Many chapters of my life have closely resembled the experience of assembling an IKEA dresser with an umlaut-riddled name: following vague instructions that read like a foreign language, jumping to step #5 before I’ve finished step #3, and never once using that little nylon safety strap to permanently affix the dresser to the wall.

But hindsight doing what hindsight does, once the clunky thing is built and my socks and undies are safely stashed away, it’s easy to understand how each piece led to the next — even if I definitely have more cam locks leftover than basic engineering logic could explain.

During the fall of 2019, with screws and bolts scattered everywhere and not even a picture on the box to guide me, my future felt like it could become anything. This native East Coaster was living on the opposite side of the country for the first time in her life, and she was eager to explore. I checked off every corner of San Francisco, my calendar was dotted with weekend trips to Big Sur and Lake Tahoe, and the billboards for $59 flights to Maui plastered along Market Street had my wanderlust wheels spinning even faster.

The irony that just a few months later, I’d be resigned to online yoga classes and Zoom happy hours in my tiny living room is not lost on me. But before anyone knew what the word “quarantine” entailed, I discovered the world-expanding magic of solo travel, and an adventurous seed was planted that would quickly outgrow its pot.

I went to Salt Lake City for a graphic design workshop, I spent a week beach-hopping in Orange County, and after visiting a friend in Vancouver, I decided that instead of flying home, I would mosey my way back down to SF on the train by way of Seattle — another city I had never been to, and a trip that would turn out to be way more significant than I realized at the time.

As a first time visitor, and with no plans besides to wander, I felt obligated to play tourist. After grabbing a grande flat white from a cute local coffeeshop called Starbucks, my next stop was predictably Pike Place Market.

Once I got past the scent of raw fish that slapped me across the face upon stepping inside, I was instantly hypnotized by the countless neon signs which line the halls of the market. It was a quintessential wet, gray, Pacific Northwest morning, so these signs really seemed to jump off the walls.

Dozens of shops thrifted, several bookstores browsed, and a gallon of clam chowder chowed down, I finally set off on the relaxing 22-hour1 train ride back home. Amtrak’s lousy WiFi became a forced digital detox, and I found myself doodling recreations of those Pike Place neon signs I was so obsessed with. Without much thought, I fired off a few sketches to some native Seattleite friends, and they nearly fell out of their chairs begging me to turn it into a poster.

The following week, I put the poster up for sale online, snuck a promotion-disguised-as-storytelling post by the r/seattle subreddit mods, and within 48 hours, I had 800 upvotes and sold over $500 worth of my little neon sign doodles.

The money was cool, but more importantly, it sparked the idea to turn this one niche poster into many, many more — it was a literal lightbulb moment.

Throughout 2020, when I wasn’t baking sourdough or drinking wine in my tiny living room, I made a few more posters, but among all of the things that seemed to go down the drain during the pandemic was my creativity. Instead of pouring my blood, sweat, and pixels into this new side project, I dragged my feet for over two more years, mostly under the procrastinational guise of letting the idea marinate and because I couldn’t think of a good name for the business. Ugh.

It wasn’t until another WiFi-less travel day when I re-read one of my favorite books2 that I would snap out of this dilly-dallying, thanks to Elizabeth Gilbert’s blunt reminder that WAITING TO TAKE ACTION ON A CREATIVE IDEA IS BAD BAD BAD (she may have phrased it ever so slightly more eloquently).

When I arrived at my destination — I’d be spending eight full weeks in the laptop-friendly-café-lined streets of El Poblado in Medellín, Colombia, wanderlust now activated to level 100 — I was pissed at myself for having made zero progress on this project during the pandemic, and knew it was time to finally get to work.

Motivation and creative juices freshly refilled, I unpacked my bags and gave myself until midnight that same day to come up with a list of names from which I would ultimately choose. And on March 11, 2022 around 11pm — four years ago today — I purchased the domain “backstorymaps.com” for $14 from Shopify.

Purchasing a domain for a side project is always a symbolic moment — it’s like naming a child, it provides a date of birth to celebrate, and it turns all of those messy scribbles in your notebook into a real, live business.

