Your work context may provide you with frequent opportunities to do that.
For instance, if you are a programmer, you can make predictions about how long a given task is going to take, or alternately how many tasks you can take on in a given period.
If you train or teach people, you can predict what they will have understood at the end of a given session, and test those predictions by asking questions at the end of the session.
More generally, predictions of the form "I will achieve objective X by time T" are a useful class, as you normally have quite a lot of the relevant information, which ought to narrow your confidence bounds.
ETA: keeping appointments is another similar class. If you're never late, you're probably underconfident. (See Umeshisms.) You should have a general degree of confidence in your timeliness, e.g. "I will seek to show up on time 80% of the time." You may adjust that depending on criticality in given contexts, e.g. "...except that I hate to disappoint employers, so I'll show up to work on time 95% of the time".
An excellent way to improve one's skill as a rationalist is to identify one's strengths and weaknesses, and then expend effort on the things that one can most effectively improve (which are often the areas where one is weakest). This seems especially useful if one is very specific about the parts of rationality, if one describes them in detail.
In order to facilitate improving my own and others' rationality, I am posting this list of 11 core rationalist skills, thanks almost entirely to Anna Salamon.