You can setup printer to rotate it for you automatically. 


For Mac

1. Open desired file (e.g. a PDF). 

2. Click "File" and choose "Print". 

3. Select "Show Details"

4. Select printing direction in "Orientation"

For Windows

1. Go to "Control panel" -> "Devices and Printers"

(Right click on "This PC", choose "Properties", then click on "Control panel"-> "Devices and Printers")

2. Right click on "Label Printer" -> choose "Printer Preferences" -> go to the "Page Setup"

3. Select printing direction under "Orientation"