Billionaire entrepreneur Sir Richard Branson is a known risk-taker whose mantra is, "Everything you've ever wanted is on the other side of fear."
Branson, 67, has already won numerous Guinness World Records and continues chasing big plans to travel to space and build one of the world's fastest transportation systems, but these are only a part of what Branson considers a benchmark of his success.
During an interview with Esquire editor-in-chief Jay Fielden for a Master Class at Hearst Tower on Tuesday, Branson said: "When you're on your deathbed and you look back at your life, you have to ask yourself, 'Have I led a good life?'"
"I don't think about it often, but you do need to think about it," he said.
That may come as a surprise as Branson enjoys to push himself outside of his comfort zone. So much so that his life flashed before his eyes when he found himself in a near-death bike crash last year.
It's how you bring up your children, it's your friends, these are the things that really matter in life.Richard BransonFounder of Virgin Group
"Leading a good life is not how much money you make, it absolutely is not," Branson said. "It's the difference you made to other people in your life."
Branson may be worth upwards of $5.1 billion, but he has never been motivated by making money, he told CNBC's "Squawk Box."
For Branson, success in life is not about material gains or losses: "It's how you bring up your children, it's your friends, these are the things that really matter in life," he said.
"I've spent quite a lot of time trying to make sure that I can close my eyes one day and feel I lived a good life."
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