Book the Damn Flight and Just Go

Issue #10 · In maybe the least surprising statement ever, I’m a sucker for a good travel blog.

In maybe the least surprising statement ever, I’m a sucker for a good travel blog.

I don’t mean those “Top 10 Things to Do in Madrid” type listicles, but rather intimate stories from adventurous folks who’ve deviated from the status quo, done cool shit and want to share how it’s affected them. Life-altering reckonings, bucket list augmenting tales and gooey self-growth type pieces — to me, that’s the good stuff.¹

I also like writing them, or trying to at least (imposter syndrome alert! 🚨) Go ahead and roll your eyes, but travel really does change you. I’m not the same person as back before I was initially mauled by the travel bug, and that’s a good thing. In fact, there’s nothing I love more than taking a peek into an old journal, a buried email or a dormant group text to remind myself exactly what that younger, naïve-r Emily was thinking.

In my very first ever blog post, I touched on my nomad origin story, but left out the nitty-gritty. Since I’m on a brief travel hiatus at the moment, I decided to soothe my itchy feet by diving into the dusty corners of my inbox, unearthing a specific exchange from the Spring of 2017, the first real concrete evidence of my travel aspirations.

At the time, I was on year six of living in Baltimore, Maryland (a decade if you count college), and things were feeling a bit stale. I love Baltimore. It’s absolutely one of the places on this earth that I consider home. I have tons of friends — family — there, and a collection of happy memories a mile wide. Contrary to it’s rough around the edges reputation, it’s a super fun, down-to-earth city that I highly recommend if you’ve never been.

But I digress, because at age 27, I was bored, single, and working a cubicle job that I loathed. The cracks in my long-term future in Charm City were starting to form — I wanted something new, something exciting, and a change of scenery that didn’t consist of moving to the suburbs and getting a dog like the rest of my friends. I wanted to see the world.

I already had a mini taste of what it would be like to live abroad. My brother had spent most of 2015 living in Amsterdam, of which I was immensely jealous. I visited him on a typical American-style whirlwind Eurotrip, squeezing four countries into just sixteen days. I only spent a few days in Amsterdam, but once I saw his cute little Dutch apartment, his two-wheeled means of transport and his favorite local café (errrr — coffeeshop), I was hooked. After two of the most fun weeks of my life, I spent the entire next year campaigning my friends back home to make international vacations an annual thing.

Unfortunately, something else tends to happen in your mid-to-late 20’s — you sandbaggin’ son of a bitch, it's wedding season! Enter extravagant bachelorette parties and expensive gowns that “you could totally wear again if you get it hemmed!” Don’t get me wrong, I had a blast on what I refer to as my 2016-2018 American Spring Break City Tour — Charleston, Key West, Newport, Scottsdale, Miami, Vegas — hilariously fun times. But those trips left zero vacation days and zero dollars in the budget for backpacking around South America or jetting off to Bali, which is what I secretly really wanted to do.

Now, back to this pivotal email exchange dug up from the Spring of 2017:

My most adventurous college friend Caitlin — who, very much like my brother, made me insanely jealous with her exotic trips to Japan and Cambodia and Cuba, and even got engaged to her lovely husband while in Ghana (naturally, they’re living in Stockholm right now) had forwarded me an article about something called Remote Year, a company that organizes trips for 20- and 30-somethings to travel abroad while they work remotely. I couldn’t believe something so perfect existed. This was EXACTLY the exhilarating “next thing” I was seeking to cure me of my Baltimore jade.

At the time, I was still handcuffed to a 40-minute daily commute and a suuuuuper important (/s) corporate job — but that didn’t matter. I scheduled a call with a Remote Year rep to find out more about the program immediately. I remember chatting with a dude named Will who joined our Skype call from a beach town in Brazil, while I joined from the walk-in closet of my Baltimore bedroom. Yep, literally from the closet.

Back then, even just scheduling this exploratory Skype call seemed absurd, so much so that I took the meeting on stealth mode in my closet in order to prevent my roommate from eavesdropping. In my mind, the one-way flight was booked, suitcase packed, passport stamped, but I was terrified to tell anyone that this was what I wanted to do. Who was I to have ambitions of traveling the world? No, I was supposed to continue going through life’s motions on zombie mode, playing by the rules that society dictated, and wasting away in a corporate job that I hated, because that’s just what adults do.

