Meet Ashley Yashinsky | Travel Content Creator & Advisor | Jetset Travelette

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

Hi Ashley, what was your thought process behind starting your own business?
I think I got to the point that many do in their career, especially post-pandemic, where we question or even realize that if we’re not working for ourselves then we’re really only contributing to someone else’s piggy bank, platform and/or agenda. That just really didn’t sit right with me but the hardest part was figuring out what to do about it.

For nearly a decade, I was a high school social studies teacher and it’s no secret how dead end that job really is. The pay is abysmal, working conditions are infamous, and career and salary advancement doesn’t really exist the way it does in other fields. As the ratchet of societal and political pressures continued to clamp down on teachers, I found myself in a job that was putting me (and my classes) in a tight, tiny, cookie cutter box. I found myself bursting with creativity, but with nowhere to put that energy. I felt that inner light of passion for what I did slowly being snuffed out by an outside force, more powerful than me. And in that realization, I felt some kind of survival mode kick on; this inner determination to protect that tiny spark that was struggling to stay alight at all costs.

There was definitely a level of not pursuing my true passions mixed into all of this. Faced with what I saw as a clash between traditional teaching and my creative wanderlust, I decided I needed to leave the field. In spite of needing to leave, I never wanted to stop being a teacher. I am one by nature. I’m always keen to share about things I love with people who are interested in listening. I didn’t always find that in a classroom. Then entered the prospects and opportunities of social media. I started putting together the idea that I could still teach but on the subject I’m most passionate about, travel, and I could find that audience who’s just as eager to participate. This was something I’d find in maybe 2 out of 30 students arbitrarily assigned to my class, and I found myself often leaning hard on those few students to fill my cup. This wasn’t sustainable. Social media opened up a world where I wouldn’t have to feel like I was squeezing blood from a stone and where I found people worldwide who wanted to learn about the same things I was into. Some of my previous students have even hung around to cheer me on. Today, my cup is filled ten times over.

The thought process behind starting my own business was simple, combining what I have a talent for (teaching) and what I love (traveling) along with allowing for my non-negotiable need to be creative. How can you go wrong with a recipe like that?

Jetset Travelette has become my platform to share my passion for travel with others and maybe even inspire them to give it a go. I absolutely believe that if more people traveled we’d have a greater collective understanding of each other and that the world could actually be a better place to live as a result.

Let’s talk shop? Tell us more about your career, what can you share with our community?
My work is based in continuing as an educator, but through the lens of travel. I love to discuss anything travel related from tips on destinations, good eats, and fantastic hotels to pointing out local culture and history. I understand that travel can be pretty overwhelming which is something I try to demystify by sharing what I learn. You’ll find that my content simply gushes over why you should love a place for that reason.

Much like lesson planning, I love planning trips. I’m happy to offer that to people looking to have the work done for them. I have an extensive network of hotels and other travel industry companies (think safaris to ski trips) that I work with to get my clients killer perks i.e. room upgrades, complimentary services, and more. My insider knowledge and personalized travel recs build out trips completely tailored to you. (More info on my website)

For those who prefer to DIY their own travel plans, I’m happy to guide their globetrotting too. I’ve designed a Traveler’s Toolkit, which has a collection of templates to help you through the planning process to set up your dream itinerary. These are the same tools I use as a travel advisor but since I was a teacher, I had to make it into a pretty workbook. It even includes a travel journal to document your trip. (More info on my website). I’m here to support traveler’s of all types, even if you simply want to be an armchair traveler through my social media feeds.

Becoming a travel content creator from a high school social studies teacher was a pretty natural pivot. The two actually have quite a bit in common. Now I get to expand and dive more deeply into cultures and history that I’m interested in. I get to learn on the ground rather than being boxed in by a curriculum guide or a textbook, which are both dictated by someone else.

I want to set an example mainly for my past students but more broadly for anyone who feels unfulfilled in their work and/or life, that running towards your passion is it. No matter what it is or how impossible it seems, your most prized passion is really the only thing worth investing your time and energy in.

My greatest struggle in building my business has honestly been an inner battle with myself. I am constantly questioning and tinkering with my own methods. But it brings me joy. Hard earned joy, I mean, if it wasn’t, would I be here writing about it? Challenges will always continue to arise, even when you become aligned with your purpose, but being present and learning to appreciate the process allows worries about the future or past fade into the background. Failing is just learning and you can’t succeed without learning (says the teacher). My best advice is to fail. Often.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
I’m actually based in Tampa Bay, Florida, yet despite living on the East Coast, I have an incredibly deep love for the West Coast. When in San Diego you can find me in a few of the usual haunts. Balboa Park being one of my favs. I love wandering around, admiring the architecture and multiple gardens. The Museum of Us is an absolute must. It’s one of the most inspiring museums I’ve ever visited. Obviously, La Jolla is super special. We don’t have sea lions or otters on the East Coast, and I’m perfectly happy spying on them from the cliffs all afternoon. The Cave Store in La Jolla is such a cool way to view the Pacific from a cave in the cliff. Then, you can grab some bougie artisanal tacos right down the street at Puesto. A sunset from the top of Mt. Soledad National Veterans Memorial gives you a bird’s eye view of the city winding down for the day, or you can check out the perfectly named Sunset Cliffs. Finally, hit up the Gaslamp Quarter. Many go there for the nightlife, but I’m more intrigued with the Wyatt Earp history that went down in this part of town. My favorite hotel I’m partnered with is the Hotel Del Coronado (contact me about perks if you’re looking to visit). Not only is it iconic, it’s beauty and history are worth a deep dive.

Who else deserves some credit and recognition?
There are so many people who have contributed to my story. My mom instilled in me early on that happiness can be achieved in life if you find something you love to do and find a way to make a living doing it. Those words ring through my mind as I continue this journey, and were the number one reason for me to walk away from a depleting career and take a shot at something steeped in personal passion. My students made me believe that I have something to offer the world and my friends have held the beacon to light the way when I didn’t believe in myself. I have a support system of loved ones reminding me daily of the importance of pressing on with passion and individuality, in a world that seems to try and strip that from us. Shoutout to the ones who’ve stood by my side and who’ve believed in me, specifically Angela, Teresa, Stephanie, and Joy. They’ve undoubtably fanned a once dying spark into an enduring flame.

Website: www.jetsettravelette.com

Instagram: @jetsettravelette

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

Youtube: https://www.youtube.com/@jetsettravelette

Other: For Travel Planning: https://www.foratravel.com/advisor/ashley-yashinsky For the Traveler’s Toolkit: https://jetsettravelette.com/shoutout-socal-special