There haven't been many wide-sweeping changes between 5.8 and 5.22 that would immediately break your program.
The most obvious changes would be the much better handling of Unicode.
The annoying stuff for migrating to a new Perl version is that you need to collect all the missing prerequisites that likely have accumulated in your old Perl installation. I keep track of my prerequisites in a Makefile.PL even if I don't intend to distribute the software ever. This makes reinstallation of all prerequisites as easy as:
cpanm --installdeps .
You can test the migration to a new version of Perl by installing a separate version of Perl using perlbrew. That way, you have a low risk of ruining your existing installation.