One of the reasons we love the USA and are planning to return there indefinitely on our big US road trip is because it was living in the US that first inspired us to create our own freedom business.
There’s a strong entrepreneurial spirit in the US and an almost absence of the tall poppy syndrome, which is prevalent in Australia and can be detrimental to success and a conditioning battle I’ve had to overcome.
When I return to the US, I feel confident, freer and like more people are rooting for, and supporting my growth and success.
In partnership with The Ritz-Carlton and their Spirit of Celebration campaign, I’m sharing the places in the USA that inspired a spirit of discovery, celebration and desire to be free of the 9-5 to live a location independent lifestyle.
It’s perfect timing as I sit typing this in at my desk in my suite at the The Ritz-Carlton, Denver. Colorado lit my soul on fire and my thirst to discover more of the US and to return here again and again.
This current trip has helped me know for sure that I don’t want to be anywhere else but here at this current stage of my life.
We’ve also just returned from the Travel Influencers Summit in Snowmass where we met and masterminded with many amazing entrepreneurs. It was a celebratory moment and not something I ever envisioned happening when we started six years ago.
Let me share with you the six places in the US that helped me stay focused and believing an entrepreneurial life was possible.
1. North Carolina
We began our travel blog whilst living in Raleigh, North Carolina in 2010.
Hopeful and excited, I sat at my dimly lit desk in our small apartment scribbling chapters of my travel eBook in a journal. I didn’t know how to make this work, but I knew it felt possible.
But, I also remember the fear. It was right in the middle of our financial disaster. We’d wanted an entrepreneurial life, but unfortunately, chased all the wrong things and failed miserably.
This time around, I was chasing something that lit my soul on fire – travel, and helping more people do it.
North Carolina is where we first had an insight into what life could become for us. Freedom, choice, a house larger than what a shed in Australia of similar value would get you, and access to unlimited travel and diversity. I was hungry to test the boundaries and discover what I was capable of.
North Carolina was where we formed great friendships and found new hobbies, like following the UNC Tar Heels, tailgating, and walking around alpine forested lakes.
We loved the college vibe, the restaurants and bars, fun parties, live music scene, and a lack of rigid rules we’re so used to at home.
We had a lifestyle we loved in a place we never expected to be great. That’s the travel life isn’t it? The places you least expect gives you the greatest memories.
It’s the same for the entrepreneurial journey – it’s full of surprises. You think some things you do will be awesome, yet never work, but others you think won’t be so great, take off.
Our desire for exploration was inflamed with our proximity to many regions: New York, Florida, Savannah, Charleston, Nashville, and our favourite weekend getaways to the beach at Wilmington and Asheville in the mountains.
We met many people excelling in different fields and doing amazing things. I learned about the value of learning, of stretching, of curiosity, service, and finding confidence in who you are and speaking up for that.
2. Puerto Rico
Technically not in the US, but an unincorporated U.S. territory, Puerto Rico had a massive impact on my entrepreneurial journey. We visited with two-year-old Kalyra in 2009 to attend a conference that was part of one of those failed businesses we were chasing.
We listened to many inspirational speakers about business and creating a free life that helps people. But, there was one man who has influenced me more than any other, Yossi Ghinsberg.
Yossi spoke for three hours about being lost in the Amazon for three weeks during the rainy season where the locals said no Indians could survive, let alone a gringo.
He spoke about overcoming fear by swallowing it, about living a life of purpose, and understanding that everything in life is set up for you to become someone great. Even the dark moments are there helping us to grow in strength and courage so we may give something great back.
This quote of his inspires me to live an unconventional life and to make sure adventure and connectedness are always a part of it.
He talks about following those dreams that hound you at night. And describes it like this:
I think anyone on a journey of travel, celebration, or creating their dream lifestyle understands the desire for this is something that keeps you awake at night.
He also introduced me to the term Dreamer Fools, which is now the name of my private mentoring group.
The dreamer intelligent spends far too much time on the couch logically thinking about the dream and the clever ways they can do it. That’s as far as the dreamer intelligent usually gets because the dreamer intelligent likes to play safe. Playing safe keeps you in the land of day dreaming and can’t take you into dream creating.
The dreamer fools are the ones breaking the rules to move from the land of safety to where it’s dangerous, yet more meaningful.
These are the ones that others tend to call foolish because there is a lot that can go wrong.
Dreamer fools experience a lot of fear, but they learn to manage it. They take responsibility for their dream and understand if it’s meant to be, it is up to them to take the risks and make it happen.
Be foolish: believe in your wild dreams and make them happen.
When we first decided to move to the US in 2004, Colorado was number one on our list as the place to live. It was calling to us long before we finally arrived to explore it on our US road trip in 2006.
We don’t have mountains in Australia, more like hills, so when we drove into Colorado, I was mesmerised and breathless – literally because the air is so thin!
I think our time in Colorado, followed straight after by Utah, was when I fell deeply in love with the US and regretted my decision to return to Australia.
But it inflamed my desire to fight like hell for this independent lifestyle so that I could return.
