Here’s what billionaire Richard Branson would tell his 25- and 50-year-old self

Richard Branson dropped out of school at age 16 to start his first business, Student magazine. By 23, the serial entrepreneur had earned his first million.

Despite his massive success early on, the now 66-year-old would still offer his younger self some advice if he could do it all over.

In a series of letters to the 10-, 25-, 50- and 65-year-old versions of himself, Branson shares what he wishes he had known at different stages of his career.

“You won’t always succeed,” the self-made billionaires writes to his 25-year-old self. “In fact, you will fail time and time again. That’s OK though because failure is an inevitable part of every personal and entrepreneurial journey.”

Nobody gets it right the first time, he emphasizes. What matters is that you “continue to take chances,” he says. “In the future how ‘lucky’ you are in business will be determined by how willing you are to take calculated risks.”

After years of calculated risks, Branson had, by age 50, launched hundreds of companies and been a billionaire for nearly a decade. “On the business front, you may feel like you’ve achieved just about all there is to achieve,” he writes to the middle-aged version of himself. “But let me tell you, there are so much more great things to come. …

“The future will be so bright if you continue to look for opportunities where others see challenges.”

To this day, Branson doesn’t feel like he’s “made it.” “The way I see it, life is all about striving and growing,” he says. “I never want to have made it; I want to continue making it!”