Sponsor: PowerPhotos – The Ultimate Toolbox for Photos on the Mac

I’m pleased to welcome a new sponsor to MacSparky, PowerPhotos. There has been a lot of action in photo management on the Mac in the past few years and PowerPhotos is that powerful utility we’ve all been waiting for. If you have photos scattered across multiple libraries that you want to merge together, have a library that you want to split up because it's gotten too large, or just want to get rid of duplicate photos, PowerPhotos can help you get your photo collection back in order.

PowerPhotos allows you to work with multiple Photos libraries and store them wherever you want, including on an external drive or a network drive. Split up your giant library into smaller ones by copying photos and albums with a simple drag and drop, preserving metadata such as descriptions and keywords along the way. Or, if you already have multiple libraries, use PowerPhotos to merge them together while weeding out duplicates along the way. PowerPhotos also features a powerful duplicate photo finder, a browser to let you see your photos without even opening up Photos itself, a multi-library search feature, and more.

You may recall an app from the iPhoto days called iPhoto Library Manager that gave you a similar set of tools. PowerPhotos is by the same developer and it’s just as reliable.

So go check out PowerPhotos today. Best of all, MacSparky readers get a 20% discount. Just use the code MACSPARKY at check out.

ComicBookFonts Annual Sale Today

If you've ever wanted to add some whimsical fonts to your library, there probably isn't any better place than ComicBookFonts.com. This is a resource for professional comic artists and there is a dizzying array of fonts available. I purchased their Hedge Backwards years ago and still use it all the times in presentations when I want something different. (I even occasionally use it as my dictation font just to switch things up.)

Anyway, these are professional fonts with professional costs. Hedge Backwards, for instance, normally sells for $129. But not today. Every year they have a New Years Day sale with fonts at a penny per year. So for today only just about everything is $20.17. I buy an additional font from them every year on January 1. Check it out. 

Productive App for Habit Tracking

Happy New Year. If you’ve been thinking about changing some habits as we head into 2017, why not game the system with an app? I have fallen off the wagon with habit tracking so I looked at a lot of the popular habit tracking apps before settling on Productive as my favorite. It has a bit of whimsey in its design and is customizable in just about every way you can think of for a habit-tracking app. 

You can have habits run multiple times a day (like flossing in the morning and the evening) or much less frequently, like paying bills twice a month. You can have reminder alarms fire off or have the app remain completely silent. I even like the way it has a selection of categorized pre-built habits the first time you run the app to get you started.

The app is free to get you started with a one-time upgrade for more than 5 habits and some other additional features. If you’re trying to get some momentum today, check it out.

iPhone City

The New York Times digs deep on the iPhone manufacturing hub in China that's capable of building 500,000 iPhones per day. It's interesting that this story comes out on the same day that the Wall Street Journal reports Apple is also exploring the possibility of manufacturing in India. Is it that the Chinese capacity still isn't high enough or that they don't want all their eggs in one basket? I suspect the latter.

The AirPods After a Week

I wrote about my new AirPods after one day. Now I’ve been using them over a week and have a few additional observations worth checking in on.

  • The AirPods charging case fits nicely in that little coin pocket in your jeans. This makes them easy to access and less likely to get all scratched up by your keys.
  • I still haven’t given them a real stressful battery test. As I go through the day, I am constantly recharging them in their case. I plug the case in at night so it’s getting charged once a day. With this method, battery simply is not an issue.
  • I’ve now used the AirPods to make approximately 70 calls with no drops, lost connections, or complaints about audio quality.
  • I use the AirPods with one ear probably 70% of the time. Specifically, if I’m on a call or listening to a podcast or audiobook, one ear is fine. I use both AirPods when listening to music. Switching between one and two ear mode is as easy as pulling them out of your ear.
  • I’ve always had an aversion to that guy that walks around with a Bluetooth things in his ear at all times. I realize that I'm leaning that way with these AirPods but my concession is that I only have them in my ear when I'm actually on a call or listening to Audio, which leads to my next point …
  • The smart connection between AirPods and the iPhone is really nice. When I'm not wearing them, my iPhone puts audio and its ringer through its speaker. When I put an AirPod in my ear it switches. With prior Bluetooth headphones, I missed a lot of calls because audio was going to Bluetooth headphones when I thought they were turned off.
  • Over a week and no cord tangles. So nice.
  • When somebody does approach me while I’m wearing the AirPod(s), I just pull one out of my ear. Double tapping and audibly telling the AirPod to “pause” while somebody is standing there looking at you is goofy. Pulling it out of my ear lets me focus on the person in front of me.
  • I received emails from a couple readers saying they don’t like the force required to double tap the AirPods. It doesn’t bother me. I would add, however, that figuring out the right amount of tap force takes a few days.
  • I’ve used them a lot more with Siri since my initial write up. It doesn’t feel to me as if Siri is any more accurate through an AirPod than it is through the built-in iPhone microphone. One big difference is you no longer have a screen to rely upon for feedback. Maybe because of this, I feel like I see the rough edges around Siri more with the AirPods than I do the iPhone.
  • They haven’t fallen out of my ears. I seem to have Apple-compliant ears.
  • I still don’t like using the double tap and Siri commands to pause or play or skip a track. I suspect I will never get used to that. Like I wrote last time, the Apple Watch helps a great deal.