Now, I never actually signed up, citing in a reply email that it just wasn’t a “good fit” (it was literally a perfect fit) and my lack of a remote job (which was a valid excuse). But the damage was done. I had dipped my pinky toe into what this adventurous alternate life could look like and there was simply no putting those wanderlust-riddled worms back into their boring old can. A year later, the travel bug inside me had metamorphosed into a rabid parasite, and I basically went through this entire process again with a competitor company called WiFi Tribe. But this time I was ready, armed with a remote job after having recently escaped the 9-5 cubicle life — it was all part of the plan.

I had my sights set on Lisbon and Barcelona, as WiFi Tribe was running trips there that fall. The stars were beginning to align — my Baltimore apartment lease was ending, I was in the clear from wedding obligations and I finally had the freedom to work remotely. But after a few weeks of overthinking things, I chickened out yet again. Societal pressure to stay on the default path (credit:

Paul Millerd

) had a stranglehold on me, and I opted for the more reasonable, yet still a decent change of scenery back-up plan of moving to San Francisco. Simply put, it was easier to justify that I wanted to live in San Francisco than go to Spain with a bunch of strangers.

I definitely enjoyed my time on the west coast, but a year in, the novelty of living in this new city had already worn off. Not to mention that one gloomy June, one frigid July and one foggy August were enough to solidify that I never wanted to live through a San Francisco summer again — Mark Twain was right. Like clockwork, the travel bug-turned-rabid parasite was making its annual appearance, and this time, I was officially out of excuses. I had already sold most of my things and moved 3,000 miles across the country — it was now or never.

Scrolling through my inbox a bit more, I found one last piece of digital nostalgia, this one from November 2019: A receipt for my first two trip bookings — Split, Croatia and Athens, Greece — alongside a comprehensive spreadsheet that detailed an entire six months of travel sandwiched between these two group trips. Seeing this email pop up was a moment of disbelief, realizing that I had finally taken the plunge — the year ahead would be unforgettable.

Except… one minor problem. Perhaps you’ve used a coping mechanism to suppress it from your mind entirely, but does the mention of "March 2020" ring any alarm bells for you?

Yeah, the trip I had spent five years working up the nerve to take suddenly vanished into thin air (plus several hundred dollars of forever unusable flight credits). Lol. Life is truly a bitch sometimes, but what can you do? Honestly, things really did end up for the best — that’s the epilogue to this story that I’ll ramble on about another day.

For now, I’m enjoying this stroll down inbox memory lane, a reminder of how intimidating travel used to feel, and more significantly, how hesitant I was to defy societal norms. These days, I seem to book a flight to Norway or Nepal or Neptune without much of a second thought, so it’s nice to look back and remember that it wasn’t always like this. Travel will leave its mark on you (and I don’t just mean the classic motorbike exhaust pipe burn or that time I definitely should have gotten stitches in Mexico).

To my travel friends: I encourage you to do the same — browse through some old emails or dig up those meticulously crafted trip plans from a few years back. At the very least, you’ll get to laugh at the late-February 2020 version of yourself who was still booking flights as if the world wasn’t about to implode. What can I say, there were deals to be had 🤷🏼‍♀️

And to anyone reading this who hasn’t traveled yet (but wants to), I leave you with one easy piece of advice: Don’t wait around for five years like I did. Book the damn flight and just go.

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Recommended related posts:

• Societal Pressure Escape Velocity — For the adventurous folks who want to book a flight and not look back, this post is for you.

• One Year on the Road: Looking Back — Reflections on my decision to leave my normal life behind and travel the world, one year in.

PS: I’d love to hear what you thought about this issue. Email me directly at hello@emilyannhill.com and I pinky promise I’ll reply back.

1. If you also like those life-altering reckonings, bucket list augmenting tales and gooey self-growth type pieces, may I recommend

Tobi Ogunnaike

? He’s an unbelievable writer and his I became a nomad essay spoke to me for obvious reasons, as well as his highly entertaining piece on Seville since I’ll be spending two months in Spain later this summer. But be warned, once you start reading Wandering the Grey, you won’t be able to stop.