Why You Should Be Using Smart Playlists in iTunes and How to Do It, Part 1

I’m a geek. That means i like to organize techy stuff so that it does cool things. This is one of those things i’ve gotten pretty good at, and i want to share what i’ve learned with you.

I have 28 Smart Playlists set up in iTunes. There are also several Smart Playlists that iTunes sets up automatically, but i mostly don’t use those. I also have 23 regular (non-smart) playlists. I’ll explain how and why to use regular vs smart playlists, and what reasons you might have to make use of both for different purposes.

There is a lot of hate towards iTunes. Some of it is even justified. I think Apple made a serious error in combining owned personal music with their streaming platform Apple Music. It gets very complex and confusing trying to make playlists when you are dealing with owned files and streaming music. In addition, the combination of iTunes Match, Apple Music and your personally owned music files has resulted in people accidentally deleting their own personally owned files. iTunes as it currently exists is bloated and confusing. However, in spite of that, iTunes is very powerful and useful, once you can wrap your fingers around its intricacies. That’s what this post is for.

According to Apple. The average iTunes user has between 2,000 and 3,000 songs in iTunes. There are music collectors/aficionados who have well in excess of 100,000 songs. I have right now, 13,768 songs. iTunes can effectively handle each of these sized music libraries when disk space is sufficient.

Examples Of The Kinds Of Things Smart Playlists Can Do

I have several Smart Playlists which i’ll use here as an example of the kinds of things you can do once you start down this path. I will show you how to actually create these Smart Playlists in Part 2 of this post. For now, these are examples of the kinds of things you can do.

Memories – This playlist plays only rock songs released between 1966 and 1980 and that i’ve rated as 4 or 5 stars. Basically, this plays my favorite songs between when i was in junior high and when i got married. That’s the age when we form our most intense musical attachments. These songs will always bring a warmth to my heart when i here them. In order to create a Smart Playlist like this you will need to rate your music, assign genres to all your music and also correct the date of the music. By default, almost every song is dated the day it was released in its most current form, not the date it was originally released. As an example, songs by The Monkees show up as dated 2011 when they were remastered by Rhino and not 1966-1968 when they were actually released. To make a playlist like this work, you will need to google each of your albums to find the original release date. I’ve found wikipedia the best place in general to get this information most of the time. This can be a daunting task when you have thousands of tracks, but is easy to do each time you purchase or rip a song.

CSN&Y – My goal for this Smart Playlist was to have a playlist with songs by every permutation containing one of these 4 musicians and only songs i’ve rated 4 or 5 stars. This is more difficult to construct than you might think, because these 4 guys have produced music in an almost infinite combination. Well, that’s an exaggeration, but not by much. The Smart Playlist must have an entry for each permutation. This includes: Crosby Stills Nash & Young, Crosby Stills & Nash, Crosby & Nash, Neil Young, Buffalo Springfield, David Crosby, Stephen Stills, Graham Nash, Manassas, The Hollies, and The Au Go-Go Singers. In case you are wondering why not just include every artist containing Crosby, Stills, Nash or Young – such an entry would get you songs by Bing Crosby, Lester Young and others. Keeping the Smart Playlist to just these 4 guys took a while and some tweaking.

Summer Music – This wasn’t as hard as CSN&Y, but i took a different approach. I wanted only songs rated 4 or 5 stars, but I wanted songs by The Beach Boys, Bob Marley, The Ventures, and Jimmy Buffett. In addition there is one particular John Denver album (An Evening with John Denver) which has summer memories for me. I also wanted to include the single song Summer Breeze by Seals & Crofts and the single song Summer’s Here by James Taylor.

I’ll show you how to actually create these and other Smart Playlists in Part 2 of this blog post.

Regular Playlists

Screen Shot 2016-09-03 at 2.57.21 PMiTunes allows you to set regular playlists by clicking on File -> New -> Playlist. You then give your new playlist a name. Once you’ve done that, you can put any songs you want into that playlist by dragging and dropping them or by my preferred method, right clicking on a song or group of songs and selecting the ‘add to playlist’ option and choosing any playlist from the list. The regular playlist is most useful for setting up specific playlists which don’t lend themselves to characteristics or data available for automatic selection. For example, i have a playlist set up for Romance which has hand selected songs which cross genre lines and other criteria. On the left is a screen capture of my Regular Playlists. You can place any song, regardless of genre, rating, artist or any other criteria into a regular playlist. The positive aspect of regular playlists is that they are easy to set up and populate. The negative is that they are static. They don’t change no matter how many times a song is played, and they must be manually updated when you get new music you want to add or tire of old music and want to remove some songs.