Overall, I’m still really happy with these AirPods. For someone like me, who spends a lot of time on the telephone and listening to audiobooks and podcasts, they’re pretty great. I haven’t used any of my other Bluetooth headphones in the past week and that’s not a result of me trying to pull a stunt for this blog but instead a result of the fact that the AirPods are just so damn convenient. (That doesn’t mean I’ll be abandoning my noise canceling headphones on my next flight.)

Thank You Carrie

I was at an impressionable age when I first saw Star Wars and Carrie Fisher showed me that a princess could be fierce, smart, and the one who does the rescuing instead of the opposite. While Carrie Fisher was so much more than her role in that galaxy far, far away to me … she'll always be royalty.

MPU 357: Workflows that Worked in 2016

It's the end of the year so Katie and I did a show focussing on our favorite new workflows from 2016. I thought this show came out great with a little something for everybody. Enjoy.

Sponsors include:

  • Fujitsu ScanSnap ScanSnap Helps You Live a More Productive, Efficient, Paperless Life. 
  • Marketcircle We help small business grow with great Mac, iPhone and iPad apps including Daylight and Billings Pro.
  • 1Password Have you ever forgotten a password? Now you don't have to worry about that anymore.

Home Screens – Rishabh Dassani

Rishabh R. Dassani (Twitter) is a creative nonfiction writer and a management consultant at Dazné. He writes short essays on personal effectiveness for design and business leaders. You can find them at right here and also sign up for his weekly Newsflash. So Rishabh, show us your home screen.

What are some of your favorite apps?

I have used most of these apps for many years now. I find them indispensable in getting work done. Please note they may not all be available on the App Store as some of them are quite old and sport older UI.

  • Things (App Store)(Website): is a list manager that I find fast and a pleasure to use. I have found its Sync feature second to none.
  • Tweetbot (App Store)(Website): Although I have used the newer version, I find myself coming back to the older version (3.6.3).
  • Simplenote (App Store)(Website): I use it with Notational Velocity on the Mac to keep small snippets of text for quick access between my Mac and iPhone.
  • Ninjawords (Website): Super fast dictionary. Sadly, the app is no longer available. But they have a website that you can use to look up words quickly. You can even add it to your iOS home screen.
  • Articles (App Store) (Website): is my Wikipedia app of choice. It has remained without update since 2013, though that hasn't deterred me from using it.
  • Due (App Store)(Website): I use it for time-sensitive reminders. Great app.
  • Dialvetica (App Store)(Website): I use it for dialing contacts quickly. It has remained in my Dock for years.
  • Fantastical (App Store)(Website) is great for quickly adding calendar events. Also, the week view is great in landscape orientation.
  • Evernote Scannable (App Store)(Website) works great for scanning documents quickly.
  • Overcast (App Store)(Website) is my podcast app of choice, though it is far from perfect.
  • Letterboxd (App Store)(Website) is great for keeping track of films watched.
  • Deliveries (App Store)(Website) app is an old favorite for keeping track of shipments.
  • Cloak (App Store)(Website) is great for keeping yourself (and your data) safe using VPN.
  • Fast (Website): Not really an app but you can add it to your iOS home screen. It shows you the download speed of your internet connection.
  • Productive (App Store)(Website) for keeping track of new habits.
  • 1Password (App Store)(Website) for managing my passwords and credit cards.
  • Find Friends (Website): I use it for keeping track of my family members for emergency/safety reasons.

Which app is your guilty pleasure?

YouTube. (Website) I spend way more time with it than I should. Tweetbot and Instagram are a distant second.

What app makes you most productive? 

