We caught up with the brilliant and insightful Kelly Tolliday a few weeks ago and have shared our conversation below.

Kelly, appreciate you joining us today. Parents play a huge role in our development as youngsters and sometimes that impact follows us into adulthood and into our lives and careers. Looking back, what’s something you think you parents did right?

My parents gave me the space to dream big as a kid. I remember as early as 6 or 7 writing out a Travel Bucket List with my Dad. I’ve always been filled with new ideas, passions and adventures for my life, and my parents did their best to allow me to see the possibility in each vision.

When I was 7, I wanted to be a Radio DJ, so my Dad set up a call with a friend who worked in Radio. When I was 12, I wanted to attend a Leadership Conference in DC. My Dad made me “pitch” to him why he should let me go and helped me make a savings plan to fund the trip.

As a teenager, I wanted to be a Music Journalist, so they allowed me go to concerts in my teens. As an adult, I created a hobby within the Travel Industry, while simultaneously working in Corporate Marketing, and this led to my current career now. My mom was the first one to sign up for my first Retreat in Costa Rica.

They never once criticized or judged my ideas, even if it may have seemed silly or risky to them.

When I decided to move to Australia after graduating college to live with my boyfriend, they didn’t squash my dream or make me feel bad about leaving. They never made their heartbreak over me leaving apparent, and they always seemed genuinely excited about what the future laid ahead. In short, they never made it about them.

Although they made their trust in me known, they still did their parental duty by asking me strategic questions to get me to critically think about my next move. This line of questioning has always helped me better inform my decision making.

I was recently asked how I’ve had the courage to go after my dreams – living around the world, starting new businesses, and taking seemingly big risks. I firmly believe it’s because of the belief and trust my parents had in me. The confidence they had in my ability to make wise decisions (even if they had their own fears around it) has been the anchor in my life that I repeatedly fall back on when I feel lost or unsure of my next move.

I strive to raise my own daughters this way.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

Travel has always been a massive part of my life. Since a young age, I was passionate about meeting new people, stepping out of my comfort zone and always learning from new cultures. I was always the kid wanting to go to the Kids Club on cruises and resorts because I couldn’t wait to meet a new friend. I was always curious about how people in other places lived – even if it was just another state away.

I received a Bachelor of Arts in Public Relations and a minor in Hospitality and Spanish from Florida State University. During my time in university, I studied in both Costa Rica and Switzerland. These experiences further instilled in me an appreciation of other cultures, new experiences and the connections formed along the way.

In 2013, I started a Travel Blog while I was backpacking in Europe, and this launched me into the Travel Industry. When I moved to Sydney in 2014, I started my professional career in Digital Marketing, but my love of yoga started to develop further as well. I completed my Yoga Teacher Training in 2017, alongside working full-time for a global marketing agency.

During this I realized I could combine my love of travel and my passion for personal development and wellness together. I hosted my first Wellness Retreat in 2017 in Australia, and have hosted 11 retreats since. In 2021, I combined forces with my business partner, Chloe Ravel, who also has a background in running events and retreats. We created RNR and have hosted group tours and retreats in 7 different countries. (Going to Peru & Greece in 2025!)

I have a deep passion for opening up the world to people who may not have experienced the world before or may not have a partner or a friend to travel with. I pride myself on offering a 5-star experience for our clients, where they get the best of what travel has to offer – cultural enrichment, authentic experiences, connection with community and opportunities for deep personal growth.

In 2023, I had the opportunity to start a podcast, and I created the Transform With Travel podcast, where we share stories of personal growth and transformation through travel, as well as episodes featuring Industry Experts to optimize and enhance your travels. I’m also a Travel Advisor, where I help clients create and curate the vacation of their dreams.

My husband and I have been living back in South Florida since 2019. We’ve lived all over the world together – including Australia and Thailand. We’ve traveled South East Asia for a year together and we both love the adventure and freedom that travel provides. We are now raising our two young daughters (4 and 2 years old) and hope to instill in them a sense of curiosity, resilience, compassion, courage and adaptability through travel. I love to challenge myself – whether it’s through triathlons, surfing, or hiking. My favorite places in the world are where the jungle meets the sea and it’s warm all year round.

