Via Entrepreneur

When was the last time you stepped out of your comfort zone? It's easy to get stuck in a routine, especially at work (more so if you've been doing the same job for a while), and taking on a new challenge is a great way of getting out of that rut. At Virgin, I use two techniques to free our team from the same old routine: breaking records and making bets. Taking chances is a great way to test myself and our group, and also to push boundaries while having fun together.

I have always loved a challenge. When my family and I went to the British county of Devon on holiday when I was four or five, my Auntie Joyce bet me 10 shillings that I wouldn't learn to swim by the time we returned home. And somehow I didn't learn while thrashing about in the sea.

I was determined to prove her wrong, so when I spotted a river during the drive home, I asked my dad to stop the car, then ran out and jumped into the water in my underwear. At first, I sank and started swallowing water, but I kicked upward and, to my amazement, soon began to swim downstream. My reward for passing the sink-or-swim test was a crisp 10-shilling note - the most money I had ever held in my hands.

That and later challenges taught me that it is important to try things that might not work, and then improvise solutions along the way. I've found that attempts to break records can result in technological leaps forward. For instance, the businessman and adventurer Steve Fossett flew our Virgin Atlantic GlobalFlyer nonstop around the globe in 2005, becoming the first person to complete such a flight solo and without refueling. Our plane was built using carbon fiber, at a time when other plane manufacturers relied primarily on heavy materials.

Following the GlobalFlyer's success, Boeing and Airbus both started using carbon fiber in the manufacture of some aircraft. This technology will make planes lighter and is likely to dramatically reduce the carbon output of the airline industry in the future. (The plane is now on display at the United States National Air and Space Museum.)

When you need a boost, it can be a lot of fun to pit yourself against one of your competitors. The most recent bet I lost was with my friend Tony Fernandes, who now runs AirAsia, but used to work with us at Virgin. In 2010, we both owned Formula One teams that were doing badly and decided to perk things up. It was agreed that the owner of the team that finished lower in the standings would work as a cabin crew member on the other's airline.

In May I honored the bet on an AirAsia flight from Australia to Malaysia, putting in a shift wearing the full stewardess's uniform, which took a few hours of preparation.

Although I've always wanted to help out on a cabin crew, I've never had a boss, so I didn't enjoy it when Tony ordered me around. I "accidentally" spilled a tray of drinks over him, and was sacked when we landed. (On the other hand, Archbishop Desmond Tutu, a passenger aboard the flight, described me as “voluptuous,” so I must have gotten something right.)

Business owners and executives usually take themselves very seriously, so the story of our wager was widely circulated in the media. Everyone had a good laugh, and nothing was lost on either side (except my pride). It was the right approach: The publicity helped both AirAsia and Virgin to build customer bases in new markets, while the charity flight on which I served raised more than $300,000 for the Starlight Children's Foundation, which provides support for sick kids and their families.

One of the great benefits of taking on challenges in your working life is that you and your team learn to confront risk together – and also to lose sometimes, because when you make a good wager, the odds are not going to be in your favor. The calculated risks you and your team take should be strategic judgments, not just blind gambles: Protect the downside by figuring out the odds of success, working out what the worst possible consequences would be, then deciding whether to accept.

You need to hone these skills, because you and your team are going to face adversity at some point. No matter what industry you work in, the nature of business is change, and so while you can prepare for every possibility, some new, unexpected circumstance is likely to thwart you. The only thing that's meaningful about such setbacks is whether you bounce back. In 1998, Steve Fossett, Per Lindstrand and I had to abandon our attempt to fly around the world nonstop in a balloon. Rather than feeling sorry for ourselves, we at Virgin continued working on some of the problems we had encountered through our other businesses.

But aside from any business concerns, one of the main reasons my colleagues and I undertake any adventure is because it's fun, whether it's a bet that ends with me serving drinks to passengers in a skirt or whether it's one that leads to the creation of a company that transforms the space industry. Should you say yes the next time somebody proposes a challenge? You bet!