Smart Playlists

Screen Shot 2016-09-04 at 6.09.11 PMSmart Playlists are where the power is. Smart Playlists can change automatically and dynamically as songs are playing and when songs are added to iTunes. You have the ability to have songs automatically added to a Smart Playlist based on all of these criteria to the left. And best of all, you can combine these criteria in many ways to both include and exclude songs from your playlist.

Organizing Your Music Collection

Ok. I know that most of you are not going to like this. Please keep reading anyway. Organizing your song data sounds like work, but the benefits are so significant that it is very much worth the time it may take.

Most people just throw everything they buy or rip into iTunes and then when they want to listen to some music, they select an artist or an album to play and skip songs that pop up which they don’t like. There is a better way, but it involves doing more than just putting music into iTunes. In order to be able to manipulate your music into and out of smart playlists, you need to add or modify some data about your songs.

Data to add to your music:  genre, rating, release date

Genre – Most music comes with a pre-assigned genre from whatever source you obtain the songs. I have two caveats. Sometimes the song genre is wrong (this happens most prevalently with artists who cross genres such as Van Morrison). More often than wrong genres are genres which are not useful to you. I suggest deciding on 5 to 10 genres that you personally want to use for your music as a way to sort and build playlists, then changing your music’s genres to be in one of those genres you’ve chosen. I tend toward broad rather than narrow genres. For instance, in Jazz there are many sub-genres such as vocal jazz, smooth jazz, swing, big band, bebop, dixieland, and many many more. I set all of my jazz music to either Jazz or Big Band because i’ve used those two genres to set up playlists. Blues can have many sub genres, but i just use Blues. I also use the genres: Classical, R&B, Folk, Rock, Christmas, Country, and Gospel (which i use for all Christian types of music from Gregorian Chant to Gospel Quartets to Contemporary Christian). Your choice of genres may be very different than mine. The key is to narrow the genres down to just ones which you find useful for setting up playlists.

Rating – I’m sure you noticed in my examples above that i often only include songs in a playlist which i’ve rated as 4 stars or 5 stars. In order to be able to do this, you will need to rate all your songs. The easiest time to do this is when you first add a song or album. However, you will notice over time that how you feel about a song may change, so feel free to change your ratings up or down for a particular song at any time. If you are using Smart Playlists, they will automatically adjust whenever you change anything about a song (its genre, rating, date, etc). I rate every single song i have, and yes, this can be tedious the first time. Please do not be reluctant to rate songs you really hate. If you are like me, you have a built in resistance to rating a song as 1 star. Get over it. For ratings to work, they have to be realistic.

For me, a 1 star song is one i will never want to listen to again. I have a Smart Playlist set up for 1 star songs. A few months after rating something 1 star, i go back to that playlist and re-listen to each song, at least enough of it to confirm i still hate it. I then delete any song i still hate. Each song with a 1 star rating will either get deleted or have its rating changed upward. Therefore, my 1 star playlist is a temporary holding spot.

I use 2 stars as a rating for things that i never want to have in a Smart Playlist. For instance, I have a regular playlist made up of songs that i use to help me fall asleep or sleep when i am in pain. Those songs are not ones i want to ever play while doing other things. So, i don’t want to delete them, but i don’t want them in any of my other playlists, so i make them 2 stars.

Songs i rate 3 stars are songs which i don’t mind hearing once in a while, like every 6 months or year or so, but songs that i’m not really excited about.

Songs which i rate 4 stars are those i enjoy listening to and never mind how often they may pop up, but usually that’s every few months.

5 star songs are those that get me very excited, make me feel happy, and songs i wouldn’t mind hearing every few days.

In my music collection, about 50% are rated 3 stars, 30% are rated 4 stars and 20% are rated 5 stars.

