Whenever you are updating your Matillion instance(s) to the latest release, Matillion's normal recommendation is to follow the best practice in this document.
In summary, the recommended steps are:
Take a backup of your old Matillion ETL instance
Launch a new Matillion ETL instance at the latest release
Use the built-in Migrate utility to copy your work from your old Matillion ETL instance onto the new one
Check everything is running OK on your new instance
Switch off the old one, and continue working on the new one
This approach gives you an easy backout strategy if you find any problems at step 4.
From v1.41 the version jump you are looking at is more than 10 releases, and almost certainly contains operating system changes. An In-Place Upgrade is definitely not suitable for a large change like that.
For information, anyone migrating onto the Matillion Hub will also need to follow the launch-new-and-migrate process.