Apple One Premier service, which includes 2 TB of data in iCloud. (We had 2 TB before but paid for it separately.) We all use Apple devices, and this allows us to manage the family accounts, and access our data from our various devices as needed. For storage, it also provides a kind of basic backup since the data is synced to the cloud.


Seven years ago, I was using Google Docs for all of my writing. In the intervening years I’ve gone back and forth between various writing apps: Scrivener, plain text (markdown) files, I’ve tried them all. Ultimately, I’ve come full circle. In college, I made the switch from WordPerfect to Microsoft Word 5.5 for DOS, and that became my favorite word processor. I have now returned to Microsoft Word, doing all of my writing there. I made this decision for several reasons:

  • It is a proven word processor that has been around for a long time. Indeed, I can open Word documents I wrote in college 30 years ago with Microsoft Word today.
  • It provides a single interface for all of the writing I do. I write these blog post in Word, as well as stories (when I am able to write them). I write letters in Word. Any kind of writing that I do happens in Word.
  • I saved myself a lot of time and headaches by creating a set of templates I use for all of my writing. I have three: fiction, blog post, and personal letter. I don’t have to worry about formatting. I took the time to create the templates to avoid having to tinker while I write.
  • I stick to the basics. I don’t need the vast majority of Word’s functions, and I’ve adjusted my toolbar accordingly.
  • It makes it much easier to archive my documents, something I have been working on for a while now.

I don’t worry as much about tracking my writing as I did seven years ago. I write, and I tend not to look at how much. That means I’ve given up most of the infrastructure I built to track my writing. It felt freeing to do that.

I still use WordPress for the blog here. WordPress is a great piece of software, one of the few that I can say has never really caused me any trouble, and has always worked well.


I’ve pared down the list of tools I use to stay productive over the last 7 years. Here are 5 that I use most frequently.

  • Pastebot. I don’t know why the Mac OS doesn’t come with a built-in clipboard manager, but it doesn’t. Pastebot fills this gap. This has been an invaluable tool for copy/paste productivity. Pastebot collects the things you copy (text, images, etc.) and allow you to instantly paste them from a history list. It integrates with iCloud so your copy history is accessible across devices. I probably use this a hundred times a day.
  • Keyboard Maestro. Great for text expanding, but it does a whole lot more. For instance, you can create useful workflows based on various events. I have one that copies the Clippings.txt file to a folder on my computer every time I plug in my Kindle.
  • LastPass. My favorite password management software. This has only gotten better in the 7+ years I have been using it. Nowadays, we use the Family addition so that everyone in the family can benefit from it.
  • Shortcuts. Once I figured out what Shortcuts were for on the iPhone, I embraced them, and I now have several that I created that have proven useful. My favorite is one I call “Let’s Nap” (as in, “Hey Siri, let’s nap). I use this when my 4-year-old and I lay down for a nap at lunchtime. When I tell Siri “let’s nap” my shortcut does the following: (1) checks for when my next meeting is, and if it is within the next hour, sets an alarm for 5 minutes before the start of the meeting; (2) puts my phone into Do Not Disturb mode for the same amount of time; (3) sets the volume of the phone to 12%; (4) turns on a playlist that we listen to as we drift off to sleep. It love it, and it works great!
  • A custom Safari home page. I created a custom Safari home page that every new tab and window opens to automatically. It has grouped jumping off points for the various things I do frequently. It’s kind of a like bookmark dashboard, but it makes it easy to get started with the most common tasks I do in Safari.
Example of my custom Safari homepage.
Example of my custom Safari home page


  • Audible. I’d been using Audible for just about a year when I was interviewed by Lifehacker. I mentioned how much more productive it made me because I could read more since I could listen to books while doing other things. That is still true today. Reading is how I continue to learn things, and Audible is an invaluable tool (and worthwhile investment) in my continuing education.
  • Kindle. If Audible has one downside, is that there is not a good way to highlight passages and take notes in the app. More and more, when I get a book from Audible, I also get the e-book. Particularly for nonfiction, this allows me to follow along, highlight passages, and take notes on what I am reading. While the e-books work on any Kindle app or device, my preferred device is my Kindle Oasis, since there are no other apps to distract me there.
  • Apple News+. This comes with the Apple One Premier service. I read a lot of magazines, and one thing I really like about Apple News+ is that many of the magazines I read are available there. For some I have separate print subscriptions because I like to read from something other than a screen now and then but having access to hundreds of magazines is useful.

Document management

  • Evernote. I don’t use Evernote for as many things as I used to, but I still use it to scan and manage important documents. Over the years I’ve pruned what I keep in Evernote, getting rid of things I never touched, and streamlining it. I almost never create notes manually. Most of what goes into Evernote these days are documents, either scanned or through some other automated process.
  • Apple Notes. This is what I use for more ephemeral notetaking. It is also where I keep various how-to notes, which I can easily share with the family.
  • Fujitsu ScanSnap 1300i. My trusty ScanSnap is still going strong after all these years.