How about pivoting – can you share the story of a time you’ve had to pivot?

My whole life is a story of pivoting. I firmly believe that your ability to pivot and change is in direct correlation to your personal and professional success.

When I was heading into the Senior Year of College, my plan was to go to New York to pursue a career in Public Relations. 4 months later, I met an Australian guy named Sam, and 6 months after that, I was on a plane to Australia to begin my life in Sydney with him. Had I been hung up on “New York”, I never would have let myself imagine a life in Sydney with the man that is now my husband.

In 2015, we were planning on teaching English in Thailand. After a few months of the job, we realized that the experience wasn’t matching up to the expectations we were promised. We decided to quit the job and travel Southeast Asia for the remainder of the year. Had I been so set on the “vision” of teaching English for a year, I would have stopped myself from making this pivot and experiencing this part of the world. The goal was to travel and explore South East Asia. I realized I didn’t need to teach English to achieve that goal. This is also where I first started to freelance in Social Media Marketing and began my side-hustle as a Freelance Digital Marketer – a career that ended up sustaining me for 5+ years afterwards.

Lastly, in 2021, I was about to sign a lease on a space in South Florida to open up my own Yoga Studio / Co-Working Space. I was ready to sign the dotted line, and I ended up in the hospital from burn-out. Raising kids, running a house & businesses, training for a race – all caught up to me. As I sat in that hospital bed, I realized that the reason I wanted to have my own space was to create a community, but I didn’t need a physical space to do that. That’s when I pivoted my business to be a travel-based wellness community, and now we run Group Retreats & Tours around the world.

In essence, pivoting show you are able to remain unattached to “how” you get from Point A to Point B. We often get so hung up on the How that we forget that what is the most important is the Why. When we open ourselves up to different routes and way of getting to our destination, we allow the potential for our success to be even greater. To take it one step further, we even get hung up on the Vision itself. We don’t often ask ourselves if that goal or vision is even in alignment to our values or current life situation. In my opinion, the ability to pivot, let go or change (without shame or guilt) is the true marker of success.

We’d love to hear the story of how you turned a side-hustle into a something much bigger.

Even as a child, you could say I was a Full-Time Student who always had a side-hustle going on. If my parents gave me $10 allowance for chores, you bet I was finding ways to diversify my income streams. From selling friendship bracelets to washing cars, I loved creating something from within my own mind and being able to commodify it.

This still rings true today. Almost every full-time job I’ve ever had, I have always had something on the side going. Most notably, when I was working in Sydney at a Global Marketing Agency, I was simultaneously running a successful travel blog, training for my 200-Hr Yoga Teacher Training and starting to market my first Yoga Retreat. I was also helping other Yoga Teachers learn how to use social media as part of their Marketing Strategy.

I had my two passions of Yoga and Travel always churning in the background, as I worked within the safety net of my Marketing Roles for over 10 years.

In 2021, I was working at a Marketing Agency in South Florida, teaching yoga at different studios and running Retreats around the world.

Eventually there came a point after my first daughter was born, that I realized I couldn’t keep going at the rate I was going. I was burning out fast, and I actually ended up in the hospital. It was there that I realized it was now or never. I either used this opportunity to quit my Marketing Role and jump full time in my side hustle. Or I keep continuing to burn the candle at both ends forever. Because I knew, I was never going to be the type of person that was happy with working a traditional 9-5. I needed something to call my own.

I took that opportunity to jump head first into my side-hustle, and now 3 years later, I have multiple businesses – RNR (Retreats) and Transform With Travel (Advising & Podcast). These businesses work cohesively together within the Travel & Wellness Industries. This took time to build , and I am still working to continue to grow our communities and offerings. However, through showing up consistently and authentically for over 12 years with a similar message for my audience (Travel can transform your life) – I’m now at a stage where people trust what I have to offer.

Contact Info:

• Website: https://www.transformwithtravel.co
• Instagram: kelly.tolliday
• Linkedin: https://www.linkedin.com/in/kellyschwantes/
• Youtube: https://www.youtube.com/@TransformWithTravel
• Other: Podcast: https://transform-with-travel.captivate.fm/

Image Credits

Melanie Gomez
Morgan Brosch