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Along these lines though when I did a lot of wood cutting I would buy the foam ear plugs, cut them shorter then use a hole punch to create a centre through hole that fit my earbuds. Replacing the stock rubber/silicon pads.
I would then compress the ear plugs with my fingers like you normally would and slip the earbuds in.
I would guess the earplugs efficacy was slightly reduced but it let me listen to music and podcasts while slinging a chainsaw for hours at a time without having to have ear damaging sound levels. I always used a helmet and earmuffs over the top for extra isolation.
Slackware 7