The first to swim the 23 and 1/2 watery miles from Dover to France was a steam ship captain, Matthew Webb, who in 1875 made the crossing in 21 hours and 45 minutes, despite jellyfish stings and unforgiving tides.

It took 36 years and 80 failed attempts before someone could replicate Webb’s success. On Sep. 6, 1911, Thomas William Burgess had ham and eggs for breakfast and on his 16th try swam the English Channel from Dover to Gris Nes in 22 hours and 35 minutes. In 1926 Gertrude Ederle became the first woman to cross the Channel. There was the first to swim both directions (1934), both directions non-stop (1961), the first to swim it three ways (1981). The first paraplegic swam the Channel in 1998; the first quadruple amputee, 2010.

So, we’ve found ways to make it more challenging, but swimming the English Channel is not easy and requires serious training. I know because in 2007 I did it too. As athletic endeavors go it’s perhaps less risky than BASE jumping, but more challenging than the Ironman Triathlon in Hawaii. It’s the Everest of open water swimming.

Over the years tens of thousands have attempted to cross the English Channel and only about a thousand made it — as with startups only 1 out of 10 tries is successful. I’m sure it won’t surprise you to learn that swimming has shaped my worldview. As an entrepreneur who has been part of four successful startups, I know much of what I have learned about tackling challenges came from being one of 1,000 people to have swum the English Channel.

The three most important lessons:

1.    Keep going (sounds obvious but bear with me)

2.    Give up on success

3.    Swim with the tide

Beyond physical challenges, swimming the English Channel is like a startup in terms of the risks you run, how personal a challenge it is, and how exhausting and exhilarating it can be.

Lesson 1 – Keep going

The primary goal of swimming the English Channel is to get to the other side, naturally. Beyond the physical challenge, and luck, it’s a test of commitment.

My support team on the boat had emergency medical gear and clear criteria under what circumstances to pull me out. If my stroke rate suddenly dropped, they were to ask me pre-arranged questions to check my alertness, and look for blue lips and neck — signs indicating hypothermia. Having set up a framework for making that decision, I didn’t have to worry about making it anymore.

I was committed to keep going until I was judged to be in no fit state to continue. It became someone else’s problem, which is good, because I had plenty of my own. What’s more, careful years of preparation, a support team that I didn’t want to let down, and charitable goals, along with a thirst for glory and pride, meant I knew I really wanted to make it.

In a startup, you need to be fully committed. Dilettantes run out of juice and teams fall apart under pressure if there’s no shared passion. Agree on what you are signing up for and be transparent about progress. You have to plan on the basis of success; otherwise, failure becomes self-fulfilling. As Vinod Khosla says, “Invent the future you want,” or you are guaranteed to get one that you don’t.

Lesson 2 –  Give up on success

A few hours into swimming the English Channel I gave up.

To paraphrase Mike Tyson, Everyone has a plan until he gets punched in the face. The frigid waters and feisty tides had stripped me of my training. I was caught in the four-hour doldrums when I suddenly realized I had only traveled five or six miles. Unless the tides changed I was looking at a potential 18-hour ordeal.

I had just come to accept the possibility that I wasn’t going to make it, when a beautiful thing happened. With the weight of expectation lifted from my shoulders, I was free to fail. Instead of thinking about how far I had to swim and how long it would take, I told myself to keep going for just one more half hour.

Thirty minutes always seemed doable, and when I got to the end I simply started another cycle, and another. Stroke after stroke after stroke. Eventually I caught a good tide, which propelled me through the currents. I stepped on French land after 10-and-a-half hours.

Everything had became easier when I was freed from worrying about succeeding.

At almost every startup most of your time will be spent failing, so learn how to give up on having to succeed all the time. Don’t worry about whether your startup is being successful – worry about making the product better enough to please a customer enough to get you your next customer. Build a path to success one stroke at a time. Don’t give up on your dream – just be willing to be flexible in how you get there.

Lesson 3 – Swim with the tide

Swimming the English Channel is made up of things that you can control and things that you can’t. When the tide was against me I had to maintain my position as best I could, without expending too much energy. When I was getting a push, I could take the opportunity to make progress. So it is a balance of swimming your race, and not fighting the prevailing conditions.

With startups, you are usually tackling something hard and seemingly counterintuitive, which is why there is an opportunity. The skill comes in swimming in a new direction, while still using the prevailing tide of a current trend to help you.

As I have traded in my swim goggles for a sports coat, I keep reflecting on my successful swim across the English Channel. Even though I am not likely to catch hypothermia inside the offices of my company, the challenges are real in this new venture. But I remind myself to keep going, swim with the tide, and to know when to quit.

It doesn’t feel like a quitting day today. I think I see France.

[Image via Wikimedia]