OmniOutliner 5 for Mac

I write a lot, both at home and at work. For something short (like this blog post) I don't always need an outline, but for longer posts and reviews or to take notes in meetings an outlining program is a must have. So I have been using the OmniOutliner tools (both on Mac and iOS) for years and I find them indispensable. Last month the Omni Group released OmniOutliner 5. There are a couple of significant features about the newest OmniOutliner that are worth highlighting:

  • Customizable Keyboard Shortcuts
  • Distraction-Free Mode
  • Typewriter Mode
  • Password Protection
  • Excel Export
  • New Pricing

The most significant feature from the list above is the new pricing model. There are two different versions of OmniOutliner 5, Essentials and Pro. Essentials is the reason the new pricing model is so significant...its only $9.99. Before Omni came out with Essentials the price for entry into a professional level outlining app was a bit cost prohibitive. Not any more. The Essentials version of the app has enough basic features to keep most people more than satisfied. I love this new model because I think a lot of people would really benefit from using a dedicated outlining app and now more people can justify paying a few bucks to have a really great to help them create outlines. So if you find yourself creating outline from time to time and would like a better way to do it I highly suggest buying OmniOutliner 5 Essentials. Omni Group also offers a free 14-day trial so you don't have to take my word for can test it for yourself. If you are new to using an outlining app, the Omni Group has a great blog post that walks user who are new to outlining with a dedicated app through the basic features of OmniOutliner 5 Essentials.

Customizable Keyboard Shortcuts:

Now for the really fun stuff...the more advanced features. Right off the bat OmniOutliner brings a pretty amazing feature with customizable keyboard shortcuts. One of the difficult things with relying on professional apps day in and day out can be remembering some of the powerful shortcuts they have. Now that you can create your own keyboard shortcuts with OmniOutliner 5 Professional you can make just the ones you need and give them shortcuts you will remember. For those of you who don't outline as much as I do you probably think I'm a little crazy for making such a big deal about this, but trust me this is really nice.

Distraction Free Mode:

Distraction free mode is nice too because it removes the sidebar and the toolbar from the view so you can just focus on the text you are writing. This can also come in handy when you have a bunch of windows open and you need to shrink down the outline window to just as small as possible. Taking out the tool and sidebars make that easier to do now.

Typewriter Mode:

Speaking of optimizing screen real estate, the new Typewriter Mode does this exceptionally well. With Typewriter Mode it keeps the current line you are on in the middle of the page/window so it is in an optimal place even as you add line, after line, after line...

Password Protection:

You can't swing a dead cat without hitting a story in the news about stolen or compromised data. Now you can password protect individual files you create with OmniOutliner 5 Pro.

Excel Export:

This feature may not seem like that big of a deal, but if you have ever started listing things out and then later realized that you really need that list in Excel so that you can do more with it...this feature is really handy. I love having both outliner and brainstorming apps export out to formats that can be sucked into other powerful apps so I really love this feature.

I can't say enough good things about the OmniOutliner app. Even if you don't think you would use an outlining app enough to really justify buying a dedicated app I think you should give the new OmniOutliner 5 a try. For $9.99 you are getting one heck of a powerful app for a very reasonable price. I hope the Omni Group carries over this new pricing model to more of their apps as well because I'm a huge fan of all of them and I think more people would be too if their entry level prices were a little more approachable.

Replacing Circus Ponies Notebook

replacing circus ponies notebook.jpg

I am way over due in writing this post, as I promised to do so back in my January 2016 article "Saying Goodbye to Circus Ponies Notebook." The Circus Ponies App for Mac and iOS is no more...quoting the developer that "Circus Ponies has gone to that great Alphabet company in the sky." So now what?

