Life was good in some people’s eyes for Sean Conway – a successful business, a good social life with all the trappings of a middle class émigré to England. What then made him sell his business for £1, buy a boat to live aboard and cut loose to become a world class adventure athlete? Could happiness be something to do with it?

Who is Sean Conway?

Sean’s website tells his physical story from end to end. The day came when he threw off his shackles:

“Sean famously sold his photography business for just £1 to pursue his dream breaking the world record for cycling around the world, Sean gained sponsorship from and set out on this epic adventure on 18th February 2012. After three weeks he was ahead of schedule averaging nearly 180 miles a day. His dreams were shattered in America when a driver hit him causing severe whip lash, concussion, torn ligaments and a compression fracture to the spine. Despite this, Sean continued on dropping to 140 miles per day, changing his goal to get back to London in time for the Olympics and raise money for charity. He made it back with a week to spare, having covered 16,000 miles - 12,000 of them with a fractured spine.”


In 2013 Conway bought a boat that served in Dunkirk in 1940 as one of the ‘Little Ships’ that Kavas Yachting told you about recently.

Over the years he has rebuilt her as a home for himself and his partner. This meant he didn’t need to pay a mortgage to a bank to survive, cutting one of the major chains that bind so many of us in life. Why and how does he do what he does? How does someone become free in this world?

First person to sail, run, cycle and swim the length of the UK

Conway said, “I have a sailing world record. I hold the record for sailing from Land’s End to John O’Groats.

In December 2015 the BBC reported, Conway “was part of a three-man crew, with skipper Phil Sharp from Jersey and boat owner Alex Alley. They completed the journey in just under three-and-a-half days. The trio left Land's End in their Class 40 racing yacht at 08:55 GMT on Friday and arrived in the north of Scotland - 620 nautical miles (1,150 km) way - 83 hours and 53 minutes later.” While an average speed of seven knots doesn’t make you think of the flying multihulls that blast around the world in a month or two, the huge tidal currents adverse weather conditions year round on that passage make this a very good time. I for one have been beaten back by the winds and tides around both Land’s End and the NW corner of the UK (Cape Wrath) – I have never made it around Land’s End despite five attempts on a yacht!

What drove Sean to do these things?

Conway explained, “I consider myself lucky enough that I was so miserable that I had to do something about it. The stability, the money, the lifestyle, the income just wasn’t worth the misery. Being cash rich and time poor is a retarded way we have fallen into. For the most part we all strive to be cash rich and time poor. You can live a much happier life by being cash poor but time rich. However, you can’t sit about in your underpants as you’ll be just as depressed!”

In his opinion however, we do need people to make this world happen. “We need those people you and I probably despise in this world, all those investment bankers and such like as they pay a lot of tax and that feeds down to services you and I use.”

Conway pointed out, “I feel sorry for those people who are not miserable enough, but not that happy and live in a state of mediocrity. They don’t really know what the options are out there.”

At this stage I mentioned to him that I am reading a book called Creating Freedom – Power Control and the Fight for Our Future by Raoul Martinez, and referred to the state of slavery where people don’t know they are in bonds. Conway agreed and responded, “There’s another book by James Wallman called Stuffocation. It says that as mammals we have a need to show off. We attain social status by buying stuff. For the most part the stuff that Capitalism has created has made our lives better. We eat too much. We buy good clothing. We are warm. We aren’t starving to death. It has worked to some extent – we are living longer… and were happier. Buying things has ceased to make us happier however and thanks in a large part due to social media we are able to buy fewer things and do more things to show off. I read somewhere recently for example that Millennials are not going for their driving licenses any more. It is moving from materialism to experientialism.”

This led to my next question:

If someone is sick to their heart about their lives, what would you advise?

Conway responded, “I sway between two very opposing philosophies. I still don’t know which one is the right one.”

He continued, “The first one is some say ‘If you find what you love you’ll never work a day again in your life.’ That is very true. Alan Watts did that famous speech of ‘What would you do if money had no object?’ It’s a wonderful philosophy. If you’re in with social media you can make your hobby pay. I’ve been getting into knife making and woodwork in the last year and there are 20 year old kids on Instagram making kitchen knives in their shed and they are selling them for £300 each. 10 years ago that would have been impossible. Now there are loads of people doing it.”

Being happy doesn’t mean sitting on your backside doing nothing – you have to work hard for it. Conway cautioned, “What I’m wary of is the perception that I am on an eternal holiday. I get to spend a lot of time outside, I eat well and I am healthy. I believe it is necessary for you to have a physical life outside of work. I’m not on holiday though. I don’t just go out and do it. I’m spending a lot of time on my own, in the rain, and have no workmates to share it. My girlfriend may go out to work at 7 in the morning and I will slog it out on the rowing machine or run up the hill – it’s what I do and I love it. However if someone just quit their job and went travelling, for the first six months they would love it but if you have no purpose you will end up depressed again. I found my purpose by breaking records. I’m not saying everyone should do that as it is not the cure to everything.”

The other philosophy is somewhat contradictory to the first one – perhaps what the investment banker should do with their money? “The second philosophy is if you love something, keep it as a hobby. If you love making knives should you make a living from it?” Conway enjoyed being a photographer until he made it into a business and started to hate it with a passion. He loves his full time hobby / job now though. “Perhaps if you are earning a quarter of a million a year from your 30 hours a week as an investment banker you could give some of that money to build 10 schools in Africa? Is that better than quitting your job and building half of one school? What makes you happy? You might be happier earning all that money!”

What it comes down to in Conway’s opinion, is “Life’s too short to do shit you hate! Everyone’s different – breaking records makes me happy, but you need true purpose to make you happy. Wandering aimlessly around the world wouldn’t do that for me.”