But the funny thing is, that it wasn’t this self-imposed deadline or any baby-naming book that suddenly got the creativity flowing. Instead, the actual backstory of how Backstory became Backstory is much more ridiculous than that:

True to the name I accidentally stumbled upon finally decided on, Backstory Map Co. was built on five continents, in a dozen countries, and now sells to customers around the world. Already in 2026 I’ve re-infused new life into things by launching a brand new website, several new poster designs, and just earlier this week, Backstory was approved as an official wholesale vendor on Faire.

None of this came with an assembly manual or grand master plan. In fact, from the funny naming miscommunication to the idea falling into my lap in the first place, I’ve been winging it at every step and building my eCommerce skillset as I go, with lines of code and pixels acting as my screws and nails.

Creativity, motivation, and free time have come and gone in waves, but four years into it — six and a half if you count back to that initial Seattle trip that inspired the whole thing — I’ve learned that when it comes to side projects, some months you sort out the pieces on the floor, other months you learn how to build the drawers, and sometimes, you spend an entire month just searching for that damn Allen wrench that keeps going missing.

Because even if things take a little longer than expected, or even if you don’t know what to name it, or even if you don’t quite know how those wooden slats will eventually all fit together, you just have to start building — otherwise you’ll never know which of the hundreds of pieces to pick up next.

Happy birthday, Backstory Map Co.!

Thanks as always for following along as I grow my eComm empire in 2026.
-Emily 👩🏼‍💻🏗️

PS: If you’ve got a side project idea of your own that you’ve been sitting on, I’d love to hear about it — please please please reach out!

PS x2: Was this another promotion-disguised-as-storytelling post? You bet your ass it was! No, definitely not. But as a thank you for reading this far, here’s a $10 code good towards any purchase at Backstory Map Co: STORYTIME10 📍🗺️

Related Side Project(-ish) Posts:

They say time flies when you’re having fun.

Well, the past six months have certainly flown by, with my version of fun involving disappearing into a cave and spending 12+ hours a day working on a smörgåsbord of creative side projects.

Here’s a quick rundown of what I’ve been up to:

• I gutted and re-built my personal website entirely from scratch.

• I designed my first 6 fonts (for what I plan to eventually be a collection of 100+) and opened a storefront on Creative Market.

• I hit record-breaking sales with my printable calendars shop, Tidy Plans, in October, again in November, again in December, and again in January.

• I fully resurrected Backstory Map Co. by giving it an entirely rewritten codebase, a dozen new products, and lots of other shiny bells and whistles.

And maybe even more significantly, on top of all of that, I’ve finally unpacked the metaphorical nomad suitcase and have officially settled down in Valencia, Spain — I just picked up my temporary residency card last week. 🥳

Oddly enough, even though I’ve just blown up my life and moved to a new city, on a different continent, in a second language, it feels like the puzzle pieces are starting to fall into place. It’s definitely a jumbo 5,000 piece-r, but I seem to have at least dug out the four corners.

Because with the newfound stability of a visa approval, a long-term apartment lease, and no boarding passes in sight, my focus is now entirely on my creative projects: Those listed above, plus a half-dozen others I’m tinkering with, and approximately 87 other half-baked ideas waiting patiently in my Notes app which I will dive into once I figure out how to clone myself.

There’s an endless amount of work ahead, but by spending the past few months writing thousands of lines of code and becoming completely fluent in Shopify, I feel like I’ve finally finished pouring the foundation for my side project empire.

In fact, this past weekend, for the first time ever, I answered the question “So Emily, what do you do for work?” by leading with my side projects.

This is the work that makes me feel most alive, that I could talk about for hours, that I pour my heart and soul into, and that willingly keeps me working until 2am most nights — and idk, something about hiding all of that passion behind my usual default reply of “I’m a freelance graphic designer” no longer felt right.

And not to mention, someday soon I plan to drop the word “side” from the term “side project empire” entirely. That’s my goal for 2026, at least.

Thanks in advance for following along as I keep laying more bricks.

-Emily 👩🏼‍💻🏗️

PS: If you’ve got a project idea of your own that you’ve been sitting on, I’d love to hear about it — please please please reach out!

September 9, 2025: As I write this, it’s 7:30am, I’m enjoying a cup of coffee and a quiet morning on my balcony — and I am absolutely sweating my ass off. Go ahead and show me all of the cute back-to-school photos of your kids that you want, but I am unconvinced and unwilling to accept that summer is over.

