Good Luck, Have Fun, Don’t Die

A solo female travel essay about fear, friendship, reinvention, and the strange rituals that carry us into the unknown.

It ended the same way it began: with a dimly lit pool game on the second floor of a hostel in Chicago.

It’s February, and rows of green paper hearts line the wall of windows overlooking the busy street, each one carrying some small, scribbled confession. Beyond them, the city presses itself against the glass, thrumming with life and love inside the cold dark of night.

I arrive dressed in black, a ballcap pulled low over my brow, headphones in, listening to the same ten songs that have carried me through the past couple months. The hostel is more or less empty; a blessing in disguise. I grab a pool cue and rack the balls the way I always do: solids and stripes alternating around the rim, the yellow one at the top, the black eight at the center, and the two bottom balls switched in the lower-right corner. My hands move slowly, following the familiar sequence. As silly as it may seem, these small, seemingly insignificant gestures have become something of a ritual for me. Somewhere between the break and the last shot, my scattered thoughts always seem to organize themselves into a shape of their own.

My flight leaves at 10 a.m., and despite having only decided to leave for India a week and a half prior, I am obnoxiously prepared. All pertinent travel documents have been saved offline and printed out, my passport still exists in the zippered pocket of my carry-on after the seventh double-check, and the details of my airport pick-up from New Delhi IGI have been confirmed. Regardless, the wait keeps me awake.

I recite how to ask where the bathroom is in Hindi several times, wondering if all the intel Yogi fed me about his mother country was more or less correct: Can I really get by with just English? What’s the deal with only drinking bottled water? And is the air pollution really that bad? Later, he and his wife Shivani will call, providing an additional layer of context: what markets are worth hitting up on the way (and when to negotiate a fair price), how to stay safe in a taxicab, who to call if I need help.

The message is clear — I’m a solo female traveler heading into a country with a Level 3 Travel Advisory — but there is a warmth in their voices that reminds me fear is not the intended destination. My imagination, having never known ordinary parameters, blooms at the thought that this feels less like a trip and more like a defection: not from a country, exactly, but from the life I had been living for the past six months.

After the Colorado Trail, I’d thrown myself headfirst back into my work, no longer convinced I’d need to come back up for air.

Thru-hiking had proven to me that I was capable of far more than I had given myself credit for. The debris of other people’s opinions — about what I should do with my life, how I should present myself, and the priorities I should be adopting moving into my thirties — had begun to erode, and there was no stopping the evolution taking place inside me. No going back from the knowledge I’d unearthed while in the backcountry.

But what to do with that knowledge? Up until just last year, I had been putting my all into the rat race of conventional goals (albeit at a crawl). If asked what I wanted out of life at that time, the answer would have been simple, mundane: someone to love, and a way to survive inside the cage I’d created for myself. The comfort of success, the distraction of wealth. The fairytale version of love.

Betrayal was (and perhaps always is) what made that old operating system collapse. Several updates have taken place since.

Besides, I’m certainly not the first to raise my white flag after suffocating under the heap of pressure modern life creates — especially when it’s met with outdated tradition. There were many conversations, held with hushed voices in the corner of some nondescript cafe or house party, that led me to this juncture. Sincere people with honest reservations about starting a life they weren’t sure they’d finish, so they created one beyond the manual. It was impossible to ignore the way my heart leapt at this beguiling periphery. I wanted in.

The buy-in was simple: set fire to fear.

But now, standing on the precipice of a life I am meant to design, I find myself oscillating between sheer, brute-force confidence and the terror that something else may come along and wipe it clean once more. Is this a practical way of life, I wonder, or just another game of survival in disguise?

It seems that no matter how many times I strike down fear, it rises again to challenge the courage I have fought so hard to keep. The pool table becomes a battlefield of my own thoughts, marred by indecision and doubt. I knock the balls around and around, holding onto the hope that, somewhere in the chaos, they will find their way home.

And, in their own time, they do. I place the cue back on the wall rack and pick up one of the heart-shaped Post-it notes near the window. On it, I write:

Go with love. — Freda Heights

And press it onto the glass pane so it falls in line with the others. The same ten songs carry me back to my 10-bed hostel dorm room, and in the morning, the CTA blue line, where I’ll connect to the free Airport Transit System towards O’Hare International.

Before I leave, I run through one last checkpoint, ensuring I have everything I need to depart. All seems to be in order, but considering I’ve accidentally brought a pocketknife with me to TSA three separate times, I decide to perform my own screening, running my hands through every compartment.

My fingers brush up against something cold and squishy deep inside one of the pockets. I pull it out to inspect. During a recent Galentine’s Day event, my friend Claire had given me a stretchy little red bear with a white heart for a stomach, which I had decided to stow away in my luggage.

I wouldn’t exactly consider myself sentimental, but it seemed appropriate (and small enough) to bring. Claire’s friendship represents something sacred to me: the sanctity of sisterhood. In turn, so does this little bear. I stash it back inside, zip everything up, and head to the front desk to return my room key.

On the way out, I see a formidable yet fitting poster of a hand hovering over a red button. It reads:

GOOD LUCK HAVE FUN DON’T DIE

I snap a picture. It’s a movie poster for a film directed by Gore Verbinski, but it reminds me of the basic instructions my family and friends gave me before sending me on my way to India. Which, in turn, reminds me that they are all waiting for an update.

I pause for a moment there on the bustling city street, surrounded by my luggage, sending out a series of mixed messages from my phone:

I’ll be okay, see you soon, to my parents.

I have no idea what the fuck I’m doing, to my brother.

I’m not sure when I’ll be back, to all the loose ends and responsibilities I’ll be leaving behind.

I arrive at the airport terminal around 9 a.m. and am pleasantly surprised to find that the departure process for an international flight is not vastly different from that of a domestic one. I drop off my bright pink suitcase, clear the passport check and airport security, and just barely make it to my gate before they start calling up the line.

Air India’s plane is easily the oldest aircraft I have ever boarded, which feels appropriate for an international voyage built almost entirely out of vibes. The touchscreen on the seat in front of me is cracked beyond repair, so I can’t read the monitor, let alone use it. The seat seems damaged as well, or at the very least, not operating how it should. The speaker system overhead warbles in and out like something from a B-list horror movie.

My nervous system doesn’t really seem to register any of this as a concern, though. It’s a blip on the interface of much bigger concerns, like speedballing myself toward a country (and culture) I can’t even pretend to understand.

I look out the window and wonder what the next 48 hours will look like instead, thinking back to Yogi and Shivani’s words of wisdom:

Be very careful whose car you get into.

Don’t go out at night.

And try not to worry too much.

That is, until D.K. sits next to me.

---

Before we go any further: have you ever made a decision that looked reckless from the outside but felt necessary from within? Tell me in the comments. I want to hear about the moment you knew you were leaving one life for another.