Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover. ~ Mark Twain

Today we chat to a man who swapped a career in UK politics for a life on the ocean wave.

Will Bruton is a freelance captain who specializes in running beautiful cruising yachts and organising sailing charters all over the world. In his free time, as well as exploring the many beautiful places he visits, Will provides political insight to the marine sector and dabbles in journalism as a regular contributor to Yachting Monthly and Sailing Today magazines.

Will has just moved to Japan where he is immersing himself in the culture, building his own location independent travel businesses and teaching English. It’s been a pleasure to speak to him and find out how he’s consciously, and continuously, steering his life in the direction of his dreams.  ~ Rachel

Will Bruton profile

1. Tell us a bit about your background…

I was born in London, but I grew up in rural Lancashire, both about as far from the sea as you can get. At school I struggled to apply myself. Fortunately, I went to a school where I was allowed (perhaps too much!) freedom to pursue constructive interests outside the classroom. Education is fundamental, in the broadest sense.

After my GCSEs I did some parachute jumps on a course run by the British Army. An opportunity available then to school leavers, but one that most had never heard of. A skydiving course in Spain followed the next summer. I met a few people that were living a legitimate long-term existence, whilst doing what they really wanted. That’s when I realised you could put something like ‘skydiver’ on your tax return. One guy I learned to skydive with, Sam Hardy, has gone on to be a professional BASE jumper. I look on in awe.

I was quite straightforward in my ambitions though for the next few years. Sandhurst and a commission in the Army was the plan until towards the end of university. I spent three months in Canada attached to a regular regiment. A brilliant experience riding around in the turret of a tank, but one that made me realise I wasn’t great in such a hierarchical organisation. I envy the relationships people in the army build though. Freelancing has some lonely moments.

I studied Politics at university. Whilst I had no ambitions in that direction career wise, the subject interested me. The humanities have taken a real hammering in recent years. We’re all supposed to be producing a reason for our existence in the system. Tangible proof of why we study a subject and an end goal.

I spent a year working in Westminster for one of the House of Common’s more colourful characters between my second and third years. It was an election year and proved particularly interesting. I saw my boss lose his job and mine in the process. Working in Westminster was a real privilege. There’s an electric atmosphere there when something big is happening.

Last year, in one of travel’s bizarre coincidences, I ran into Lembit Opik (my old boss) at Marrakech airport. I was there to run the half-marathon. We found an afternoon to catch up. The main topic of conversation was the madness of politics and the joys of self-employment.

2. What was the catalyst for changing careers? Why sailing?

Whilst looking for countless lobbying jobs I didn’t really want to do, I launched my own lobbying start-up, appropriately called Black Sheep. I’d built up a knowledge of some legislation whilst working at Westminster, so I wrote to the companies concerned by it and made a business out of trying to change it for them.

Lobbying has always been seen as some kind of dark art. In truth it’s about articulating an argument effectively. That business was all about capitalising on specialist knowledge to build a few very strong bridges. I didn’t have the manpower to write to every politician. It all gets put in the bin by the researcher anyway. I know, because I was one. I focussed on identifying a few natural advocates that didn’t need their arms twisting. There’s still great scope for that model of lobbying. However, I was in a suit too much, and my heart wasn’t in it for the long run.

It struck me sailing would be a great way to work and travel. A mechanism to the kind of slow travel I knew I most enjoyed. A gap-year in the traditional sense has never really appealed.

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3. What does training to become a skipper involve?

To earn money as skipper of a small yacht, the bare minimum is really a Yachtmaster certificate these days. You need to spend a lot of time on the water and have a solid grasp of sailing. How to manage crew is a big part of the job. As you move up it’s about managing an expensive asset and all that goes with it.

I took an intensive ‘CELTA’ sailing course on the south coast. I used to keep quiet about it because the old sailing guard seem to hate the idea that you can learn to sail in a few months. In reality, if you’re sailing every day in crap weather, you learn a lot more than someone sailing at the weekends in good weather for fun. I finished the course with a very cautious approach.

