“Well, that’s not right!”, I remember thinking as I looked down at my left foot in confusion. My little toe was sticking out at an awkward 45-degree angle – something I was pretty sure had never happened before. Not knowing what else to do, I tried to push my toe back into its original position – just like I’d seen in movies dozens of times before. Of course, in the movies, it was usually an arm that was snapped back into position, not a pinkie toe, but, whatever.

I was in the British Virgin Islands on a business trip when my colleague and I decided to take a day tour to the beautiful island of Virgin Gorda at a place called “The Baths”. The beaches at The Baths feature white sand, giant boulders (also called batholiths), beautiful sheltered pools of waist-high, crystal-clear water and narrow caverns just begging to be explored. Each year, tourists from all over the world flock to The Baths to explore its natural beauty, climb its boulders and take a dip in its dozens of pools. But how did an excursion to explore one of the BVI’s best kept secrets end up with me being in excruciating pain? For that, we’ll have to travel back in time about 15 minutes before I realized that my toe was broken.

My colleague and I had just about completed a tour of The Baths. All that we needed to do now was to stand in line and patiently wait our turn to go through a narrow cavern on our right that was clearly marked “exit”, and that would lead us out of the network of caves. But, sadly, like many entrepreneurs, patience isn’t one of my virtues. Due to the large number of tourists on that particular day, and to the narrow size of the exit cavern (which would only allow people to pass through in single file), it would be at least fifteen minutes before we could make it through the exit cavern. I figured that would be enough time us to explore another cavern on our left, just opposite the exit sign.

My colleague, let’s call her Jane, wasn’t in the mood to explore caverns that no one else seemed interested in investigating, and begged me to stay put and wait our turn to exit the maze of tunnels. Ignoring her warnings, I set off on a solo expedition of the cavern on the left. After a few minutes of exploring, I came across what was undoubtedly one of the most beautiful sights that The Baths had to offer – a crystal clear pool with knee-high water set in white sand and surrounded by several boulders that separated the pool from the open ocean. My solo expedition was clearly worth it! Such a pity that Jane wasn’t brave enough to join me on my expedition.

Up until that point in time, I had been navigating through the waters of the pool cautiously, gently using my toes to figure out where I should plant my feet and where I should take my next step. But, unfortunately, lulled in by the soft sand that covered the bottom of the pool, I had let my guard down and took one confident (and careless) step forward. As I brought my left foot down, the pinkie toe on my left foot clipped the edge of a large rock that lay beneath the surface of the water, just a few inches off of the bottom of the cavern. While my other four toes made it safely to the bottom of the pool safely, my pinkie toe snapped upwards, dislodging it from its usual position and causing a painful break in the bone of the toe.

For the rest of our tour of Virgin Gorda, I hobbled along in excruciating pain. Jane, rather predictably, showed no sympathy. After all, she had tried to convince me not to wander off on my own. When I tried to convince her that “What happens in the BVI, stays in the BVI” and that this little story shouldn’t be shared with the rest of our colleagues, Jane, matter-of-factly replied “Sorry! That’s not in my contract.” I remember mentally running through Jane’s contract of employment and sadly, I had to admit, it wasn’t in her contract – not even in the fine print!

Within 20 seconds of us getting to a Wi-Fi hotspot, Jane had, in great detail, described in our company WhatsApp group how I had ignored her warnings, how I had wandered off on my own and how I had broken my toe. The reaction from team members was swift, and ranged from words of genuine empathy and concern, to hysterical laughter at Jane’s vivid description of the episode.

Fortunately, thanks to a kind doctor who treated me back on the island of Tortola where we were staying, my pinkie has now completely healed. It no longer juts out at a bizarre angle and I no longer have to hobble along in pain. In fact, apart from some good-natured ribbing every once in a while from my friends, family members and colleagues, I’ve pretty much forgotten that I’d ever broken my toe!

Entrepreneurs have a tendency to wander off and go exploring narrow caverns on our own – even if it means ignoring the warnings of well-meaning, level-headed colleagues. And even if it means there is a chance that exploring these narrow, less-travelled caverns may lead to failure in one form or another. Exploring narrow caverns, breaking a toe or two, accepting the chance of failure – those are some of the things that makes entrepreneurs, well…entrepreneurs!

