Filing System Complete - Hazel adds Dynamic Mavericks Tagging

The latest update of Hazel, version 3.2.3, add dynamic tag support.

New features: Added "Dynamic Tags". You can now create and remove tags based on a file's metadata and custom attributes.

Thank you Noodlesoft! My basic filing system is now complete. See these posts for more discussion on tagging and my system.

The system is summarized here:

Folder Processing System

  • Inbox, Outbox, and Now folders located on my sync folder
  • Filing Cabinet in Together 3

Files go into the Inbox via the downloads folder of via this script. They are evaluated and go into the Now folder or the Outbox.

The Now folder is semi-organized into folders corresponding to my omnifocus tasks and some recurring items like to read items.

The Outbox is watched by Hazel to autofile via tags to a shallow folder system by project.

 Dynamic Mavericks Tagging in Hazel! Dynamic Mavericks Tagging in Hazel!

Slight delays on finalizing my filing system

We got the OK at work to go Mavericks. The upgrade was great and I was primed and ready to update my filing system as outlined here. Basically, I autotag files from emails with who sent the file which is a big help for me in finding stuff.

Then came the crushing realization that I am still stuck with comments. The good folks at Noodlesoft haven't yet implemented dynamic tags in Mavericks.

So in the meantime, I'm slowly mirroring the typical open meta tags Hazel rules to include the Mavericks tags I have been applying by hand, like some sort of Neanderthal. I put in a request with Mr Noodle for dynamic tags here and I am am hoping this comes through.

All said, I do like system wide tags and they help a bit in finding files. I can't wait for the dev community to blow this out. Here's to hoping its simple enough I can make use of it. Brett Terpstra outlines what he is doing on his site.

More thoughts on minimalist wallets

I've been using a few of the newer minimalist wallets and finding them to be fairly good. In keeping with the design, I am having to choose what I carry with me. Overall, I really like having a slim wallet to carry. As I stated on this post, handling cash is an issue. I went through a brief stretch of using cash more than usual and found that I was annoyed at a couple of things: working with bills pretty much showed everyone how much money you were carrying (there are some ways to not do this) and that putting bills back "into" the wallet was slow. I often just shoved the bills in my pocket. The slow and unorganized handling isn't enough to make me go big on the wallet again. It does make me use cards in favor of cash. I'd rather that each work well.

This issue with folded bills is that you can' shuffle through them. Particularly, if they are folded twice to fit on or in a card sized wallet. You can fold each bill separately or, you know I'm not that interested in figuring a way to make this work out with a given wallet. There are wallets that are beginning to address this with in between designs. Here are a couple:

The most rad wallet is big enough to have cash only folded once. This was better. It still not good enough to beat out the smaller card wallets to me. It's a well made product but just that much bigger and thicker than I want.

There is one more style, the wrap wallet, that is getting a ton of backers on kickstarter. This is probably too thick when all is said and done. However, it may solve the cash issue enough to tip the scales for folks.

The more I think about it, I think I need a cash sleeve that is separate from my card wallet. Feel free to run with that.

Update on Minimalist Wallet

After a bit more usage, it is clear that these an small wallets are great card wallets. They will not work if you use cash with any frequency, they will be annoying at best. At worst, they will not work for you. Basic guidance would seem to be that for cash usage the smallest size will be slightly larger than a singly folded bill.

Minimalist Wallet Thoughts

Like a bunch of folks, I am in the minimalist wallet camp. As cash isn't used as much today as even 5 years ago, the requirements for the wallet are changing. The strategy i use is the everyday carry wallet for my license and a few main cards. I have a second wallet with other items I want to carry. Kickstarter is a haven for these things today and I've picked up 2 wallets this way, with two more on the way, and am considering a couple others. I did the same thing with wallets about 15 years ago to figure out what worked for me. Then I stuck with a basic style until now. No need for disclosure here as I am not getting any samples or being paid to write anything. This is becoming a bit of a hobby over the last 6 months so I thought I would share.

