This quote by Mark Twain, often attributed to him in various forms, emphasizes the importance of taking risks and embracing opportunities, suggesting that the regrets of not trying something will outweigh any disappointments caused by failure.
The idea is that in the long run, people tend to regret the things they did not do more than those they did, even if those actions didn’t turn out as expected. The message is a call to action, urging individuals to step outside their comfort zones and explore new opportunities, as the fear of missed chances can be far more painful than failure itself.
Twain’s perspective here aligns with his broader views on life and adventure, which often appeared in his works. He was a man who traveled widely, experienced various walks of life, and did not shy away from expressing his thoughts on living fully. His encouragement to act reflects his belief that life should be lived with boldness and an open mind, not constrained by hesitation or fear of failure.
Mark Twain, born Samuel Langhorne Clemens in 1835, is one of America’s most beloved authors and humorists. He wrote iconic novels such as The Adventures of Tom Sawyer (1876) and Adventures of Huckleberry Finn (1885), the latter of which is often considered one of the greatest works of American literature. Twain was known for his wit, humor, and keen observations of human nature, often combining them to offer social commentary on issues such as racism, inequality, and the American experience.

Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did……Mark Twain
Though Twain’s work contains elements of humor, he was also deeply insightful, offering profound reflections on life’s challenges. His exploration of themes like the importance of adventure, self-discovery, and personal growth permeates his writing.
The quote fits into this worldview: it’s better to take chances and pursue what you’re passionate about, even if there’s a risk of failure, than to let opportunities pass by and later wonder “what if.”
In his lifetime, Twain was also a traveler and lecturer, engaging with diverse ideas, cultures, and people. He lived in various places, including the United States and Europe, and his experiences shaped his understanding of the world. Twain’s life included many ventures that were both successful and filled with failure, but he consistently learned from those failures and used them to fuel his future endeavors.
This quote underscores a core lesson from Mark Twain’s life and works: it is better to act and experience life fully, even with the possibility of mistakes or setbacks, than to live with the regret of never trying.