NJMOMpreneur: Anna Fishman, Olegana Travel Boutique


Anna Fishman grew up in a small town in Eastern Europe, studied abroad in Spain and Israel, and lived in New York City for 16 years before settling down in the suburbs of New Jersey. With her natural urge for globetrotting and exploring, Anna Fishman, began helping families enjoy curated travel experiences through her company, Olegana Travel Boutique. Today, she travels alone or with her family and scouts out the best hotels, tours, and resorts at destinations all over the world, so when her clients are looking for the best all-inclusive beachy resort in Mexico, she knows precisely which one to recommend. We’re inspired by her go-getter approach to life and her passion for helping others create life-long memories. Anna sat down with NJMOM to discuss her plans to take educational destination courses next year, as well as her favorite spots to visit with her family around New Jersey, like Van Saun Park.

Creator of Olegana Travel Boutique & NJMOMpreneur Anna Fishman

Fulfilling her wanderlust via Anna Fishman

NJMOM: What do you offer to your clients and how is it different than other professionals in your field?
Anna: My company, Olegana Travel Boutique, makes families happy. I believe every family deserves stress-free vacations that they remember and talk about for years to come. I create trips with unique and authentic experiences for the dads who work overtime to get that promotion and can’t add another item like a vacation planning on the to-do list, the moms who do not have enough time after work and the activities of their children to have to plan one more thing, the newly wedded couple who is busier than ever making plans to bring their lives together. They all pour into their family and work, and there isn’t much time left for travel or adventure. They desire a family getaway to make memories and take a break from the pressures of the outside world, but the research and planning involved are too much. It’s easier to just let year after year go without taking a break or to throw together travel plans with the short amount of time they have but never getting the most out of their trip. 

I offer them unparalleled first-hand experience of having traveled to a lot of destinations myself and with my family, where I have relationships with the local travel companies that can take care of any unpleasant situations, who know the lay of the land and will create completely custom made experience tailored to that family’s interests and dreams. These types of experiences can’t be bought with a few clicks online. They are created for that specific family in mind.

Don’t wait for your kids to be 5 or 15 or 25 to travel with them. Just go. Go for a week or a month or a weekend. It will be the best thing you have ever done with them. I promise you that. But also embrace slow travel: breathe, listen, indulge.” – Anna Fishman, NJMOMpreneur

NJMOM: What inspired you to get into your line of work?
Anna: After getting married and having my son, the corporate world in which I spent many hardworking years soon lost its appeal. No longer was I making time for the things I loved. No longer was I waking up feeling alive and ready to tackle the day ahead. I had so much to offer but no direction for my go-getter approach to life. I knew I needed to make a change. I always wanted to have my own business, but I thought that I had to discover a unique idea or product that had never been seen or done before. Then I decided to ask myself this hard question: “If money wasn’t an option, what would you do?” The answer was simple: travel the world! Traveling has always been in my blood. I’ve been globetrotting since I was five-years-old and have been to 25 countries and counting. I grew up in a small town in Eastern Europe, studied abroad in Spain and Israel, and lived in New York City for 16 years before settling down in the suburbs of New Jersey.

I was met with immediate obstacles — a young child, a mortgage, and a working husband. Picking up and traveling the world wasn’t the easiest option. But I refused to extinguish the dream. I asked myself another question: “What was the next best thing to traveling the world?” Boom. It hit me. The next best thing was helping others plan their next adventure and using my travel expertise to gift families a chance to make memories that last a lifetime. My business track was set. I started with little knowledge other than my personal travel experience and a Google search about how to start a travel agency. But I knew it wouldn’t take long once the go-getter within me had her way in my business. Soon, I felt alive for the first time — pouring into my family and my business and working harder than ever. I would do research on my commute to and from work, and I would miss my train stop because I would be so immersed in what I was doing. I was so excited to learn about the travel business and to use my already long list of personal travel experiences to benefit others. 

Anna with her family in Portugal via Anna Fishman

NJMOM: What is your favorite part about your business?
Anna: The flexibility of living my life, being with my family and son and running my business on my terms is priceless. Also working in my PJs and commuting for 15 seconds from my bedroom to my home office.

