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

Hi Jessie, can you walk us through the thought-process of starting your business?
I started my first travel blog, Jessie on a Journey, in 2011, with the goal of empowering women to confidently travel the world solo.

Funny enough, I never really dreamed of traveling solo myself; however, during college my friends bailed on a summer backpacking trip through Europe. Instead of giving up the trip, which I was incredibly excited about and had spent weeks planning, I decided to go on my own.

It ended up being the best decision I’ve ever made, and ultimately led to me realizing that I truly had the power to design my own life. As a travel lover, I didn’t need to wait on others to visit the places I wanted to go. I could book the trips that I wanted, and enjoy them in the way that I wanted.

For me, it felt like ultimate freedom, and I really wanted to share the joy of solo travel with others who may be nervous to travel alone.

And while my business has shifted over the years to also offer travel blogging courses and NYC photo tours, at its core it’s still about empowering people, especially woman, to see the world.

Let’s talk shop? Tell us more about your career, what can you share with our community?
As a travel blogger, my goal is always to create content that truly helps people. When I’m writing a story or travel guide, I always start by thinking “What do I want to help people accomplish by writing this, and what questions do people need answered to make it happen?”

Coming from a place of service is something that really excites me in my business, as it’s ultimately what helps me feel like I have a purpose.

Additionally, listening to the questions and needs of my audience has led to the birth of other exciting projects.

For instance, after having countless readers ask me how I actually went about starting a profitable travel blog, I started an online blogging school that currently has over 7600 students.

This school includes my Travel Blog Prosperity membership, which I affectionately call “my baby” as it’s one of my proudest creations. I believe that along with education, having a community to learn from, network with, and lean on for support can really be *the thing* that helps us get to where we want to go.

Additionally, after having many readers ask me to show them around my home of New York, I started NYC Photo Journeys, a photo tour and experience company that always provides people will professional photos around the city. I’m passionate about showcasing the beauty of New York, and it’s especially fun when doing this with fellow travel lovers in my community.

In terms of lessons I’ve learned along the way, one of the most important is to listen to the needs of your audience. Personally, I keep a running list of the questions, comments, and DMs I receive. From there, I look to find the most common questions and problems — and then create products that solve them.

Also, if you’re starting a blog specifically, realize that writing in itself does not lead to income. Yes, your content can be profitable; however, you’ll need a plan to really make money blogging. This means implementing revenue streams and using your content to support those.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
With a week in NYC, I’d mix a few of the popular sites with some non-touristy activities — and I’d definitely suggest exploring beyond Manhattan to experience the other boroughs as well as nearby destinations like Long Island for beaches and wine country and the Hudson Valley for hiking and countryside fun.

A few of my favorite popular sites include the Statue of Liberty and Ellis Island to really understand New York’s history, as well as Central Park, which is beloved by locals and visitors alike. Have a picnic near Turtle Pond for a view of Belvedere Castle, go bird watching in The Ramble, and check out what events are happening on the park’s website. If you’re visiting during summer, SummerStage brings loads of free concerts to the park.

That being said, know that Central Park is one of over 1700 parks in NYC — the largest of which is actually Pelham Bay Park in The Bronx. If you enjoy nature, spend time exploring some of the other parks. Personally, I love Randall’s Island, Prospect Park, and the waterfront Carl Schurz Park.

If you love museums, check out the many museums on Museum Mile in the Upper East Side, as well as other incredible institutions like the Tenenment Museum, the Brooklyn Museum, and the City Reliquary — possibly the quirkiest museum in NYC.

Looking for fun free things to do? Wander the street art of the Bushwick Collective, take in a Statue of Liberty view from the Staten Island Ferry, or walk the art-filled High Line — an elevated park that used to be a rail line.

Of course, food and drink is also part of the NYC experience. Have a rooftop cocktail at Westlight, enjoy a budget-friendly boozy brunch at Siena Cafe, dance all night at Brooklyn Mirage, and discover some of the city’s best eateries at Time Out New York Market in Brooklyn and Chelsea Market in Manhattan.

As an NYC local, tour guide, and tour operator I could talk about things to do in New York for days. These are just a sampling of my favorite experiences.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
In 2011 when I started Jessie on a Journey, the idea of blogging as a career was pretty new. And while my parents didn’t quite get it, especially as I had a Master’s Degree that they thought I should be using, they also supported my dreams once they knew I was serious.

It certainly wasn’t easy seeing their young daughter fly off to Europe, South America, Asia, and beyond on her own, and while they expressed their concerns, they also excitedly shared in the trip planning process.

Once I launched my blog, they were my first readers, email subscribers, and social media followers — not to mention my dad carried my business cards around and handed them out to literally everyone he spoke to (lol).

Starting an online business can be difficult and isolating, and having support and people who believe in you, especially before you’ve grown an actual audience, can mean everything.

Website: https://jessieonajourney.com

Instagram: http://instagram.com/jessieonajourney/

Twitter: https://twitter.com/JessonaJourney

Facebook: https://www.facebook.com/jessieonajourney/

Youtube: https://www.youtube.com/user/jessieonajourney/videos

Other: TikTok: https://www.tiktok.com/@jessieonajourney TripAdvisor (for NYC Photo Journeys): https://www.tripadvisor.com/Attraction_Review-g60827-d9826452-Reviews-NYC_Photo_Journeys-Brooklyn_New_York.html

Image Credits
Jessie Festa (I own the rights to all of these images)

Nominate Someone: ShoutoutSocal is built on recommendations and shoutouts from the community; it’s how we uncover hidden gems, so if you or someone you know deserves recognition please let us know here.