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Choose Your Own Career Adventures with Ryan Connolly

My name is Ryan Connolly. I'm a 32 year old Scotsman living in Iceland. I run an adventure tour company in Iceland, called Hidden Iceland. I am the Marketing Manager and co-founder of the company along with local expert, Dagný Björg Stefánsdóttir and Australian geologist, Scott Drummond. I am currently running a boutique adventure tour company called Hidden Iceland that specialises in glacier hikes, ice cave exploration, northern lights hunting and off the beaten path travel.

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 interview Ryan Connolly of Hidden Iceland, a certified glacier guide and Wilderness First Responder, guiding on multiple glaciers across the south of Iceland. Ryan has spent many years working and travelling the world. He achieved his life goal of travelling to all seven continents a few years ago, but remembers the final moment like it was yesterday.

Thanks, Ryan, for speaking with us to tell us all about your career adventures that have taken you from Scotland, to Austria, Australia, Iceland, everywhere and anywhere. 🙂

Tell us about yourself

My name is Ryan Connolly. I’m a 32 year old Scotsman living in Iceland. I run an adventure tour company in Iceland, called Hidden Iceland. I am the Marketing Manager and co-founder of the company along with local expert, Dagný Björg Stefánsdóttir and Australian geologist, Scott Drummond. 

What are you working on now? 

I am currently running a boutique adventure tour company called Hidden Iceland that specialises in glacier hikes, ice cave exploration, northern lights hunting and off the beaten path travel. We have been running Hidden Iceland for around 2 years and started making a profit by the end of our first year. We now hold a near flawless record on TripAdvisor and are actively sought out by the more discerning traveller to give them a real experience they won’t forget. Despite the tourism downturn in the country this year our brand continues to strengthen which is bringing more and more customers on a daily basis. We have no grand aspirations to take over the industry. We are happy for continued organic growth and to keep providing a very high level of service. 

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 started my professional life after university as a career banker working in the International Relationship Management side of business lending. I learned a lot of valuable skills while there, including what the term ‘long hours’ really meant. But around three and half years into this career I realised it was not my passion. I didn’t know what my passion was. But I did know I wouldn’t discover what it was by staying in that job and getting too used to the banker lifestyle. 

So after one very mediocre day at work I felt enough was enough. I decided that choosing another career path immediately following this one wasn’t a good idea. I decided to ‘take a break’ from developing my career for a little while. I managed to find a job that paid literally nothing in a ski resort in Austria that would cover my expenses. In return I could ski every day and figure out what I wanted to do with my life. 

It turned out that travel, outdoors and adventure was what I wanted to do. I’d previously had guiding jobs part-time while studying and had loved to travel too, but always saw these things as something to experience when you were young. Not something I could make a career out of. Now I finally had time on my hands to figure out if that was actually true, or if I could take this passion and turn it into a career. The ski season was a fantastic break but I wasn’t ready to go back into the real world. So I turned down another job back in the UK in favour of getting a working visa in Australia. 

Before I knew it I was serving cocktails on a beach bar in a sleepy town called Coral Bay on the West coast of Australia. It was here that I set myself the goal of travelling to all 7 continents before I was done with this whole travel thing. In less than 2 years I had achieved my goal by working while travelling. I took jobs doing anything I could from cleaning toilets and fixing boats to working for an accelerator fund and teaching kids how to rock climb at an outdoor adventure camp. I think I racked up around 20 different jobs as I went just to keep some cash rolling in. Whatever was needed to get me to the next place is what I would do. 

Three years into my travels I found myself working as a glacier guide in Iceland. It was here that I met who would become my future business partners, Scott and Dagny. Between the three of us we possessed a lot of the characteristics needed to set up our own business so we got to work creating a personalised tour company that would eventually be named Hidden Iceland.

Photo courtesy of Hidden Iceland.

What past projects / what have you worked on in the past that spark joy for you when you look back at what you have worked on? 

In university myself and a number of close friends ran a student enterprise called iCUE (Innovative Consulting University of Edinburgh). It was here that I really honed my skills as an entrepreneur. It was a society that effectively ran as a business. Each project had two goals; firstly, give students the chance to experience real business with a safety net and secondly, try to turn a profit just like in real life. So many of the projects failed. And the less said about my foray into clothing design the better. But for every failed business idea there would be another that turned a profit to cover the loss like the Edinburgh Apprentice competition.