Data protection

I have a 3-tier approach to data protection that has evolved over the years:

  • Tier 1: iCloud. All of my working documents, notes, archive, etc. is stored in iCloud and so it is always synced between the devices I use.
  • Tier 2: Time Machine. My Mac Mini—which acts as our home server, has two 3-TB external disks. One of these disks is a Time Machine backup, that is backing up data hourly.
  • Tier 3: CrashPlan for Small Business. This backs up all of our home computers (including the external disks) and provides an added level of data protection that has come in handy on several occasions over the years, most recently when Kelly’s laptop got stalled on a system upgrade.

In addition, I use Express VPN when connecting my devices to networks that are not my own, for instance, when staying at a hotel, or connecting to public WiFi in a local park.

Development tools

I never mentioned the development tools I used back when I did the LifeHacker interview, but I figured now was a good time to correct that oversight.

  • Homebrew. The first thing I install upon setting up a new machine is LastPass. The second thing I install is homebrew, which installs all of the good packages that a Mac Unix system is missing.
  • Visual Studio Code. For years I used GitHub’s Atom editor for editing code. But in my day job, I’ve been using Visual Studio for years (decades, really). Now that Visual Studio Code is available on a Mac, I’ve been using that to do local development work, and I’m pretty impressed by its capabilities.

My workspace, circa 2021

I was primarily working from home even before the pandemic hit just about a year ago, so that was nothing new for me. But about 2 years ago, we sold our town house, and bought a house nearby. That house came with a sunroom that in turn became my office. So today, my workspace looks a lot different than it did 7 years ago. The desk is the same (although I’m looking to get a new one). But I now have a table that forms a U-shape that I sit in and provides me with a surface for writing on paper.

Annotated image of my workspace.

I am also surrounded by my books, and often use the old rail chair for reading the newspaper in the morning. I like bright spaces, and the windows on 3 sides of the room let in plenty of light.

The other side of my office, surrounded by books.

The only thing my workspace is missing at this point is a set of French doors that we’ve been telling ourselves we’d install ever since we moved into the house, to create more of a separation between my office and the living room.

My favorite to-do list manager

Well, it feels like I’ve tried them all over the years (most recently Things 3), but none of them prove to be much better than a pen and paper. So beginning this year, in order to have some semblance of order, I’ve switched to Apple Reminders—keeping with my philosophy of keeping things simple, and using system tools wherever possible. So far, that is working just fine. I often scribbling items in my Field Notes notebook, but if I need them beyond a day or so, I’ll add them to Reminders.

Besides phone and computer, what tool can I not live without?

My Field Notes notebook. I’ve had one of these notebooks in my pocket since 2015 now, I believe. They are useful for all kinds of things. Jotting notes and ideas, a convenient ruler for small measurements, a straight edge for drawing a straight line. Remembering someone’s name I just met (because I try to write names down, lest I forget). I have an annual subscription which I’ve happily renewed year after year and I look forward to each quarterly shipment of notebooks to see what creative thing the Field Notes folks have come up with.

My current Field Notes "Heavy Duty" notebook.

That’s how I work as of January 2021. I’m always looking for ways to improve so if you have suggestions or recommendations about things that work well for you, let me know about them.


  1. This is an awesome update! I love the “How I Work” series and always wonder how the interviewee’s working methods change over time. Would love if this type of post were a tradition for you!

  2. Hi Jamie, i’m really enjoying reading your articles. I remember reading some of your work years ago on Evernote but then I stopped using it, now i’m back with evernote i find how you use it more valuable than anything else. How are your notebooks / tagging systems currently setup? i’m like you where i strive for simplicity and found using evernote for note taking makes it an overcrowded workspace, separating evernote as my document filing cabinet / read later hub from apple notes has been a game changer. I am however still lokking for the perfect way to structure my notebooks in evernote, any recommendations or tips would be most welcome.

  3. Nice overview again, Jamie!
    I like to read about the way you evolve in your working procedures.
    I missed reading about the Bullet Journal you started using a year ago. Did you stop using that? I stopped with mine starting this year. Too much work and not enough “ROI”. I missed the scheduled Reminders-function.
    I suppose you use Microsoft Office for work, but I find the office tool of Apple (Pages, Numbers and Keynote) sufficient for private use.
    Also would like to mention Agenda of Momento in my workflow. In the late 80s, early 90s, I was a passionate user of Lotus Agenda and have been looking for replacement since, which I found to a large extent in Agenda, working on macOS, iOS and iPadOS. It keeps me alert!

    1. Jaap, my paper-based Bullet Journal faded out, but I’ve been using a “digital” version in OneNote for work and that has worked out pretty well for me. Yesterday, however, I started experimenting with Obsidian and today, I began replacing my OneNote bullet journal with Obsidian. (I also started a “personal” bullet journal using Obsidian. I’ll let you know how it goes once I’ve been doing it for a while.

  4. Thank you for this great update, Jamie. I remember reading your first ‘How I work’ in 2014. You should know that your posts have encouraged me over the years to go paperless and read audiobooks! I also noticed a trend toward simplicity in my own workflow. For me, Alfred and Alfred-triggered scripts have replaced many other tools I have used over the years. I also love Beeminder and Complice to keep me grounded and focus on what matters to me.

    1. Giovanni, thanks for sticking around and reading for so long! You’ve probably seen a lot of my productivity evolution over the years. I’m delighted to hear that you found some of my posts helpful.


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