I have to upload a passport photo. My photo is 814kb. It has to be converted to a .pdf and shrunk to 300kb in order to upload.

I have found converters and file reducers online, but none of them will get the .pdf to below 300kb. Any SUGGESTIONS?JPEG Files
JPEG files are perhaps the most commonly used type of image file for both sharing online and within document files. They are popular because the degree of compression on the image can be adjusted, so the storage size and image quality can be played around with to get the best solution for the user. The more compressed a JPEG file is, the lower the quality. With this in mind, you can fit a fair amount of JPEG files into a document, but the smaller they are, the worse they will look.
... from https://www.iceni.com/blog/which-is-the-best-image-type-to-embed-in-your-pdf/

Most photo editors let you reduce the print size of a photo. Also, the file size can reduced by adjustable compression. Try a factor of 12.
Irfanview?
Hey,

If you have MS office installed you can ALWAYS a open a word document. Then insert the image you want in to the document and save it as a pdf.Depending on how your computer is configured, you may be able to find your photo in File Explorer, right click on it, and select Convert Picture to PDF. Your right-click menu will probably also show one or more options to edit the photo, and this would probably give you an option to crop and/or resize your image. If you want to retain an original version of the photo, be sure to rename it when shrinking it so that you still have the original, plus the smaller version of it. You can use PaintDon't need any software. Right-click the picture and hit Print, then you can SET the output size.

Here is a possible answer to the question.
A JPEG picture can be edited by most photo programs, such as Microsoft paint.
The picture can be RESIZED to a suitable number of pixels. Then to convert the program to PDF, you would simply invoke the print command and select the option to print to a PDF file.
If you do not have that option in the print command, you can install a PDF editor that includes that FEATURE. One such is Fox PDF editor. And there are others that also have an option of turning a print output into a PDF file.
And of course, the other easy option would be to open a new PDF document in a PDF editor and then simply insert a JPEG image into the document and adjust the size. This is rather straightforward and should not require any expertise except just basic familiarity with a PDF editor.
I hope this helps.