This is a very good question and one that applies to a lot of candidates. Thank you for posting it so that it can be discussed in its proper context.
In the ideal world, you would take the GMAT exam once, get the score you desire and then move onto your applications. However, this is frequently not the case. The actual process of taking the GMAT is stressful and often no matter how well prepared you are, your scores fall short of expectations. Please do not let this deter you from pursuing your goals.
Many candidates take the exam 2 or 3 times -- it is not uncommon and business schools are use to seeing this. In fact, most top business schools look at only your highest score. Once you take the exam more than 3 times, things start to look a bit suspicious to some in admissions, so I would not recommend taking the exam over this number of times. Before you take your exam (or retake your exam), figure out what areas you are weak and causing the score to remain lower than expected and get the help you need to address this area (yes, a tutor). Often times it just take a bit of intervention and investment to make a big difference in one or two areas. Also, I cannot emphasize enough the importance of practice (in fact, practice, practice, practice....), especially in those areas that are causing you problems. Attack them head on and I am sure that in short time, you will see marked improvement.
Just to give you some encouragement, four years ago I worked with a candidate who had taken them GMAT 12 times over the course of 2 years. Her sole goal was to get into HBS and her GMAT score kept on coming up short (her life over this time was studying for the GMAT). I was unsure of how HBS admissions was going to accept this fact, but was shocked when she was granted and interview and was later accepted. I guess tenacity does pay off - but I would rather that you be more strategic in approaching the test and achieving your desired score.
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