Career Adventures Travel

Choose Your Own Career Adventures with Rachel Biggar

Rachel's adventurous and unconventional career has taken her skiing in France, cooking in Ireland and back to sailing in Greece, Corsica, USA and all around the world. Rachel's story is a strong reminder to ignore the naysayers, always keep learning and growing your skills, the importance of trying as many things as possible to discover what is NOT what you want in life as well as what you DO, as a big reminder how good things don’t come to those who wait, they come to those who work!

You could say that you are on a “career adventure” instead of a career path. Welcome to “Choose Your Own Adventure”! Our “career adventure” interview series charts the joys & challenges, and many different directions our career adventures can take us. Anything from career changes, working remotely, freelancing, contracting, self-employment, starting your own business, working on your own projects alongside your day job, having a side hustle or a portfolio career – all depending on what choices we make, what steps we choose to take, what opportunities or challenges that come our way in the most unlikely of places that help you to choose your own adventure.

We met Rachel Biggar in Greece in Spring 2019 when we took a one week live-aboard Introduction to Sailing/Competent Crew course near the Greek Island of Lefkada with Sailing Ionian. It was one of the many things we did that Spring that had been adventure trips we had wanted to take for years! Rachel’s adventurous and unconventional career has taken her skiing in France, cooking in Ireland and back to sailing in Greece, Corsica, USA and all around the world. Rachel’s story is a strong reminder to ignore the naysayers, always keep learning and growing your skills, the importance of trying as many things as possible to discover what is NOT what you want in life as well as what you DO, and a big reminder how good things don’t come to those who wait, they come to those who work!

  1. Tell us about yourself

So, I’m 32, originally from Scotland but now living almost full time in Greece. I started sailing when I was about 7 years old, and took to it like a duck to water. Over the years I have trained as an instructor and now work with sailing schools in the Ionian. 

2. What are you working on now?

Over winter I trained for and passed my YachtMaster Instructor exam, which was all with the plan that I would be running a yacht sailing school this summer, however due to Covid-19 that has all been put on hold. So, in my spare time now I have adopted three beautiful kittens (who were abandoned on my veranda). This summer has been a tricky one, as it has been for so many people. Fewer tourists and less sailing, however it has fuelled my enthusiasm even more for summer 2021.

3. Could you tell us about how your career adventure(s) started, about what experiences, challenges or opportunities you came across over the years that led you to choose your own adventure? Where has your career adventure taken you in the past leading you to where you are now? 

I was never the academic kid at school, I was always more interested in the practical stuff and sports. As such I wasn’t very good at exams either. In fact, I was just never very good at sitting still for more than 20 minutes at a time. I even had teachers who told me that if I didn’t focus on the work then I wouldn’t get to university, and if I didn’t go to university then I’d never really amount to anything. 

From the age of about 8, I knew I wanted to sail all summer and ski all winter, and I was pretty strongly warned that it might not be the most financially secure of careers. Despite this, when I finished school I embarked on a Gap Year and spent the first part of it working to save up some money before going to France and training as a ski instructor. The following spring I went to Ireland and completed a 12 week cookery diploma. I knew perfectly well at this point that it wasn’t going to be the cooking that kept me going, however it was enough work to push me through the summer to the following winter. 

It was a couple of years later that I returned to sailing, having spent much of my summer holidays on dinghies at the local sailing centre. I passed the RYA Dinghy Instructor course when I was 21 and went to Australia. The next few years were spent teaching dinghy sailing during the summer, always in nice sunny places; Greece, Corsica, upstate New York etc,.. and taught skiing in Austria every winter. Then one year I applied to be a guest manager at a yacht charter company. This was where the real change in career came. I loved being on yachts, I understood how they worked and how they sailed. However, a member of the team I was in told me that I’d never be able to do his job – and that was like a red rag to a bull. The following winter I went to Gibraltar and did my YachtMaster Offshore and by the summer I was in Croatia as a flotilla skipper. From there I moved back to Greece, continued working as a skipper before being sponsored to become a RYA Cruising Instructor. This was when I knew that sailing was about to take over my life. Three years and two sailing schools later, I have just passed as a YachtMaster Instructor and am now in a position to open my own sea school. 

4. What past projects or anything that you have worked on spark joy for you when you look back at what you have worked on?

