That's the situation Kurt Long found himself in earlier this month.
Long, founder and CEO of cyber-security company FairWarning, visited Neckar Island, which Branson owns. The two met and played a few friendly tennis matches. After the last match, Branson invited Long to participate in the Virgin Strive Challenge.
Organized by Branson, the ultra-marathon involves biking thousands of miles, scaling live volcanoes, and navigating steep mountains in a fundraising effort to support start-ups focused on helping young people.
"You learn to think of something bigger than yourself," Long told CNBC. "You learn to try big things and manage the risk of it. You experience some failure, you pick yourself up and you keep going."
On the journey, Long realized he wasn't only learning how to cycle more miles than he had ever before. He was learning some key business and career lessons.
For this CEO, the big goal was to bike 300 miles along the coast of Italy in just a few days. In order to do that, he had to think small and focus on pushing the pedal every second.
Success rarely comes overnight. To achieve your next business or career goal, Long recommends breaking big goals into small to do's.
"The key is to keep the ultimate goals in the back of your mind at all times, but have a plan for every day and even every moment as to how you will get incremental progress," Long wrote in an email to CNBC.
There were a few times when Long didn't know if he would finish the race at all. Over the course of the difficult trip, he found that the worst thing he could do was compare himself to others.
"When other riders are cruising past you up a hill, or blowing past you down a hill, when it feels like you are really doing something wrong, you have to trust your own instincts about the right plan for you," he said.
Focusing on yourself allows you to be realistic and alleviates stress.
With only a couple of weeks to prepare (on a beach cruiser bike, no less), the entrepreneur sought advice from people who had experience doing long distance cycling.
After sitting down with one avid cyclist, Long learned several important lessons about everything from the importance of setting goals to the importance of wearing padded bike shorts.
"Listen to people who have done it," he said.
Whether you're recovering from a broken bike gear or a disappointment at the office, it's important not to dwell on the past, Long said.
"Roll the bike forward," he said. "Looking over your shoulder or dwelling on the past doesn't get you anywhere."
Working hard at something will drain you, Long realized. It's important to give yourself time to bounce back.
"Recovery isn't optional, recovery is mandatory," he said. "Surprisingly, if you pay attention to recovery, you actually can improve your performances even when riding long daily distances."
Whether it's getting extra sleep or prepping yourself mentally for the next day, it's important to take care of yourself, according to the entrepreneur.
When Long was in physical pain on the journey, he found that maintaining the right attitude helped.
"For whatever reason, just smiling and having a sense of humor about an outrageous endeavor works," Long said. "Your body responds to positive input even when it is just your own outlook and smile."