Release Date – When i say “release date” i’m only interested in the year. I haven’t found any use for knowing the exact date of a song’s release. By default, almost every song is dated the day it was released in its most current form, not the date it was originally released. You will need to use google and wikipedia to get the correct release dates. If you want to use release dates in your Smart Playlists like i do above in my Memories playlist, then you will need to correct their dates. The albums which always need this done are Greatest Hits albums. You may need to google each individual song to find its release date. Often the original release date will be in the album booklet of the CD. If not, then you’ll need to google each song.

Part 2 of this post will contain actual “How To” construct these playlists.

I’ll add a link here when it’s ready.

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Update on eBay and 5k iMac


It has been 3 weeks since i last made a blog post. I’ve been spending all my time focusing on selling my CD collection to raise money to buy the 5k Retina Display 27″ iMac and also reading this 2″ thick tome Switching to The Mac.

I can announce success on both counts! I am typing this blog post on my new iMac, and i completed reading the book which i highly recommend to anyone switching from the Windows world to the Mac world.

In addition, my experience selling on eBay has been surprisingly positive. With only a few small glitches I’ve sold my most collectible and expensive CDs. I still have a few hundred plain old normal CDs left to sell, but everything is going very well and I have a number of very satisfied customers.



I am extremely impressed with the iMac. Briefly, here are the high points:

  • The display is simply incredible. Bright. Sharp. Crisp. The blacks are the deepest darkest blacks i’ve seen on any monitor anywhere. In fact, this is easily the best computer monitor i have ever seen or used. For someone with bad vision, this is a HUGE deal. Seriously.
  • The Mac OS X operating system is very different from Windows and in almost every case, that is because it is better, more flexible and more capable, especially with regard to graphics and audio.
  • The hardware itself is in a universe of its own. The aluminum case the computer and display are in is solid and light. No plastic in sight other than the actual keys on the keyboard (which are set in an aluminum frame as is the trackpad). The Mac has superior audio output because of better audio components as well as the way the operating system handles audio. Mac’s cost more than Windows PCs, but it is my opinion that it is more than worth the cost for the far superior hardware.

I’m very pleased with the time and work it took to make this transition. I would do it again in a second.

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John’s Apple Conversion

The Beginning

I started in the world of computers in the late 70’s. As part of my MBA program i had to pass a test proving i was proficient in either Cobol or Fortran. I didn’t want to waste time taking a class, so i bought a book and taught myself enough Fortran to pass the test. I’m one of those strange ducks who always reads the manual, and is able to learn stuff better from a book than being shown. My mind just processes things better that way.

A year or so later, MBA in hand, while working for General Electric’s Mobile Radio Division, microprocessors were making their way into our products so i took a hands on class in assembler programing of 8088 processors. That’s machine language programming using hexadecimal.

We then moved to NC and i got a job at a community college teaching television repair (my undergrad degree was in Broadcast Engineering). They asked me if i’d also like to teach Introduction to Computers and also Programming in Basic (on Radio Shack TRS80’s). The Intro to Computers course was no problem because i’d taken that in my MBA program, but i did not know Basic Programming. How hard could it be after teaching myself Fortran and taking a program in assembler programing. So, i bought a book on Basic Programming for TRS80’s and in a month i was good to go. Around the same time i bought a Commodore 64 for myself, and learned Commodore’s version of Basic Programming on the C64.

A few years later, i got a job teaching Basic Programming on the IBM personal computer for a local business college. I then also learned MS-DOS and writing batch files. A few years later Windows came out and i moved down that rabbit hole. I am very proficient with all things related to Windows hardware and software and have existed solely in the Windows world for almost the past 25 years.

The Present

I am now preparing to move into the Mac world. My six year old Windows 7 computer is at the end of its useful life and i simply see nothing compelling or interesting in the world of Windows, so i’ve decided to get an iMac later this summer. Guess what i did? Yup, i bought a book! It’s called “Switching to the Mac”. I must confess to being extremely impressed with the Mac’s approach to computing. As i wade through the two inch thick tome i find myself continuing to think “Why doesn’t windows do it this way?”