Definitely passing the instructor courses as they are achievements for which you’ve got a piece of paper confirming that you are of a skill level which is not necessarily obtainable to everyone. However, sailing from Greece to Antigua will always be a highlight of my saying career. I may not have enjoyed certain aspects of it at the time, but looking back and telling people about it, it was a surreal experience – the realisation that all you can see is water and you are totally on your own out there. 

5. How do you choose what to work on?

With my job it’s not necessarily what to work on, rather where to work. One of the defining things that makes me look for work in a certain company or area is the people. I learnt pretty quickly that if you’re working with the wrong people then it can lead to an unhappy work space. 

6. What advice, practical or otherwise, would you give to someone looking to start a career adventure similar to your own?

Don’t expect to come into the industry knowing everything – no one knows everything! Every day you will learn something new, whether you’ve been sailing for 5 years or 50 years. Get some qualifications as soon as you can – there are so many courses in so many parts of the world, and unfortunately experience won’t get you far unless you have the bits of paper to back yourself up. And I guess most important of all is have balance. In a very male-dominated industry (although this is slowly getting better) female skippers need to be able to stand on their own two feet and know when to have the courage of their convictions, but also to be humble and accept help when needed. There are some really physical elements and sometimes its nice to have a bit of help, however that doesn’t mean that you need to question all your other efforts. 

7. Could you describe your day-to-day at “the office(s)”? 

There is no standard day. Every day will be different and every week will be different. I guess in the simplest form it would be something like:

0730 Get up

0800 Breakfast – either onboard or in a local cafe

0900 Get the boat set up for the days training

0930 Leave harbour

After leaving harbour we can be training any part of the appropriate syllabus, whether it be mooring, sailing, man overboard etc,.. 

1230ish Stop for lunch in a bay or cove, or maybe even have lunch whilst we are still sailing

Then we continue training, usually with a bit more wind in the afternoons.

1600/1630 Head into harbour for the evening. Pack away the boat. 

1700 Chat with students about the day, sometimes on the boat or sometimes with a nice well deserved cold beer. After this students have time to relax, or maybe do some homework depending on the course we are doing that week.

1930/2000 Dinner in a local taverna

2200/2300 Back to the boat and off to bed

These timings are very vague. If I have a group of Day Skipper students then we usually start earlier in the morning and finish later in the evenings. We are also required to do some night navigation with them, so one evening we will leave the harbour when it is dark and sail to another harbour or bay. These nightsails usually finish around 0130/0200.

8. Where do you feel you work best and thrive the most? (This could be ways of working or environments)

I feel that like most people, I thrive in a working environment where I feel like I’m making a difference. As such, I cannot pinpoint one aspect of teaching. Whether it is students who are totally new to sailing and I am taking them on their first adventure (and really hoping that they’re going to love it as much as I do), or it could be a group who have had some sailing experience and I am spending my time coaching them through certain aspects and taking their skills to a higher level. 

9. What inspires and drives you every day?

The fact that I am so lucky to be doing a job I really love. I once read a saying which was “Find a job you love and you’ll never work a day in your life”, and I really believe that.  

Having worked some pretty awful jobs only to find out that it wasn’t what I wanted to do, makes my job now even sweeter. I guess waking up every morning to a beautiful view over the sea also helps.

10. What advice would you give to your younger self, knowing what you know now?

 Don’t listen to the naysayers. You don’t have to to go university. You don’t have to get a degree. You just have to work hard at what you want to do – good things don’t come to those who wait, they come to those who work! 


You can follow Rachel’s nautical adventures and creations on on Instagram at @rachbiggar, @long.blonde.silver, and @lebateau_enpapier.


Feel free to contact us at Project Anywhere if you have any questions about any of our career adventure stories. Come back soon to read more career adventures! Contact us here if you’d like to be featured here to share your own career adventures story or if you would like to write a guest blog for Project Anywhere.

Project Anywhere icon

Subscribe to our mailing list!

Processing…
Success! You're on the list.

Project Anywhere icon

I’m often working on stories and blogs from cafes or co-working spaces while fueled by copious amounts of tea and coffee! 🙂 If you’d like to support Project Anywhere by buying me a cuppa you can do so by clicking on the button here. Thank you! Becky x

Buy Me A Coffee

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s