It can surely be beneficial when one is being skeptical. Some people simply tend to have a more difficult time when they are trying to take advantage of a person, when that very same person is being skeptical.
Still, unhealthy for anyone's well-being would be to get pessimistic over every single thing that is going on around them.
Always being able to see the light down the end of the dark tunnel, this is what is known as being optimistic about situations. Even if one has always been a pessimist for their entire life, it is never to late to become optimistic.
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