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Dreaming that you overcome an obstacle, means you will be able to congratulate success.
To dream that you need to overcome obstacles, suggests in reality you will feel disillusioned and be disappointed with someone's service.
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added / Sam on 2010-09-29 for Obstacles
Dreaming of obstacles to your progress can indicate that you are uncertain of your ability to achieve your goals in life. You lack self-confidence and may feel unable to do the things you want to do. You may feel that you are being tested in some way. The barrier may or may not be self-imposed.