Productivity and Organization

Over time I’ve acquired a reputation for being an organized (and, presumably, productive) person; occasionally, people ask me for tips.

Be as efficient as you can.

In the interest of following my own tips, I’m writing this up as a blog post so I have something I can quickly send to folks when they ask. Automate things where you can; if you’ve got the time to learn it, Workflow is a wonderful tool.1 I’ve got a good chunk of my morning routine compressed into pressing a single button on my phone and, depending on how complex my calendar is for the day, answering a question or two.

Don’t trust your brain to remember things

The human brain is a wonderful machine! Unfortunately, it’s terrible at remembering things, but also convinced that isn’t the case. The good news is, we invented writing, and then computers, both of which make it much easier to remember things. So don’t just put stuff in your head and assume it’ll stay there; it doesn’t matter what you use, but have somewhere permanent that you can put stuff. Depending on what you prefer, you can use a planner or notebook, or go all digital like I have. Personally, I use a combination of the system-default Calendar app, syncing through Google Calendar, with Drafts 42 as my “writing thoughts down in the middle of the night” app, Day One as a journal, and Ulysses for any longer-form writing or note-taking.3

Have a to-do list

Technically speaking, this is an extension of the above, but don’t trust yourself to remember things you have to do in a day. If they’re at a specific time or meeting with someone, they go in your calendar; otherwise, they go on the to-do list. Again, this can be on paper if that’s your style, but if you’re a big ol’ tech nerd, you’ve got a bounty of options. The built-in Reminders app is… there, and it’s not great, but it’s free and meets the bare minimum of functionality. Personally, I’m a big fan of Things 3,4 but Omnifocus is also a big name in the field, if (in my opinion) over-complicated. That said, task management apps like that are a huge market on the iOS and macOS app stores, as well as just online, so you should be able to find something you like.
Once you’ve started using it, I recommend the “vaguely Getting Things Done” style, which consists of “write stuff down as soon as you think of it, and file it away in the proper place when you’ve got time.” The important thing is to not go “oh, I’ll remember that later,” because there’s a really good chance you won’t.

Figure out what you’re spending your time on

You know that feeling like you’ve wasted a whole day? That’s stupid, but it’s also hard to convince your brain you’ve been productive if you don’t actually know what you’ve been spending your time on. Having a to-do list helps with this; you can look at your list for the day and see all the things you’ve checked off.5 Beyond that, you may want to try time tracking; I’m a fan of toggl and use it all the time. I keep the website pinned in a tab on my laptop, and rather than use their app, I’ve got some Workflows built that interact with their web API.6 It works pretty well for me; I know what I’m spending time on, and I can also use it for some very accurate billing, should I need to.

Clean up

Finally, staying organized is not only helpful for quickly finding things, it also just tends to make you feel better about everything. Take time when you can to organize your work and living spaces. If you’re currently in college, you’ve probably got ten thousand pages of various papers drifting around; next time it’s time to buy textbooks, I recommend going digital (it’s slightly cheaper, and then you only have to carry around your laptop/tablet, which you were probably gonna be carrying anyways, and you can search in your books, which is quite helpful). For the zillions of pages of handouts you get, invest in a scanner that can do duplex scanning and a recycle bin; it’s amazing how much space you can save by getting rid of all the papers.7 Once you’ve got things digitized (or, preferably, as you get them digitized), come up with a neat organizational system and stick to it. For school stuff, semester/term lines are a nice dividing line; if you’re doing the whole ‘adult life’ thing, the tax year is a good one.8

I’m going to call it done there. If you skipped to the end, the single most important thing I’d like you to get from this is brains are bad at remembering things; write stuff down. That’s my number one tip, so if you only take one thing from this, that’d be it.
If you’ve got any questions, I’ve recently brought back the ability for people to leave comments, so go ahead and do that.9 And hey, maybe I’ll do more posts like this, I enjoy doing the writing, and it’s fun to be able to support the various apps I use.10

  1. In September 2018, or thereabouts, it’s going to disappear and be replaced by Shortcuts, but from what we’ve seen in public betas, Shortcuts has the same functionality, some new features, and a new coat of paint, so if that link doesn’t work, just search the App Store for ‘Shortcuts.’ 
  2. Drafts 5 has been out and received very good reviews for its automation capabilities, but all I really want from the app is a dark color scheme and the ability to open directly into a new document, so the old version works for me. 
  3. That link is to Ulysses’ iOS app, but thanks to their subscription system, you pay for it on one platform and get it on iPad and Mac as well; mostly I use it on the Mac, but it’s nice to have it available wherever. 
  4. That’s their macOS app; they’ve also got separate iPhone and iPad apps. 
  5. This is why I’ve got Things set up not to sweep things away as soon as I check them off, but to leave them there until the end of the day. If I look at my list and it’s empty, nothing to do and looking like I’ve done nothing, the “oh god I wasted the whole day” feeling gets so much worse
  6. If you’d like to know more about those, leave something in the comments that I’ve just remembered I opened back up. 
  7. You don’t necessarily need to do what I did, which was a roughly five-year-long process of clearing out every paper I own, but then, you’re hopefully less of a pack-rat than I was, too. 
  8. Oh, and don’t leave those files in a single place; the nice thing about being digital is that it’s easy to make copies, and when you’ve got copies, you don’t have to worry that you’ll lose the original. These days, I throw all the current stuff into iCloud Drive, but I used to use Dropbox; older things get moved from whichever cloud to an external hard drive that’s backed up with Backblaze
  9. It’s one of the only ways to get in touch with me. Bonus productivity tip, for those of you reading the footnotes: social media sucks, stop using it. 
  10. Shameless self promotion: as an app developer, I know how danged hard it can be to actually make a living from the App Store. Support the people making the stuff you use. 

