Dare to be free, dare to go as far as your thought leads, and dare to carry that out in your life.
Did Vivekananda say "Take risks in your life. If you..."?
Not in his works
No. "Take risks in your life. If you win, you can lead. If you lose, you can guide." does not appear in Swami Vivekananda's Complete Works. Searched vols 1 to 8 with a fuzzy match, and Wikisource (all volumes, including vol 9) by phrase. No passage comes close.
The version people share
“Take risks in your life. If you win, you can lead. If you lose, you can guide.”
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Lines he did say
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Is "Take risks in your life. If you..." in the Complete Works of Swami Vivekananda?
No. We searched volumes 1 to 8 with a fuzzy match and Wikisource across all nine volumes by phrase. Nothing comes close.
How do you check a Vivekananda quote?
Search a distinctive phrase in the Complete Works (Advaita Ashrama, nine volumes; the text is on ramakrishnavivekananda.info and Wikisource). If only quote sites carry it, with no volume or lecture named, treat it as unverified.
Sources and method
Matched against The Complete Works of Swami Vivekananda, Mayavati Memorial Edition, vols 1 to 8 (9,239 paragraphs, Bengali translations checked separately), with Python difflib. In his words: 90 or more out of 100. Paraphrase: 70 to 90. Not in his works: under 70, and no hit in a phrase search of Wikisource across all volumes, including vol 9. This line scored 54.