I’m building a live set right now, so I can’t tell how it works out yet, but I thought I share what’s my strategy while building it. I’ve played in a jam band for some years so I’m building on this experience.
TL;DR: Perform and listen to your performances when you build up a live set. Start off with a very crude version of a track (like a single pattern) and then automate things you are not happy with and iterate.
There are two things which are important to me:
A) I need to to feel like I’m in control of what’s happening in the set
If I get the feeling I’m not in control of the live set it would feel like ‘acting’ instead of performing and I know that I’m a terrible actor. Also performing is much more fun than acting for me. How much actual control I need to have over the things happening to achieve that feeling depends in my opinion simply on skill and in the exact opposite way one might think. I consider a real musical Zen master who is able to perform live by just pressing play and let an mp3 run for an hour while still having the feeling of performing and being in control. Beginners like me however need a lot of boxes and knobs which do stuff to achieve that feeling, but I hope to get closer to actually DJing once I get better as a musician. Having actual direct control means to me being insecure in how things should sound.
(I know this might be controversial and you can disagree with everything I wrote; It’s just my opinion)
B) What I do shouldn’t be annoying to people listening to what I play
Of course there will always be someone who doesn’t like what I’ll be doing, but at least I shouldn’t be annoyed listening to what I play. What I learned from the jam band sessions is that you can have an amazing jam and feel like Joe Satriani the whole time, but if you listen to recordings afterwards you want to through up. It’s really easy to fool yourself while playing, so, even if it seems like a no brainer, I think it is important to actually listen to what you are playing when you are not actually playing.
The trick is now to find the balance between A) and B) as they are opposed to each other: More freedom means more can go wrong and potentially be annoying. Less freedom means being less in control. What I do to build the set is the following. I jam out at home until I arrive at a pattern of 4,8 or 16 bars that I like (most of the time it will be 8; It is very hard for me to come up with something that is 4 bars or 16 bars that is not annoyingly tedious because it is too long or to repetitive). This would be the basis of a track. Then the performance of a track will consist of building and deconstructing the pattern. I usually record several performances of a single track and then try to get rid of the most annoying hickups by automation and try different ways of constructing and deconstructing until I converge to something which I’m confident with. This I do with every track in the set. When I’m done with that (which currently is not the case) I go and tryout transitions between tracks in a similar manner.