Things on the iPhone (App Store)(Website) works great for me to capture items on the go. Later I use Things on the Mac (2.2.6) to process them.

What app do you know you're underutilizing?

Drafts. (App Store)(Website) I only use it for a handful of things right now, though I know it can a lot more.

What is the app you are still missing?

I want my Apple Watch to track my sleep automatically. There are apps out there that let you do that but you have to turn them on/off manually.

More than an app, the feature I most want in my Apple devices is Proaction. I want these devices to learn from my use patterns. For instance, it knows that when I am at home, I turn off the Cellular Data (and turn on wifi), and when I am away, I turn on the Cellular Data (and turn off wifi). It would be great if it learns from you without you having to do it every time.

How many times a day do you use your iPhone?

I use my iPhone a few times (10+) during the day. I am trying to cut it down.

What Today View widgets are you using and why?

  • Fantastical (App Store)(Website) for viewing today's calendar.
  • Battery widget (iPhone and Watch).
  • PCalc (App Store)(Website) for doing quick calculations.
  • Activity for keeping track of Move, Stand, Exercise.
  • Shazam (App Store) for quickly identifying music I come across.

What is your favorite feature of the iPhone?

3D Touch: I use it all the time on my most-used apps. For instance, I use this feature with the Phone app to turn on/off Cellular Data and to put phone in Low Power Mode quickly.

If you were in charge at Apple, what would you add or change?

I would have longer cycles (more than a couple of years) between hardware and software releases.

I would also make the new macOS more mac like. One of the reasons I haven't upgraded to the newest OS is because I found its UI to be less pleasing to the eye. I also find the older iTunes 10 better. I am happily using Mountain Lion (10.8.4).

Show us your watch face.

I use the Modular watch face most of the time as it can have as many as 5 complications. The complications I use are Activity, Timer, Day and Date, Time, and Calendar. I also use a Utility watch face with the same complications. Although, there are now third-party complications available, these are the ones I have found to be essential.

What's your wallpaper and why?

I use wallpapers from a collection called Focus Backgrounds (no longer available) designed by my friend, Joe Darnell. I have been using them on my Mac (10.8.4) and iPhone (iOS 10) for quite some time.

Anything else you'd like to share?

I am excited to share that earlier this week I put out my 100th piece for my weblog. Please have a look at the Archive page to see what tickles your fancy. And if you like something, please share it with others.

Thanks Rishabh.


Default Folder X: Still Awesome (and Updated)

It has been years since I’ve mentioned it but I still use the heck out of Default Folder X. This is an application for your Mac that updates the open/save dialog boxes. It gives you an easy way to navigate to recent folders and files, favorites, and otherwise speeds up working on your Mac. If you like to tag files, it also fully supports tagging in the open and save dialog boxes. If you’ve never heard of it, I recommend downloading a trial and given it a shot.

If you have heard of default Folder X, you’ll be pleased to know that they just released a significant update that allows you to create folders in your Library folder for Default Folder X Favorites, Recent Folders and Recent Files. These are actually aliases to the folders and files shown in Default Folder X's menus, and can be used as a way to access Default Folder X's data from other applications. I love it when an app this mature can still surprise me with useful new features.

Yahoo Hacked Again for Another 1,000,000,000 Accounts

I'm a little late with this story but thought it worth sharing anyway. Yahoo announced last week that they had another security breach (in addition to the 500 million hacked accounts earlier this year). This newly disclosed breach, which happened in 2013, involved 1 Billion Yahoo accounts. As seen in the title, that's a lot of zeros.

It appears Yahoo's user data has been compromised multiple times in recent years. If you've used Yahoo in the past and cancelled your account, please make sure you didn't use the password you had at Yahoo anywhere else. If you have a Yahoo account, why are you still reading this? Go cancel it .... now.

25 Million Marios

According to Sensor Report, the new Mario game for iOS has already had 25 million downloads. That's a lot of Marios.

Super Mario Run is an interesting angle for Nintendo. The game isn't a traditional Nintendo game but instead a taste of one. If you really want a proper Mario platform, you'll still need to buy Nintendo hardware and that is probably the point.

The most annoying bit for me is their extreme copy protection. The app actually has to have an Internet connection to work. It's not requiring Internet data to play the game but instead it's a copy protection mechanism. I hate it when a company makes a product significantly worse for paying customers in effort to avoid software piracy. As an example, I was in line at Disneyland a few days ago and thought I'd play the Mario game while waiting. Unfortunately the Internet sucks at Disneyland and instead I got this.

