Truth in Travel & Tradeoffs


Free as a bird with no place to land.

You’re twenties can be a difficult time even if you’re having fun. Trying to navigate which path you want to go down when for many of us, the options are truly endless. Post school things can look very daunting. Like you’re in the middle of the forest and you don’t know how to get out. Should you drop everything & travel the world while you’re young? Should you put that expensive degree to work? Should you move home or move out? If the answer is move out the question becomes where. It can all be very overwhelming. You’re told for years where to be, what classes to take, what friends to have and how to be. For probably the first time ever you are in control. Or out of control. If you have even minimal savings, a whole lot of will, or a car… something… you can do anything you want to.

When I graduated college it was May 2020. Peak Covid and no job lined up I started waitressing a few hours from home at a club that provides free housing. With accommodation taken care of and a 6 day work week I was able to stack up a decent amount of dough. Seeing as it was just a summer job, I left in early October. I had just found out my first love had another girlfriend. It’s funny to look back on this because I was truly devastated, but now I can barely remember what he looked like or a single conversation we ever had together. I always knew I could do anything, but with turning 20 and for the first time having a credit card and financial freedom, I booked a one way trip to a small island in the middle of the Pacific Ocean called O’ahu. If anyone knows anything about Hawaii those islands are expensive and my savings depleted quickly. I managed to supplement income though and between very minimal yet very profitable online work (wink wink) my 4 hour work week brought in hundreds a week. I was running around the island in a bikini all day every day. I would surf and watch the sunrise and the sunset. I hiked until my legs were shaking. I was genuinely very happy with not a single care in the whole world. It was not a realistic way of life though. It wasn’t fake per se.. but it wasn’t real and it certainly wasn’t sustainable.

I soon grew tired and weary of selling what I was selling online. I grew tired of the men and bored of the sun. I got increasingly agitated sharing a small space with a too many girls and a big part of me wanted to go to work. Turns out you really can have too much of a good thing. I decided to head back to my job in the Hamptons for “one more summer.” I met a boy. Moved him to Hawaii. Learned a lot, far too much to disclose here. Reality hit me. Harder than he did. Most of my friends had move off the island, many got jobs and weren’t free to frolick around the place like we used to. People were growing up. Life isn’t just an endless beach party, I so sadly discovered. Out of money, out of options, and desperate to get away from my relationship, I went back to my comfort working at a club on the beach in New York. One more summer I said, then I’ll get a “real” job.

In your twenties you really can do anything, despite what books or people may tell you. This is why you should make all of your major decisions with meaningful intention behind them. I didn’t always do this, I still struggle with it now because I want to fly and I do. I tend to fly so high and far I don’t realize I’ve no place to land. I woke up one morning in October and realized I was 22 and had no idea what I wanted to do with my life, I didn’t even know where I wanted to live. So without any real planning or job out West, I hopped in my car and drove from New York to Las Vegas in my 2009 Nissan Versa. No surprise I only lasted 10 days out there. I hated the desert. I spent the rest of my savings moving myself to LA. I liked LA a lot better. There was so much to explore and I took weekend trips whenever I could. The service industry gives you a lot of flexibility to do things like that. I made enough in tips and hourly that I worked Thursday through Sunday and had off Monday through Wednesday. If I ever needed more money I could just pick up a shift. Similar to my experience in Hawaii, this isn’t really a sustainable way of living.

I did a lot of trips over that winter, I drove to the Grand Canyon, Zion National Park, San Diego, San Francisco, Yosemite National Park, Joshua Tree, Maine/ New Hampshire, the Big Island, and a few more day trips but you get the idea. I took every opportunity I had to go see the world around me and explore everything I wanted to… and still, I had trouble. Financially all these trips drained me down to my last dollar every month. I thought “well, I make enough to cover my bills and my trips” and in reality I did. However, would only have about $30 maximum left over to “save”. See, no matter what way you look at it, traveling costs money. It just does. Really everything costs money. Take my trip to Joshua Tree for example. I slept in the desert in the freezing cold in my tiny beat up car by myself to save money on accommodation for the evening. This trip still wasn’t free though, it cost me at least $200 in gas, if not more. There are absolutely ways to cut costs but you can’t eliminate them completely. Even with work exchanges or programs like world packers, there will always be some sort of cost.

Tell you what though, I’d rather pay $500 for a plane ticket and do a volunteer/ work exchange in a foreign country than spend $1,500 in rent plus utilities. And a car payment. And groceries. And gas. And whatever else people are paying for these days. No matter how you live (unless you’re realllly living off the land) you need money. May as well spend it on seeing the world if that’s the sort of thing you’re into.

My life looks amazing on Instagram, I’m proud of the photos that I’ve taken and the part of my life that I’ve shared. People reach out every now and then to ask how I do it and I never really know what to say. On one hand I do love my life and how I live it but there are drawbacks that people don’t think about when they decide to “quit their job and travel the world.” Firstly, I’ve never had a job besides being a waitress. I’m not trying to diss the service industry, it’s given me so much freedom and experience, just not something I personally want as a “forever career”. It’s a slippery slope when your “summer job at age 20” becomes your only job at age 27. I always say “one more summer” and in the blink of an eye I was the most experienced server there. Everyone else had moved on and I found myself surrounded by teenagers who weren’t sure if their fake ID would work to buy drink. My best friend from high school (who is a year below me) got her first big girl marketing job out of college two weeks ago and moved to Ft. Lauderdale. My little sister just finished grad school. Everyone else is making moves in their professional life and while I thoroughly enjoy what I do, I know that I have not one thing on my resume that future employers and a company will look at and think “we have to hire this girl!”