Overall, I'm choosing small size and weight. I'm sacrificing on ease of cash handling while maintaining easy card usage. With that in mind, a quick tour of the wallets I've looked at.

The classic minimalist wallets that I've used:

This style is my go to for the past 15 years. You can usually find some cheap versions of these. They are reasonably good until the leather starts stretching. When this starts happening, cards start falling out which is the main failing of this wallet. In addition to being light and cheap, I like having a window for my license for some reason. This one works for that.

money clip style any of the inexpensive money clip version wear out too soon for my liking. Any clip the has the strength to hold cash and last adds too much weight in my opinion. if you favor this style, this is the best I can recommend in terms of style: best money clip wallet of the bunch. I choose this style although it lacks a bit in the clip longevity category to keep a small size and low weight. Of minimalist wallets, this style has the best handling of cash of the bunch. Not as easy as a traditional wallet but still close enough if that is a primary need fro you. I didn't have this exact wallet so you may want to see one of these in person before buying.

I've had at three of each of the classics above so I do rate them as more than workable.

Beyond these, I have a few I've tried and not liked these are mainly one general style, the "card sleeves" like this one. These are too minimalist. I recommend passing on this style. No visibility for my license here. This has the biggest disadvantages of cash handling of the bunch.

Before I found minimalist wallets showing up on Kickstarter, I looked at some on the Web that I didn't buy:

slimmy. Too expensive to me for what I see in the ads.

Dosh . This one has more "design" built in. In the end, it looked to bulky to me.

That brings me to where I'm at now. Kickstarter had over 20 "minimalist wallets" via a quick search on the site. They mostly are getting funded and I saw a few that caught my eye. The Kickstarter Crop:

Most of these wallets rely on some sort of elastic bands so I have some concerns about how long the will last. Many of the designs are thin machined Al plates with various cut outs to allow access to the cards. These work fine for credit cards which have raised portions that minimize the interaction with the cards next to it. Credit cards slide out fine but things like insurance cards don't. I like this style the best to date for a light weight carry wallet. Watch out for weight! Lighter is better in the pocket. There is also a side benefit of RFID blocking if you need that.

My current favorite is the Dizmio wallet has been my carry wallet for about 4 weeks now and I am loving it. Watch the video for how it works on the kickstarted site. I keep my license on the outside of the front for visibility and a bit of cash on the back. 5-6 cards sit on the inside. It is light and sits in my front pocket comfortably. Getting the cards does take some getting used to. I prefer the solid hold this has on my cards vs my previous go to wallet.

This style of wallet is the smallest being basically a stack of cards. Anything with fold is adding additional layers and the hinge point. Unless this one wears out too quickly, it is in the drivers seat for my favorite

I haven't gotten the Crabby Wallet yet. I have high hopes for this bit of a mash up of fabric and elastic with a more traditional housing for the cards. It doesn't have the window but I like the concept of using the elastic to keep my wallet with my phone.

There is one style that's not making the cut for me. The Solido is a fixed size and too heavy to meet my requirements. I do like the fusion of the leather strip and the metal body which is why I tried it out. Unfortunately, its never made it out the door with me. I'd stay away from any "fixed" size minimalist wallets for either bulk or weight reasons.

I'll end with a few others from Kickstarter that are interesting.

This one despite the name may be a good conventional style minimal wallet.

Wally Case may be too much bulk for the nicely balanced iPhone 5. That said, I'm intrigued by the concept of and ID and 1-2 cards connected to my phone.

The Dollar Wallet is cheap! if you're on the fence, this is the one to try.

Minimo has a twist on how you access your cards.

Business Card Scanning

So business card scanning was ridiculously easy. Simply had to use my equipment at home. Fujitsu ScanSnap S1500M into CardIris (comes with the Scan Snap) exported to vCard to to Cobook on my work machine. No need to even get out a thumb drive. There are some obvious errors so I also sent over all the images as HTML file from CardIris

Thoughts on Systems

I am not one to enjoy designing or implementing systems. As such, I greatly appreciate well designed systems and loath poorly designed ones. My evaluation of a good system involves the system getting out of my way the boring or unpleasant tasks and, in general, eliminating my need to spend energy or spend too much energy doing.

