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I have read some post about the meaning of かっていうと and i understand it should be read as 2 separate particles i.e. か+っていうと

However, I can't seem to understand what the this phrase means in the below sentence:

実は初めから宇宙飛行士になるつもりだったかっていうと、そうじゃないんです。大学を出たら、医者になろうと思っていましたから。

Any help would be appreciated!

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First of all, 「~~かっていうと」 is the informal form of 「~~かいうと」. Both 「って」 and 「と」 are quotative particles.

実{じつ}は初{はじ}めから宇宙飛行士{うちゅうひこうし}になるつもりだったかっていうと、そうじゃないんです。大学{だいがく}を出{で}たら、医者{いしゃ}になろうと思{おも}っていましたから。

To place imaginary quotation marks, it would look like:

実は『初めから宇宙飛行士になるつもりだったか(?)』っていうと、そうじゃないんです。大学を出たら、医者になろうと思っていましたから。

In the construction:

「Phrase A + か + と/って + いうと + Phrase B」

"Phrase A + か" is always an embedded question and Phrase B is always the speaker/writer's own answer to that question.

If you remember the sentence in bold above, you will be able to come up with a valid translation. An example would be:

"If you ask me if I wanted to become an astronaut from the start, no, that is not really the case. I was actually thinking of becoming a doctor after graduating from the university."

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