In learning to improvise, what are your challenges?

[webacademyofmusic]

I know the challenges are different for everyone. What are your challenges? Knowing what to practice? Lack of a teacher? Motivation? Inspiration?

As a teacher and a student, I'm continuously trying to get to the bottom of this.

https://webaom.com/blog

[pianist88]

As an improvisor myself, I actually found it hard to create countermelodies. I started off with just basic chords. After I studied harmony and counterpoint, I finally felt confident enough to add countermelodies into my improvisations. I improv a bit of blues (lots of 7ths and such) classical (I can turn Twinkle Twinkle into a Mozart-sounding sonata) and such.

[rjarsenault1101]

I'm just learning to do improvised composition. I got a new teacher and that's what he's getting me to do. 

[ted]

With improvisation learning passes from freedom to order. This is the precise opposite of the whole of formal education and what we are used to. By far the worst obstruction to learning improvisation is inhibition, and a habituated concern with "ought tos" and "shoulds". Flow must occur first, prior to any assessment of quality. Therefore initially the actual material is best kept very simple. For example one way is to take just two or three scales and play any phrases and rhythms within them in uninterrupted flow. Something like that gives infinite scope for invention, no requirement for mental arithmetic, and if it is in one scale it must sound all right in the conventional sense.

Yes, a teacher is good. Trouble is, hardly any trained musicians or piano teachers can improvise themselves except the odd one or two who are restricted to jazz.