Make a backup or two, clone your boot storage to a scratch test environment, boot that, and upgrade and test that.
And is it wise to perform a production upgrade to Catalina, absent some Catalina-only requirement? Without testing?
Then let us know which (presumably) iMac you have, and whether it works with Target Display Mode. Or what (else) breaks.
We’re all still sorting out what works, and what doesn’t, and what works differently, based on the churn here in ASC.
~60 different questions either new or new replies in the past ~hour, mostly Catalina problem reports.