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Olga Maria – A Latina Digital Nomad Traveling The World

I met Olga Maria a few months ago on Facebook. We connected and right away had a very interesting conversation where we realized that we have a lot in common. We both became adoptive daughters of the city of New York, we both are passionate about this digital world, and we are both natives of Latin America, which we comically realized after our entire conversation had been in English, a language that we have both learned as immigrants and continue to improve every day.

¡Clic aquí para leer en español!

I loved Olga’s story, what a brave woman she is! It reminded me of 2004, when I told my parents that I was going to a “strange” country (Spain) for three weeks, to stay with my cyber-friends who I met in a forum at an entertainment web portal. A lot of people thought I was crazy. Nowadays, my mom keeps saying that she doesn’t understand how she let me go and I keep telling her that “crazy trip” has been the best experience of my life. So much so, that there began my love for Spain, the culture and its people, and as a result of that same trip, the following year I packed my bags again and moved to Barcelona to study my master’s degree.

Olga’s story is very similar, but she has gone even further and today she is a digital nomad with three postal addresses. Through her blog, she is opening the world to many Latinas through her travels and experiences, and what I like the most is that she is breaking many taboos like “you can’t travel alone being a woman” or “traveling is only for the rich.”

A few months ago, Olga and I had the opportunity to meet in person at the “Unstoppable Latinas” event in New York, and after hearing her speak at the event, I confirmed that she was one of the “Latinas in Media” I wanted to feature in this section of my blog. I hope you enjoy her story as much as I do!

Latinas in Media – Who is Olga María?
Olga Maria Czarkowski – I am a small town girl from Bayamón, Puerto Rico living my dreams in heels around the world. I left my island at 18 years of age with a suitcase full of dreams, no family and without speaking English. I decided to take a leap of faith and build (from scratch) the life I’d dreamed of (and I can proudly say that it is now beyond my hopes and dreams).

My first stop was Miami, Florida, but not for too long, followed by NYC, which has been my home until my recent move abroad. Ironically, I was born in Brooklyn, New York, but my mom (originally from Naranjito, Puerto Rico) returned with me (at 6 months of age) to Puerto Rico and raised me there. My father is from Havana, Cuba, which makes me Cuban-Puerto Rican.

Similar to most, I had lots of struggles in my path, but I moved past them and didn’t take ‘no’ for an answer. More than anything I’m a Latina who was born with wanderlust, who found value and a purpose in traveling, and who wants to inspire others to join her on adventures around the world. It began with a study abroad opportunity and I never looked back. Expanding your horizon, even if it’s in your own country, is key to personal growth. By submerging myself in other cultures, I learned more about myself and developed a deeper appreciation of my own heritage.

Photo provided by Olga Maria Czarkowski

LM – Why “Dreams in Heels”?
OMC – The concept for Dreams in Heels was born in New York City. My brand name literally came to me in a dream, words that later became one of my mantras: “I am Living my Dreams in Heels.” The most obvious answer and the one that most people realize right away when meeting me is that I am always wearing heels. Many people wonder: “How can she be in heels all day long?” The truth of the matter is that most people think that I am only a girl who is fascinated with style, beauty and just wants to always look well put together (which is not totally false). Some people even judge me, or at least look at me strangely, since I not only run all over NYC in my heels but anywhere I travel. For example, my adventures have included: Europe, South America, The Caribbean, Asia, United States and Canada. I’ve ridden a bike in heels multiple times, walked on cobble stones (trained in Old San Juan, ha-ha), made it to the top of the Blackcomb Mountain, to the Equator…all in my heels! Basically, I am really living my dreams in heels!

However, the real story behind it is that I was born with a leg condition whereby my Achilles tendon is shorter than average. I cannot walk with my feet flat on the ground; I can only walk on my tippy toes. Thus, heels are much more comfortable for me. Growing up, I was mocked in school (in Puerto Rico) because my condition resulted in my having to wear boots with metal braces, even to sleep. Kids bullied me because of the way I walked. But eventually, the boots and leg braces came off but resulted in little improvement. More of my story can be found here. Obviously, this experience made me stronger but it also taught me never to judge others based on their looks.

I am Living my Dreams in Heels – @itsolgamaria Click To Tweet

Back to DIH…. Dreams in Heels “caters to all types of adventurous souls, including those who are already exploring the world, those who plan to travel (even on a budget), and lastly, it’s especially for those who message me to say that living vicariously through my journey brings them joy and inspiration. My goal is to inspire all, regardless of their circumstances, to live life to the maximum! Anyone can start by exploring their own neighborhood. You never know what adventure awaits just around the corner!

