The Upside of Cringe

Celebrating fifty issues and against all odds, actually sticking to something for once.

Hi there, I’m Emily! 🙋🏼‍♀️ For those who are new, here’s a quick catch-up:

Five years ago, I packed my entire life into a suitcase and hit the road, moving to a new city every few months. Now I write stories about the quirks, chaos and realities of living abroad, intertwined with my attempt to create a happy, meaningful life.

June 16, 2025: It’s easy to overlook progress when it comes in small doses. But if we don’t recognize the baby wins and mini milestones along the way… what are we even doing?!

So today, we are popping champagne on a Monday and celebrating the golden issue of Extracurricular Pursuits — because consistency deserves confetti, too 🎉

Back in 2021, I started this newsletter as a way to storytell my travel experiences since even some of my closest friends didn’t understand what the heck I was doing in Istanbul, Hong Kong and Guatemala City (to be fair, half the time I didn’t really know either). Writing helped me map out where I wanted to go next, and understand why I was even wandering in the first place.

But these days, now that I’m not on the move as much, a few things have changed:

1. I have a lot more time on my hands

2. I have a lot fewer travel stories to tell

3. I have an itch to figure out what’s next

Fortunately, I’ve never been the type to stay in just one lane, and restlessness has always been part of my rhythm …perhaps that explains all the passport stamps? I’ve got a textbook case of Shiny Object Syndrome™ and a graveyard full of abandoned creative projects to prove it — so the fact that this newsletter has reached fifty whole issues is nothing short of a small miracle.

We’ve laughed, we’ve cried, I’ve overshared. Somewhere along the way, this stopped being a travel diary and instead morphed into something much more personal: a place to think out loud, explore my creative whims, and follow the detours that would eventually rewrite the original plot entirely.

Don’t get me wrong, I’ve enjoyed writing about my no-frills long-haul schleps to the other side of the world¹, romanticizing slow mornings at my beloved Mercado Zicatela², and even recounting a spontaneous road trip to a delightfully bizarre, anarchic enclave in North Macedonia³ — but honestly, these ‘travel stories’ were never really all that travel-y. Reading through old posts, I now realize that most of my writing has just been me (very publicly) figuring out what I want to do with my life while eating the occasional street taco.

Cringe as oversharing with strangers on the internet may be, the public-facing nature of this newsletter is exactly what has kept me showing up for fifty issues. Publishing under my own name acts like a built-in anti-ghosting mechanism, and the dopamine hit when someone asks when the next issue is coming? I am a woman of the people, I mustn’t let my fans down!

But beyond just accountability, the simple act of broadcasting my personal interests to the world has been a magnet, attracting dozens of unexpected and rewarding encounters. Writing online has invited me into rooms that I would never have found otherwise, and has summoned opportunities that continue to surprise me — events, jobs, friendships — no romance yet, but I am accepting referrals.

So even without quirky travel anecdotes as my muse, what’s going to get me to publish fifty more issues is the proof that good things happen when you pursue your curiosities — and even better things happen when you let other people in on them.

Unsurprisingly, I’ve got a laundry list of creative projects, side quests, and hobbies that I’ve been itching to build, tinker with, and explore — and this newsletter just so happens to be the perfect place to document the journey and see what unfolds. The process will probably be a little messy, but that’s precisely when the magic of experimenting in public tends to reveal itself.

I guess it’s a good thing I named this newsletter Extracurricular Pursuits 😉

Some housekeeping:

· Credit to

Matt Cyr

for this post’s catchy title, born during a recent Write Hearted gym session — one of my extracurricular pursuits I’ve been investing time into lately and that I plan to talk more about in coming weeks.

· A link to my bridal shower baby shower housewarming Milestone Newsletter gift registry which has been thoughtfully prepared for your perusal, should you feel so inclined as to commemorate this special occasion with a token of your kind-hearted benevolence and everlasting generosity.

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1. Issue #12: Schlepping It

2. Issue #24: Stacking the Happiness Odds in Your Favor

3. Issue #14: Follow Me to Weird Places