Ask Jessie: Your Weekly Dose of Wisdom and Wit for Life's Questions

Ask Jessie - Week 1, July 26, 2025

Question from Sofia in Denver:

Hi Jessie,

I’m writing this the day after my passport got pickpocketed at Quinta da Regaleira in Sintra. We were at the entrance trying to figure out the ticketing system, and I was so focused on talking with my girlfriends and helping everyone buy tickets that I completely let my guard down. Bag unzipped, wallet out, totally distracted by our conversation. I felt so safe with them there.

Why me, though? I keep replaying it - there were tourists everywhere, but somehow I was the target. Probably because I was the one fumbling around the most, clearly not paying attention to anything except having fun with the girls.

The panic comes in waves. But here’s the weird part - underneath all the panic, there’s this strange feeling that maybe the universe is trying to tell me something. Like maybe I needed to slow down, to stop rushing through everything. But that sounds crazy when I’m stuck in a foreign country without documents, right?

I don’t know what I’m asking for. Maybe just someone to tell me this will be okay? That I’m not stupid for letting this happen?

- Sofia

May 14, 2025

Send your questions to Jessie at askjessie@inkandbranch.com. Every week, one question gets the space it deserves—honest, unfiltered, and written from the heart.

What Jessie Has to Say

Oh Sofia, sweet girl. Yes, things happened! And before we dive into what the universe might be whispering to you through a Portuguese pickpocket, let’s get you home first.

Step 1: The Practical Stuff (Because Panic Doesn’t Pay for Flights)

First, breathe. Then get online and find the U.S. State Department website. As a proud American abroad, you’ll discover there’s a U.S. Consulate right there in Lisbon. Lucky you - no need to trek to Madrid or wherever the nearest embassy might be.

But here’s the thing about foreign bureaucracy - it loves paperwork more than I love my morning coffee. Start with a police report. Yes, I know you probably already did this, but if not, get yourself to the nearest police station. They’re public servants, and even without documentation, they can help validate who you are. It’s their job, and they’ve seen this song and dance before.

Now, this is where past-you either becomes your hero or your cautionary tale: Do you have a photo of your passport saved on your phone? A copy tucked in your luggage? If yes, you’re about to feel very smart. If no, well, consider this your expensive education in travel prep.

Call the consulate and make an appointment for an emergency passport. You’ll need a passport photo (there are photo booths all over Lisbon, or any pharmacy can help), proof of your identity (this is where that police report comes in handy), and money - because freedom isn’t free, and neither are emergency travel documents.

Step 2: The “Why Me” Question (Spoiler: It’s Not Really About You)

Now, let’s talk about why this happened to you. You asked “why me?” as if the universe held a committee meeting and decided Sofia from Denver needed some character development.

Here’s the truth: You got pickpocketed because you were present. Fully, beautifully, messily present with your friends, fumbling with tickets, laughing, living in the moment instead of clutching your bag like a security blanket. The pickpocket didn’t choose you because you’re stupid or careless - they chose you because you were joyfully distracted.

And here’s what I find funny: You’re sitting there wondering if the universe is trying to tell you something, while completely missing what it actually just showed you. You know how to be present. You know how to let your guard down and just be with people you love. Most of us spend our whole lives trying to learn that.

The Plot Twist

So yes, maybe this forced pause is exactly what you needed. Not because you deserved punishment, but because sometimes life has to steal our passports to make us sit still long enough to notice what we usually rush past. You mentioned slowing down - what if this isn’t the universe punishing you, but rewarding you with a few extra days in one of the most magical cities in Europe?

You’re not stupid for letting this happen. You’re human for living in the moment. The only stupid thing would be letting this experience teach you to never open your bag, never help your friends, never get lost in conversation again.

Sometimes the best stories start with “So there I was, stranded in Lisbon without a passport…”

You’re going to be okay, Sofia. More than okay. You’re going to have one hell of a story.

P.S. - Eat something. Anxiety tastes better with bread.

Send your questions to Jessie at askjessie@inkandbranch.com. Every week, one question gets the space it deserves—honest, unfiltered, and written from the heart.