I’ve only now just returned to Colorado and, again, I’m breathless! And so in love.
We’ve just been chatting with Kaitlin in the lounge of the The Ritz-Carlton, Denver about her life in the city after growing up in Florida. She’s almost convinced us that Denver might be a possible place for us to settle down.
At the very least, we decided we’d have a holiday house nearby so we could experience the outdoors lifestyle in both the winter and the summer.
Colorado is vibrant and people are passionate about living here. They’re friendly, grounded, and healthy. I think to embrace a life of travel, or creating your own business, a passion for living deeply is a requirement.
We spent three days in Snowmass at our conference, but also had time for hiking, bike riding, campfire BBQ’s and art evenings. It was truly magical. And now in Denver we’re exploring the food and craft beer scene, river bike riding and just about to indulge in a Colorado river stone massage.
Now I’m working in my comfortable suite and ducking outside for walks up and down the 16th Street Mall to grab a quick smoothie and meal, I’m happy this is the life I’ve created. I envisioned it in Raleigh, not knowing how to make it work, but we got there with an entrepreneurial spirit of discovery.
It’s worth every failure, lesson, and challenge and it’s wonderful to be truly able to work and travel anywhere.
Being in Colorado reminds me just why I’m working on our business and being the best I can be – because I love life, and if I can’t get amongst it like they do here, then I don’t survive.
The air may be thin, but the living is rich in Colorado!
4. Orlando, Florida
One of our other failed business ventures led us to a conference in Orlando.
Can you see the pattern here?
On your quest to create a life free from the 9- 5 you will have many failures. Part of overcoming this and getting to the eventual rewards is to understand the failures are lessons in disguise guiding you to your perfect place.
I can look back and see how many of my failures happened so I could learn from certain people, who were instrumental in getting me here.
The conference in Orlando was one of the first we attended. I found the city of Orlando to be pulsating with vibrancy, fun, and active living. I loved hanging out with other like-minded people, masterminding and networking in the hallways. I’m now pretty addicted to conferences and go to them whenever I can to reconnect to this spirit.
At this conference, we met Todd Falcone, a very successful network marketer and business man. He said something in our talk that changed the way we approach our work and how we build relationships with people.
In his speech, he said that many people approach him with the attitude of, “You’re rich, you should buy me a drink and tell me everything you know.” He said how wrong this is and if you want to pick someone’s brain then you should be the one buying them a drink!
When we met in the bar after the conference, he was surrounded by people trying to pick his brain. He walked near us, and we found a space. “Hey, Todd. We loved your talk today. Can we buy you a drink?”
He stood at the bar with us, and we did not ask him one question about business. We chatted about surfing, skiing, Australia and travel. We hang out with him for the next several hours, partying until 3 am.
When we left, he said, “You’re the most fun entrepreneurs I’ve ever hung out with. Here’s my number call me anytime.” What a buzz we felt being called entrepreneurs and fun ones at that!
I learned the importance of being real in relationships and making it less about you and more about others. Don’t try and do business and get all you can from someone on your first interaction. Build a connection, become friends or better acquainted, and then you can get help further down the line.
It’s been instrumental in building the successful business and lifestyle we have. We have many solid long term relationships that have lead to many opportunities.
We had such an incredible time at our conference in Snowmass following that same approach. People I know we can help with their business and which will be returned to us as well.
You cannot beat authentic, in-person connection. Be yourself always.
While a lot of this does happen in the bar, don’t worry if that’s not your thing. Coffee, lunch or just chatting in hallways works wonders too!
5. New Orleans, Louisiana
I had to include New Orleans in this post as it was the first place we wrote about when we started this blog.
It was our first trip we took as family travel bloggers (minus unborn Savannah). I realised then how much I loved this choice we’d made. I was doing what I had done for years before via emails and letters to friends, but this time on a potentially larger scale.
I could write my stories of travel, but also help inspire others to do the same. We could give them the tips on how we found great accommodation deals, got around the city, the exciting things we experienced, and how to have amazing memories as a family.
I remember exploring by tram with Kalyra, watching buskers in the street and sitting in the park in New Orleans and watching Kalyra sing and dance in the middle of the park like no one was watching.
We found it hilarious and laughed so much at her spirit, wanting to live life in the same way.
Then we laid down together on the grass for our first family selfie snap.
I was in love with having these experiences as a family and became determined that this would be our life forever more.
Now we travel with the girls all the time, and as I’ve said to many people, parenting is much more enjoyable for me, and filled with so many more memories, when I travel with my girls instead of chasing the settled life.
Like Colorado, Utah is my favourite state in the US and full of surprises and wow moments. I fell in love with the journey in Utah, twists and turns through surreal landscapes and a rich palette of colours.
We still can’t believe that it’s not as promoted as many of the others states in the US and we’re delighted to dive more into it to showcase it through this blog on our road trip.
We rode horses through Bryce Canyon (one of the most beautiful places I’ve ever seen), we hiked Angels Landing and The Narrows in Zion National Park, were blown away by sunset at Dead Horse State Park, and had the thrilling experience of a lightning bolt crashing on the ground beside us as we drove through the Canyonlands.
