Today we’d like to introduce you to Jenny Oswald.
Jenny, we appreciate you taking the time to share your story with us today. Where does your story begin?
In May 2023, I embarked on my first real post-pandemic international adventure- Australia for a family wedding! It was on that trip to Australia, between touring the Sydney Opera House and snorkeling in the Great Barrier Reef, that I realized how much I had truly missed traveling the world: meeting new people, trying new foods, and learning about new places and cultures. I decided then and there that I needed to find a way to make travel a bigger part of my life again.
When I returned home to the States, I immediately began to research. Maybe I would be a travel agent? I didn’t know much about it – did anyone even use travel agents any more? In short, I learned, the answer is yes. But it seemed that most travel agents were highly specialized. Many were focused on luxury experiences, plenty focused on cruises, and even more were experts in Disney or other theme parks. Don’t get me wrong, I love a Disney trip as much as the next person, but it seemed to me that these set ups weren’t addressing the type of travel that I loved to do. I knew there had to be a way to help others who travel more like me. I dreamed of helping to build all types of trips – maybe a luxury honeymoon too, but also a European backpacking adventure, a hidden gem staycation road trip, options for those with varying budgets and interests. To build a niche of my own – essentially, no niche at all.
And so, Go with Jenny O was born! I provide a fully customizable service that fits the needs of each client individually. Consider me your travel research assistant. I help clients with as much or as little of their trip as they request. Sometimes that means we start at square 1 with a brainstorm on where to go based on the type of vacation they are dreaming of. Other times it means only doing some research on activities for an already half-planned vacation to help get them over the finish line. No matter what the trip is, I make sure to understand who my clients are. A key step in my process is the intro call. On this call, we go through questions to help define what I call your “travel personality.” It’s not just “what do you like to do” but it’s also “are you an anxious traveler?” “are you an early bird or a night owl?” “how busy do you like to be throughout the day?” “how often do you want to move between sleeping locations?” And so on.
The reason for this is that travel is not one size fits all. A dream trip for one group could be a nightmare for another. Some people want adrenaline and others want as much ease as possible. There is no one “best” recommendation, so I need to truly get to know you so that I can recommend what is best for you. The only recommendation I can make that is true for everyone is that you can and should travel. It doesn’t have to be far or for long, but you will only grow from getting a change of scenery.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Go with Jenny O has been a small side project for me for the last few years. However, a few months ago I was laid off from my full time role and decided to use this moment as an opportunity to try and expand my business. Learning about marketing and reaching new folks who could benefit from my services has been the biggest struggle of starting my own business! There is no clear instruction manual to working for yourself and building a client base – and it takes time!
Can you tell our readers more about what you do and what you think sets you apart from others?
What sets me apart from others is that my professional background is in event planning and leadership development. As a result, building strong relationships is at the core of everything that I do. My travel planning work with Go with Jenny O is fully customized – every itinerary is based on the individual client and their own wants and needs. I truly work to get to know you and make sure that we design the perfect trip for YOU.
What do you like best about our city? What do you like least?
I have lived in the Philly area my entire life! I love how proud everyone in Philadelphia is to be from here. There is so much to do and see – and we have such an amazing food scene. We can often be underrated by outsiders but we know how great it is here and are not shy about making sure others know it!
Contact Info:
- Website: https://gowithjennyo.com
- Instagram: https://instagram.com/gowithjennyo/
- Facebook: https://www.facebook.com/gowithjennyo
- Other: https://substack.com/@gowithjennyo
