What determines the amount of difficulty an obstacle creates for you is not so much the obstacle itself but rather the way you think about the obstacle, especially in terms of a concept called locus of control.

People are either "external locus of control" meaning that they believe (at least subconsciously) that their life is controlled by influences outside their direct control, or they are "internal locus of control" meaning that they believe that their life is controlled internally by thoughts and actions that they are responsible for. Many people consciously express that they are internal locus (IL) but their behavior shows that subconsciously they are external locus (EL).

What's all this have to do with obstacles?

EL people with describe an obstacle or problem in terms of external control or simple fact, and as such they find it more difficult to overcome that obstacle, as overcoming requires an internal solution that is then applied to the obstacle. Let's look at some examples.

EL statement of obstacle: I don't have enough money.

This is actually an external description as it is describing your circumstances and is a simple statement of fact. The problem with viewing obstacles in this manner is that it avoids the reason for your circumstance, which is always some action that you are taking or are avoiding. Let's look at rephrasing this to an IL perspective, where you are taking responsibility for your circumstances.

One possible IL restatement of this obstacle is "I am not taking the right actions to acquire the money I need".

Notice that the IL description of the obstacle is in terms of what you are "doing" or "failing to do" and as such it points you in the direction of the "action" you need to take to solve the situation. It is forcing you to take responsibility whereas the EL description conveniently bypasses your responsibility for your predicament.

Here's another example.

EL: I'm overweight.
IL: I am eating in a manner that is inappropriate for by desired bodyweight.

Being overweight is only the result of inappropriate eating. You have to change your eating habits in order to lose the weight.

You could take the IL approach to a more basic level and describe the situation as; the way I am thinking about my food and eating is leading me to eat inappropriately.

Notice that all the IL descriptions are in terms of present moment actions that you are personally responsible for. This is the key to this method.

Think of the obstacles that you are facing now and write out a description in terms of present moment actions that you are personally responsible for. Now look at how much easier it is to see the way through those obstacles.

If you develop the habit of seeing your whole life in terms of present moment actions that you are personally responsible for, then you will be firmly planting yourself behind the steering wheel of your life and obstacles will quickly become minor inconveniences that you easily sail through.