4. What was your first job after qualifying?

I was very conscious my qualifications needed bolstering with more experience, so I signed up with all the yacht delivery companies to help deliver boats. To begin with, for expenses only. That was tough, but a brilliant learning curve. After quite a few deliveries I got a summer job as a skipper for the now ubiquitous Yacht Week in Croatia. I learned a lot and the sailing in Croatia is fantastic.

5. What does your work involve these days? And how has your business as a freelancer grown and evolved?

My business comprises several things that dovetail reasonably with each other. All involve travel.

I have got to the stage with the sailing where I can comfortably freelance. That provides the most reliable income stream. However, it’s also the most professionalised work I do. There are some qualifications I have to keep in date and without experience I would quickly get rusty anyway. I take on interesting yacht deliveries, charters, and some short term projects for yacht owners. It’s great to get on a boat and apply myself to something so different for a couple of weeks.

In parallel, I’ve worked very hard at getting my writing published, which is finally starting to pay off. Fundamentally, I pitch to editors about what I want to write about- so my enthusiasm doesn’t really wane. To begin with I set myself a target of getting in the major yachting titles. I’m now doing more travel writing as well, with a focus on how a yacht is a mechanism to fulfilling travel.

Finally, I am starting to build a travel company. It’s a long term project with no public face as yet. Fundamentally, it’s about fulfilling travel fueled by deep local insight. Unparalleled experiences and immersion in a place.

6. You specialise in sailing Oyster Yachts. What is it about them that captured your heart and where has life onboard them taken you?

Oysters are built in the UK, and whilst they are beautiful yachts, they are also built to cruise long distances. That in itself is a mechanism to meet interesting owners game for big adventures. Thirty-two Oysters are setting off on a circumnavigation together next year – I am hoping to join a couple I used to work for for a leg of the The Pacific. It’s also great to sail a British built yacht. It’s like a Bentley before people started painting them orange. A bit of an understated magic carpet.

Oyster yacht

7. What kind of clients do you work for?

All sorts. On charter, you’re essentially working for holiday guests who’ve hired the boat. When you’re sailing for the owner, it’s a little different. You also build a relationship you wouldn’t on a motor yacht. It’s first name terms in many cases.

One guy I worked for was a former bank chairman. Really not what I expected. On one charter I had two former professional football players, a journalist just off the plane from Syria, and a ski guide. It does vary enormously.

8. What have you been doing over the summer? Talk us through a typical day…

This summer I have been getting ready to move to Japan… so it’s been a bit different.

I spent a month taking a CETLA English teaching certificate, before getting some practice teaching at a language school in Brighton. Whilst I’ve no plans to teach for a living, I’ve set up a micro-business providing English language training to people in the marine industry trying to pass maritime exam papers set in English. Very niche. In Japan I’m going to teach couple of evenings a week to get me off of my laptop and meet some locals. I like learning new things.

Just before leaving Europe I sailed on a yacht to the UK from Palma as the First Mate, or Second in Command. It was great to not have all the responsibility of being skipper to be honest, particularly as the skipper had sailed round the world twice, so there was lots to talk about.

A conventional day on a long trip like that is a bit unusual. We work in shifts or watches, usually three hours on, then six hours off. A lot of keeping a yacht safe is pre-empting things that could go wrong, so we are constantly checking everything. A lot of time is spent trying to adjust the sails to make her go as fast as possible… eight miles an hour if we’re lucky!

On this trip we saw whales, dolphins and basking sharks in the Bay of Biscay. There were some spectacular sunsets and sunrises – fantastic time to think, take stock, and come up with the next plan. It’s a totally different rhythm.

On charter the pace is pretty mad and the days are very long. A great charter is a swan, effortless above the waterline, the crew frenetically paddling below. Two weeks is ideal as most guests with busy lifestyles take the first week to relax properly. The key is to have a loose plan that goes with what the wind wants to do, not that all guests come equipped with a capacity for loose planning!

