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The Digital Organizing Toolbox

Los Angeles based professional organizer/Apple tutor Deron Bos's digital organizer's toolbox.

Inevitably when I’m teaching one of my clients one app, I’ll mention other apps that help me keep me organized in Apple Land. One client strongly requested that I compile all of this tools into a list…and being a gentleman who likes to help, I have done so!

Mac Apps and their iOS counterparts

One of my favorite categories of apps are those that allow me to work with the same data on any device that I own. That’s possible mostly through this service:

Dropbox: while I certainly use iCloud to back up my iOS devices it’s DB that I use to sync all my data between devices because it’s done so with nar a hitch for last few years. I often think one of the easiest metaphors for understanding some (not all!) of its possibilities: is that it’s a thumb drive in the sky that can be shared with as many folks as you like (or none at all.) One of my favorite uses of it is as a replacement for your Documents folder, outlined in this post.

1 Password: the 21st century equivalent for me of “I’d like to buy the world a Coke” is I’d like to teach the world to use 1 Password. We all have too many passwords at this point and trying to manage them in our heads or in unprotected text files or notepads is not only inefficient it’s downright dangerous. You might as well wake up every morning and walk down the street buck naked. I go into deeper detail of my love in this post. The iOS version is equally as great and is now free so you could start there and then sync it all over to your Mac through Dropbox or iCloud.

Textexpander: this runs right alongside 1Password for me for as an essential app and I write about why right here. And it has an iOS app that just keeps getting better. Its logo is a balloon and so I give you:

Byword: if writing apps were Wes Anderson characters: MS Word (and to a lesser extent its Apple counterpart Pages) would be Max Fisher overly committed and overburdened while Byword would be The Fantastic Mr. Fox: sleek, light-weight, while still having plenty of tricks up his sleeve. It offers a distraction free writing environment that will do more to helping you focus on the task of writing that you thought possible. Complimented as all apps in this section with iOs versions.(iPhone and iPad)

Day One: like Byword, this app offers a distraction free writing zone, but it’s specifically geared for journal writing. Even if you think, “Oh, I don’t need a diary” at this point in your life I would encourage you to check this out – this app is so well designed and so FUN to use even if you only listed 4 things you did that day or threw an occasional picture into it with a two sentence caption, it’d pay you back for the investment for years. Simple, but powerful. Start it on your Mac in the morning, finish it on your iPad or iPhone at the end of the day.

(I’d like to thank my seven year old for the idea for this clip:)

Evernote: one of the main strengths of this app has always been that it’s available everywhere: on the Mac, on the web, on iOS, Android, – almost any situation where you have a digital connection it’s there. It’s my digital filing cabinet for my paperless workflow, but it’s also a great place for project inspiration and notes. Don’t be intimidated by all it can do, just try to do one thing with it and go from there.

Todoist: for a few years I thought the simplicity of Reminders was enough for my task management, but recently I’ve had a renewed love affair with Getting Things Done and went looking for something more powerful to put this system into action. Todoist is the current winner. A great tool for GTD, these articles by Mike Vardy were incredibly helpful to me in setting up and continue to be a touchstone that I go back to as the tasks stack up. Like Evernote it’s everywhere: iPhone, iPad, web, and even a Chrome extension.

Chrome: I rocked Safari for years until it kept beach balling on me with my usual array of tabs. Since then I’ve used Chrome and it’s very stable, plus offers a lot of killer extensions. I like the iOS app too and how they work together, but wouldn’t fault anyone for sticking with mobile Safari: it’s a damn good mobile browser.

Tweetbot: if you’ve only used Twitter through the web interface or its native apps, you’re in for a treat with this suite of apps. The most up to date version is the iPhone one but the older iPad and Mac versions sync with all of them and are still sharp. Beautiful interface, pleasurable swiping interface, and cute robot sounds are three of the many reasons this remains one of the most dee-lightful apps to use.

Fantastical: I struggled with digital calendar apps, before I found this one which like Tweetbot has Mac, iPhone, and iPad versions. They all make adding and checking out your week super easy and fun. Mine syncs no problem with my wife and I’s Google calendars. Essential, so well done.