Sponsor: Straighten Out Your Email with SaneBox

This week MacSparky is sponsored by SaneBox, the email service that can start saving your bacon today. As the end of the year approaches, it’s a good time to look at your workflows that work … and those that don’t. For a lot of folks, email is a constant pain point and it doesn’t need to be. With SaneBox at your back, you add a powerful set of email tools that can work in just about any email client. With SaneBox you can:

  • Wake up everyday to find the SaneBox robots have automatically sorted your incoming email for you so you can address the important and ignore the irrelevant. 
  • Defer email for hours, days, or weeks so it is out of your life until a more appropriate time.
  • Set secret reminders so if someone doesn’t reply to an important email SaneBox gives you a nudge to follow up.
  • Automatically save attachments to the cloud (like Dropbox).
  • Use their SaneForward service to automatically send appropriate emails to services like Evernote, Expensify, and Kayak.
  • Move unwanted email to the SaneBlackHole and never see anything from that person again.

The list goes on. Why not straighten out your email in 2017 by getting a SaneBox account and bringing a gun to a knife fight. If you sign up with this link, you even get a discount off your subscription.

The Apple AirPods After a Day of Use

My Apple AirPods arrived. Hurray! I don’t think you can call this a “review” after just a day of use. Instead, it’s a list of observations from a new user. Before getting started, I should say a little bit about me and bluetooth. For several years now I’ve been carrying around a variety of bluetooth headsets throughout the day. I use them to listen to music and podcasts. I also use them to make a lot of telephone calls. So as an AirPod customer, I am looking for something that sounds good but is also useful for phone calls. With that in mind, here goes…

About the Case

  • I like the idea of a battery case. I'm always carrying these Bluetooth headsets in my pocket and the idea of one that can charge them while in my pocket is a great idea.
  • The case is heavier than you think it is.
  • It’s a good thing the hinge is chrome or I'd never know what side is front … really.
  • Since you know which side is front, you also know exactly which AirPod is for the left and right ear when you open it up. This is helpful if you use just one AirPod at a time, which it is already clear I will do often.
  • The Magnetic latch for the case is more satisfying than it should be. At some point I started to feel like Captain Queeg and his ball bearings so I put it back in my pocket.
  • Overall, the case design is great. It’s about the size of a dental floss container but the edges are much more rounded, making getting it in and out of your pocket much easier.

About the Pairing Experience

  • A lot of folks are losing their minds over the pairing process. It is more convenient but I'd consider a side benefit and not a good enough reason to buy AirPods over some other Bluetooth headphone. All of my recently acquired Bluetooth headphones hold a pairing pretty good.
  • Setting the previous point aside, using these with multiple Apple devices is far superior to any other Bluetooth device I’ve used. I jumped between iPhone, iPad(s), and Mac(s) at will with these AirPods. None of my other Bluetooth headphones could do this without a lot of work (if at all).
  • I couldn’t get the AirPods to pair to the Apple TV automagically. I can get them to pair to Apple TV as a standard Bluetooth headphone but where is the fun in that?
  • When you flip open the case, iPhone displays a panel showing the current charge status of each AirPod and the case. Super-slick.
  • Once you pair the AirPod's with any iCloud connected Apple device, they are automatically paired to every other device in your iCloud account. 

About the Fit

  • This is the second time I’ve used AirPods. Again I jumped and shook my head like a crazy man. Again I was unable to make them fall out of my ears. I took a hike with no problem but I wouldn’t use them while playing tennis or climbing a mountain.
  • Thinking about how I usually have corded Apple EarPods fall out of my ears, it usually involves some hijinks with the cord. These new AirPods don’t have a cord so–in large part–problem solved. You know that feeling when your EarPods yank on your ear because the cord got caught on a door handle, right? No more.
  • The fact that the AirPods fit nicely in my ears doesn’t mean they’ll fit in yours. I have several friends with ears that are too big or too small (or too odd-grin) for EarPods. I expect they’ll face the same problems with AirPods.
  • Changing clothes with the AirPods in your ears is a lot easier than any other headphone or Bluetooth headset I've ever used. I can actually change my shirt without having to stop my song or podcast.

About the Battery Life

  • It is too early for me to report on battery life. I'm just getting started with these things. However, because so often I use them one at a time with the other one charging in the case, I don’t expect losing battery power to be an issue.
  • The fact that the case charges by lightning cable is convenient for me. I have lightning chargers everywhere in my life including next to my bed, in my car, and even a battery that I carry in my bag.

