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I recently read on stack overflow that getting two PhDs just shows that you're unfocused and you don't know what you want to do. However, I'm at a small school with a 5 year Computer Engineering bachelors/masters program I feel like I should take advantage of, but I'd also like to go on to do another part time grad degree in the same field or Computer Science at a larger, better established school, while I work.

If I went to a larger school like University of Illnois or MIT or similar, will having a masters and going back for another be frowned upon, or is this a non-issue?

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I don't think it is going to help your career much, so I would only recommend to do it if you enjoy the classes.

  • I have never seen a job asking for two Masters. If any employer would be impressed by two Masters, it would be because they are in different disciplines. (e.g., a Masters in CS and a Masters in Finance might look good if you are trying to get a particular position at a financial company)

  • Two CS Masters is redundant. The only time I have seen this is when a PhD program gives a MS en route to a PhD and the student already had a MS.

  • Industry is going to value experience over multiple Masters

If you do just enjoy the classes, you might think about a different field that still interests you and is relevant to your day job (e.g., HCI or math).

Or you may just want to look into a PhD program :)

EDIT: According to the responses to this very similar qeustion, Can a masters student apply for a second masters in the same field at another university?, it appears that a lot of schools may not even accept a Masters student that already has a Masters in the same field.

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    @JFA The goal of a PhD isn't to get a salary increase, it is getting a job that would be not possible with a Masters (i.e., faculty and research positions). – Austin Henley Apr 16 '14 at 22:07
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    In particular, Illinois will not admit you to a Masters program in X if you already have a Masters degree in X. – JeffE Apr 16 '14 at 22:32
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    @JFA No, I would say that is not helpful and is almost always unnecessary. – Austin Henley Apr 16 '14 at 23:14
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    It would be. Don't get a master's from your first school then. – user2258552 Apr 17 '14 at 0:23
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    +1 for "Industry is going to value experience over multiple Masters". – Burhan Khalid Nov 25 '15 at 6:23

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