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How do I shred the data on an external HDD? I am trying shred "/media/me/New Volume/" but I get failed to open for writing: Is a directory. Why?

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You need to run shred on the device, not on the mount point.

Type mount and get the device name (e.g. /dev/sdb1, likely it will be /dev/sdXY where X is a letter and Y is a number), then unmount it (run umount /your/device) and run shred /your/device.

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shred runs on block devices or files.

So it is either (if /dev/sdx is your external HDD):

shred -n 1 /dev/sdx

Or, in case of a file (if the filesystem is 2TiB large):

truncate -s 2T "/media/me/New Volume/shredfile"
shred -n 1 "/media/me/New Volume/shredfile"
sync
rm "/media/me/New Volume/shredfile"

The file will not shred the entire HDD, just the free space in the filesystem.

The option -n 1 makes sure shred uses only a single pass - multiple passes are a waste of time.

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