When It Rains In Palermo


Real talk


Want to know my biggest fears?

Not having money. Not having a nest of nice things. Not being able to communicate. Not having a plan. Not having familiar faces near.

So when I quit my job, got rid of my apartment, sold my material possessions, and bought a ticket to a foreign country—where I know no-one, that speaks a language that is not English...I was knowingly crawling into the belly of the beast.

Put your vileness up to a mirror and weep. That’s when the real art, the real making, begins. A tailor must have a torn shirt to practice his expertise.
— Rumi

sharing news of blowing up my life


“You’re so brave.” Feeding me words they thought I wanted to hear.

Trying to swiftly eliminate the air of self-righteousness, I’d reply, “I don’t know about that, I’m just trying to live the life I want to live.”

“Aren’t you scared? I’d be so scared,” people remarked over and over and over.

“Nah, everything’s gonna be alright,” I’d snarl with a confident Robert De Niro grin.

Here’s the weird thing, I wasn’t scared. A sane, level-headed person would be ulcer-ridden with nervous anxiety, appropriately so, and turn back because there are too many unknowns with this massive life risk. But I’ve always been a fool.

I had lived a life of “playing it safe” long enough. I suppose I just got fed up with fear of the unknown eating at me.

If I continued to focus on worries, I’d get pivoted back towards comfort—the opposite direction of a life I’d actually enjoy living. So, I just kept going, one foot in front of the other.

Guilt and fear hold people back.
— Megan joiner

I changed the way I think. I didn’t cling to uncertainty that was brought by fear, I clung to the possibilities that could be. Instead of spending my time calculating the possible monsters lurking behind the door, I started to focus my vision on the warm light shining beneath the door.

This change of thinking forced me to reevaluate my life:

  • Friends? People who heard my news of blowing up a cushy life thought I was crazy and judged me for now being poor (cough cough, no job means no money) — I realized those weren’t people I wanted to spend my time with anyways;

  • Money? I was forced to rearrange my priorities and where I spend my money—which made me reevaluate what I value;

  • Time and energy? Thinking about what I value made me question how one figuratively votes for the things they value—with their most precious resource: time and energy.

Your daily energy is a limited resource, be intentional with how you spend it.
— Hector Sanchez

In order to truly grow and even have a shot at being a better person, I knew I had to look my fear in the eyes, head on. I had to do the things that scared me most. So here we go…




$325 in the off season, can get you from freezing-rain in Chicago to sunny Palermo in three connecting flights. Unless you can afford a $3,000 direct flight from NYC, but my unemployed-self certainly could not.

I packed two PB&J sandwiches on processed “whole wheat bread” (to learn that this would not be considered “bread” in Italy, but fit for cat food), an empty water-bottle, and five mini-bags of m&m trail-mix. A great homage to American food.

Layover in Iceland. Then slept on the floor of the Malpensa Milan airport for a 2nd layover instead of getting a hotel. As a form of much deserved penance for my radical decisions. What can I say, I was raised Catholic...

Thirty-two hours later, I finally arrive at my end destination of glorious Palermo, Sicily!

Hallelujah! The world is my oyster! I risked it all for this moment! This is it! This is the first day of the rest of my life!

So what happened the first week in Palermo that was surely going to be the most positively hyperbolic seven days of my new chapter of grabbing life by the horns?!


Cold rain and disappointment.

Wow, did my time in Palermo seriously suck. I’m one to go to extremes to find a silver-lining in the most wretched circumstances, but even with the rosiest glasses on, all I saw were grey clouds and a naive, disillusioned girl begin to bury her head in the sands of defeat.

Let me be clear, I don’t blame it on the city itself. It was my fault.

Completely alone, in a city with people who aren’t used to crappy weather, in the coldest, rainiest week of the year. The atmosphere of bad moods permeated the streets. No one was friendly, except the creepy vendors at street markets, who’d nearly grab my ass as I’d peruse the seafood and fruits. I was unable to explore restaurants or do cool tourist things. “But I didn’t want an ordinary tourist experience anyway,” I said as I ate an entire humble pie to myself.

Friends and family were eager to hear updates of my new adventure. Many of them naturally had scenes of Under the Tuscan Sun running through their minds, as if I had packed my bags and bought a magic plane ticket to live in an alternate-Hollywood movie reality that they desperately hoped was possible.

What am I supposed to say to them?: “The dream that many of you secretly fantasize about as you stare out desk-job windows on long, frustrating days, ‘Screw it, I’m gonna run away to Italy! Life will be better there!’—turns out ain’t so good! Sorry to crush each and every one of you!”

No, I couldn’t say that, of course not.

But enough about protecting the psyche of others—what about me?! I clearly dreamt this fantasy up so much that I forced it into reality by breaking some fourth wall. I risked it all for this dream...and turns out, maybe it should’ve just stayed in the dream-realm, never to get brought to life in the dreary, rude, rainy streets of Palermo.


Now what?!


I tried to make the most of it...with no money. May I remind you that money is a pretty critical resource to do things. I checked out a couple markets, grabbed espresso down the street (but in Italy, you don’t grab espresso and people watch, you pound your espresso at the counter then get the hell out), I walked around city parks with umbrella-in-hand, I took the bus to the beach on the only sunny-but-cold day, I cooked out of a Sicilian cookbook using local ingredients, and did lots of lonely Yoga. But doing these things all alone brought me no fulfillment. I had truly and madly lost my ever-loving mind.

Check out the photo gallery from this Palermo trip.

Alone watching Jerry Seinfeld’s Stand-Up special,     I’m Telling You For The Last Time

Alone watching Jerry Seinfeld’s Stand-Up special, I’m Telling You For The Last Time

Jerry Seinfeld became my only friend.

I watched re-runs of Comedians In Cars Getting Coffee, various Seinfeld stand-up, and his 2002 documentary, "Comedian” on repeat. I had learned after getting my heart crushed by guys over the years—so much so that it pretty much became a sport for me—that comedy always cheers me up. So I turned to good ’ole Jerry Seinfeld. His dry sense of humor kept me sane on the rainy days, er at least distracted me from my misery.

There was a point mid-week where I considered just buying a ticket back home and admitting failure.

But I knew I couldn’t.

This trip was bigger than me and my selfish fantasy. Just about every person I told my plan of running away to Italy for a food adventure was heart-wrenchingly charmed with twinkles in their eyes: “I want to live vicariously through you! Out of one of my dreams too! Please do it and don’t ever look back!”

What I set off to do gave people hope. I imagined they thought, “If this silly young girl can muster up the courage to live the life she always wanted, maybe I can too.”

I had to balance doing this YOLO trip for me, while also being aware of my impact on others. I had to show everyone that everything was alright and things did in fact work out after my big leap, so that they could feel empowered to chase their dreams too.

You can’t sit around waiting for the sun to get handed to you, we must make our own light.
— Jeff Poole

This depressing week in Palermo taught me that sitting back and letting things work out does not mean be totally passive and wait for opportunities and answers to get brought to you. It’s a harmony of being fiercely positive, knowing that things will be okay, while also being proactive and putting yourself out there.

The most action-inspiring advice I got during this rough patch came in an email from a wise friend with three little words: “Keep moving forward.” A short message, but powerful.

Keep moving forward.
— Vince Shavers

That’s when I paused Netflix and took Vince’s advice.

In my tiny Airbnb room in Palermo, I acted on a decision that had called to me like a river Siren for three years. A decision that would forever alter my life.

With the silent tap of my Macbook mouse, stars aligned, my heart beat louder, and things radically changed. Just like that, I finally understood the real purpose of my trip…


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