To dream that you are skiing suggests that you are pushing yourself and putting your mental and/or physical ability to the test. You are your own fiercest competitor.
If you dream that you are wearing skis and going about your day, then it points to your daily challenges. The dream may also imply that you are feeling awkward in a situation. Perhaps you are headed in the wrong direction. In particular, if you are trying to climb up a ladder while wearing skis, then it indicates that you are succeeding despite those around you telling you that you will fail.