A good system is something like I always put my keys in the same spot so I know where they are. When followed, I never think about the system or the keys, I just know where my keys are. When not followed, I can spend some time trying to find my keys. I'm looking for simple systems like this. It's not going to come from just buying an app, although that can be a great start. It's more along the lines of identifying a need that can be solved by a quick Hazel rule that adds tags or renames files as well as Text Expander snippets that do date math. See this example from David Sparks.

I've explained my thoughts on what I want my filing system to do in a lot more words than needed here. Short summary, I don't want to spend much time filing and want to find files quickly. I noted that I often revert to email to find a file because I usually remember who sent me a file. In this case, I did enjoy figuring out how to do this. Making this simple observation was exciting enough for me that I wrote about it here.

I'm looking for things that get time drains and energy saps out of my way. Unfortunately, many of the published automation examples are by bloggers and other online writers streamlining their work flow. I have yet to adopt these tools as the handful of posts I make really doesn't warrant it. That said, I am enjoying typing this post in Editorial after reading this review from Frederico Viticci. It does make the process of getting links for this post easier through the integrated browser. The integrated browser feature is not unique or new feature to text editors. The workflows could be. If I read Federico's article a few more times, I might be able to wrangle a few more personal workflows to help me out. I really like the navigation feature of being able to move the cursor by simply dragging on the extended keyboard top row.

At the end of the day, I will have to do some more observation of how I do my work to look for patterns that simple systems can improve. So far, I spent time on note taking for meetings and begun on filing.

Candidates include: * getting system for team member lists probably via Cobook. * capturing contacts from business cards and signature lines

Why, because several times over the course of the last few weeks, my progress on a primary task has been side tracked while I look for contact information or needed to adjust a team list to send out emails.

Ouya and the Implications for Gaming on AppleTV

I backed the Ouya's kick-starter because I'm a long time gamer beginning back with the 2600 and now up through PS3 and Wii U. I got in late to the OUYA campaign as it gained success and mainstream press coverage. It remains an interesting concept. Will it disrupt the major consoles? Maybe? I like the idea of a system designed to play casual games on my TV. It's a better gaming experience on the TV by far than on any handheld option, phones included. I also like the lighter and less time demanding stories and games in the casual segment. There is only so much time for a game like Infamous) for example.

For the most part games designed for phones and tablets play differently and need different control schemes and concepts to be successful. The classic games (Pacman and Donkey Kong notably) play better with buttons and joysticks. Point and click adventures and board games are better with touch screens. Some games can indeed crossover such as Canabalt or other runners that only require 1 "button" or control input.

The OUYA has fun games and I would recommend No Brakes Valet as an example. It was inexpensive and still gets a play or two every time the OUYA is on. It's two player mode is satisfying as well since it involves screeching tires and crashing cars. The machine can provide entertaining content and I hope the folks developing and OUYA can make the needed return to pay their bills and feed their families so I can continue to enjoy it. It's also likely to spur Apple into the mix.

What's missing in today's status quo? I grew up using a giant dot in Adventure to battle simple dragons on the 2600. Adventure) and the rest of the 2600 games didn't translate well to the iPad because of the controls. That said, Missile Command does work well on the tablet. Even with an iCade controller and air play, it's still not quite there. There is room for someone, be it OUYA or Apple, to get the experience right. OUYA doesn't yet have the content. Apple isn't playing yet.

My biggest excitement was the realization that this is very, very, very, much doable with an Apple TV and the announcements at WWDC about controllers. I expect that an Apple ecosystem would bring a critical mass of developers making games suited for the First Screen. While there are several fun games for the Ouya, the one's with the most polish are ports like Final Fantasy III and the recently released Sonic games. It proves the concept has some legs but doesn't yet deliver on the full experience. The OUYA likely won't get there in my estimation. However, I hope it does.

