Happy Friday @Derek_Kelly 
Please have look at the following thread: Do you track your time?
You might find some of the answers provided useful!
Regarding your My Task view, it is currently not possible to view Custom Fields from your My Task.
This is a very popular request in the Forum: Custom Fields in My Tasks. You might want to cast your vote to it.
Please have a look at this post Custom Fields in My Tasks - #151 by lpb. It might help in the meantime.
Please let me know if there is anything else I can help you with Derek! Have a great weekend!