Years ago, I was in the US visiting an old friend of mine, Denise. We had a lovely dinner, catching up with each other, and were relaxing in her living room when she decided to put on some music. To my near horror, she started loading the CD changer of her stereo.

Now this was a while ago, but still well after the advent of the iPod and firmly in the era of MP3s and digital music. I tried to explain to her that she should do herself the favor and digitize her music collection. I pointed to her shiny, new MacBook Pro and described how easy it was to do and convenient to use once done. After some comments to the extent of it not being worth the effort, we continued enjoying some drinks over music and the periodic clack of the CD changer changing albums.

I still remember that lovely evening, but apparently the experience with the CD changer left a sizable impression as well, because after I got home, I did the only thing I knew to do: I wrote a how-to guide documenting how to digitize her music library.

I recently ruminated how important writing is to me and how long it took me to realize that importance. Writing that how-to guide was an important step along that path of realization. It allowed me to exercise a skill that I enjoyed while also adding some personal flair. It showed me how I could explore writing, even technical writing, as a method of personal expression.

I only recently rediscovered the guide while doing some digital housekeeping. Though clearly dated, I have reproduced it below. You know, for fun. Consider it a (strange) example of what you can do when following a whim and sharing your curiosity with a friend.

Bones’ Guide to Pulling Yourself Out of the Audio Middle Ages


It is generally well-accepted that most people like music. You undoubtedly like music. The ultimate irony of this axiom is that, even though everyone ostensibly likes music, on the whole, other people’s music sucks.

Take the youth of today. Their music is terrible. It is the din of moral decay. Experts estimate that over 90% of the time a person spends listening to music, they are listening to other people’s ghastly music. The fact that each and every person spends their whole life listening to other people’s abominable music is in all likelihood the largest contributing factor to old people rarely dusting off their gramophones and listening to the ragtime favorites of their adolescence. After living a life surrounded by loathsome music, a person grows disenchanted.

Consider this Venn diagram. represents MTV and similar public disservice. represents modern radio. C represents the shit that punks today pump out of the tinny speakers of their mobile phones. Naturally the aural effluent on MTV is generally also what is heard on the radio (1). What is heard on modern radio is also some of the appalling drivel that little twerps play on their mobile phones (2). And the slackjaws who watch MTV probably also listen to their obnoxious music in public places on their mobile phones (3). That leaves you (4) stuck in the middle of this shitstorm of sound.

One’s passion for music should not be allowed to wane. And given the technology available today, it is amazingly easy to enjoy good music (i.e. your music) whenever and wherever you feels like it. Whether it be in the peace of your own home, in the car, or anywhere else. It is easy to fight back against these unabating and egregious assaults to your sense of taste by being armed with your own artillery of sublime sounds. To that end, a person must pull their music catalogue into the modern age. Although those Counting Crows and Oasis CDs were the hot items to have back in ‘96, it is time to dust them off and bring them into the 21st century.


The purpose of this document is to detail how you can convert their once prized CD collection into a respectable digital library using iTunes and have the entire collection available on demand. Naturally this will also make the reader instantly cooler.


This document details the steps necessary to convert a CD collection into digital format using iTunes. Although similar methods could be employed to convert LPs or cassette tapes as well, these media are outside the scope of this document. If you even know what a gramophone is, just throw this document away and keep on listening to Paul Harvey on the radio.


The intended audience of this document is anyone who has an extensive CD library and is tired of listening to other people’s vile music. Such people are usually also tired of being derided for having to reload their CD changer when friends come to visit.

0. Preparation

The following items will be required:

  • A collection of CDs
  • A computer with the latest version of iTunes installed
  • An Apple Airport Express (optional, explained in step 3)
  • A standard male RCA to 3.5 mm stereo connector (necessary length defined in step 3)
  • A stereo with an auxiliary RCA audio-in connection available