My most prized success while there was creating a ‘Student Market’ that would allow all the other struggling student entrepreneurs to present their concepts and ideas to investors and the general public. The student entrepreneur paid nothing for this service. We made our money from partnerships and sponsors for the physical events we run. The sponsors gained exposure in the student market while the entrepreneurs gained a community to promote their business. Win/Win. 

How do you choose what to work on?

My biggest passion is to be in front of people. That could be doing a presentation in front of students at iCUE business society, negotiating with clients at HSBC, preparing investment speeches at Techstars, volunteer teaching in Africa or guiding guests on glaciers. To me it’s the same. My passion is in that human connection. There’s no greater feeling than when you realise you’ve had an impact on someone from your words alone. In the latter years I realised my ability to present could be coupled with adventure (guiding) and be used as a mechanism to travel the world. It married up all the things I love. So my choices, career or otherwise, always seem to revolve around creating connections in some form or another. Being stuck behind a computer screen all day is a nightmare scenario for me. 

I didn’t really choose to run this company, Hidden Iceland. My time as a glacier guide in Iceland was supposed to be temporary. Another stepping-tone as I travelled the world. But the idea and the opportunity arose at the perfect time. I found great business partners who I trust implicitly and who fill the gaps in my skill set. If I was to offer one piece of advice it would be trust the people you work with. 

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

The other thing I realised during that time is that a good business idea is thought up every 5 seconds. It doesn’t mean they will be a success. Many people go into these projects/businesses with all the gusto and energy in the world. But when you start to realise that it may be years before you turn a profit, that enthusiasm starts to dwindle. So I always say, find your passion first. Then figure out a way to make money from it after. I could have stuck it out selling custom t-shirts online if I really put in the time, but how is that any different from when I worked in the bank? Now I get to hike on glaciers as my job and run my own business at the same time. I might never become a millionaire doing this but I’m happy and I’m in control of my own life. What else can I ask for?

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

I will answer it in 3 stages as I wear many hats for Hidden Iceland.

Day 1: I take a small group of clients with me on an adventure across Iceland. That might be hiking on a glacier, hunting for the northern lights or discovering new ice caves. 

Day 2: Working with journalists and travel agents to promote Hidden Iceland. This might be writing articles, networking, attending events or running press trips. 

Day 3: Responding to emails and helping out with the day to day logistics of the company. This is mainly done by my partners but I help out whenever I can. 

Where do you feel you work best and thrive the most?

I need to be on the move. If I’m sat behind a desk for too long I go insane. I’d rather network at an event than send 100 emails. I’d rather run a trip onto a glacier than write about it. 

Photo credit: Amy Robinson Photography

What inspires and drives you every day?

We maintain the best TripAdvisor reviews in Iceland for private and multi-day tours. This is because we create bespoke personalised tours that we know people will love. Maintaining that level of service is key. For most people this is a once in a life-time trip to Iceland. It’s up to us to make sure we give them that.

It pushes me to keep going during the harder days. As I write this we are in the midst of a storm. When you see that someone was so moved by our tours or guides that they sit down long after the tour has ended and write what can only be described as an essay about their experience is so eye opening. We clearly make an impact on people. Couple that with the importance we play on educating people about climate change and I personally believe we can make a real difference in people’s live and inspire change. 

My personal daily inspiration is to push myself that little bit further out of my comfort zone. Winter driving, glacier guiding, crevasse rescue, wilderness first aid. All of these things were new to me when coming to Iceland and I have no intention of stopping there. If you are not testing yourself regularly you will start to retreat back into old ways and that’s not something I want to do. 

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

Stand up in front of people and talk. Do it all the time. Do it daily if you can. Go to skill sessions. Listen to experts. Practice, practice, practice. Because whether you are meeting a client, negotiating a new contract with a supplier, or presenting at a crowded conference, it’s all about how you present yourself to the people in front of you. Nothing else will help you to differentiate yourself as much as your personal brand will. 


To find out more about Hidden Iceland, or if you would like to join on a tour with them in Iceland click here. Ryan shared his tips on marketing your business without a budget with us in his insightful article here!


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.

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