It’s hard to come across examples of successful entrepreneurs who, at one point or another, haven’t experienced painful episodes as a result of exploring unchartered territory. Richard Branson, the billionaire founder of the Virgin group of companies, has experienced tremendous success in the business world. But he’s also failed in many of his ventures. Virgin Cola, a product designed to compete with Coca Cola is no longer on the shelves. Neither is Virgin Vodka, Virgin Cosmetics, Virgin Clothing or Virginware (which was meant to compete with Victoria’s Secret).

Google, the Internet behemoth responsible for successes like the Chrome browser, the Android operating system, Gmail and Google Maps also has a slew of failures including Google Knol, which was designed to compete with Wikipedia, and Google+ which was Google’s ill-fated attempt at developing a social media platform.

But despite these failures, Google does everything it can to encourage its employees to continue taking risks, even if there is a chance that these risks may end up in failure. According to a FastCompany.com article, Google employees are publicly applauded by their co-workers and supervisors for their failures, and are often rewarded with time off to contemplate what their next project will be. Supercell, the gaming company behind the popular online game Clash of Titans, celebrates employee failures by cracking open a bottle of champagne. And P&G, the billion-dollar global consumer goods giant, is known for its prestigious “Heroic Failure Award” which is given to employees with the biggest failures.

But…why on earth would companies known for their successful track records and high rates of innovation actually reward people for failing? Doesn’t that encourage employees to lower their own expectations and, instead, produce mediocre work? Not so, say leaders from Google and many successful companies that encourage their team members to fail. These companies recognize that atychiphobia (the scientific name for “fear of failure”) can be paralyzing and can be a tremendous threat to their competitiveness.

Companies like Virgin, Google, SuperCell and P&G understand that failing, sometimes spectacularly, is part and parcel of the journey towards success. That’s partly why I don’t feel so bad about the string of business failures that I have under my belt. So far, I’ve has a music, entertainment and fashion magazine that ceased publication in the early 2000s, a tee shirt label that has been “on hold” for years, and an import company that only managed to deliver one shipment to Barbados. But, each of those failures (and the additional failures that will probably happen in the future) helped to teach me some vital business lessons.

That’s also partly why I’ve made “toe-tal” peace (see what I did there?) with the painful experience of breaking my toe in the BVI. My experience exploring that cavern really was a valuable learning opportunity! If I ever come across another cavern similar to the one in Virgin Gorda, you can bet that this time around, I’ll be sure not to let my guard down! No matter how soft and welcoming the sand under my feet may be, I’ll proceed as if there’s a sharp underwater boulder in my path!!

Would I still have made the decision to explore that cavern If I had known in advance that I would break my toe? Probably not. It would be bizarre of me to actively seek out pain. Do I regret exploring that cavern on my own? Not one bit. For one thing, I got to explore one of Virgin Gorda’s most beautiful sites that other visitors to the island had missed out on. For another thing, I’ve learned to always, always walk cautiously when exploring unfamiliar territory. Heck, I might even return to Virgin Gorda to go back to that same cavern so I conquer my old adversary (the rock that caused me to break my toe) and, this time, come out unscathed.

In the grand scheme of things, I broke a toe. It was embarrassing and painful, but it wasn’t the end of the world! If I had lost my toe, or my leg, or my life exploring that cavern, then the cost/benefit ratio would clearly have been unacceptable. But I didn’t lose my toe, my leg or my life! I just broke a toe and I learnt an important lesson in the process.

If you’re at the point in your life where you’re hesitant to walk down an unexplored cavern of starting a new business, finally writing that book you’ve had in your mind for years or applying for a job that you’ve had your eye on for quite some time, chances are you’re afraid that you’ll break a toe – metaphorically, of course! And that’s a valid fear! Wandering off on your own can lead to painful consequences. But, if you do decide to take the plunge and explore that cavern, you’ll also have an opportunity to experience something great, exciting and beautiful that others around you may be missing out on.

In the world of theatre, people often wish actors good luck by telling them to “break a leg”. I’ve never broken a leg, but it sounds even more painful than breaking a toe! It also sounds like nothing I’d ever wish on a fellow entrepreneur. But I have broken a toe, and I can tell you from experience that after the initial shock, panic and pain, it’s not all that bad. With the right medical treatment, after a few weeks, you’ll be as good as new.

So, go ahead. Explore that cavern. Put pen to paper and start the first chapter of your book! Boldly apply for that job you know you deserve! Follow your entrepreneurial calling and start your own business! From the bottom of my heart, I wish you the best of luck with your ventures. Or, in other words, “break a toe!”