What about people in debt?

Debt isn’t the only way an individual can move forward in life, though nations don’t have to conform to the same idea. Is someone who can just about afford a top end Audi (but skimps on life at home with his family to pay for it) genuinely free? What about someone who’s more concerned about living in a certain area of town and cuts their living expenses budget to the bone to pay their mortgage? What about those who earn enough to have to pay their mountain of student debt, yet not enough to thrive after the repayments - can they break free too?

Conway pointed out, “I could have bought a house, had a mortgage. I purposely didn’t. To survive on this planet you need three things – shelter, food and warmth. You can provide for your family for cheaper. I moved in with my mother and slept on her sofa for a while and then bought a £2000 boat to live on.” In living on a boat, so he didn’t have to pay €€€ to the bank, and is arguably doing the world a service by bringing a Little Ship back to life.

Conway continued, “Look at the Meek family with their wonderfully inspiring 10 and 8 year old daughters and had this amazing adventure. They did it! It isn’t easy but there’s nothing wrong with giving it a go. There’s nothing worse than waiting around and suddenly realising that 10 years have gone.”

Society in Conway’s eyes has become about quick fixes. “Everything’s disposable! Dating? Swipe someone on Tinder. Have your food delivered to your door!” In the UK, he said, “Because we are for the most part earning more than we need, one of the reasons we don’t have disposable incomes is that we are chasing this idea of earning more money and buying more expensive things. This is one of the reasons why property has become so expensive it takes up all our incomes. If you time travelled to 50 years ago and told someone that in 2017 you would have to save until you were 40 to buy a house they would think you were crazy!”

Putting the work in

I’m lucky to have got to know people in the elite yachting world in my time. For the few giants sailing these amazing races there are hundreds who have tried to get sponsorship and failed. While a west about solo round the world record might be relatively ‘cheap’ at £1.25 million (one case I know) Conway’s business is quite mercifully cheaper. He certainly won’t need €15 million as Alex Thompson is rumoured to need for his next Vendee Globe campaign. Conway said, “My adventures are nowhere near as expensive – the most expensive adventure I did was £25,000 to cycle around the world. Most of the stuff I have done is closer to £5,000 – maybe £10,000 if I have splashed out on accommodation. Accommodation is the most expensive thing on these trips. Sponsorship is a big side of all sport,” from Olympic sailors to footballers, everyone has to pitch to sponsors no matter what they want to do in life.

Conway has to raise funds from private companies to go off and do it. While living supposedly free of the bonds that tie us ordinary folk, he is certainly not free from the bonds of relying on those with wealth to enable him to do things that inspire us all at home.

He explained that unlike other athletes, he doesn’t seek to make a living for between those adventures. “I think that would make me hate my job. If all I was doing was doing the sponsorship round and wearing the tee shirt I would just be an employee of that company. I don’t over-commit. I like working with sponsors as they often have a good foundation or charity. They also bring an audience. When I swam Britain I had Speedo sponsoring me and that meant that 5 million heard about me. It’s not all about earning the money with my stuff because it’s a lot cheaper. Often the sponsorship angle is the reach you can have and the impact you can have on people is more important than the money side. Anyone who is self-employed will know that you have to think on your feet and put food on the table.”

A continuum of adventurers

There are two types of adventurers in this world. Conway explained that there is a continuum with, “exploration at the left hand side of the spectrum and athleticism at the right hand side. You have the explorers who might not have a time limit and are just wandering around exploring things, perhaps collecting data as they go. Then you have people on the right hand side who are after the ‘Three Fs – be first, furthest or fastest. I gave up my most recent record attempt because I got injured and had to take a day out – there was no way I could get that day back to break the record in my challenge so gave up.”

Mark Beaumont has just cycled around the world nonstop in 78 days, 14 hours and 40 minutes. Conway isn’t the only one in this business! Is there a little competition between people of his kind? “Mark Beaumont’s record doesn’t excite me so I won’t go after it! The stuff he has to do behind the scenes puts me off that, as do all the Polar expeditions. No one else does big swims. If Mark had a sponsorship deal with Land Rover then I’m pretty sure they wouldn’t sponsor me so I wouldn’t go for it.”

There is an appeal in the idea of racing someone else, perhaps on a race across Europe. “If there was a race I wouldn’t appear just to be a middle aged, middle class white guy riding a bike!”

Do older adventurers ever stop?

At 37 years old Conway admits that his body isn’t the same as when he started his antics. Is the time coming when he is going to take £50,000 to do after dinner speeches about taking one step at a time and pressing on when all seems black? “I know I’d be miserable again! He laughed. With regard my physical abilities I won’t be able to achieve what I want to achieve physically and I don’t know how I’ll cope. I don’t think there is any sportsman in the world who can answer that question. I have a lot of hobbies I enjoy. I love old Land Rovers – maybe I’ll get into that. Maybe I will move along the scale from being an athlete looking to break records and on to being more of an explorer like [73 year old] Ranulph Fiennes who’s still doing things into his 70’s. I could never move into just earning money!”

Perhaps that’s Sean Conway’s secret to life – you do something for the sake of doing it, as opposed to gritting your teeth just to achieve the ending. While for him the success of achieving one of the three Fs – First, Farthest or Fastest – is core to his work today, this isn’t a form of slavery. He is in control and isn’t at the beck and call of someone he despises and being forced to do something he hates for a veneer of happiness. “Life is too short to do shit you hate!!!”

Richard Shrubb

See also ↠ Sailing solo around the Southern Ocean, Ken Fowler - Race to Scotland