Hell, claude even makes that part of the standard workflow, with /compact; cleverly using the llm itself to summarize the previous context
I much prefer to choose tasks that can be done with 25%+ context left and then just start the next task with fresh context.
If I'm getting low on context I have it summarize the plan and progress in a text file rather than use /compact and then start a fresh context and reference that file, which I can then edit and try again if I'm not getting good results.