To dream of an obstacle in your path represents feelings of being unable to make progress or move forward in a situation until a problem has been dealt with. Feeling thwarted. Feelings about needing to overcome something. Negatively, you may be experiencing self-doubt. Feeling the potential to lose an opportunity or important chance. A fear of losing out on something. Frustrations.
Alternatively, experiencing obstacles in a dream may reflect your feelings about other people intentionally making your life harder than it needs to be.
To dream of overcoming represents your ability to use your skills to cope with a problem you felt was thwarting you.