I could turn this article into its own book, but instead I am going to keep this as short as possible (which is still going to be relatively long) and tell you what I have done and mention some of the really great options there are out there. Here are the steps I recommend you take:

  1. Export all of your existing Circus Ponies Notebooks into formats that are a bit more future-proof
  2. Examine your specific needs and based on those needs choose an app or several apps that best fit those needs
  3. Stop using Circus Ponies Notebook and move on

Exporting Your Circus Ponies Notebooks

Freeing your precious data from the crumbling prison of the Circus Ponies Notebook app should be your top priority. Using the term "crumbling prison" is probably a little harsh as the Notebook app has several really simple and powerful ways to exports all your data from a given notebook with just a few clicks. But even so, it is VERY important that you do so quickly. While the Circus Ponies Notebook apps will continue to work on iOS and macOS for at least for a little while, you still need to sever the tie to this dead platform. Here are the export actions I took:

Export to a webpage:

This is all done through the Circus Ponies for Mac app from the "Export" menu option. This creates an "index.html" file that you can open in any web browser and then interact with your Circus Ponies Notebook just like you could with the app, at least from a reading and browsing perspective (you can't search or edit). This was a really key thing for me because I had a ton of embedded images in my notebooks and exporting out to OPML or to Word just didn't help because they don't retain the embedded images. So if you know approximately where in your notebook you are looking for data this export option is by far the best way to get to your data.

Export to Word:

As I mentioned above, exporting out a complete notebook to Word doesn't retain the embedded images but it does nicely take the entire text content and structure and stick it into a Word document. Images and files that were attached or embedded to the Notebook are still listed in the Word document so can still eventually get to those files (more on that later). Because Word is such a powerhouse app it is unlikely to completely disappear from the Earth any time soon, so this is a good long term format for your data. Just like the export to a web page option above, this is done through the Circus Ponies for Mac app from the "Export" menu option.

Extract All Images and Attachments:

This is a very important step because the only way to ensure you get absolutely ALL of your content out of the Circus Ponies Notebook format you need to grab all the "non-text" content that you added into each notebook (things like document and images) and this is done manually. Here is how you do it...

  1. Find the Notebook on your Mac you want to grab all the data from. It will have a ".nb" file extension.
  2. Control Click the file and choose "Show Package Contents" from the menu that pops up. Circus Ponies Notebook files use the Mac OS package file format, so the attachments and files that are embedded in a Notebook are all stored within the folder structure of that Package file.
  3. Now you will see a bunch of folders, but the one you are really looking for here is "attachments." This folder contains everything from your Notebook that was added in as an image or attachment.
  4. Copy and paste all of the files from this "attachments" folder into a folder on your computer so you can search and find these documents later.

Examine Your Needs and Choose Replacements Apps

Ok, great. You have rescued all of your precious Notebook contents. Now what? There is no single "one size fits all" answer here. The replacement app for you depends on what features of Circus Ponies Notebook you were using. So start by looking at what you need our of a "Notebook Replacement App." Once you have figure out your "can't live without it" list of features it is time to look at the options.

Microsoft OneNote:

If there was a single app out there that had the best chance of meeting most people's needs for replacing Circus Ponies Notebook this would be it. Best of all, this is a "free" app. Free is in quotes here because Microsoft is pulling in some profit from the app because the app is helping them to drive up their Microsoft 365 subscriptions. Because the app is not paid for upfront, there is a chance that Microsoft will stop supporting it in the future but that can be said of any app. OneNote has been a solid app for quite a few years and I suspect it will continue to be for quite a for more years. Seriously take a look at this app. If it does what you need this a great choice. Unfortunately this doesn't work for me for one very silly and simple reason...syncing. For whatever reason (probably the reason I mention above), Microsoft does not offer local storage as an option on their Mac OneNote app. It is an option on the PC and on mobile devices but not on the Mac. If you use OneNote on the Mac the data must be stored in Microsoft's cloud which is called OneDrive. The reason this doesn't work for me is that one of my biggest use cases for a Notebook is to capture data for work and almost all of that data is sensitive data that can't be stored on a cloud service.

OmniOutliner for Mac and iOS:

This is the solution I have settled on. It is a bit on the pricey side, but you get what you pay for. I spend so much time taking notes and ferreting away information that the solution I choose has to be very powerful and stable and I need to know that it is going to be around for a few years. OmniOutliner hits all of those points for me. I recommend biting the bullet and buying both the iOS version (OmniOutliner 2) and the Mac version if you are like me and need to take notes everywhere you go. For my work purposes I only use the Mac version and keep all the data locally on my machine to get around the sensitive data issue I described earlier. I recommend buying OmniOutliner for Mac directly from the OmniGroup's website rather than the Mac App Store because you will get discounted upgrades when new versions of the app are released (and discounts are not possible through the Mac App Store).

