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When do I need a mask while working?

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I'm mostly filing, sanding, scraping, and that sort of stuff. I have a high powered fan going while I am doing this. I wear an N95 mask and can smell some certain things when I am wearing the mask. I know there are some things when working and building guitars where you don't need a mask, but where is a mask needed and not needed?

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Wearing a mask every time you create dust or act with chemicals is good practice. That includes sawing, filing, rasping, sanding, painting...

As you have been previously told, a fan is not  a dust extractor. Instead a powerful fan raises the dust in your working space into the breathing air, making the mask even more important to wear. A dust collector vacuum would be a good addition on your power tools list. You could use that for your bandsaw as well as with your router etc. One with an automatic power outlet would allow for starting the vacuum remotely by the tool.  -In the workshop we're using there's a 6" industrial piping system with fire extinguishers and all, yet the belt sander table is dusty. Learn to wear a mask as naturally as your undies!

Hand planing is the most dust free process in guitar building, followed by drilling. Even those create inhaleable particles. Always wear a mask if you want to live a long life as a professional guitar builder.

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