Today, our guest post comes from Kiera Ogden, a travel enthusiast, entrepreneur, and member of the NYC chapter of The Nomadic Network. Not long ago Kiera was stuck in a full-time position at a brick-and-mortar shop with the normal two-week vacation each year. Once she discovered her love of travel in her 20s, she dreamed up a much bigger plan for her life. Somehow, within a matter of years, she went from never having traveled alone to obsessing over travel, to building a business that allows her to travel whenever she wants.
We love featuring stories like this and hope they inspire you to find a creative way to incorporate more travel into your life as well.
Four years ago, I moved my life from Virginia to New Jersey for a much-needed change of scenery. My commute took hours, so I left my house at 5:30am and got home by 11pm (just another twentysomething living that glamorous NYC dream). Once I got my own studio apartment in the Bronx, I felt like things were looking up. Nothing like an overpriced 500-square-foot apartment in a sketchy neighborhood to make you feel like your life is coming together, right?
Even though I have a degree in fashion design, I actually worked at bridal company directing and managing its bridesmaids’ sales, buying, and creating its social media profiles. It wasn’t my first choice, but I wanted to work in NYC, so I took it.
After one measly year, I felt miserable and frustrated. As winter grew colder, I remembered a perk that I had insanely forgotten: 10 days’ paid vacation between Christmas and New Year’s, when we were closed. In an attempt to really relax and do something different, I decided to go on a vacation. Since it was Christmastime and everyone I invited with me already had plans, I sucked it up and booked my first-ever solo flight.
My trip to Italy was nothing short of magical. And solo travel wasn’t as daunting as I had made it out to be in my head (can anyone else relate?)!
Oddly, at this time I had a fear of flying, so it took quite a bit of wine at the airport for me to relax, and even still, I was the last one to board the plane. Once I landed I worked my way through the airport, caught the train to Milano Centrale, got a taxi to my hostel, and walked into a warm welcome from (still) my favorite hostel employees (shout-out to Ostello Bello!). I knew I would be happy there.
Simply being able to navigate airports and public transportation while not knowing the language really felt empowering. It’s something that I now see as just a part of the adventure, but I sometimes and look back and remember how daunting it felt that first time.
My first hostel experience was also pleasant. I got a friendly welcome from the man lying in the bunk next to mine. He and another hostel-mate immediately invited me to dinner; we became fast friends and even ended up traveling to Venice together!
Fast-forward 10 days and I’m sitting at the desk of a job that I dreaded, living paycheck to paycheck and feeling totally unfulfilled. Something had to give.
That taste of travel had seeped into my bones and left me thirsty for more. But how could I travel more?
First of all, I couldn’t at my current job — so I quit.
I moved to New Jersey and started managing a much lovelier bridal salon, where I calculated my precious vacation days and planned trips as often as I could. I set off to Italy a few times. Over these few short years, I also made my way to Iceland, Sweden, Ireland, Croatia, Greece, Germany, Portugal, Thailand, Canada, and Spain, to name a few destinations. I even took my first non-European, non-North American trip to Morocco!
As I traveled more and more, I found myself testing the limits of what I thought was possible. I found a level of confidence that seemed to be buried inside me. Traveling gave me a whole new lease on life.
My primary goal became one thing and one thing only: travel more.
I also had a newfound obsession when it came to the international bridal market and found myself visiting bridal shops all over the world on every trip I took. It became a central theme for my trips.
Somehow, I had managed to convince my boss to let me be the one to travel for work, so I got a few all-expenses-paid trips alongside the ones I was saving up for!
I spent two years in this job feeling like my life was pretty good alright. But I had this nagging thought in the back of my head that something wasn’t quite right.
I’d spent my career up until that point as a bridal store manager and buyer, but I was feeling thwarted creatively. As I said, I have a bachelor’s of fine arts in fashion design, so I started to think about how I could do that as a side hustle to get my creative juices flowing.
Hand-making accessories for brides was where I found my stride: beaded belts, veils, hairpieces, and other pieces used to embellish brides on their big day. The salon owner graciously allowed me to sell my creations in both of her stores. It started slow — like really slow, a couple of belts a month — and that was going to be it. I had no intention of actually making any real income from it when I started.
That all changed when my pieces started selling. When I saw my creations come to life, I felt alive inside — a feeling that I’d dreamed of for so long!
New plan! What would it take to make this an actual, viable business? A purpose. A website. More output. A photoshoot. A social media presence. I started reaching out to my network and asking for resources in all of these areas. Soon enough, Worldwide Wedding Style was born!
This side hustle was really taking off. By day, I was working full-time at the bridal salon. By night, I was creating products and building my brand.
I dreamed of the kind of life I’d lead if I could support myself on only this “side hustle.” How great it would be to own my own company?! Like Nomadic Matt, I dreamed of a business that would be the vehicle that would allow me to travel the world!