So how does OmniOutliner replace Circus Ponies Notebook? There is an excellent article over at Organizing Creativity that goes into great details about how you can do this. I have no intention of trying to duplicate any of that great work here so just give that article a read. I will warn you that using OmniOutliner for replacing Circus Ponies Notebook is not for the faint of heart. It is going to take a bit of fiddling and you will need to create some templates in order to really do it right, but in my opinion this is the best "power user" solution moving forward and it keeps your data in a format that quite future proof.

Outline by Gorillized:

There are actually quite a few app that have "notebook" features and Outline by Gorillized is just one those app. But there are two things that make this app stand out. The first being that they actually developed a Circus Ponies Notebook importer, so you can directly import all of your old Circus Ponies Notebooks into the Outline app. Here is a link the the support article that explains how to do this. The other reason to take a good look at this app is that they offer a discount for all of us "Circus Ponies Refugees." The discount only works on the Mac version of the app, but all you have to do is go to their website and purchase the Mac app and at checkout enter the discount code "CIRCUSPONIES" for 30% off the purchase price. I will probably end up purchasing this app and using it for two main purposes. One is to have a user friendly version of all my previous Circus Ponies Notebooks and the other is to use the app replace how I used to use Circus Ponies Notebook as a digital notebook while sitting on console for rocket launches.

Notebooks by Alfons Schmid:

I really like the clean look and simplicity of this app. I haven't personally used this app yet, but everything I have heard about it has been positive. Depending on your needs this app might be a good solution for you.

Move On

The last step in the the process of replacing Circus Ponies Notebook is to move on. You must sever all ties to the now dead Circus Ponies app and move forward with the application(s) you have chosen as (a) replacement(s). There is no such thing as a permanent application , at least not in today's fast moving technology world. Don't be afraid to experiment with different apps and use multiple apps for replacing Circus Ponies Notebook...using a single app to replace just one or two key features at a time. It is also important to think about the longevity of your data in these replacement applications. How is the data stored and how easily can you export that data into a format that can be read and used by another application. After all, Circus Ponies Notebook won't be the last app that goes off into that great big gig in the sky...

Pushing the iPad Pro to Its Limits

I've written quite a bit about the iPad Pro here at 1Wayswim:

All of those pieces have led to this one... what are the limits of the iPad Pro? Where does it start falling behind a more traditional computing system like a laptop or a desktop? Can it really be used in a "professional" capacity?

In the fall of 2014 I went back to school to finish my masters degree in Space Systems Engineering. So for the past two years I have been fighting my way though a heavy course load on top of my normal workload in my day job. For most of those two years my weapon of choice was my trusty 11" MacBook Air. But after the iPad Pro was released I decided that with most of my school work behind me, the iPad Pro was going to be the more functional device for me. But there was one wild masters thesis/project. My final project for my final semester in my masters program is a very large paper (60+ pages). As you can see from my article history on this site I have no issues with writing, so length was never a concern for me. But the project I chose is graphic Intensive...lots of figures and diagrams. Not only did I need a way to produce very professional looking diagrams, but I also had to manipulate those diagrams within the construct of the paper I was writing. I wasn't so sure how the iPad Pro was going to hold up under those conditions. The results were mostly positive, but there were a few pain points along the way...


I spent the first 3-4 weeks of my project doing the research portion. Once I found a document or paper I needed to read I would save it off to a folder on DropBox. When I was ready to start reading documents I would then, from right within the iOS DropBox app, copy the document over to PDF Pen 2 for iOS and start reading, making notes and highlighting text with the Apple Pencil. As I would run across items that fed into my paper I would start outlining the concepts and content. The one pain point here was the file system interface with the DropBox app. It would cutoff the full name of each file sometimes making it quite difficult to find the file I was looking for. I have no idea why the DropBox app does this, especially given the enormous screen of the iPad Pro. DrpBox needs to update their app.