LM – How did you get involved in the digital world?
OMC – Everything started when I was going to college. I used to have two jobs to be able to support myself in New York City. Between jobs and university, during my precious little free time, I started building my online presence and my personal branding.

Initially, I was very active on Facebook. I built a network and cultivated friendships. I also started volunteering for events involving fashion, beauty and non-profit organizations. Eventually, I quit one of my jobs and finally started organizing fashion shows, fundraisers and started doing public relations on the side in the fashion and beauty industry. All of this lead me to quit my job and start a small PR company. Simultaneously, I was always writing, because I’ve loved to write since I was a child (starting with poetry, music, journaling and then eventually sharing my experiences). All of this gave me the opportunity to attend many prestigious events, such as New York Fashion Week, Colombiamoda, MIAMI Swim Week and even The Oscars. But after a few years, I noticed there was much more than PR and fashion for me. I noticed that one of the things that made me happiest was to travel and learn about different cultures.

Olga Maria Czarkowski speaking at the Unstoppable Latinas event in New York – Photo: Alex Tabar

This is how my career as a travel and lifestyle writer started more than 4 years ago. I changed all my branding to be more focused on this niche; I immersed myself in everything travel-related: networking groups, conferences and more. Suddenly, based on all the work I’d already done with my personal branding in the past, doors opened, opportunities appeared and when I least expected it, I was getting invited on trips by tourism boards, airlines and hotels to destinations around the world. Eventually, I chose the Digital Nomad lifestyle since I love the freedom, creativity and the independence that came from having a flexible location. This is why, after almost five years as a blogger, influencer and freelance writer traveling all over the world (while based in NYC), I decided to take a leap of faith about a year ago and stay in Europe. I now have three addresses (one in Germany, one in Austria and one in NYC), since I always travel back and forth for business opportunities. And more than anything, I’m a citizen of the world! I’m someone who is constantly exploring new traditions, cuisines, basking in the magical company of locals and just living life to the maximum, as everyone should!

LM – What are the biggest achievements of your blog “Dreams in Heels”?
OMC – Some of the biggest achievements of Dreams in Heels include having readers and fans from so many different parts of the world. When I travel, I meet so many amazing people that follow our Instagram or other social media channels and they reach out to me and offer to show me their city. For me, that is the magic of traveling and doing what I do – meeting new people from all over the world.

In addition, it’s the partnerships we’ve built. We have been able to partner with prestigious airlines such as Swiss Air and LAN Airlines. We have worked with amazing tourism boards such as: Luxembourg Tourism, Switzerland Tourism, Ecuador Tourism and more. Most recently, we partnered with an amazing tour company in the Ukraine. We have worked with many hotels such as Hard Rock Hotel Riviera Maya, Beau Rivage Palace in Lausanne, Plaza Grande Hotel in Quito, Chelebi Cave House Hotel in Cappadocia and more! As well as with powerful brands such as Prudential, Dove, Ketel One Vodka and more. Recently, I’ve been featured in different media outlets such as Bravo TV, HuffPost, Expedia UK, and more. I’ve shared all of these experiences with readers/followers in an attempt to inspire them to find their passion. In addition, I’ve been invited to be a speaker at conferences like Hispanicize, Unstoppable Latinas, NY Trav Fest and even to H.S. schools, where the majority of students are Latinos and of color, to inspire them and help them understand that they can do what I do or whatever it is that they want to do. Nothing is more amazing than giving back to the next generation. It is a lot of work but pays off when you are committed to growing your brand.

Photo provided by Olga Maria Czarkowski

LM – What has traveling meant for you?
OMC – Traveling has changed my life. It made me see the world through another’s eyes. I had not only learned so much about other cultures along the way, but also about myself. I’ve grown personally and professionally. I have discovered that there are good people in every corner of the world and that you cannot judge people in one country by their politics, their leadership, religion or beliefs. When you travel, you understand many things are not as black or white as the media will lead you to believe. Everywhere you go there are new people to meet and learn from; you just have to be open to experience new cultures, to listen to another’s story, to learn new words in different languages, to just basically embrace traditions and beliefs that can be different from your own but just as special. Life is too short to live in/inhabit the same space forever.