As I use my Apple TV and OUYA, I will impatiently wait for the controller development for iOS 7 to unfold. I'll look to those more connected and with better insight into the workings of Apple to comment on the likelihood of the Apple TV hobby to expand into the gaming area.

I do hope the Apple TV gets its own Gaming Apps as I will want to play different games on my TV vs my iDevices.

Holding on Doing More Filing Workflow Until Mavericks is Out

I'm pretty sure my workflow will get really simple with the building blocks already in place and whatever Devs come up with in over the next few months. Specifically, I expect Hazel from Noodlesoft will solve the autotagging issue by giving official support for tags. I should be able to use this strategy auto tagging with Hazel. Also, Clark's Tech Blog indicates there should be some quick scripts to move my open meta tags to the new system tags here. Tack Quicksilver on top and I think I should be good to go!

Folks are Missing the Opportunity of Tagging - Filing and Finding in the Future will be Great

So a number of folks have been poking at the overall utility of tagging vs. nested folders your favorite system like big pile-o-files. Clark's Blog Here; and here.

from Dr Drang here

I can think of few things less exciting, and less useful, than tagging. In the example Apple gives, the user clicks on a tag in the sidebar and all the files with that tag appear in the main area of the Finder window. If you have only a few dozen files, this may be just the thing for you, but I actually use my computer, and this is absurdly inadequate and the reason I’ve never cared for tagging. If you restrict yourself to a small number of broadly applicable tags, each tag is likely to apply to hundreds of files. If you use more specific tags, the number of tags explodes and they become impossible to remember. Either way, the tags don’t help you find your files.

Some of the points that folks are making regarding tagging are reasons why they themselves do not use tagging. Some are illogical arguments that tagging systems fail if you don't tag every file or some other variation. I find that nested folders are the same way for me in that I mis-file something and can't find it. Yadda, yadda, yadda skip ahead to ever popular there is no perfect system argument.

There are positive articles on tagging see this one by Jason Snell at MacWorld . See this one at Engineered Eloquence

It goes back to a simple need to develop your filing system to use the tools that work for you. Tags can be part of this system and will continue to be part of my system.

I don't have a perfect tagging system nor a perfect folder system. I rely on a mix of Together (previously Yojimbo), nested folders, and Tags to try and find my files. To date this year, I have chosen to file over 2000 files. Too many I am sure. However, when prepping for a review or meeting, I find myself digging for some random file a lot. Of course not every one I filed and often not the files I thought I would search for. So I will continue to use tags and folders and whatever else I can to find these files when I need them. I view it this way, I am more likely to find a file I tag and put into a nested folder in Together 3. I outline a couple of ways tags will be great for me in this post. Namely that I tend to remember files by a number of ways including who sent the file to me and about when. I could imagine that geo-tagging files could work for some folks. Think something like I started that file at the office or coffee shop or in The Chemistry Bldg. or whatever. The main point is that however you tend to think about files, there are some good auto tag ideas to build a great filing system.

For all of you corporate types I offer one simple tag idea: fromYourBossesName. I think you know what I'm talking about. Run with it and please share tips to me. The auto tagging script from email is a great first step. I am also looking forward to seeing how Trickster and others help me quickly find and parse my files on a daily basis.

We will see a lot of creative stuff coming from folks as they begin to use tags now that they will be system wide. Ditto for when creative Devs get behind this. I'm up for beta

Update on Notetaking both iPad and on Mac

Overall my workflows described in my notetaking posts have remained reasonably the same. There are a couple of notable exceptions.

Notes to Mail

As I moved to MacMail, I have needed to switch to cut and paste of RTF as I saw quite a few of the HTML cut and pastes coming back to me garbled.

So I have been using marked - a fabulous app from Brett Terpstra which if you've found this, you probably have a copy. Using marked is pretty easy and gets the job done.

iPad Notes

Mostly, I capture notes on my Mac as I type quicker there than on the iPad (well just read my separate posts for background - here and here and here ). For smaller meetings, like 1-on-1's or meetings I'm not running, I use Notability and simply output the PDF to my Box account. I use a star next to follow-ups and transfer them to Omni-focus about once a week. PDF's go into a archive folder on my Mac. This equates to what I used to do with my paper note books.