In my opinion, there is only one real option for professional outlining in iOS and that is OmniOutliner 2. I started with a very high level outline of the paper structure and then started filling it in with content from my research efforts. But traditional outlining wasn't my only approach. Sometimes I would need something a little less structured to just get my ideas down. For that I turned to my favorite mind mapping app iThoughts for iOS. I would use iThoughts to literally capture a stream of "stuff" I needed to get out of my head and collect it somewhere. Once I had those ideas and concepts I could then group them together and once I made sense of it all in iThoughts I would port it over into my paper outline in OmniOutliner. But that still wasn't enough. I was still struggling to figure out how I was going to do certain aspects of my project and I needed to physically draw things out. So I turned to the built-in Notes app in iOS and used the Apple Pencil to start getting an idea down by sketching out the concept. I am NO artist, so I am being generous with the term sketch here...

I told you...chicken scratch

I told you...chicken scratch

Sometimes a sketch would eventually get transferred into text in my paper outline and sometime it would be the start of an actual diagram I would use. Either way, the Apple Pencil allowed me to physically transfer ideas into something. In the digital age we are in today we have lost a lot of the art of that tactile creation and sometimes you just have to go back to it. The fluid lag-free implementation of the Apple Pencil with the iPad Pro allows you to go back to the old-school ways but still capture it digitally. This ended up being a huge bonus for me as I fought my way through this project.

Writing the Paper

I started writing the main content for my rough draft in an app called Ulysses. Ulysses is simple yet powerful app for writers that gives you some really useful writing tools while at the same time getting the hell out of your way so you can WRITE. With a 60+ page page ahead of me I didn't need any more barriers than necessary. Ulysses just within the last week or so just got an update adding in features specifically for the iPad Pro. But even before those features were added I still found the app quite conducive to the work I needed to do. I was able to draft up about the first half of the paper section by section and then export the document out to Apple's Pages app so I could get the rough draft reviewed. This isn't a review for Ulysses but overall it performed like a champ and I can see myself using it quite a bit even after I finish up with school.

Pages was where my final paper ended up. I've been using Pages since day one for all my school papers but this was the first time I had used Pages exclusively on iOS, where as before I used it on my MacBook Air. Is Pages as powerful as Microsoft Word? No. But it is so much more elegant. And did I mention reliable? One weekend I spent over 30 hours writing on my paper in Pages on my iPad Pro and then had to spend a few hours creating some slides for work the next day. So I hopped on Microsoft PowerPoint and about 45 minutes in PowerPoint hung and I lost all of my work. This type of thing just doesn't happen in Pages, Numbers and Keynote. So I used them anytime I can and I don't look back.

I have yet to encounter a feature missing in Pages that I have to go over to Microsoft Word for. When I needed my group at work to peer review my rough draft I was able to export my document out of Pages into Microsoft Word. And when it is time to completely hand in my finished project I can export it out to PDF right from Pages. Also, Pages on the iPad Pro links into DropBox for iOS for inserting graphics I have captured and stored there and it also allows for direct exporting of graphics via the clipboard from other apps within iOS. So with even greater ease than on my Mac I am able to plug in the graphics I need. I will say that I have heard some amazing things about Microsoft Word for iOS. So if you aren't comfortable with Pages but are with Word I think that is an excellent option for you.

Creating the Graphics

For the graphics for my project I rely on Omnigraffle 2 for iOS. I own Omnigraffle Pro for my Mac as well, but after spending a little bit of time with the new Omnigraffle 2 for iOS I have found the experience of building graphics through the touch interface to be much more rewarding. I guess there is something to be said about being able to touch things. Omnigraffle 2 for iOS does take a bit of time to learn properly. There is a ton of functionality built into the touch interface for that application and it is almost like learning another language. Luckily the Omni Group put out a free iBooks book for Omnigraffle 2 that walks you through absolutely everything. There were two graphics for my paper that I ended up creating on my Mac, but that was only because I already had a similar graphic within the Mac App that I wanted to base the new graphic on.

