World-Record-Breaking Sailor Dee Caffari on Epic Voyages and Leadership
On board with her crew, trailblazing yachtswoman Dee Caffari relies on open communication and positivity to make it to the finish line.
Nowadays, when seemingly everything has been done, it’s a feat like no other to do a world first. GamePlan A met with Dee Caffari, the first woman to sail single-handedly and non-stop around the world “the wrong way”; westbound against the prevailing winds and currents.
The former Physical Education teacher turned professional sailor never thought twice when she, in 2005, embarked on the epic voyage only done by four men at that point. To date, Dee is the only woman to have sailed solo non-stop around the world in both directions, as well as the only woman to have sailed around the world three times, non-stop.
More recently, she skippered a mixed gender youth team in the 2017-18 edition of Volvo Ocean Race. Throughout the eight months, the international crew raised awareness on ocean health with their ‘Turn the Tide on Plastic’ campaign.
How does the pioneering sailor maintain her focus and lead a diverse team through changing tides? Read on to find out.
Let’s rewind to 2005. What made you decide to sail solo around the world “the wrong way”, becoming the first woman to do so?
It’s not something I set out to do at all. I was happy as a school teacher, but soon realized that the big decisions you make are those which you grab with both hands.
The year before, I was on the Global Challenge race. We had 12 identical boats, I was the only female skipper, and our crew were amateur sailors who had paid for the opportunity to lose themselves, to find themselves, to find other people. We were taking them around the world westward, against the prevailing winds and currents.
Towards the end of the race we were in Cape Town with a 7,000-mile leg across the Atlantic to Boston ahead of us. In the middle, you go through an area called the doldrums where it’s very hot with little wind. It’s a tense time for frustrations as it’s hard to keep the boat moving. By then, my crew had learned a great deal and got confident to question our decisions. It went from a sailing exercise to a man management exercise, and I thought, “Maybe I should sail on my own next.”
Also, only men had ever done it, so a big catalyst for me was the opportunity to do a world first. Three months after finishing the Global Challenge, in November 2005 I set off solo and did what was my impossible voyage at the time.
Where does your determination and resilience come from? Is it something you were born with or have built over time?
Somebody said I have a stubborn streak, but I say I’m driven by finding the extraordinary. Sure, 98 percent is good, but what about the 2 percent? My father would always say, “Do your best and go out there to be the best you can be.” This mindset was encouraged with me at a young age, so I’ve always lived to push my boundaries a little bit.
I think this mentality can be practiced, but don’t expect it to be easy. You have to find your strength from within.
When everything goes well on a boat, I imagine the highs are extra high. Then again, the lows must be really low. How do you lead a team through those waves?
A high-performing team is all about consistency – constantly ironing out highs and lows. It’s also about managing expectations and setting the tone for the team.
Open and honest communication is important. Sharing good news is easy. “We’ve gained miles. We’re ahead of so-and-so.” But often you have to say, “It’s not looking good for us.” The team needs to know the full picture.
Then it also becomes a case of not letting the team get discouraged by bad news. If one person reacts negatively, it has a knock-on effect on others.
Huddled in a boat for a long period of time, personalities are bound to clash. What’s your approach to conflict management?
It’s an intensely emotional environment. There’s extreme fatigue. You’re hungry, you’re cold, you’re wet, you’re homesick. The tiniest thing might wind somebody up, and you need to identify issues before they escalate. That awareness is critical, I think, as a leader. Everybody has the same goal, after all.
Crew members are also responsible for putting their hand up and going, “I’m sorry, I’m just really tired today.” Sometimes people don’t recognize how their habits can annoy others.
Always exercise open communication. It doesn’t matter what environment you’re in, a workplace or a team sport. Even when you’re part of a remote team, how you communicate and what you communicate is critical.
Women are still a minority in sailing. Have you ever had to fight prejudices?
Though I’ve never had a barrier, I’m sometimes still intimidated to sit in a room with my male peers, which is crazy. Though they wouldn’t consciously treat me differently, they can underestimate the image and the character they portray, sat around a table with their mates, being happy, confident, and chill, while a female peer is thinking, “Whoa, that’s very unapproachable.” I don’t think men always realize how much power their presence has.
Generally, when you’re sailing, everyone is equal and respectful. But there’s a reluctance to be accepting, which is why women still have less opportunities. We’re slowly making changes, but like in any sport, it takes a long time.
You must be an expert in stress management. What tips would you give to our readers who are tackling challenges on dry land?
Make a list, be proactive in your goals, and enjoy the sense of achievement. For me, it’s important to have goalposts to meet.
Another tip is to use positive language. Rather than saying what you don’t want to happen, you need to be able to say what you do want to happen, articulate what you want to achieve. It’s easy to be in a negative language mode, but hard to turn that around. A good management tool is to be positive, prioritize, and focus on things you can action.
What do you enjoy more: starting a race or finishing a race?
Has to be starting. I love the preparation, the training, the nervous anticipation of start day. The end of a race is actually quite sad. There’s a huge glory and triumph and celebration, but it’s the end of an intense time you’ve had with this group of people.
At the end, people always ask: “What next?” That’s a big void to fill when you’ve been so consumed with this one thing. You’re like, “I have no idea, I haven’t even thought about it yet.” So, for me, the beginning is the exciting bit.
Knowing some time has passed since Volvo Ocean Race, I’ll ask the dreaded question: What’s next?
In the short term, the power and the momentum behind the plastic message is huge. I’m a proud advocate for ocean health and, seeing companies doing valuable work in that arena, I’m encouraged to go and make sure everybody knows about it.
In the UK, we’re not great at developing offshore sailing talent, and I hope to use my notoriety to help improve the situation. Also, I want to keep going out and doing something special. I definitely want to do another round-the-world as part of a team that’s out to make a statement and push boundaries.
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