I stuck my toes into the world of Apple with my first iPod in 2009 followed by my first iPad in 2010 and i have found myself enthusiastic about the intuitive way their products “just work”, so now i’ll be jumping into the Apple pool with both feet.

The Reasons

So, what are the reasons for my Apple Conversion? They are twofold.

Things Microsoft has done (or not done).

  • Windows 8
  • Focusing on ‘touch’ for computers to the detriment of everything else
  • Moving to a subscription model for Office products
  • Naming mutually exclusive computers and operating systems the same to completely confuse their customers who can’t understand why their new windows computer can’t run windows programs
  • Innovation so bad that the majority of their home and business customers are still using very old versions of their operating system, a significant number using versions 12 years old and no longer secure
  • An inherently insecure operating system so bad that they single handedly caused a new category of software to appear just to fight viruses, trojans and malware.

Things Apple has done.

  • Innovate – the iPad was so well done that it created an entirely new aspect of mobile computing
  • Understanding that while some aspects of their mobile computer operating system (IOS) can be used in their other lines, they never merged IOS and OS X, keeping them separate and distinct
  • ‘Touch’ on mobile computers but not on desktops
  • Trackpad innovations like gestures
  • It’s trite, but it’s true. Their products just work
  • Maintaining complete control of the hardware production
  • Free upgrades to the operating system resulting in a much higher percentage using more current and more secure operating systems
  • An almost non-existent market for anti-virus and anti-malware software for their operating system because it mostly isn’t needed.

The Result

The market share for Windows computers has been sliding for several years and manufacturers of windows computers are either stopping manufacture of Windows computers or cutting back on their product lines.

The market share for Macs is growing each year and they are adding new products and options each year.

Lest i seem like a total fanboy, let me say that Apple is not perfect. There is much i’m learning in the “Switching to Mac” book, but the overwhelming number of shortcuts to do things on a Mac is so great as to become absurd. While it’s nice that you can use a shortcut to do anything you can do with a mouse click, it is not possible to learn the thousands of shortcuts needed to accomplish this, at least not for this aging computer guy. There are so many shortcuts that many of them have no mnemonic (a device such as a pattern of letters, ideas, or associations that assists in remembering something.)  relation to what they do making strict memorization the only possibility for many shortcuts. For example, on windows ctrl-c copies, ctrl-x cuts which makes sense. Macs have so many shortcuts that the use of the option, shift and command buttons individually and in combinations coupled with a number or letter key ends up without the ability to hang your hat on which keys to use to accomplish each shortcut.

Lastly, the most significant aspect of the Mac is that it is inherently visually based. You can see PDFs, pictures and videos in their icons! And that’s just the tip of the iceberg. Also, the monitors are so crisp and bright that it makes your jaw drop. Apple pioneered the very concept of a retina display. For my aging eyes, that’s a huge plus.

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How to Evernote John’s Way!

I’ve been putting all kinds of information into Evernote for 5 years now and i’ve stumbled upon some pretty great/easy ways to grab information and easily get it into Evernote, and i’m gonna share those tricks with you.

I’m going to divide this post into 2 parts: how to get information into Evernote from a desktop (Mac or PC) and how to get information into Evernote from an ios device (iPhone or iPad). Sorry, i do not have an Android device. If you do, it is likely that many of the ios methods will be transferable to Android.


I work mostly on my iPad Air. However, there are a few things i do on my desktop pc and the way i usually add information from my desktop is by using an add-on/extension for my browser called Evernote Clearly. Evernote Clearly is a free Evernote product and there is a version for Chrome, Firefox, Opera and Safari. It does two things: it gives you a clean reading version of almost any web page, minus advertisements, banners, etc. and it has a side panel that lets you highlight and then post the page directly into Evernote. It will even learn your posting habits and post directly into the appropriate Evernote notebook you usually use for a given type of information. You also can print your highlighted reading version of the page. Here is an example of a page before and after Clearly.

Before Clearly

Before Clearly

After Clearly

After Clearly

As you can see, Clearly has removed all the cruft  and left a clean and readable page. This cleaned up page can then be highlighted and directly posted into Evernote by clicking on the side panel on the right (not showing in this screen shot).