I just got back to Valencia after spending the past two months in Southeast Asia, which has only made my internal calendar even more useless. My circadian rhythm — or whatever the equivalent is for seasonal awareness — is officially fried. One thing I am aware of though, is that it’s been way too long since my last update, and while it might seem like Side Quest Summer has fallen by the wayside, that couldn’t be further from the truth.

Last we chatted, it was the end of July and I had my metaphorical backpack packed, ready to head off to Font Camp. Well, the bus to camp took a sudden detour, because the very next day, I woke up to record breaking single-day sales and a 20x spike in traffic to Tidy Plans, one of my other side projects. Font Camp was immediately put on hold while I scrambled to figure out what the hell was going on, and celebrated my sudden windfall of like, $60.

Back in the spring, I had done a ton of SEO work on Tidy Plans — like, hours and hours and HOURS of blindly tinkering with keywords and building landing pages and trying to figure out how Google’s black box algorithm works. And after a few months of letting that SEO juice marinate, it finally began to pay off.

Buuut there was one tiny problem: Having just launched Totebrag (my newest ecom shop full of Shopify’s latest and greatest 2025 bells and whistles), it was painfully obvious how archaic my older sites were. As it turns out, my existing shops were still running on a codebase from 2015 (!!!) which, in internet years, is essentially carving HTML into a stone tablet — and it was unknowingly limiting the upside of my newfound SEO glory.

Enter my next side quest (just not the one I had planned):

Quest #3: A Spontaneous Vibe Coding Bootcamp 🤖

Given that August is low season for calendar sales and that I had plenty of time on my hands in Bali, it felt like the perfect opportunity to give Tidy Plans a quick facelift. But once I began pulling out some of the old code, the whole site unsurprisingly collapsed like a house of cards. Before I knew it, I had stripped it down to an ugly Craigslist-esque shell of its former self, and began rebuilding the site almost entirely from scratch.

After a month of 14-hours days spent at ZIN Café1, the site was back online — faster, cuter, and no longer held together by the duct tape that was my decade-old code.

The wild part is that before any of this, I literally didn’t know how to code. Like, I could fumble my way changing colors or heading sizes with basic HTML and I had some familiarity with CSS, but that was about it.

I learned simply by feeding chunks of code into ChatGPT and asking for fixes — it’s what the kids call ✨vibe coding✨ these days, but with one important distinction: Rather than just blindly copying and pasting the repaired code that ChatGPT spat back out, I went through line by line — more than 4,000 lines of code 😵‍💫 — asking it to explain what each element does, and trial-and-errored things until I understood.

It was messy and super tedious at first, but about three weeks later, I was no longer relying on my robot professor and was able to write full, functional sections of code myself. Oh, and it’s already working — even with the site being fully inoperable for ~10 days,2 August was my second highest month of revenue of the year (after January, obvi), which I’ll happily attribute to both the increasing SEO momentum and the site’s shiny new paint job.

As for Font Camp, even though it got hijacked by this rogue crash course in front-end development, I’m still planning to attend (I’m now aiming for later this month). The cool thing is that I now have the perfect use case for it, as the newly designed Tidy Plans website is in need of a pretty, custom accent font to replace the cookie-cutter script placeholder I currently have in there.

And as for Side Quest Summer overall, my list of project ideas is now twice as long as when I started, and I’m having so much fun tinkering and learning that I’ve decided to continue this indefinitely, well beyond the summer.

The beauty (and benefit) of side quests is that simply working on one idea tends to surface the next. So what began as a fixed experiment — seven projects in fourteen weeks — is evolving into something slightly more flexible. That original self-imposed deadline served its purpose of getting me moving, but now, my goal is to follow the momentum rather than force things to fit an arbitrary timeline.

What’s Next:

Last week, I started what is likely to become Quest #4: Migrating my personal portfolio website off of Weebly (where it is currently hosted, and which has an equally archaic code base) to… somewhere else, tbd.

I’m doing so with the help of CodeFast, an online course created by Indie Hacker legend Marc Louvion. I figured now was a good time to get a bit of slightly more formal coding education under my belt, and so far, it’s as equally entertaining as it is helpful.