1. Configure iTunes

  1. Start iTunes
  1. Open iTunes preferences either under the iTunes menu selecting Preferences or press ⌘-Comma.
  2. On the General tab:
    • Change When you insert a CD to Ask To Import CD.
    • Tick Automatically retrieve CD track names from Internet.
  1. Click on Import Settings. In the Import Settings window:
    • Tick Use error correction when reading audio CDs.
    • Change the import method from AAC to MP3.
      • Note: Although the AAC format is superior to MP3, it is not compatible with most non-Apple music players. It is the preference of the author to use the de-facto music format standard of MP3. Should the reader ever choose to migrate their data to a non-Apple platform, MP3 is usable across platforms.
  1. Under Settings choose Custom. In the MP3 Encoder window:
    • Select 192 kbps for the stereo bit rate.
    • Check Use Variable Bit Rate Encoding (VBR).
    • Set Sample Rate to 44,100 kHz.
    • Set Channels to Auto.
    • Set Stereo Mode to Joint Stereo.
    • Tick Smart Encoding Adjustments.
    • Note: These settings are widely accepted to offer a good balance of superior sound quality and resulting data file size. For a true audiophile, Apple Lossless would be the ideal setting. However, the resulting file sizes will reflect the fidelity of the format.
  1. Click OK in the MP3 Encoder window.
  2. Click OK in the Import Settings window.
  3. Change to the Advanced tab.
    • Tick the option Keep iTunes Media folder organized.
  1. Click OK in the Preferences window.

2. Import CDs

This is the most time-consuming task. It is recommended to do this over the course of a couple of days or weeks, depending on the number of CDs to be imported.

  1. Insert an audio CD into the computer.
  2. When iTunes prompts what to do, choose to import into iTunes.
    • For an average CD, this will take around five minutes.
    • If the CD is damaged (e.g. scratched or dirty) this may take significantly longer.
    • A severely damaged CD might require over an hour to import.
  1. iTunes will automatically retrieve album and track information from the internet for most CDs, usually for even those that are rather obscure. Unless the CD is a homemade single you bought from that band your cousin’s friend’s friend from high school is in that played one Tuesday evening three years ago at a local coffee bar, iTunes will likely find it.
  2. Once the CD is imported, the music can be seen in iTunes. Click on Music under the Library heading in the left sidebar. In the sort panes, the album can be found by either genre, album name, or artist name.
  1. Album art can also be added to iTunes. Click on the Show Item Artwork Viewer button at the bottom left of the iTunes window.
    • It is easiest to find the album on Amazon and click and drag the album cover image from the web browser into the album art area.
    • More than one track can be selected (e.g. the entire album) and the album art can be copied en masse.

3. Connect Airport Express

The Airport Express is Apple’s lower-tier wireless access point. However, it also offers a feature called AirTunes, allowing a person to stream music wirelessly to external speakers or a stereo.

  1. Plug the Airport Express into an ordinary outlet as near as possible to the stereo.
  2. Using the RCA audio cable, connect the stereo jack of the cable to the Airport Express.
  3. Connect the other end of the RCA cable to an auxiliary-in connection of the stereo. The length of the cable needed will be dictated by the distance between the outlet where the Airport Express will be plugged and the stereo.
  4. Run the Airport utility on the computer form which the music will be streamed and follow the on-screen instructions.
  5. Open iTunes and see a pop-up menu in the lower-right corner of the iTunes window. Select the Airport in the pop- up menu and begin streaming.

An Airport Express is not required to connect an iTunes library to an external stereo. Instead of connecting the stereo to the Airport using the RCA cable, the RCA cable combined with an extension cable could he used to connect the computer directly to the stereo. However, this negates the coolness factor that wireless streaming offers.

4. Next Steps

Not only does iTunes make it easy to store and organizer a music library in one place, making finding and playing music almost instantaneous, it also offers ways to discover new music and rediscover one’s existing library.

  • Enable iTunes Genius
    1. In iTunes, under the Store menu, select Turn On Genius. You will be required to create an iTunes account. iTunes will then scan the iTunes library and upload a profile of it to Apple’s servers. iTunes will then download data including information about what music in the library goes well together.
      • Note: Yes this does mean that information about your library now belongs to Apple. Calm down. No one cares that you secretly listen to Blink-182 or any of the other numbered bands from the late nineties.
    2. Now when an item in the iTunes library is selected, the Genius will display selected music that complements it. In addition, iTunes can create mixes by genre based on similar music that goes well together, or when playing any track, select to create a Genius playlist to create a compilation of music that goes well together.
  • Extend the Library
    • By setting up an iTunes account to enable Genius, one can now also directly buy music from iTunes.
    • However, be aware that music in iTunes, although of high quality and also free of DRM, is in the Apple AAC format.
    • One can also download music directly from Amazon in MP3 format and also of a high quality.
  • Take It Along
    • For the love of god, buy an iPod. Plug it into the machine holding the iTunes library and synch the music to be taken anywhere.
    • An iPod nano is recommended for those who are active as it is a great exercise companion.
    • Also, if the user drives a high-end modern car (e.g. an Infinity G35), it likely has an auxiliary-in jack. Using a simple 3.5 mm male-to-male stereo cable, the iPod can be connected directly to the car stereo.