About the Sound Quality and Range

  • Overall I would rate the sound quality as "pretty good". If you're super picky about audio, you'll probably not want AirPods. If you think the EarPods are good enough, you'll find these wireless versions good enough as well. I tried really hard to compare wired EarPods to wireless AirPods and they sound about the same to me. I guess that's the point.
  • I'm sure it has something to do with the Apple W1 chip but the range on these is better than any Bluetooth headphones I've ever used. Because I spend so much time on the phone and listening to Bluetooth audio, I have a really good idea of how far I can get away from my phone before things start falling apart. The AirPods sound better and I was able to get much further with the AirPod's then I was any other Bluetooth device I’ve used in the past.

About Making Phone Calls

  • I love the fact that you can just use one of the AirPods in mono-mode. I made several phone calls with the right one in and then stuck it in the case and pulled out the left one out and started using that for hours. They've got the same hardware for both the left and the right. If you're making a lot of telephone calls, this allows you to be charging one while using the other. Clever.
  • The call sound quality is acceptable. I did a test with one friend between my AirPod's and my BlueParrot Bluetooth headset and she reported that both sounded the same.

About The Controls (and Lack Thereof)

  • Every other Bluetooth headphone I've used has attached controls similar to those on the existing EarPods controlls. Pausing with a click is great. You don't get that with AirPods. Instead, to pause, I just pull an AirPod out of my ear and the audio stops. Volume up and down is more frustrating. You can use a Siri command or you can use volume controls on your iPhone or Apple Watch but all of those things take more steps than a simple click. Indeed, there is no way to adjust volume with the AirPods as easily as you can with the EarPods that come free with your iPhone. While that sucks, AirPods bring Siri to the game, which is pretty awesome.

About Siri and the AirPods

  • Getting Siri with a couple of taps to your ear is really useful. Granted, I am in the Siri camp already so I'm comfortable giving commands to my personal digital assistant and getting some results. The double tap is more convenient and easier than the long press on the center control button on my existing Bluetooth headphones. Moreover, Siri is just more accurate and responsive with the AirPod's then she is with any other Bluetooth headset I've used. Audio playback/volumes/next track issues aside, having Siri in my ear is pretty great.
  • There's a setting that allows you to toggle the double tap between Siri activation and play/pause. If you use Siri at all, you'll want to leave it on the default Siri activation.
  • I hope at some point they find a way to give you more control with taps. Why not a single tap or triple tap?
  • Interestingly, the AirPods improve dictation accuracy. I ran test with both Dragon Anywhere and Siri dictation and found it more accurate when using the AirPod microphone then using the built-in microphone. I think a lot of work went into the AirPod beam forming microphones.

In Summary

I fully expect these AirPod's to take over the vast majority of my Bluetooth headphones duty. The convenience, the easy access to Siri, the ability to carry them in my pocket and always be charging make the AirPods a clear winner for me. While I am certain I will miss the better audio controls you get on a corded headphone, the other features AirPod provide more than make up for this for me.

If you need noise canceling or something over the ear for more strenuous workouts, the AirPods won’t cut it. However, for most people I think the AirPods are going to be a great solution. Best of all, this is only the first generation of Apple’s AirPods. These things are only going to get smarter and more useful over time.


MPU 356: A Fresh Look at DEVONthink

DEVONthink has made some significant strides in the last few years. Most impressive to me, is the way they've implemented iOS syncing. You now can have your entire DEVON library on your iPad and iPhone. This week we're joined by Stuart Ingram, a busy guy that is getting the most from DEVONthink to hold it all together. We talk about the app basics, how to set it up and get started, and some interesting advanced features.

Sponsors include:

  • 1Password Have you ever forgotten a password? Now you don't have to worry about that anymore. Save up to 20% using this link.
  • The Omni Group We're passionate about productivity for Mac, iPhone and iPad. 
  • Sanebox Stop drowning in email!

1Password for iOS 6.5 Gets an Improved Watch App

This week 1Password released version 6.5 of the iOS app. There are several big improvements including a better onboarding experience and better group management. What really struck me, however, is the new Apple Watch app. It’s what I would refer to in my 80’s vernacular as “a sweet upgrade”.