Spending the past two months mostly solo threw me into hardcore introvert mode — between living at the coworking space and training for the Valencia Half Marathon (another side quest!), it was the most productive stint I’ve had in years, and I am going to try my damndest to not lose that momentum. But now that I’m back in Spain, I also want to make up for my lost summer. So while I do love a cozy flannel shirt and a pumpkin-spiced anything as much as the next basic bitch, I’m going to squeeze in a few more beach days with a tinto de verano in hand first.

I’ll also be back soon with a (highly-requested) full recap of my Bali trip, assuming I don’t take another unplanned month-long detour 😉

Thanks for reading!

-Em

1

Haters will say the illustration at the top of this post is unrealistic, so here’s a photo of what my actual work setup was like: An open-air coworking space 30 seconds from the beach, bottomless $2 unicorn lattes and a fresh fruit bowl every morning. Okay, maybe I didn’t hate everything about Bali.

---

Greetings from a still very gray and overcast Bali, now with a side of smoke!

I chose to spend July and August here for the promise of sunny days and the occasional tropical downpour, but so far I haven’t had many of either.

What gives? Has anyone been here in August who can offer a dose of optimism? I feel bad complaining from paradise1 but this kind of almost sunny but with a thick layer of gray cloud cover weather gives me the WORST headaches.

On the bright side (lol), not being lured to the beach has done wonders for my productivity. I’ve been here for almost a month, and at the risk of sounding like an Eat, Pray, Love cliché, it genuinely feels like this trip could be a major life inflection point.

Maybe it’s Mama Bali working her magic, or maybe it’s just that I’ve gone a full month without a single sip of booze (the more likely factor). Either way, for the first time in ages, I have clarity on what’s next: professionally, creatively, existentially, all of it.

I’ll send a post about that next week, because today I’m here with a recap of Quest #2, and to finally introduce Quest #3.

I was feeling a bit mehhhh earlier this week, so I gave myself a few days to take a mini breather before diving into the next thing. And after generally feeling like I had been screaming into the void, yesterday I received two separate encouraging messages asking when Quest #3 was coming — consider my motivation fully restored 🥹

Quest #2, also known as Cinematic Storytelling was my attempt to learn how to use the video editing software CapCut and experiment with making reels for Instagram.

Contrary to the build-in-public mission of Side Quest Summer, I quietly published my first reel into the wild last week — partially because I don’t believe Substack is the right medium for video, and partially because I wanted to create a new, separate IG account for Extracurricular Pursuits, so only a few dozen people saw it. Here it is, if you missed it:

I had a big head start thanks to a basic familiarity2 of Adobe Premiere Pro which is basically CapCut’s older, more professional sibling. Once I figured out where all of the settings and controls lived, it came together pretty quickly. Though I later realized I’d been using the simplified web version of CapCut instead of the more powerful desktop app — I'll have to test that out before deciding if I should stick with it or actually learn Adobe Premiere for realsies.

Either way, I really enjoy video editing and it’s something I want to do more of. Beyond the cringe of filming myself, it’s surprisingly intuitive — and that includes thinking through storyboarding, pacing, transitions, sound effects, etc.

Making reels as a beginner is the perfect challenge in overcoming perfectionism, and it’s also a good lesson in not caring about my appearance: All three clips I used of myself in that video were placeholders that I planned to reshoot with better lighting and a face full of makeup. But in the end, I didn't feel like re-doing everything, said screw it and hit publish, my sweaty gym clothes and lack of mascara be damned.

The original goal was to post three videos which I didn’t do, but I still count this project as a win. I don’t have the time (or interest) to become the content factory that Instagram or TikTok’s algorithmic overlords demand, though I could see myself publishing one solid video a week — maybe two, if they’re less complex. My one major takeaway from the whole thing: Even making a 30-second video is much more time-consuming than meets the eye.

I likely won’t be posting future reels on Substack or on my personal IG account, but you can follow along with all of them here: @extracurricularpursuits

Now, on to Quest #3! 🏕️

But first, a quick backstory (I swear we will get there):

My most profitable and favorite side project to date is Tidy Plans, an ecomm shop that sells printable PDF files of calendars, planners and journaling tools. I launched it in late 2022 and it became profitable about a year later.

