I planned long sets when I was first starting out simply because I didn't have the experience and confidence necessary to make those quick decisions, read a crowd, and converse with people at the same time.
A very effective way to play middle ground here is to plan sets of 3-5 songs that work really well together. This gives you the fluidity and complexity of well-rehearsed transitions, but also gives you the ability to quickly change your set altogether if the crowd isn't feeling it.
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