Abuse of Productivity Systems

Example 1.
Bob's dream had always been to learn French, and to live in France after he retires early from his high-paying management job. Recently, he used the flashcard program Anki to help him with learning French, and had considerable success with it.
In fact, he has learned French to complete fluency in around one and a half year, and he attributes much of this result to using Anki effectively. His habit of learning Anki every day is very strong, and he always does it first thing in the morning without fail.
Now he thinks, "if I could have done it with French, what stops me from learning, like, 10 languages in the next 15 years? It'd be so cool!". And so, after his daily French workload has dropped significantly, he downloads and imports a huge database of German flashcards.
Pretty soon, his notices that he is losing his motivation to learn every morning. "What is wrong with me? Am I becoming lazy?", he thinks, and pushes himself to work harder. Learning gradually becomes more and more unpleasant. Bob's resentment builds, and soon is too large for him to overcome.
When he finally gives up on Anki altogether, it comes as a huge relief.
Example 2.
Sally is very satisfied with how the pomodoro technique helps her with productivity. She has several projects on which she wants to work, and using pomodoros gives her a well defined framework for time-sharing those projects. Having a more tangible measure of progress (the number of pomodoros done) provides pleasant reinforcement, and she has reduced her total procrastination to acceptable levels.
In the meantime, she is considering a move to another city, and wants to look for a new job. With dismay, she discovers that when it comes to looking for jobs, she is not procrastination-free. It doesn't fit with her new image of herself as a procrastination-free person.
Sally thinks about the problem, and comes up with a great idea: she is going to use pomodoros to search for jobs! She decides to spend one of her pomodoros every day to browse job offers on the Internet. The next day, when she remembers about the plan, she feels slight displeasure and annoyance, but pushes those feelings away quickly. She sets the pomodoro timer and opens her web browser.
25 minutes later, the timer rings and she realizes that she has procrastinated away most of the pomodoro. This is the first time it has ever happened to her. But she keeps up the positive attitude, and tries the second time. She is able to do a little bit more, but it's still nothing like the concentrated work she had been getting out of her pomodoros before.
Questions
What mistakes are Bob and Sally making?
What would you change, so turn those mistakes into successes?
(Note: the definition of "success" is broad here. If Bob can decide to not learn German with zero wasted motion, it's a success.)
How does this generalize?