Until there is a native Mac or easy to use handwriting app that's not putting my content up on someone's server, I'll have to forgo being able to search my content beyond the title.

More on Autofiling and Tagging items from Email for my Filing System

So I've been using a filing system from my email that autotags the files in spotlight with Hazel with who sent the file to me and when I received it. I explained it in this post and this post.

I've yet to be able to get the system to work with open meta tags but I'm happy with the progress so far. Here are the basics on how I autotag with Hazel.

Everything is explained in this post in the Hazel forums about going into subfolders Hazel SubFolder Post by MrNoodle

Here are screen shots of how I applied for my locations and what I wanted to do.

What this means is that I'm able to do a spotlight search for fromBossesName and a descriptor and find files pretty quickly. Like I mentioned in my previous post, the key for a system is recognizing how you remember something about the file. For me, I'm often remembering that document that Jimmy sent about Project X timeline. Searching for timeline and project x is usually not enough.

Some discussion of the system:

Files are saved via applescript to subfolders based on the senders email from MacMail. These are in a Attachments folder in my documents folder. From there, Hazel can autotag by folder name. The 3rd picture shows the detail of how I am doing this. Once tagged, the files are moved to my inbox for further processing.

 Rule #1 Rule #1

 Rule #2   Rule #2

 Detail on the naming of the comments coming for the folder names

Detail on the naming of the comments coming for the folder names

Filing System - Automatically Saving Mail Attachment to Folder Named for Sender

Recently I was excited to make a few breakthroughs on my filing (reference system for you GTD folks) system. By breakthroughs, I mean finding a couple good nuggets via web searching variations of “automatically saving attachments in mail.”

This post on The Cocoa Quest is right what I was looking for. This issue I had was figuring out Applescript enough to make it work for me when I don’t want a rule to fire off the script. In hindsight, its pretty simple but it took me monkeying around with it quite a bit.

I modified the script from Mark Hunte to take out some of the functionality and suitable to fire off via a keyboard command with Quicksilver. You can use Alfred which is en vogue these days or Launchbar. I simply select the messages I want to ultimately tag with the sender’s name, execute the script and then let Hazel do its magic.

Modifications are to parse out and email address that for the vast majority of the time is The script will take the first part of the email if there is no “.” in it. Here it is:

– Adapted from a copyrighted script by Mark Hunte 2013
– Changed script to parse out the first part of the email address as the folder name, eliminated time stamp folder
– Changed to run as triggered script vs email rule
– explanation of what and why at

– set up the attachment folder path

tell application “Finder”
set folderName to “Attachments”
set homePath to (path to home folder as text) as text
set attachmentsFolder to (homePath & folderName) as text
end tell

tell application “Mail”

set theMessages to selection
repeat with eachMessage in theMessages

– set the sub folder for the attachments to the first part of senders email before a period
– All future attachments from this sender will the be put here.
– parse email name by @ and . to get to first part of email name

set subName to (sender of eachMessage)
set AppleScript’s text item delimiters to “<“
set fName to text item 2 in subName
set AppleScript’s text item delimiters to “@”
set fName to text item 1 in fName
set AppleScript’s text item delimiters to “.”
set subFolder to text item 1 in fName

– use the unix /bin/test command to test if the timeStamp folder exists. if not then create it and any intermediate directories as required
if (do shell script “/bin/test -e ” & quoted form of ((POSIX path of attachmentsFolder) & “/” & subFolder) & “ ; echo $?”) is “1” then
– 1 is false
do shell script “/bin/mkdir -p ” & quoted form of ((POSIX path of attachmentsFolder) & “/” & subFolder)

end if
– Save the attachment
repeat with theAttachment in eachMessage’s mail attachments

set originalName to name of theAttachment
set savePath to attachmentsFolder & “:” & subFolder & “:” & originalName
save theAttachment in file (savePath)
end try
end repeat
end try
end repeat

end tell

In Search of a Better Filing System - Vision and Hints at a Breakthrough

So I’m thinking of how to be able to find folders more quickly in my reference system. Most of the files come in from email, are written by others, and I may need to pull them together in a summary document to present up to decision makers. In this context, what does productivity look like to me: it means I can find a document quickly. If I evaluate how things are going with my nested folders based on project name and a couple sub-folders, its a very mixed bag.