On a charterOn a charter

9. Life on the sea must be liberating, exhilarating, and at times, challenging. What big life lessons have you learnt along your journey to doing what you love?

Sailing lends unparalleled perspective on life. Ocean sailing in particular. The challenges and rewards are big. There are a lot of parallels with entrepreneurship and both are ultimately exercises in self-reliance.

There’s an old expression gentlemen don’t sail to windward, which essentially means they don’t go against the natural forces acting against them, but there’s more to it than first appears. It’s not about giving up, it’s about working with what you’ve got. You can zig-zag into the wind and tide to get to your ultimate destination, but it’s pretty miserable. When one idea I am pursuing starts to stagnate, or I get writers block, I quickly change tack onto something else. It’s about making efficient gains in the long run. When there’s no wind sometimes I’ll just let the boat drift for a couple of hours. Have a swim!

Will Bruton swimming

10. You love writing; how are you pursuing your passion for journalism and what have been your biggest ‘proud ofs’ to date?

I’ve just written a piece for Yachting World, a magazine I never imagined being published in and really the leading voice in yachting. I wrote to the editor last year. To my great surprise, she invited me to Time Inc’s gargantuan office on the Southbank. That she took the time out to meet me for a coffee and give me her two cents on how to get into magazines meant the world at a time when I felt I was banging my head against a brick wall. Rejection is par for the course and you have to just keep submitting copy you believe in.

Will Bruton The world is my officeThe world is my office

Norah Ephron was a journalist, director and all round larger than life Hollywood character. Her son made a film about her recently. Her mantra ‘Everything Is Copy’ was the title. It kind of sums up the feeling of being compelled to write. Every nuance of life has the potential to be a good piece of writing. I’m quite self-conscious about what I put out there, but I do it anyway.

Will Bruton officeBelow deck: my office 

11. You’ve just moved out to Japan. What are you doing over there?

Japan has always been somewhere I have wanted to live for a while. My partner has just finished a Japanese degree, so the stars have aligned somewhat. I’m going to write a lot, do some sailing, and immerse myself in the country. I’m now about 70 per cent location independent, so being based here is fine.

The yachting market is expanding apace in Asia as well so I have trips planned to Singapore and Hong Kong.

12. What does the future hold for you? What’s the ultimate dream?

To carry on building location independent businesses conducive to long-term travel. In particular, slow travel. Immersing myself in countries and taking unusual routes between them is what I find most fulfilling.


I’ve travelled at the sharp end of the plane and realised you’re still in a tube at 40,000ft breathing the same recycled air. I’ll happily take two weeks to sail from Southern Spain to the UK though. Dipping a toe into places has always been crap, you’ve got to get amongst it to really understand it.

The ultimate dream? I’m not sure. Perhaps sail, fly, and drive myself around the world?!

Will Bruton helicopter

13. Who is your biggest inspiration?

Difficult to say, but despite being clichéd, I’d say Richard Branson. He is proof you can create business, break records, and have enormous fun. He also works very hard, that’s the old fashioned bit cynics tend to forget. I’ve seen him kitesurfing early in the morning off Necker a couple of times.

14. What advice would you give anyone who isn’t doing what they love?

At the crux of it is how people think about work. You don’t have to 9-5 anymore. I’m in Japan now. The friend we’re staying with has recently ditched his salaryman job for flexible hours. He’s working from home with his two-year-old on his lap. If it’s possible to confront the status quo here, a lot more is possible in the west. Sideline businesses people do outside a regular job are often some of the most interesting.

15. Finally, is there a quote you try and live by?

Don’t grow up. It’s a trap.

Will Bruton sunset

To read more about Will’s extraordinary experiences visit his website. You can also contact him by email [email protected] or follow him on Twitter @WillBruton