NJMOM: What is your background in your business expertise?
Anna: Having traveled since I was a little child, I have close to 30 years of first-hand travel experience that I draw from every day to create experiences for my clients. Now, I travel professionally, where I go to a destination for a few days just for the purpose of inspecting hotels or meeting with tour operators. For example, last year I spent 5 days in Jamaica and 5 days in Mexico touring and inspecting 4-5 star all-inclusive resorts. In those 10 days I have visited close to 30 resorts so when a client calls and says I want a lush tropical resort, with amazing food, hammocks on the beach and peaceful wellness vibe I know exactly where to send them.

NJMOM: What are you most proud of in your career?
Anna: Having the guts to follow my heart and quit my corporate job/life.

NJMOM: What is something few people know about you? 
Anna: When I was 15 years old I was featured on the cover of NY Times magazine in an article about my family and our first year in New York as immigrants. 

Exploring Sintra, Portugal via Anna Fishman

NJMOM: What can we expect from you next year – personally and professionally?
Anna: I love this business because it allows me to continue growing, learning, experimenting. I am going to be traveling a lot, alone and with my family, my husband and soon to be 4-year-old son, inspiring other families to travel no matter what. Nothing compares to the gift of travel, showing your kids the world outside of where you live, opening their eyes to other cultures. It is priceless. I am planning on taking some continuing education courses specific to Hawaii, Italy and Greece destinations so I can be a true expert.

NJMOM: What charitable cause are you most passionate about?
Anna: I am most passionate about St. Judes Children’s Research Hospital. It breaks my heart to see sick kids, especially now that I am a mom I can relate so much more to the families that are going through rough times with kids battling cancer.

Seeing Nazare, Portugal via Anna Fishman

NJMOM: Do you have a favorite quote you live by? Why is this quote so important to you? 
Anna: It’s not a quote, more like a mantra, not to have any regrets. Things happen for a reason and if you make a mistake, try to learn from it and move on, tomorrow is another day.

NJMOM: What are your favorite things to do in New Jersey with your family? 
Anna: We are always exploring. I love that NJ has so many parks, farms, outdoor areas. My son, who I call an outdoor cat, loves being outside so when the weather is cooperating we are always exploring a new park. Our favorites are Van Saun Park and Turtleback Park. Both have train rides which my son loves.

NJMOM: What is the best part about being a mom for you?
Anna: I remember when I was pregnant, it felt so surreal that I was growing a human inside of me. I remember telling my husband that if I never get to do anything else with my life just being able to create a human is such an accomplishment. Now, that my son is almost 4 (and my hormones are back in check ;), I love watching him grow and discover the world for the first time. It is so priceless.

NJMOM: What are your favorite businesses in New Jersey?
Anna: We spend a lot of time at kids gyms – 1Gym4All in Waldwick, JumpingJax in Paramus, because my son can’t be cooped up indoors when it is cold. Restaurants – if not for Red Bowl Asian Fusion Restaurant that is around the corner from my house I would probably starve. In the summer we hang out at the Waldwick Whistle Stop Ice Cream Shop. It is right next to the train station so my son can watch the trains come in and they have a wooden train on their lawn for the kids to play with and crawl on top so it’s always fun.

Anna, her husband, and son via Anna Fishman

NJMOM: Where do you reside and vacation in New Jersey?
Anna: We live in Waldwick but vacation worldwide. I love the peacefulness of our town, but also the proximity to the hustle and bustle of New York City.

NJMOM: What advice might you have for a fellow NJMOMpreneur who is just starting out?
Anna: Don’t give up, you are in this for the long haul so patience is the key. Set up goals from weekly goals to annual, 5, 10, 15 years out goals because you can’t know if you got there if you don’t know where you are going. There will be hard times, there will be times when you will feel like no one understands you, you will be questioning everything you ever knew, but if you believe in yourself and your dream, just power through it, tomorrow will be a better day.

NJMOM: Anything else you’d like to tell moms in New Jersey?
Anna: Don’t wait for your kids to be 5 or 15 or 25 to travel with them. Just go. Go for a week or a month or a weekend. It will be the best thing you have ever done with them. I promise you that. But also embrace slow travel – breathe, listen, indulge. When you do get to go on vacation, don’t try to jam 5 cities in 10 days. It’s not about passport stamps, it’s about lifelong memories! 

For more information on Olegana Travel Boutique, follow along on Facebook and Instagram.


About Author

Erika is a yogi, writer, coffee enthusiast, and world traveler. If she's not at the beach or chasing the sunset, she's looking for the best iced coffee she can find and planning her next adventure. Her favorite NJ spots include The Saint, Island Heights, and Lava Java House.