SQL Server 2014’s end of support date is coming in less than two years: July 9, 2024. I know that sounds far-off right now, but consider the work you have to do between now and then:
Pick a new version to migrate to Set up development SQL Servers for that new version Start developing & testing with it Get users to sign off that it’s working as expected Design your high availability & disaster recovery strategies for it (something I recommend folks revisit with each new release) Set up production/HA/DR SQL Servers Migrate over to the new servers