Should I Tell My Boss I'm Unhappy -- Or Just Start Job-Hunting?

There are times when it makes all the sense in the world to tell your boss you're unhappy.
If your biggest workplace problem can be solved with one decision — for example, if you're frequently allocated a work schedule that doesn't mesh with your life and you need a different timetable in order to keep the job — then it is logical to recommend a resolution.
If a simple schedule change could melodramatically change your job for the better, then by all means suggest a schedule change.
If you like everything about the job excluding one thing that is comparatively easily solved, then you may as well give your boss a chance to solve the problem before moving on.
You're better off starting a stealth job search than laying your cards on the table by telling your company boss that you are unhappy. People who insist on doing things their way and who keep tight control over other people are not typically folks who are open to condemnation.
There is nothing to gain by telling your boss that he is too bossy and controlling. Keep your unhappiness to yourself, and get your resume out on the talent market instead.
Now you know to ask more questions on job interviews, including questions like these:

1. Can you please tell me what an emblematic day in this job would be like?
2. You mentioned arts and crafts activities for the residents. I have some favorite arts and crafts activities and others I've heard are good but haven't tried yet. Are you open to trying new activities and seeing what works best?
3. How do you keep your schedule of activities fresh and novel over time? How do you learn about and integrate new activities into the schedule?
   Don't worry that a prospective boss might not like some of your questions. If they don't like your questions, you wouldn't like working for them either!
   This experience working for Eileen has been tough learning, but at least you get the learning. Now you know that not every manager deserves your talents.
   Only the people who get you deserve you!
   All the best,