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How Generation Y & Z Is Defining Itself Through Experiences, Not Things

Updated: Jul 31, 2019

INTERVIEW // OLIVIA O'CONNOR - FOUNDER OF DONTTELLSUMMER


Welcome to Compass Studio's fifth instalment of our 'Explore More' series where we dig into the stories and inspirations of those people that are conquering uncharted grounds right now - whether physical, environmental or social, in the hope of spreading the good further. 


We learn more about DontTellSummer, a community founded to inspire generation Y & Z to do what they would love to do now, rather than waiting for some point in the future. We talk with founder, Olivia O’Connor, about how travel has changed through generations, the concept of travel as a form of wealth, and the first steps to getting out on the road – all whilst doing what you love.

  • Let us know more about yourself, and DontTellSummer?

I’m originally from Portland, Oregon. I moved to California for University and it was there that I decided to study abroad in Australia. I loved Sydney and knew that I wanted to come back as much as possible. The only time I could do that was during my summer breaks, which was Australia’s winter. Consequently, every year for three years, I missed summer!


This period was the time of my life because I felt like I wasn’t waiting for anything to be myself, and to do what I would love to do. I took that freedom-based lifestyle and mentality and launched DontTellSummer as an online platform and blog to inspire others to do what they would love to do now too, rather than waiting for the future.


Through DontTellSummer, I launched #RadLivin – a unique annual festival created to inspire you to do what you love, now. It’s a community of incredible, passionate people following their dreams and doing good in the world.


  • How do you think Generation Y and Z look at travel compared with their parents' generation?

I think travel is seen as more accessible. It’s much more affordable and you can book trips at the click of a button. These generations place a lot of emphasis on travel for being an important part of discovering who you are, what you’re passionate about, and meeting like-minded people out in the world.


Having the internet at our fingertips also allows for a lot more spontaneity. We are also a generation who has embraced the idea of the entrepreneur, meaning that a lot of people can work from the road, rather than needing to wait to travel until specific holidays.


  • How would you consider travel a form of wealth?

As far as acquiring things in life, travel brings you great confidence in yourself, new experiences, memories, and genuine friendships.



  • What are the benefits of doing travel now, rather than later?

I believe we’re drawn to certain places in our life at different times, and for different reasons. If we don’t listen to that gut-instinct or excitement towards somewhere, we may miss out on what was there for us. For example, when I was a Junior in college, I was drawn to Australia. Rather than waiting until after I graduated, I did a semester abroad at the University of Sydney. It completely changed my life and gave me a new set of passions, confidence within myself, and now a new home. Had I waited, a lot of things in my life wouldn’t be here right now. It’s important to listen to the call of a certain place. Of course, we might feel called to a million places and that costs a lot of money, but generally one place draws us in more than others. Go there!



To me, living the dream is living based on feeling good; feeling happy, excited, and inspired. It’s living out a roadmap that I created for myself with my dreams, and living in alignment with what those dreams are.

  • What’s the first step in packing your bags, and working from the road?

The first step is having a form of income that allows you to work remotely. If this isn’t an option, consider what kind of odd jobs you could do abroad that could make it happen. For example, working at a bar in Greece for three months while you save to go to your next destination.

If you’re working from the road, it’s important to have your groundings in your business and structure set out. Knowing when things need to be done, how much time it might take you, etc. – because sometimes while on the road it can be hard to get WiFi. Also figuring out what type of person/creative you are, and what you need. Usually you won’t know this until you get out onto the road and give it a try. Although maybe challenging to find those spots between leisure and work at first – it’ll get easier after time, when habits are formed, and you get into a routine that works best for you.

  • What’s your definition of ‘living the dream’ – and how do you think this term has changed over time?

To me, living the dream is living based on feeling good; feeling happy, excited, and inspired. It’s living out a roadmap that I created for myself with my dreams, and living in alignment with what those dreams are. It also means enjoying the journey along the way. I think the term has changed because people are more focused on how they’re feeling nowadays, rather than what they’re getting – whether that’s a new car, money, a house, etc. People are putting their happiness above everything else, as well as purpose.


  • Are social influencers who live on the road, really as disconnected as they appear to be?

It depends on the person – I would say yes. I remember being out on a camping trip with a few friends for a collaboration and I needed to post something to social media. There wasn’t any WiFi near our campsite and so my friend and I had to trek 30 minutes with a lantern to get one bar to post!


  • How do you think social media has changed travel? Do you think it has made remote and hidden destinations too accessible?

I think it’s opened up possibilities for people to explore places they may have thought weren’t possible before. It’s also nice when you’re in a new place and don’t know anyone, to be able to look at social media and see who’s around. With that said, I think that it’s important to remember to experience the synchronicity of travel; that’s what makes it fun. Not knowing how everything is going to play out, going with the flow, and jumping into the unknown. Now when I go to a place, I like to do little research about it before going so that I can experience it firsthand to the fullest.


  • Where to next? What are the top three destination on your wanderlust list for 2018?

Heading to Vanuatu, Greece, and America. Aside from those, my top destinations are Sri Lanka, Peru and seeing the Northern Lights.


Want to learn more about DontTellSummer, and join their every-expanding community? Check out donttellsummer.com or follow on Instagram.