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Right now I'm looping the changes to autumn leaves and practicing playing different chords/intervals over the changes.

So for example I'll just play the 7th of every chord or I'll play the 3rd and the seventh in a double stop.

I've been told I should try to learn songs in different keys but I'm still struggling doing this in the original key.

Would it be counter intuitive to try it in a different key before I have a firm grasp of it in the original key or do you think trying it in another key would actually help more by growing my vocabulary so to speak.

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Generally, it's good to practice everything everywhere. This helps you get to know the instrument you're playing better (this doesn't apply only to guitar) and helps you learn how to transpose the songs.

But, if you still cannot play a song in a certain key, there isn't much point in transposing it. It might help if you transposed it into something that had easier chords for the guitar, but this might not be easy in all the songs.

I would advise to transpose a song when you can play it fluently. What I mean is that you should be able to:

  • Play the chords
  • Play the melody
  • Accompany someone else that is soloing
  • Be able to solo yourself

When you are able to do all of the above, you should try to transpose. In Jazz, you're going to need all of the above (or most of them) in every song. So, if you cannot play them in a key, there isn't much point in trying to learn the song in another one.

In conclusion, I don't think it's counter productive to practice it in a different key before you have mastered it, but I don't think you'll get the most of it.

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  • The importance of playing everything in every key is also mentioned in MArk Levine's Jazz Theory Book Jun 20, 2015 at 20:22
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Moving toward transposition of whole tunes

As a step between learning a tune and transposing it to all keys, it's helpful to have a few basics already under your fingers (and in your ears). These can (and should) be practiced the same way as described for practicing "Autumn Leaves": just the 7th of each chord, 3rd and 7th of each chord, etc.

This post has four main headings: ii-V, 12-bar blues, Rhythm changes, Concluding tips.

ii-V

"Autumn Leaves" is a great tune for this particular question, because it is largely ii-V based. So as a step transposing, you would do well simply to practice ii-V progressions, which lend themselves to moving cyclically through all keys.

There are many different ways to do this, but a few basics to get started:

Major

  • C-7 F7 Bb-7 Eb7 Ab-7 Db7 ... D-7 G7 (this takes you through six keys)
  • B-7 E7 A-7 D7 ... C#-7 F#7 (this takes you through the other six)
  • C-7 F7 Bbmaj7 Bb-7 Eb7 Abmaj7 Ab-7 ... D-7 G7 Cmaj7 (as above, do this one also starting from B-7)
  • C-7 F7 B-7 E7 Bb-7 Eb7 ... Db-7 Gb7 (this covers all 12 keys)

Minor

All of the above, but substitute min7b5 for min7, and when the I chord is present, of course that would also be minor.

Tri-tone substitution

Again you can use all of the above patterns, but here, instead of the dominant 7 chord, you substitute the 7 chord a half-step below the ii chord. For example, the first patter:

C-7 B7 Bb-7 A7 Ab-7 G7 ... D-7 Db7

12-bar blues

Blues is so ubiquitous in jazz, that you should be proficient in all keys. This will give you a leg up on lots of blues-based tunes, even ones that further vary from the simplest forms. 16-bar blues, modal blues, bebop blues (which typically use lots of ii-Vs) all have their underlying basis in the basic 12-bar progression.

For practice purposes, I use this form, because it's simplest.

| C7 | C7 | C7 | C7 |
| F7 | F7 | C7 | C7 |
| G7 | G7 | C7 | C7 ||

Or, if you prefer:

| I7  | I7  | I7 | I7 |
| IV7 | IV7 | I7 | I7 |
| V7  | V7  | I7 | I7 |

If you want to practice continuously "around the cycle", just change the last I7 to be a ii-V into the new key.

I-VI#-ii-V / Rhythm changes

The chord progression for "I Got Rhythm" is also ubiquitous in standards. Both the A-section progression (I - VI - ii - V) and the form as a whole are good to know in all keys.

You can find the chord changes on Wikipedia.

iii-VI-ii-V

Note that this common variation on I-VI-ii-V is really just the ii-V pattern from above.

I-I#o7-ii-V

Another common variation. For example:

C C#o7 D- G7

Concluding tips

  • When practicing through cycles, remember to start in different places within the cycle so you don't just learn it one way.
  • When you are confortable with, say, tri-tone substitutions, you can add them into the other patterns you're learning. For example, instead of I-VI-ii-V, try I-bIII-ii-bII.
  • It isn't necessary to fully master these before you start transposing. Rather, they just give you a leg up, but you can be working on both at the same time.

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