IOS (iPhone/iPad)

I do most of my information capturing using my iPad.  There are two ways i use most often for getting information into Evernote, and several other ways i use less often. I’ll focus on the two i use daily.

Using the Reader View

When using the Safari browser on an IOS device, in the upper left of the center section there is a four bar (usually used for menus) icon. In this case, the button is not used for a menu, but instead to toggle the safari view from a web view to a reader view. This is a very powerful and underutilized function. Here’s how it works.

iPad 1

Before pressing the Reader View button

Now, press the Reader view button and all the cruft is removed, very much like what Evernote Clearly does in a desktop browser.

iPad 2

After pressing the Reader View button

The next step is to click on the Share button to bring up the options.

iPad 3

Now select the mail button, and the IOS device places the Reader View version of the web page into an email. Now for the cool part! You’ve already set up your Evernote email address in Contacts (right?) so you just type the first few letters of Evernote into the To: box and it will autocomplete and your email is all ready to send directly into Evernote, formatted in an easy to read view. I use this process every single day at least 4 or 5 times to save web information i come across.

iPad 4

Using the Drafts App

Drafts is one of the most powerful apps available in the IOS app store, along with Evernote and an app called Workflow (topic for a future blog post). For now we are going to look at using Drafts to move information from Safari into both Evernote and Facebook (it can also be used for tweeting and sending information to other apps).

First, highlight something in Safari and tap Copy. For this example i’m using a quote i found.

iPad 5

Now, go to the Drafts App. It opens to a blank screen just waiting to be written on. In this case, instead of writing, we are going to paste the quotation we just copied from Safari.

iPad 6

You will notice below that when it pasted the quotation into Drafts, it removed all the formatting. Drafts is all about text. Yes, you can use markup language in Drafts if you want, but it really shines at stripping all the junk away and leaving you just the text.

iPad 7

Now for the cool part! Tapping on the little square box in the upper right brings up the Drafts menu. You can now send this text to any or all of these options. The menu is user configurable and there are actually hundreds of possibilities you can add. Many of you will select your twitter feed to add to this menu. My norm with quotations is to Post to Facebook, then Save to Evernote, and then Delete. Done!

iPad 8


Remember from our previous post that getting information into Evernote is just so that we can have access to it wherever and whenever we need it by using Evernote’s search function. The key is to get everything you will need to have into Evernote after installing Evernote on every device you use. Then the fun starts and you can keep adding stuff and adding stuff knowing it will be there wherever and whenever you need it.

Here’s a link back to the first Evernote post: Why Use Evernote?

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Why use Evernote?


Evernote’s motto is “Remember Everything”

  • What does Evernote do?
  • What devices can run Evernote?
  • Why would you use Evernote?
  • How does John use Evernote?
  • How much does Evernote cost?

Most people have heard about Evernote. Usually from someone who uses it and is excited about it. Also, most people don’t ‘get’ why people are so enamored with this app/program, not seeing what they could do with it, nor thinking they have a need for it. I aim to disabuse you of those ideas by answering those questions above in a straightforward way. I have no affiliation whatsoever with Evernote other than being a happy user for the past 5 years.

What does Evernote do?

It’s tempting to answer: everything, but that’s an exaggeration. However, it does do a lot.

Basically, it’s where you can save almost any kind of information you want. Such as:

  • links to web sites
  • full content from web sites (also excerpts from web sites)
  • blogs
  • lists of things, like: a shopping list, a list of books to read, a list of movies you want to rent/watch
  • notes of any kind, like from classes, sermons or political debates
  • to-do lists with check boxes you can mark as you finish things
  • quotations!
  • personal information like your driver’s license number, your license plate number, the entry code to your gate
  • you can scan all kinds of things into Evernote like your lease agreement or your social security card
  • you can also scan business cards into Evernote
  • Evernote can access your camera so you can take pictures of white boards or quotations from the page of a book
  • you can save pdf files directly into Evernote as well as office documents

Once you put all this stuff into Evernote, what then?

Evernote has a blazingly fast search ability. You just type a word or phrase into the search box and up will pop every piece of data with that word or phrase in it! Or, you can narrow your search to a particular folder in Evernote (folders are fully configurable, and you can set up hundreds if you want, or go minimalist with just 4 or 5). An optional feature actually will OCR and index pdf files, Office files, and jpegs (such as a picture of a white board).

