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What If You Always Wonder “What If”?

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Stop Living With Regret & Instead Ask Yourself This One Simple Question It was just two months — actually, 57 days, 10 hours and six minutes — before an epic summer backpacking Europe. The trip was pretty much all my roommates and I talked about; the adventures we’d have abroad. Or maybe I imagined that. Because as I woke up and mentioned over breakfast that it was time to book our plane tickets or risk paying exorbitant fees, they both sharply turned their heads down. “Is there something interesting in your cereal?” I asked, already realizing what they were going to say next. “I can’t go anymore,” they said in unison, the air in the room suddenly stifling. They both gave me excuses — boyfriends, work commitments, lack of funds — but I couldn’t hear them. I just felt an uneasy mix of disappointment and panic. I didn’t want to live with regret, but I didn’t want to go alone. What was I going to do now?  I spent the entire day alone, pondering. Flipping through the notebook I turned to my Bucket List page. Eat pizza in Naples. Take a Flamenco class in Barcelona. Go bungy jumping in Interlaken. This was my summer. I was going to expand my horizons, immerse myself in other cultures, experience things I’d only read about in guidebooks. By this point I practically listed Rick Steves as my emergency contact I’d read so many of his articles. Months of planning and excitement. Gone. Or was it? 
living with regret

Pondering life on the waterfront in Williamsburg, Brooklyn

What If I Always Wonder ‘What If’?

Now I was faced with a decision: stay in New York for yet another summer waitressing and doing what I always did, or hit the road solo and have an unexpected adventure. The idea terrified me; but it also excited me. This was just a couple years after Eat, Pray, Love was published, and I knew the possibilities for self-growth were limitless once you left your comfort zone. I also had anxieties swirling around my mind, so strong my sweaty palms tattered the notebook’s thin pages. What if I lost my passport? What if I got robbed? What if I couldn’t communicate when I needed help because of the language barriers? What if I ended up spending every hour of every day alone for the entire summer because I couldn’t make any friends? And then, the most important question…

What if I always wonder ‘What if?’

That question has stuck with me since this trip, making my decision whenever I feel doubt creep in. It’s the question that led me to book my plane ticket that unforgettable, absolutely amazing summer and it’s the question that leads me to take the often rewarding risks I take today. Because what if I didn’t go to Europe, and always wondered what I’d missed? To me, that thought was the scariest of them all.
living with regret

Taking in the beauty of Lake Bled in Slovenia. Imagine if I would have stayed home instead?!

Never Living With Regret

This is also the question I asked myself when I decided to pursue blogging as career. Now, keep in mind this was 2011, and blogging wasn’t as common as it is today. Instagram and Snapchat weren’t invented yet. Facebook was only for those with college emails who wanted to see where the campus parties were at. Graduating with your Master’s Degree in Communication and then telling your family that, no, you would not be looking for a job with benefits but would be traveling and “blogging” about it for the foreseeable future was not well received. “What’s a blogging?! Is it contagious?! Does it bite?!” is more along the lines of the response I got from loved ones than “Go girl and follow your dreams!” Looking back, I must have seemed absolutely insane to everyone around me. My friends were getting salaried positions with health insurance in Midtown Manhattan and I was booking plane tickets to hike through Chinese rice terraces and do a homestay in Ghana. But these people didn’t see my vision because they weren’t in my head hearing the question bounce from my cerebellum to my frontal lobe.

“But what if I always wonder ‘What if?'”

living with regret

Doing a rain dance in El Yunque. It worked.

Stop Wondering. Start Doing.

I’m not saying you need to quit your job and be a blogger; but if you feel passionately about a certain path in life, take it. And if you want to go to a certain destination but have nobody to travel with, book the ticket anyway. Sure, you may reach for the passion career and fail; but you might also succeed. And you may book that solo trip and hate it; but you might also fall in love in Amsterdam, see the most amazing sunset of your life in Cinque Terre and learn the joys of time spent with oneself and having ultimate control over your itinerary. Honestly, anything is better than wondering “What if?” And if you’re really unhappy on the road, take comfort that paying to buy an early flight home is a whole lot cheaper than living with regret.

Additional Resources:

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About Jessie Festa

Jessie Festa is a New York-based travel content creator who is passionate about empowering her audience to experience new places and live a life of adventure. She is the founder of the solo female travel blog, Jessie on a Journey, and is editor-in-chief of Epicure & Culture, an online conscious tourism magazine. Along with writing, Jessie is a professional photographer and is the owner of NYC Photo Journeys, which offers New York photo tours, photo shoots, and wedding photography. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

Jessie Festa standing in front of grafitti wall

Hi, I’m Jessie on a journey!

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1 Comment

  1. April on at 5:51 pm

    You are absolutely right. Any of us who have traveled solo had the same thoughts when contemplating of traveling abroad for the first time. It is a scary thought. So many unknowns. But that’s life – full of unknowns that we try hard to take control of in our “normal” day to day routines. After traveling solo for many years now, I don’t even hesitate about booking the trip. I want to do it. I want to experience it. I’m going. Going past that initial hurdle is hard, but once gotten past, the world is yours.

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