It’s my pride and joy, the thing that I secretly work on while I’m procrastinating on everything else, and a business that I’d probably never sell (though I’m happy to hear offers!)

That’s because a profitable digital product is the holy grail. Of course it requires work upfront, but that dopamine-inducing cha-ching notification from every sale? Receiving four new orders while you were taking a nap? Knowing the cash will be in your bank account tomorrow without you having to lift a finger?

There’s nothing quite like it.

I’d take a $10 digital product sale over $100 of freelance client work any day of the week.

The problem is that viable, money-making digital products are already scarce — and they're only getting harder to come by as AI becomes more mainstream.

Why would anyone pay even $3 for an e-book written by a subject-matter expert when ChatGPT will provide 10x the output, tailor it specifically for their situation, and do it all for free? Gone are the days of selling simple icon packs or gradient backgrounds — Midjourney murdered those business models with a single prompt.

Still, there are some digital products that AI will have a tougher time replacing, and I believe that fonts are one of them. Hear me out:

• Fonts are complex file types with tons of nuance that I don’t think your average Joe could spin up even armed with a ChatGPT Plus subscription

• They are heavily used in branding and nobody is launching a company with something that feels even remotely AI-generated or generic

• Designers who purchase custom fonts are generally anti-AI and value work made with human hands + brains

• It’s gotten better in recent months, but if there’s one thing AI image generators struggle with, it’s letters, words, and type

• Even if AI-generated fonts do eventually flood the internet, my hunch is that most will be mediocre

Consider me convinced. Plus, I’ve wanted to dive into font design for years.

Tomorrow I’ll be enrolling in Abby Leighton’s online course Font Camp, and putting my iPad, Apple Pencil and Procreate to work. The goal: Create my own custom font by next Thursday, August 7th.

Off to camp I go! I just hope s’mores are involved 🏕️ ✍🏼

There’s something hilariously tragic about pouring your soul into a personal 5,000-word magnum opus written straight from the depths of your soul in an era when most of the world is hypnotized by 12-second videos.

I love writing (obviously). The problem is that most people don’t love reading.

Sure, plenty of people claim to love cozying up with a good book. But when it comes to actually sitting still long enough to scale that towering wall of text otherwise known as the prologue — oops, there’s that bottomless dopamine slot machine, right back in your hand again!

And just to make sure you’re still with me so far:

TL;DR: BIG PARAGRAPH SCARY… ME WANT CHONKY CAT VIDEO…

But hey, no judgment, I’m absolutely talking about myself here, too.

Anyway, after launching my first Side Quest last week, I did some reflecting — what went right, what didn’t, what I’d do differently. And to be honest, things went incredibly smoothly — except for the part where I once again learned that ‘If you build it, they will come’ is a complete and utter lie.

For the rare few who hang out with me on the nerdy corner of the internet known as Substack Notes, my constant progress updates probably felt like I was beating a dead horse. But outside of that bubble? 🦗 🦗 🦗

So for my next quest, I’ve decided to go where the people are (don’t worry, I’m not making an OnlyFans account). Hypnotic doom-scroll vortex aside, Instagram is where the eyeballs are, and having launched a half-dozen side projects that looked great on paper but never gained much momentum, I have to admit it: Marketing is always my downfall.

So this time, I’m trying something different — and here it is, hot off the press:

✨ Quest #2: Cinematic Storytelling 🎬 🍿 ✨

…which is just a fancier way of saying that I want people to actually see what I’m building so I’m going to experiment with making reels.

Start Date: Right now lol
End Date: July 20 (one week)
The Goal: Post three behind-the-scenes / build-in-public style reels

No Oscars will be won, and they will likely be a little cringe. Whatever.

In a *~signs from the universe~* kind of way (forgive me, I’m still in Bali 🪬🔮🧘🏼‍♀️), I keep stumbling across what I can only describe as people doing cool shit on the internet and documenting it as they go:

Note: #2 and #3 are fantastic, but they’re in Spanish. Though I bet you’ll still get the gist.

1. Bowling Alley Dude — His deadpan delivery gets old, but it’s a sweet project.

2. Veneno House — A gutsy twenty-something gal used her life savings to turn an abandoned warehouse into a gastro-cultural hub in Valencia which opened in April (coincidentally, two blocks from where I was just living).