How I Organize My Digital Life

This is written in response to a post of the same title that my friend did on her blog: normally I would’ve responded in the comments, but it seemed like such a fun concept for a post that I felt like doing my own write-up.
In a similar vein, I am fairly immersed in the Apple ecosystem, though not entirely: my primary machine is a Macbook Pro running OS X Yosemite, and I’ve also got an iPhone 6 to which I am attached. However, a lot of my sync services are handled elsewhere – I use OneDrive, Dropbox, and my own server(s), as well as Google Calendar and a variety of email services.
For the apps that keep me organized, though, the list is as follows:


Apps that I use on both my Macbook and my iPhone.
1. Calendar. Mine is a multicolored mess, but each color corresponds to a calendar for specific things. My main Google Calendar is full of obligations – work, club meetings, classes. I’ve got an iCloud calendar of practice time and meals, things that are important but not quite as critical, another iCloud calendar for my free time, and another that I use for stuff that I might do. Plus, three calendars stored on my school’s Exchange server, which I use to keep track of the hours for the dining hall, the campus mail room, and office hours of my professors.1
2. Things. I wound up with this app after it was part of a bundle of software I bought at one point, and I’ve been using it ever since. The sync is well-done, and I enjoy having a ‘per day’ sort of system rather than the specific-time setup that Apple’s native Reminders app uses.
3. Pocket. The Share extension in iOS is beautifully-implemented, and the service is very reliable. I tend to binge-add, and then read through things slowly. Pocket is what I use for all of my linked-lists style content.2
4. Excel. I use spreadsheets to keep track of my budget and which classes I’m going to take and when. They’re intense spreadsheets.
5. Day One. Not technically for keeping organized but more for keeping sane, I use Day One as my journal of choice. Every day, about an hour before I go to bed, I’ll write up anything notable that happened that day. I’m outsourcing my memory.
6. Dropbox. To be honest, I almost forgot about this one because of how seamless it is. Dropbox is the glue that binds my life together and I could not function without it.3
7. myHomework. It’s technically possible to do everything that myHomework does using a combination of other apps on this list, but the ease-of-use of having it all in one place is worth it to me. Especially considering that I’m taking about a billion classes and I need to keep track of what project is for what class.
8. Mint. It’s got less functionality than my bank’s website does (in terms of what I can actually do with accounts and stuff) but it’s helpful to put my balance next to the balance on my student loans. Keeps things in perspective.


Not available on my iPhone, unfortunately.
1. Airmail 2.4 Email is an important thing that I use a lot. Airmail 2 is host to all 8 of the email addresses – spread across six different email servers – that I use regularly.5
2. Ulysses. I do all of my writing in Markdown6 and Ulysses is my favorite editor out of all of the ones that I’ve tried. It’s got a few idiosyncrasies, but half the time they’re features that I enjoy – the footnotes, for example, are wonderfully executed. And when I say I like it, I mean “I have more than 50,000 words written in it to date.”7


Those things that are iPhone-only.
1. Outlook. The best mail app I could find that supports my varied email providers. It’s actually a pretty good app, too, not just a ‘the only thing that would work’ – I’ve got one or two things I would change, but it’s all fairly well-implemented.
2. Health. I somehow became one of those Quantified Self people, to some degree or another. I’ve been on the iOS 9 beta for a while, and I really enjoy the Health-native support for water tracking. I also using Withings HealthMate to put in my pulse sometimes, because why not, and Lose It! to track what I’m eating.8

So yeah, that’s how I keep myself organized. It’s a complicated system, but it works for me.

  1. There’s no central place where all professors list their office hours, which I find strange. It’s an idea I’m fiddling with as a potential for a capstone project in my computer science major. 
  2. The Daring Fireball-style quotes-with-links posts I’ve been doing a lot of lately. 
  3. It’s gotten to the point that I now install it on the computer I use in the Computer Science lab, in spite of the fact that the machine has Deep Freeze on it. Long story short, I install and sign in to Dropbox at least once a week in that lab. And it is worth it
  4. Apparently they’ve got an iOS app coming out soon. I am very excited. 
  5. Don’t ask why I have that many functional email addresses. It just… happened. 
  6. John Gruber has been more of an influence in my life than I thought. Hmm. 
  7. I’m guesstemating here, but I’ve got about 100,000 words stored in it overall and I did anywhere from 30,000-50,000 of that in other editors and later imported them into my Ulysses file structure. 
  8. Fun fact: I started using Lose It! during the fall of last year, not because I felt like I needed to lose weight, but because I needed a reminder to eat enough that I wasn’t starving myself. I forgot to schedule myself time to eat meals. Whoops.