You have to reinstall the update manager. First, remove/purge it:
sudo apt-get purge update-manager-core update-notifier-common
Then have a look at the console output. If it tells you, that some directories could not be removed, delete them manually. In my case:
rm -rf /var/lib/update-manager
rm -rf /var/lib/update-notifier
If you are on 13.04 or later, you should also do this to clear cached update messages:
sudo rm /var/lib/ubuntu-release-upgrader/release-upgrade-available
Then update your sources:
sudo apt-get update
Reinstall the update manager:
sudo apt-get install update-manager-core update-notifier-common -y
Only if you are currently on an LTS and want to upgrade to latest LTS, make sure that in /etc/update-manager/release-upgrades
you have set:
Prompt=lts
Otherwise (upgrading any version to a newer version) set:
Prompt=normal
Now dist-upgrade should work:
sudo apt-get dist-upgrade
Best Answer
I'm still running 16.04 myself and the support only ends in April 2021 so you have to upgrade before that, unless you're willing to pay for extended support in which case you're fine till April 2024.
I like to skip LTS releases because upgrading is 40+ hours of work in my case as my system is highly customized and does exactly what I want and looks the way I want (Steampunk).