My vision is 2-fold:

  • I can find those files quickly to pull them out.
  • Once I pull any file out of any folder to the desktop or current working folder. I can have it automagically go back to where it should be filed.

This will be my current fiddly quest now that I have note-taking basically sorted out. I’ve made a bit of progress on both points just today.

I've been keeping track of how I've been finding and not finding files. Spotlight isn't really cutting it for a lot of cases. If I'm in a crunch, I usually go back to mail. Why? it is because I usually know who sent the file to me and about when they sent it. It turns out that often times, the contents of the file aren't enough for me to narrow the search down. Another problem I have is that I often have several versions of the documents in various stages of preparation (these are usually multiple drafts from multiple contributors) and outright duplicates in the system. This is a sub-problem that I’ll be going after later.

So what was the breakthrough? It involves a mail rule to automatically save attachments to a folder with the name of who sent it to me and Hazel to auto spotlight comment tag the file. Hazel also moves it to my “inbox” folder for further processing. This type of approach has been done before (insert here some of the stuff I found) but not in ways that worked for me (they weren’t simple enough for me). I'll have to extend the auto-tagging to my current nested folder structure and I should be there.

I’m going to have to clean up the script a bit and get some screen shots to illustrate it so that will be another post soon. In the meantime, I thought I would outline my current system in slightly more detail.

My go to setup for a while which has been infinitely better than the past is as follows:

4 main folders:

This set up comes from this post at Lifehacker

  • Now - these are currently active projects (think GTD projects here not my work project codenames).
  • Inbox - these are documents I have to figure out what to do with or need to get parsed into projects or filed.
  • Outbox - this is where stuff gets put to get filed or deleted. I have a large amount of Hazel rules mainly by subject title that move files to the right work based project folder in my last folder.
  • File Cabinet - Things get filed here by project with a couple of sub-folders.

I keep Now, Inbox, and Outbox synced to so that I have access to these files anywhere.

Update on Notetaking on iPad Flow

My workflow on notes with my computer is my go to flow for large meetings.  For the balance of my note taking, it varies between nvALT workflow AND using my iPad.  The nvALT workflow works great for me and the only change is ending mostly in mac Mail.    

The workflow is now using an stylus and Notability.   I've gone with the Adonis Jot Pro vs. the Jot Touch and Wacom Bamboo (see below).  Notability is a great note-taking app. The UI is good; it works with, and it has a magnification writing area that is a must have in note-taking.  The other App I used a lot was NoteTaker HD.  It writes better but the UI isn't as smooth and Notability.  This has been a stable process for about 3 months.  

The workflow is as simple as can be.  I write my notes marking follow-ups with a star.  I export them to in a specific folder.  I review the docs on my Mac and capture the follow-ups in OmniFocus.  That's it.

I've passed on using a keyboard.  If I want to type, I use my Mac.  That said, I do use the keyboard a bit outside of work.  

Stylus Comments

The Jot Pro works well.  It has good precision and glides well on the iPad.  Also, its got a nice magnet that keeps it attached to the iPad 2 or 3 well enough to walk around with it.  I really like this feature.  The only draw back is that it makes a bit of noise when writing.  All said, I still prefer to the Bamboo.

Wacom Bamboo gets a little messy with the tip wearing off after a while.  It has a replaceable tip so its workable and I used one for about a year.   

Jot Touch is a bit too much for work and I don't need pressure response.