That would mean that I could weave travel into the brand and get to go wherever I wanted, whenever I wanted. I’d be my own boss! After all, that’s why I picked the name Worldwide Wedding Style (#WorldwideWeddingStyle).
In March of 2019, I handed in my resignation. Four months later, I was a full-time entrepreneur.
My first order of business? Book a flight to Thailand.
For what? Of course, my first international photoshoot for the launch of my collection and website at NY Bridal Fashion week that October.
Why Thailand? Why not? I was the boss. I was calling the shots. And if they’re my shots to call, I’m going to make them as international-leaning as possible!
Planning this shoot in Thailand was an exciting challenge, since I had never been there before and I wanted to produce it with local models, makeup artists, hairstylists, and photographers. Giving back to the community I was traveling to meant a lot to me.
I reached out to a well-traveled friend of mine (having a travel community is so important), and she connected me to a Thai friend of hers in Bangkok who was able to help me connect to all of the people I was looking to work with on the ground. Together with the local talent, we picked the beach and long-tail boats, and booked everything before I even stepped foot on the plane.
I made all of the arrangements for my business trip to Thailand from my laptop in New Jersey. The challenge of it all was exciting, and I feel like it taught me so much about running my own company that I didn’t even realize I needed to know. Sure, I could have easily done this photoshoot at home, but I wanted to create the life of my dreams!
For Thailand, I packed up some bathing suits, flip-flops, a few wedding dresses, and some handmade bridal accessories and I headed to Asia for the first time! After a day of flying, I landed in Phuket a day before the photoshoot, found a local flower shop, and had them create a bridal bouquet with flowers native to Thailand.
Everything was going smoothly. I felt like my life was finally “together” like I was hoping for. There I was, visiting a gorgeous, warm foreign country… for (my own) business! I had created what that original trip to Milan years before had spun into motion. I was the owner of a company that did business around the world. This was my life now.
Not so fast! A few hours before our perfectly planned Thai photoshoot, the sky opened up and a typhoon hit our island, Phuket. I stared out my window, wet from raindrops, and had this sinking feeling in the pit of my stomach for what felt like hours. The rain showed no signs of letting up. That meant no beach photoshoot. No long-tail boats in the background. No place to have everyone meet me in the morning. All my plans were ruined.
At 4am, after feeling bad for myself for not having a backup plan. I realized that this was no different than the time when the hostel in Morocco didn’t have my reservation on file. Or when I missed my flight home from Italy after a business trip. Or that time I got my phone stolen on the streets of Florence. I realized that this was just another travel mistake. Sure, it felt heavier because it was a business mistake, but I knew I could handle it just like I had handled all of the other misadventures I’d gotten myself into since I started traveling solo.
I sucked it up and started Googling places to host the photoshoot inside. After an hour, I had booked a dreamy villa at The Shore at Katathani. The next morning, I dragged my luggage there in the pouring rain.
There were a lot of bumps in the road — mainly the language barrier, my lack of sleep, and a heavy dose of jet-lag — but we prevailed. The Thai photographer Nattapong Get Jantarat captured beautiful shots of the sweet, helpful, patient model I hired, Medploy. Even though I was in a new country, surrounded by new people, a new language, and a new kind of weather (that was my first typhoon), I felt like we actually really got each other. As a team of people who had never met before, we were flexible and made the best of the situation!
Once the shoot was done, I spent two weeks island-hopping all around Thailand and getting to really experience solo traveling and the beauty of the Land of Smiles.
Thailand made me realize how easily I could really marry my two passions: working in the bridal industry and traveling the world.
Seemingly out of nowhere, I started getting requests to style weddings that were nowhere near my home in New Jersey. I booked business trips to Florida, Georgia, New York, and Belfast, Ireland.
Along with styling weddings and business photoshoots, I get to jaunt around the US for all sorts of business reasons. It’s only been a year since I took off on my own, and while it’s had its challenges, I am forever grateful for having taken this leap. I think about the life I used to live, where I had to submit paperwork to request to use my 10 vacation days a year and smile. The life I have created truly is able to marry my biggest passions.
Thanks to my companies, Worldwide Wedding Style and the Kiera Elise Collection, I’ve been able to move my dream into reality. My business seems to evolve with every day that passes. I made the initial decision to quit without feeling like I had a clear vision for my company. I still don’t, but I am figuring it out as I go.
The journey of entrepreneurship feels strangely similar to that first solo trip to Milan that I booked on a whim. I was frightened and excited but mostly shocked at how bold I was to make such a move. My advice to anyone feeling stuck in life: take a solo trip. You’ll learn just how capable you are of creating a life that you love.
Note: We love featuring our travel-loving members, if you’d like to be interviewed or write a guest post for this blog, send us an email at info @ thenomadicnetwork . com with the subject line “TNN Blog.”