Meet Jessica Gray | Travel Concierge

We had the good fortune of connecting with Jessica Gray and we’ve shared our conversation below.

Hi Jessica, can you walk us through the thought-process of starting your business?
As someone who is fueled by individuality, creativity, time freedom and independence, I’ve always struggled with working in a corporate environment. While running a business is certainly not easy, I am always grateful for the ability to work how- and when- I choose. I also love the fact that my business, and the way I run it, is a representation of who I am as a person and as an entrepreneur.

Alright, so for those in our community who might not be familiar with your business, can you tell us more?
I am a luxury travel advisor, specializing in crafting customized itineraries all over the world for destination weddings, honeymoons, families and groups. I believe my 15 years in the hospitality industry, as well as my experience as a certified wedding planner, sets me apart from other professionals in the travel industry.

Don’t be fooled by what now looks like a cushy, work-from-anywhere job! It took a lot of hustling, long hours, late nights, early mornings, side gigs and phone calls to get to where I am. I started this business around working full-time, so I had to fit the work in wherever I could. There were many weeks I was working about 80 hours! As my business grew, I was slowly able to back off my other obligations until it became my main focus.

One of the most important lessons I’ve learned is that your happiness should be number one. My husband and I have a saying: “If you’re constantly complaining about it, you need to get rid of it.” I know so many people who stay with jobs, schools or even people when they’re absolutely miserable! I did this for the longest time. Life’s too short. There’s other ways to make money. Figure out what you love and DO THAT! Give up anything that isn’t part of it. If not immediately, then take baby steps to get there. You’ll be happier and thrive in the long run.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
I live on Long Island, about an hour from NYC. I’d tell them to visit at during the holidays, because NY at Christmas is just MAGICAL! We’d see the Radio City Christmas Spectacular, Broadway shows, go ice skating at Rockefeller Center, shop and dine around the Bryant Park Winter Village, walk through Central Park, go window shopping and visit some museums. I’d also take them for grilled cheese and tomato soup at Sarabeth’s, brunch at Boqueria and dinner at Becco!

Who else deserves some credit and recognition?
I’m a firm believer in that “everything happens for a reason.” That being said, there are so many people and instances that have lead me to where I am! I specifically need to shoutout Amanda Bisack, The Chica Travelista, for her incredible mentorship in this industry, as well as Marriott International for inspiring my love of travel when I was first hired with the company back in 2011! I’m also extremely grateful every day for the support of my husband, Jason. Whether he’s keeping me fed or caffeinated, or just being my cheerleader, he is a big part of why I continue to be successful.

Instagram: @travelistajessica

Linkedin: Jessica Gray