Traveling has changed my life. It made me see the world through another's eyes. –@itsolgamaria Click To Tweet

LM – Which has been your favorite destination so far? Why?
OMC – That’s always a hard question to answer since I fall in love with different destinations. But one of the countries that has captivated me so much, since I have a special connection with it and it was my lifelong dream to visit, is Turkey. It was definitely high on my bucket list, especially riding in a hot air balloon in Cappadocia.

I decided to visit Turkey (although being warned against it) and ‘yes,’ I traveled solo around Turkey as a female, for over 8 weeks, during the fall of last year (2016). I originally was going for a week and I loved the country so much that I decided to stay. Many people (such as readers, family, friends) kept messaging me while I was there, concerned about my safety. But I never had any issues. Of course, I took the same precautions as I would have taken in visiting any other country. Some people in Turkey were surprised when they saw me, since they said that they do not get many American tourists any longer, and even more rare, a solo latina traveler. The locals were so happy nonetheless and welcomed me with open arms. The people are the friendliest and most helpful that I’ve met in a long time. They welcome you similar to Latino culture with a cafecito, but their version (Turkish coffee) or with a cup of their amazing Turkish tea. Felt a little like being home.

Photo provided by Olga Maria Czarkowski

Turkey has so much to offer: Vivid colors, the delicious food, a rich history, architecture and culture, along with beautiful views, buzzing streets, great hospitality and the opportunity to learn about so many traditions….what’s not to love?! I can personally vouch that solo females can travel to Turkey. I even wrote an article recently about this topic and I am developing a series of articles to be showcased on my blog about this country and others that I recently visited, like Ukraine. Many of these countries are overlooked as tourist spots but have so much to offer. I hope to inspire others to visit.

LM – How does a travel blog become a business?
OMC – It definitely takes a lot of hard work and dedication. First, you need to recognize who is your audience, what they need help with, what’s your niche, etc. Second, a travel blog is not about staying in free hotels or drinking and eating like most people think. As a travel blogger, you review destinations, experiences, you highlight what you see, so that your readers can experience it through your eyes and hopefully be inspired to take their own adventure, to experience it for themselves.

Like with any other business, you must wear many hats and know and cultivate different skills sets: social media, marketing strategy, negotiation skills, networking, storytelling, finance and more. There are different ways to make money with a travel blog, some are: affiliate marketing, ads, social media campaigns, brand ambassadorship, become a spokesperson, partnerships with destinations, and freelance writing. I am writing more blogging tips on my website and explaining how I started. I have a recent article I wrote entitled, “You call me lucky? I’m self-made…” It’s about how I created a job that allows me to travel full time and do what I love. I wrote it because often times people call me ‘lucky’ and think that I have the perfect job without really knowing the amount of work that goes on behind the scenes. They don’t know how many days I spend on my laptop working on the website’s look, strategizing my next moves, editing videos, writing, etc. I’m not paid for sick days and traveling for work is different than traveling on vacation. When you work predominantly from home and/or on the road, it’s important to strike a balance between your personal and professional goals.

LM – What do you think is necessary for a travel blog to stand out from so many others that exist?
OMC – I believe that it not only needs to have great content, but you must have a unique voice, a niche, and great strategy. Also, developing lots of ways to market and drive traffic to it is key because you could write the best content but if nobody sees it, then what’s the point?!

Photo provided by Olga Maria Czarkowski

LM – Latinas Who Travel, more than a blog is a community … What is the mission and purpose of this project?
OMC – Latinas Who Travel is a bilingual travel community created to inspire and empower Latinas and women of color to travel more and expand their horizons. But all women interested are welcome. That is the beauty of our community, many people identify with our music, passion, cuisine and want to even learn our language. This is why in the community we welcome honorary Latinas. For example, there is a lady from India married to a Latino, or a woman from Luxembourg who loves Latin culture and speaks Spanish fluently, and African American women who were raised around Latinos. This is why this community is not open exclusively to Latinas, but it’s more of a movement and a sisterhood between all ladies who appreciate Latin culture. NOTE: Sorry guys, it’s for women only.

Join Olga Maria and the “Latinas Who Travel” on an adventure to Spain and Morocco this December 2017. Click here for more info!

The idea came about because I realized that during my extensive travels I often did not meet other Latinas. In addition, many times the locals would comment that I was the first person they ever met from my country, and many of my friends and acquaintances always tended to travel to their homeland and/or the same places over and over. Many of them acknowledged not feeling comfortable enough to travel on their own or to travel to unknown countries (which were totally out of their comfort zone). Thus, Latinas Who Travel was born to create wanderlust, to share travel hacks and showcase that traveling is not only for rich people; that travel does enrich you culturally and in many other ways.