The new Apple Watch app is a native Apple Watch app taking advantage of the the watchOS 3 update and running much faster. It’s now easy to set up and move key items from any 1Password vault (including 1Password.com vaults) to your wrist. I’ll be using 1Password on my wrist a lot more now. As an example, I still occasionally need to get my credit card PIN number when making a purchase. Now it’s on my wrist.

There has been an evolution with Apple Watch apps. With watchOS 1 and 2, watch apps felt like an experiment more than a finished product. With watchOS 3, Apple Watch apps have the possibility of being useful. That doesn’t mean that they all actually are useful. I think getting the user interface and feature scope on an Apple Watch app is a tricky thing. It’s a small screen and app developers need to think of it primarily as a consumption experience for getting data out of their app. 1Password nails this.

Building Custom Apple Watch Faces

I mentioned in yesterday’s OmniGraffle sponsorship post that I made some cool new Star Wars Apple watch faces. That resulted in several emails from readers asking exactly how I did that. So here goes.

Custom Apple Watch Faces

Apple’s not big on custom watch faces. In fact, I would be surprised if they ever open the watch up for just anybody to make their own watch faces. Apple does, however, allow you to make a watch face based on your photo album. The idea is for Apple Watch owners to use their favorited photos on the background of a basic digital watch. If you love your dog, you can have your dog on your wrist every time you check the time.

I tested this watch face and didn’t like it because my favorited pictures (largely family pictures) don’t look good on a small screen and definitely don’t make a good background for a digital clock. That got me thinking about what would make a good background. Specifically, could I make something that approximates a custom Apple watch face so long as I’m willing to stick with the digital clock available on the built-in photo watch face? The answer is that it is absolutely possible to make interesting custom watch faces this way. The trick is to have a simple graphic and a pure black background.

Icons Are Key

As you may know, I love Star Wars. So I decided to make myself a series of Star Wars watch faces. Images shrunk down to a watch face size look pretty odd and anything with too much detail compresses into just a blob of pixels. Icons, however, are different. They are usually graphically fairly simple and can easily scale down to a small size for your watch face.

So I did a Google search for Star Wars icons. Specifically, the search was “Star Wars icons PNG”. It turns out there is a treasure trove of Star Wars icons on the Internet. Below is a more refined search of “Star Wars icons R2D2 PNG”.

A lot of icon files, particularly in the PNG format, are saved without a background making it really easy to drop them onto a black background to make your Apple watch face. To add a layer of difficulty for this tutorial, I picked this one that has a bright orange background. I then open the file in Preview and used the Instant Alpha feature to remove the background. It’s fairly simple. Just drag the mouse enough to remove the background and nothing more. When you’re done, save that file and then you’ll have a background-less PNG file of R2D2.

Removing the background in Preview.

Removing the background in Preview.

A Black Background

Next I needed to get that icon on a solid black background. This is the part where I use OmniGraffle. In OmniGraffle, I made a black square. Notice it is not gray or partially black. It’s solid black. When the watch face displays on Apple watch, anything other than black looks off. I tried using gray backgrounds and other colors and they all look silly because of the way the watch is made. A pure black watch face fades right into the background. If you look at Apple’s own watch faces you’ll note that almost all of them also use the pure black background.

Then I simply drag the R2D2 PNG file on top of black square in OmniGraffle. The photo watch face displays the time in the lower-right corner of the watch. Therefore, that section always needs to be solid black. (You can make an adjustment to display the time at the upper-right portion of the watch face if you prefer but I want the icons on top.) While respecting the area for the time display, you can set your icon anywhere else on the black square. I center larger icons and place smaller ones to the left but do whatever blows your hair back. Don’t make the icon too small. Don’t forget that watch face is still pretty small. Once I got things laid out exactly how I want in OmniGraffle, I export the images as PNG and then import it into the Photos application.

By default, the Apple Watch imports your favorited photos. However, in the Apple Watch preferences app on the iPhone, you can change that to import any album you choose. So I made a new album called, appropriately, “watch”. Now I have the Apple watch sync the watch album over instead of my favorites. I’ve loaded that album up with various bits of Star Wars themed custom faces I made in exactly the way I described above. It usually takes a few minutes but eventually the new images will sync over your watch and if you set the photo face as your default Apple watch face, you’ll suddenly find you got some nice custom watch faces. If you aren't feeling like makinig your R2D2 watch face but would rather just download mine, here you go.

Obviously, you don’t have to just use Star Wars icons. You could also simple icons from your interest (or fandom) of choice. The Internet is full of interesting, cleanly designed icons. Put any one of them on a solid black background and sync over to your watch and enjoy.