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People make choices everyday. From the food they eat, the clothes they wear, the classes they take and the person they wish to marry. All of these choices may become overwhelming. I think that it definitely matters what you choose. My aunt is constantly reminding me about "choices and consequences". She'll talk to me about her daughters and how she tells them, "do whatever you want; I'm not going to stop you, but remember that there are always consequences to the choices you make in life." In sense, I would have to agree with her, however there are choices that matter more than others. Choosing what college to attend, choosing your significant other, choosing what to major in: those are choices that matter more, because they are more long-term. On the other hand, choosing what to wear in the morning, what to eat for breakfast, those things aren't necessarily a matter of life or death. They aren't exactly significant to long-term; they are more short-term. 

I also think that some choices should be more thought out than others. However, overanalyzing choices and comparing the "what ifs" may change your initial thoughts about a choice. Therefore, I find it better to make choices based on that gut instinct. Make the choice and don't look back.