I felt so alive in Utah. It sparked my desire to stay in greater connection to the land and adventurous experiences.
Utah is about intensity and surprises and vibrant living. I think it describes the entrepreneurial life. You just never know what’s around the bend, but you love journeying around it as you know it will be something unique, new and worth diving into.
People connected to travel through celebrations of many kinds, whether it be anniversaries, birthdays, or celebrating major milestones and life changes. Travel enriches our lives, transforms us, and gives us rich memories.
Our Entrepreneurial Journey in Podcast
- Episode 1: Solo Travel and Working Abroad before we met
- Episode 2: Our 5 year honeymoon living and traveling the world
- Episode 3: The Dark times and Birth of the girls and travel blog
- Episode 4: Embracing Family Travel and our 18 month Australian road trip
- Episode 5: Getting a green card and traveling the US (our dream realized)
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I’d love to hear in the comments how certain travel experiences have transformed your life and allowed, or inspired you, to become who you are today.
10 thoughts on “6 places in the USA that inspired our entrepreneurial journey”
Caz, I loved this. It touched very close to home with me as I left my job 5 months ago to chase the entrepreneurial dream as well. After leaving my job, I went to Italy for 2 weeks, then Denver Colorado. Going to Italy reinforced the idea that I wanted to maintain a job where I could see the world as I pleased. Then going to Denver for just a weekend, I met a handful of dreamers just like myself who were chasing their dreams. It is always great to hear about the experiences of others as this life is uncertain, but so fulfilling.
Our 2 week honeymoon to New Zealand changed us. We went sky diving, bungee jumping, canyoneering, heli-hiking on a glacier. We are planning to go back in 4 years for our 10 year anniversary but my husband would love to move there. While I certainly don’t mind that idea, I’d love to travel the US in a motorhome on our own schedule.
I really enjoyed this post. I actually like hearing about how you failed in a few business ventures (even if that’s a hard story for you to tell). We also have a failed network marketing business behind us– It’s been difficult to move forward and persist with dream-building, so I appreciate your vulnerability. Sharing your experience in New Orleans was so sweet, too. It’s those little times we see our kids come alive that encourages me to hit the road more- and gives me the urges even more to pursue the nomadic lifestyle.
Oh God the failures and the network marketing! They sure do teach you a lot. It’s so hard to overcome them but I think if you look at them as being a very important part of your journey for how it makes you grow, you can accept them and move forward to better things.
Very inspirational post for budding travel entrepreneurs. Loved the fact that you used the places which inspired you, to inspire us.
New Orleans looks like a fairy tale!
Wonderful post. I am so glad to see someone highlight traveling in America. It seems that the travel blog community is inundated with reasons that you must travel in Southeast Asia. America has so much to offer travelers from here or abroad. It is a vast expanse covering so many climates and cultures.
Even more though, I appreciate your definition of “The Tall Poppy Syndrome”. I have never heard this before but is sadly a spirit I have started to notice in America as well. My whole life the “American Dream” was about making yourself whatever you dreamt. Suddenly, I hear an attitude of “who do you think you are?”, “steal from the successful because they must have cheated somehow”. Where I was most saddened by this attitude is in our public education system. In an effort to serve all student populations (which I understand is a tough task) the gifted and/or successful students have become pariahs. They are subject to ridicule by their peers and scorn from the teachers that see them as extra work.
I don’t like to see people become successful on the backs of less privileged, but if anyone has created success legally and through their own initiative and hard work, then I say: MORE POWER TO ‘EM!!
Such a great comment Janet and so true. That’s so sad the Tall Poppy Sydnrome is creeping in. It’s a horrible thing. The term comes from back in the convict days in Australia. As a form of control, the British soldiers would punish the entire work gang if one of the convicts spoke out and was cheeky. They’d come in from a day of work, and their faces would be all burnt and look like a poppy. If one would stand up and give the soldiers cheek, the rest of the gang would shout out, “sit down you tall poppy”
So the syndrome comes from way back then. Standing out was one of the worst things you could do. It’s really sad.
We’ll be road tripping around the US later this year for the next couple of years. We’re excited to share so many wonderful things about the country. Australians tend to spend so much time seeking to explore outside our own country. We loved road tripping around Australia and inspiring many people to explore their own backyards. We hope to do the same in the US for our US readers!
Colorado is amazing! I had the chance to snowboard there which fueled my love for the sport. Beautiful state. Living in Amsterdam I miss the mountains. But we’ve made it a yearly family vacation to do a snowboarding trip here in Europe.
I really hope to see Zion Canyon at some point, and your blog really inspires me to take leaps towards that! Thanks!
Oh, Caz, so inspirational as ever. Just as I was sitting down to chase unpaid invoices and deal with how to manage someone stealing almost all my money from my bank account! Thanks for the boost – and for the reminder that the US is full of wild open nature as well as gritty cities. Wishing you all the best in the next stage of your journey!