I don’t know what career I want. I know that I love to write but the odds of getting a book published in this day and age is somewhere between 1%-2%. I have no clue what I want to do. The “I can do anything in the world” mantra I’ve lived off of for years is becoming less of an inspiring manifestation and more of a daunting terror. Realistically most people start at the bottom of the food chain in any job. Doing full time travel and focusing less on a career means that if I do want to join the work force one day, I may be a 28 year old answering to my boss who’s 24. I always used to pride myself on being the youngest in the room. Graduating high school and 16 and college at 19, people were in awe and impressed. Even at my country club job I was the youngest.. until this year. Time moves on, newer and younger move in. I don’t want to be doing this in 2 years which means change has to happen now.

I guess I’m sort of pouring my fears and uncertainty into this piece and I hate to be so anticlimactic but I don’t have an answer yet. See, the trade off for traveling the world is that I’m working in the service industry which provides me both the funds and the flexibility to have this life I love. I would find it difficult to do World Packers (which I love doing because I meet new and like-minded people in hostels) and also have a remote job. Time zone changes, travel days, lack of privacy… Not exactly the ideal environment for taking a meeting. The job would have to be very forgiving and understanding of my lack of wifi in parts of the world and jet lag.. working from an airport. Never mind the fact that I wouldn’t be able to log in at certain times because it might conflict with my schedule working at whichever hostel I’m staying. This isn’t to say people can’t work remotely and budget travel but without having a decent resume or a connection, I’m finding great difficulty doing so.

Living out of a backpack, 45+ travel days to get the cheapest flight, lack of privacy, lack of ability to start a meaningful career, falling “behind”, missing holidays, the life of a full time traveler isn’t an easy one. I can’t tell you how many times I’ve cried buckling under the stress of figuring my life out. The days of zip lining though the jungle and skydiving over the ocean and outnumbered by the days of looking at $12 in the bank and crying in the airport because I haven’t had a moment to myself for 2+ months. I used to think “that’s your twenties” until I saw “everyone else” at peace in their jobs and with their friends. I’m great at making friends, I do so with ease. I’m absolute shit at keeping them. I’m always moving and traveling that I miss events and birthdays and then I blink and it’s been 3 years. I find great difficulty meeting people on the same wave length as me. Like I said, I love (to the moon and back) all of my friends. I really do. It’s just hard sometimes when they don’t understand why I’m doing what I’m doing. Hostels provide the opportunity to meet people who are also doing what I’m doing and somehow things just make more sense.

It took me a long time to realize not everyone wants to travel the world. People don’t want to spend their days of a crowded budget friendly bus in Asia somewhere or share a bunk bed in a hostel with 12 other people in the room. They don’t have the desire to have no answer when asked the simple question of “where do you live?” They want to start a career and be able to buy a home before they’re 30. They want to set up a life for themselves and their partners and future children if they don’t have them already. As my little sister put it “I like getting up and going to yoga everyday. I like the consistency of knowing what my day will look life. I like consistent income and stability.” It’s not that I don’t want these things because honestly that life sounds amazing. I just don’t think I’d be happy with the thrill of not knowing what each day will bring. The excitement behind exploration and the connection behind meaningful friendship from people who understand you.

Reality is a hard thing to grasp sometimes, but before embarking on adventure it’s a good idea to reckon with it. For example, I have to be okay with the fact that because I frolicked around Hawaii for 2 years while my younger sister was in school, she will probably out earn me for the rest of my life. It’s difficult to catch up in a career path (not impossible but you know what I mean.) I have to understand that I will most likely not be a homeowner before 30. I don’t have real identity capital from the last 3 years besides waitressing (I will be changing that this year though!) I will have to stay in the flexible serving industry if I can’t figure it out remotely because it’s important to me to have flexibility while I’m traveling too (i.e. not wanting to be locked into a job abroad). I don’t want to be living im hostels when I’m 28 (not that there’s anything at all wrong with that, this is just me talking about what I want in life, live in hostels forever if that’s what you love!)

If you’ve read down this far you probably never want to get on a plane again. You’re probably already applying for jobs in another tab but here’s the curveball:

This is how I am 100% sure I am on the right path.

All of these drawbacks and “tradeoffs” the truth behind it all… I want it. Every tear shed or hard travel day I have ahead of me, every dollar I spend is worth it. I can accept all of this and still feel in soul that this is what I’m meant to do right now. Could I go get a job and save up and grow with the company and take a 2 week trip to Cancun in 4 or 5 years? Sure, I could probably stay in a really nice hotel by then too. You can travel even if you have a career but I just know i’m my heart that’s not the path I want myself on right now. There are no guarantees in life, I just feel this is right. You could start a career and have the time of your life in your 30s traveling around with disposable income. You could have the career and disposable income and wish you did your travels 10 years ago. You could be the kind of person that doesn’t want to travel at all. Just make sure everything you do is for the right reasons and make sure you understand you are signing off on these “tradeoffs.” Part of me doesn’t even want to call some of these drawbacks because I actually quite enjoy the “hardships” of travel. Sleeping on the airport floor and on a 30 hour train. I digress. Follow your heart and trust yourself, and most importantly be confident and know that no matter where you go you’re only a phone call, click, and a flight away from where you want to be.

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Moving to a New City by Yourself

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Moving Across the Country (Again)