Using Deprivation Testing as Hurdle for Tools to Make Your Work-Flows

Much talk of productivity podcasts center on tools. I try out more than my share of tools. While my productivity is at its core mainly down to a system like GTD implemented by Omnifocus, I find that some tools become integral to a smooth flow of getting my work done. How do I know if the tool makes the grade? After an initial spurt of putting a bunch of tools on my home and work machine, I settled on putting the tools first go on my home Mac. How do the they make it to the big time of installation on the work machine? The concept is deprivation. Here is a [article] ( in the Harvard Business review by Scott Anthony that should give you the flavor. Basically, if I don't "reach" for the tool on my work machine after knowing what it does, I don't need it. That's the core and I know others have similar ways of trying out new tools.

With that said, I have most of the geek standards on my home machine and many have made it to the show, notably, Hazel, nvALT , and Text Expander . These tools tend to fall into a niche in my work. There is a secondary point to my use of tools, I need the tool to fill a critical niche not usually to solve all my needs in a one stop shop. I don't need to really be a power user in all of these programs. I need to shave off time and stress out of my work life. The biggest reason that tools get installed on the work machine is that I find my self using the short cuts without the tool installed and then recognizing the time or break in my routine that causes a bit of an iusse. I'm missing something in being deprived of the tool.

So what tools made the Show?

  • A surprise tool that is in constant use is PopClip . I use the Paste and Match Style constantly in addition to simple cut and paste.
  • Text Expander is in constant use with dates being common and a big times savings in adding my conference call-in information to emails, calendar entries, and IMs. Its not really the direct time I save typing, its finding/copying/pasting that is the big time savings.
  • DragonDrop is also there to get documents into emails smoothly.
  • Of course, 1Password makes the list.

There are a few others that I use sparingly. Notably, I'm fine with spotlight as an applauncher as I haven't yet got the hang of launching multiple types of items via launch bar and I use relatively few scripts.

So for those of you looking for a way to streamline your tool use, I suggest trying out some sort of deprivation testing to find the indispensable tools.

Outlook Identity Crashes - I Look for email data portability and Migrate from Outlook 2011 to Mail

Migrated from Outlook 2011 (14.2.5) to MacMail (version 6.2)

It seems that my end of year email clean-up binge and archving corrupted my outlook identity such that it couldn't rebuild.  I have my data pretty well backed up so I didn't stand to lose any data.  Nonetheless, the failure to rebuild left me a little less confident in Outlook.  I couple of other folks had this happen and did lose some data.  So I started a new identity and moved my email archives over to the new identity.  Obviously the server data migrated over without a problem when setting up the new identity.

To note: this site has some good information when you run into issues:

Office is a great tool but it is quite frankly overkill for what I need for email etc. as I use omnifocus for my task manager and the integration to Mail is better than Outlook.  Much like data portability in via text files, I wanted to get my email data a little more portable.  As I searched, I found only sketchy recommendations for migrating my Outlook data .olm file to mac mail and it seemed like I shouldn't need a 3rd party solution to make this work.  

It turns out it is dead easy to do.  You simply drag your archive folder to another folder on your Mac and you'll get a .mbox file of the folder that you can easily import into mac mail.  I suggest you test it out yourself with a small number of emails.  It took about 10 - 15 mins. to export 2 - 3000 email folders.  I couldn't drag the archive to the desktop, I had to drag it to a folder on my desktop to make it work.

I don't want to get into a position where my email client can shut me down for 2 - 3 hours to get back up and running again.  So I'm going to manage a short term archive (I use the pile of records in a folder approach to email with smart folders) on the server for portability and have redundant archives of my older email in outlook and Mac Mail.  Mail goes belly up and I use Outlook or Outlook goes belly up and I use Mail

However, day to day I'm going to use Mail, iCal, and Address Book with Address Book being the clear weak link in the chain.  

For ease of folks who may also be looking to switch from Outlook 2011 for Mac to Mac Mail, simply drag your archives to a folder on your Mac and import the .mbox folder into mac mail.  Since I'm a corporate stooge, everything else goes over via the cloud exchange server.