#latinaswhotravel – Instagram

Currently, we have over 1,100 members who’ve joined our Facebook community. I’m so proud of how members share their experiences, provide support and encourage one another! It’s truly inspiring.

Click here and join the “Latinas Who Travel” Facebook group today!

We also have an Instagram where we repost daily pictures from latina travelers. And travel can be in your own town, city or country. You only need to use the following hashtags for your photos: #Latinaswhotravel or en español #Latinasqueviajan.

LM – What advice would you give to a Latina who is thinking of launching a travel blog with the objective of monetizing it?
OMC – I would say that it’s totally possible to monetize a travel blog, but if that’s all you are in it for, it’s not the best strategy (since you could probably earn more money doing something else). Things don’t happen overnight. It takes time so you need to have the passion and inspiration to keep going, even if you are not making any money at first. Like I said before, it’s lots of hard work but start by treating it like a business. Create a business plan, find your market, find your voice, a niche and think about how your travel blog can help others.

Photo provided by Olga Maria Czarkowski

LM – What tools do you consider essential for traveling when it comes to creating content and handling your blog and social networks?
OMC – My essentials tools are many, but to mention a few: An external hard drive to backup all my content, my MacBook Air, my camera, lens, external batteries for the camera, extra memory cards, my microphone for recording video, my iPhone, my portable battery charger, a Dropbox account, my portable wifi device (Tep wireless) since I need to always have wifi for what I do. Also, traditional things such as a journal and a pen. I also use different apps later to help me save time or to remind me when to post on certain channels like Instagram or to schedule tweets with HootSuite. You need a lot of tools as a travel blogger!

More about Olga Maria!


A book: The Alchemist by Paulo Coelho. I keep going back to it. It’s a book that teaches you so many life lessons, inspires you and gives you wanderlust. Paulo Coelho’s words are the reason why I left Puerto Rico when I was 18 years old to start my life.  

A blog: I have many that I read. I love to keep up with industry trends and to read other travel stories. I prefer authentic voices. I have to say that two of my favorite blogs (because can’t pick one) are by two fellow women of color: Oneika The Traveller and The Blog Abroad by Gloria Atanmo. I personally have met both of them and not only do their blogs have an authentic voice and useful information, but they are both down to earth people who genuinely care about other people.

I recently spent over an hour with Oneika in Kiev, Ukraine right before heading to the airport. It’s amazing to connect with fellow jet-setters between our crazy adventures around the world. It’s so important to interact with others in your industry and keep in touch.

One “Latina in Media”: Hard to pick one. But I definitely love María Celeste Arrarás, Adamari López and Rosario Dawson. All are fabulous at what they do, and humble persons.

One Social Network: Instagram. I love how visual it is. I can tell a story through it and highlight the magic of each destination, a view, a bite of food, a cup of coffee, an off beaten path site and the locals, one photo at a time.

One App: For cheap flights and random trips, sky scanner, because it allows you to enter your location & travel dates and then it gives you a list of different destinations for your consideration, starting with the least expensive.  For my travels, Google Translate because it allows me to communicate with locals without using data. I can use it offline. For communicating with my friends: Whatsapp. I just love apps!

One YouTube Channel: Currently, one of my favorite videos is not on YouTube but on Facebook, I love Nas Daily. I started watching his one-minute daily videos when he had like 3,000 followers (he and I are Facebook friends). Now, he has millions of followers. His videos are fun and address important issues, plus he is all about the people. The magic of the locals!

One brand: Depends on the type! Tech: Apple, Fashion: Betsey Johnson. I just love her! Beauty: One of my favorite makeup is Cover FX and for Travel: Lo & Sons Camera Bag and Carry-On Bag.

A quote: “Remember that wherever your heart is, there you will find your treasure.” ― Paulo Coelho

Written by Alex Tabar

With more than 10 years of experience, Alex has developed a diverse portfolio containing projects ranging from entertainment to education, creating content for digital media, television, and publications. She has been the producer and co-writer for various documentary films, some of which have been presented in international festivals and have won prizes such as “Best Documentary.” Alex is Youtube certified in their “Audience Growth” program, and is a fan of Mafalda and Willy Wonka.

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