Usually means: Manage to barely stay afloat.
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We found 5 dictionaries that define the word keep one's head above water:

General (5 matching dictionaries)
  1. keep one's head above water: Merriam-Webster
  2. keep one's head above water: Oxford Learner's Dictionaries
  3. keep one's head above water, keep one's head above water: Collins English Dictionary
  4. keep one's head above water: Wiktionary
  5. keep one's head above water, keep ones head above water: Dictionary.com

Definitions from Wiktionary (keep one's head above water)

verb:  (idiomatic) To survive or endure, especially in a situation in which one is struggling to avoid being overwhelmed by adverse financial circumstances.

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