What devices/platforms can run Evernote?

Evernote literally runs natively on everything (except linux). There are versions for IOS, Android, Windows, Mac, there is a web portal to Evernote so you can access your data anywhere with a computer and internet access even if you left your phone home. There’s even an Evernote for Windows Phone! Best of all, Evernote automatically syncs all your information and data to everywhere you have it installed so you can add, edit, or delete things on any device and it automagically happens everywhere else. That means wherever you are, you have access to all that information you’ve put into Evernote!

Why would you use Evernote?

Have you ever been somewhere like at the hospital filling out forms and you needed your husband’s or wife’s or child’s social security number? Or your license plate number for a hotel registration? Or you’re in the bookstore or the library and can’t remember the name of that book you heard about last week and wanted to read? That’s just the tip of the iceberg.

How does John use Evernote?

  1. I have a notebook set up in Evernote where i collect quotes (one of my passions). I currently have around 2500 quotes in the notebook and every author is tagged by name so that with one click i can see every quote i have from Benjamin Franklin, Abraham Lincoln, Albert Einstein, or anyone else. I have made this notebook a shared folder so that anyone who uses Evernote can have a copy of my quotes notebook in their Evernote.  Just send me a request via the Contact John page and I will send you a link.
  2. I have a Health folder where i copy and paste all kinds of blogs and articles relating to health, supplements, exercise, diabetes,and more.
  3. I have a notebook set up for articles, recommendations, reviews and more having to do with books and reading.  It also contains my books to read list.
  4. I have a notebook for music reviews, articles, information about audio equipment, audio files, and my music wish list.
  5. I have a notebook with personal and  family documents i have scanned into Evernote. Things like my wife’s teaching certificate, our driver’s licenses, social security cards, lease, marriage license, birth certificates, etc.
  6. I have a notebook set up for making daily Journal entries. I admit that this is an as yet unrealized aspiration, but the structure is there to enable me to do it. I just need discipline to make it happen.
  7. I have a notebook with sub notebooks under it that contain the Keynote presentations and all my preparation notes for the Adult CE classes i’ve taught over the past 5 years or so.

How much does Evernote cost?

This is the best part! There are three price points for Evernote. There is a free version, which for many people is all they may need. The program itself is not in any way crippled in the free version. Here is a description and costs for each of the three plans.

Basic – this is the name they use for the free plan.  Obviously there is no cost.  You can use Evernote with all its features including syncing all your data across all the places you have it installed. You can share and collaborate with others.

Plus – this is the name of the middle lever plan. In addition to the Evernote program with sync and sharing, there are several additional features. This plan costs $25 per year. Here’s what you get in addition to the Basic plan:

  • An Evernote email account. You can clip information or put anything into an email, including attachments like pdf’s and email them directly into your Evernote data. I use this feature daily.
  • You gain the ability to access all or some (your choice) of your data when you don’t have an internet connection.
  • You can put a passcode on your data to protect it from access by someone using your computer or phone.

Premium – This is the plan I have used for the past 4 years. It costs $50 per year and for me it is easily worth it. In addition to all the Plus features you can also:

  • Have unlimited uploads with no monthly data cap
  • The ability to make your notes into presentations from right within Evernote
  • Evernote will automatically show you links to content you have in other notes which relates to the note you are currently accessing or writing.
  • Ability to annotate pdf files you have in Evernote
  • Most importantly to me and the reason that i use the Premium plan: Evernote will OCR and index all of your pdf and Office files that are in Evernote. This is huge! The OCRing and indexing is done on Evernote’s servers and usually only takes an hour or so to be finished once you enter the file into Evernote. Then you can search through those pdf and Office documents using Evernote’s search function.

I hope this post has given you a glimpse into just some of the things you can do with Evernote. I will be making a second post soon which will use screenshots from my computer and iPad showing you some really great tricks of how to get information into Evernote quickly and easily.

BTW, you can get Evernote for free and also sign up for any one of the three plans at Evernote.com

Here’s a link to Evernote Post 2: How to Evernote John’s Way!

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