The Pros and Cons of the iPad Pro

The iPad Pro is excellent for being able to concentrate on a single task. There is nothing else up on the screen to distract you like can often happen on the Mac. But when you need it, you can use things like split screen mode to instantly work between two different applications. There is also the sidebar (almost like a partial split screen mode) that lets your briefly slide out a small portion of the screen for another app to quickly glance at or cut some text or a graphic out of and then go right back to the full screen app you were working in. The Apple Pencil, despite my total lack of artistic skills, has also been quite useful. Being able to write things out, easily highlight documents and make quick notes and even sketch out a rough diagram has been a great tool to use to power through parts of my project.

And now the downsides. Manipulating text can be a real pain. I use a Bluetooth keyboard when writing most of the time so my only option is to touch the screen in order to select the text I need to copy, paste or edit. If I were using the virtual keyboard on the screen I would be able to press down on the spacebar with two fingers and use it like a trackpad to highlight and select the text (and this works great), but the virtual keyboard is not feasible for large writing projects. Moving through sections of a long paper can be a bit cumbersome on the iPad Pro as well. On the Mac you can use a two finger swipe to quickly scroll up and down, but on the iPad Pro you just have to either use the table of contents of the paper to quickly jump or swipe with your fingers to scroll. There are also times that I just feel out of place on the iPad Pro and want to go back to a traditional Mac. I think it is just all the years I have spent using a non-touch interface. When I get into working there is something to be said about falling back on the familiar. This isn't really a weakness of iOS, it is just a result of it being new and therefore not as comfortable...yet.

Even after writing this mammoth of a paper, I am still only about 4 months into working with an iPad Pro. I feel like I am only scratching the surface. There are a few things that are easier to do on the Mac and there are a lot of things that I can do on the iPad Pro that couldn't do at all on my Mac. My initial assessment that I made in my article Is the iPad Pro for You? was pretty much spot on. For what I intended to use the iPad Pro for it was the most versatile and useful tool for me to choose. It is perfect for every task? No, but no tool ever is. So far I haven't really run into anything on the iPad Pro that has limited me. It has all been things that can be overcome by getting more used to the operating system and the new features and eventually new 3rd party software will come along and help fill in some of the professional features as well. But for now the iPad Pro has served me well in this final semester of school. I am anxious to push through these final weeks of school so I can put the school work behind me and start using my iPad Pro for all the other areas of my life that I have had to sideline for the last 2-years.

You Get What You Pay For

In a world full of "free" games and applications, every once in a while you have to pause and think about just what it is you are "buying" when you download a free game or app. An issue I ran into with one of my applications yesterday made me do just that.

I've been using OmniFocus as my go-to task management tool for quite a few years now and have never had a lick of trouble with the application...until now. I won't go into all the details here, but I essentially lost a good portion of my data (all of my work Contexts were somehow lost). The good news is that OmniFocus has backups, so I could just revert back to a previous backup and recover what I had lost. Except reverting to the backup failed. I was now getting into the "complicated" fix territory. If OmniFocus were like most applications out there I would be stuck with having to email tech support back and forth. But not in this case. I was able to pick up the phone and immediately speak to someone in Tech Support within the OmniGroup (the company that developed OmniFocus). Within just a few minutes the wonderful tech support person at the OmniGroup had identified the problem (it was a bug with how their syncing worked) and figured out how to work around the bug. I was back up and running with my original data in just a few minutes.

Now this will really blow your mind. OmniFocus is an iOS app. How many iOS apps do you know of that have tech support that you can call? Not very many. But that's my point here. In a world full of apps that are "free", its nice to have a few apps that are really important to you personally that you actually pay REAL money for. That way, when things go to hell there is a REAL human you can call that can help pull you out of the fire. I'm not advocating that every application out there needs to go to a pricing model similar to what the OmniGroup uses (let's face it, they charge a premium for their applications). But they provide a premium service that I am more than happy to pay for.

OmniFocus isn't the only OmniGroup iOS app that I use on a regular basis. Here is the full list of OmniGroup apps I own:

So the next time you hesitate or just flat reject the idea of paying REAL money for an app, reconsider. You just might get your money's worth...

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.