Mac Only

My MacBook Pro is still my favorite workstation and these are the apps that make me long for the Mac’s physical keyboard when I’m away too long:

Quickcast: is how I’ve recorded all my screencasts on Bos Organization so far and it’s…free. I know it’s gaining in popularity, but it still feels like a hidden jewel to me. You can record screencasts up to 5 minutes long, publish them to the web, and then embed that video or send someone the link. Not only helpful to bloggers, but perfect if you want to send someone a quick video tip or question.

Mailplane: up until Mavericks, I used Mail, the native Mac app to manage my multiple Gmail accounts. However with Mavericks the friction between Mail and Gmail became so unbearable that I took my friend David Sparks’s advice and went to a mail client that was built specifically around Gmail’s unique architecture and even offers built in access to cool Gmail plugins like Rapportive and Boomerang. Very happy with this app, which is frequently updated and improved.

Clean my Mac 2: I needed something like this app for years but probably missed it, because I was so on-guard against Mac Keeper, which is pretty evil – a heavily advertised piece of malware that you should avoid at all costs. However this app will clear the junk out of your Mac in a safe and quick manner in a user friendly and beautifully designed interface.

Hazel: is a simple to learn automated file management app that can be incredibly powerful depending on how far you want to go with it. My primary uses for it currently are to clear out my downloads folder and keep my Mac’s desktop tidy. That all makes it worth the price, but it’s possible to have it do so much more.

The Backup Crew

You must, must, must have a backup solution in place, before you proceed any further, put in any more work on your computer. You know this, let’s do something about it:

Time Machine: this is Apple’s native backup app, it’s baked right in with the OS. Simple to set up (you’ll need some kind of external hard drive or Time Capsule) and it runs effortlessly in the background. A backup solution, but mostly built for grabbing lost files or previous versions of files.

Super Duper!: if the whole ranch goes up in smoke, you can restore your Mac by Time Machine but it will take a while. What Super Duper creates is a bootable clone of your entire computer, so if your drive crashes: you can literally boot from this clone and get back to work.

Backblaze: you have backup, but what about when the big LA earthquake happens or there’s a robbery? You need offsite backup and this is my service of choice: built by former Apple engineers, affordable and easy to use.

Cloud Pull: it gives me a piece of mind to be able to have copies of all my Google data on an actual hard drive. (Sort of the opposite of Backblaze, I suppose?) This backups almost all of your Google data in the background.

Web apps:

Google Drive: I’ve kept spreadsheets for personal finance for years and GD is my app of choice because it’s easy to learn and streamlined. You can do a lot more with Google Drive (more and more it’s similar to Dropbox) but it’s worth for me for this reason alone.

Google Music: I signed up for iTunes Music Match on its launch and found it lacking in a number of key areas and frustrated that Apple seemed uninterested in working on it during its first year. That’s when I moved all my music to this comparable and FREE service. (If you don’t mind trading your soul to Google.) Although most of my listening hours go to podcasts this is a killer music solution and has a sharp iOS app to go with it.

Canva: most of the images I’ve done for this blog and social media, I created right in this app: a super easy to learn alternative to a beast like Photoshop. Presized templates, cheap clip-art (if you need it) and a great design make this a joy to use.

Pic Monkey: although you can do a lot of creation in Canva, for photo touch-up and effects (like the blurring here) I go here. The perfect companions: Canva and Pic Monkey.

Buffer: if you’re on social media for your business, this app is indispensable. It allows you to schedule and organize tweets and posts weeks in advance and in a very clean and simple interface. Love it: iOS apps too.

iOS Apps…the beginning:

Again, a lot of my favorite iOS apps are listed above, the ones with Mac counterparts. But here are some that live on that platform alone. I’ll expand this as time goes by:

Documents 5: I love this app plus the apps that work with it including PDF Pen Expert and Scanner Pro. If you like to read PDF eBooks on your iPad or iPhone then this is the app for you! I wrote all about that in detail here.

Overcast: as I mentioned earlier, I’m a podcast junkie and the iPhone is the best place to put them – this is my podCATCHER of choice. Great design(see a theme here?), Smart Speed, Voice Boost and cool discovery features.

What’s your favorite apps for digital organizing? What digital organizing challenge are you still looking for an app to solve? Let me know in the comments below. Thanks!

Note: a lot of these apps are free, for the ones that are not I’ve linked to them using an affiliate link which means I earn a few cents if you use my link but to no extra charge to you. It helps me a bit in keeping expansive resources like this for free, so thanks!

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