3. Can Balam — Earlier this year, three guys bought a dilapidated hotel in Puerto Escondido and are now winging the renovation of it with zero experience.

4. Becoming Intrepid by — It’s an essay (eeeek, more words!!) but it’s reeeally good: He tells the story of confronting the dread of filming himself in order to shoot his dream job shot.

The common thread here is raw storytelling. In fact, these accounts are part of what inspired me to embark on all of these side quests in the first place. Hey, at least my late-night scrolling habit is occasionally motivational!

Okay, less typing, more video editing — let’s see what happens.

*I’d be remiss to not shamelessly plug my Book Club Dropout tote bag by naming the title of this post as such

**And here is your chonky cat video, as promised:

July 11, 2025: Howdy y’all! Grab a coffee and get comfortable, because today there is a lot to catch you up on:

A few weeks ago, I embarked on Side Quest Summer — a self-imposed challenge to launch seven indie projects before September.

Why? Because I have an unreasonable amount of creative ideas collecting dust, and I want to see what happens if I stop overthinking and just start making things, even if it gets a little scrappy. Plus, it’s a great way to stay busy while I’m (mostly) alone on the other side of the world for the next two months — oh yeah, greetings from Bali 👋🏼 🌴

Anyway, today I come to you in a celebratory mood because the inaugural quest just wrapped, and it went even better than expected 🎉

It’s an e-commerce shop called Totebrag, and below I’ve outlined *~in excruciating detail~* exactly how I built it from scratch in just fourteen days.

In fact, I’m building all of my side quests “in public”, which means I’m posting the baby steps as they happen: brain dumps, early logo concepts, spontaneous decisions, late-night pivots, and the wins and setbacks along the way.

You can follow along with my daily progress updates in two places:

• My off-the-cuff Substack Notes

• The running progress logs for each project (the log for Quest #1 is below)

Let me explain: this here post has been live on my Substack since June 25th, and I’ve been adding to it every day — that’s everything you’ll find below. I’m only now writing this intro and sending the whole thing out to my email list.

If you want to follow along in real time with Quest #2, you can do that here.

Okay, enough blabbering, let’s get to it. This is the most fun I’ve had working in a long time, so I’m really excited to share.

One quest down, six to go!

⚠️ Note: The rest of this post is the entire running progress log for Quest #1 — it’s long and a bit chaotic, but I’d love for you to read it.

Or, if you’d prefer to jump straight to checking out Totebrag for yourself, click here 👜 ✨

Either way, your support of my writing and weird little projects means the world!

Visit the Totebrag Storefront

Side Quest Summer · Quest #1

Live Updates · Last (and Final) Update: July 11, 2025

🎬 Quick Hits

Description: An e-commerce shop with a playful vibe that sells tote bags with witty, tongue-in-cheek phrases on them. All tote bags will feature my own original artwork and be fulfilled via Printify, a print-on-demand production partner.

Shop Name: Totebrag

Project Start Date: June 25, 2025

Project Launch Date: July 8, 2025

Stack: Shopify, Printify, Photoshop, Illustrator, Midjourney

Cost to Launch: $75.03

• Domain: $17.76 (annual fee, purchased directly through Shopify)

• Shopify Plan: $0.79 (what a steal1)

• Cost for samples: $56.48 (ordered one tote in each color to confirm color accuracy)

⏳ Pre-Launch To-Do List

• Choose a product ✅

• Order samples ✅

• Come up with a concept/theme ✅

• Come up with a shop name ✅

• Buy the domain, claim social handles ✅

• Design logo and branding ✅

• Add new Shopify store to my account + setup backend ✅

• Finalize phrases for products + create artwork ✅

• Setup up Printify integration and load in all products ✅

• Customize Shopify storefront design ✅

• Add bells, whistles + boring compliance stuff ✅

• Place test order ✅

• Viola! Grand opening ✅ 🏆

🚧 Daily Progress Log

‣ Day #1: What the Heck Am I Going to Sell?

[June 25, 2025]

Hello from Singapore! No better way to kick things off than with a healthy dose of jet lag. But let’s leave my travel tales for later, because I’m ready to dive into Quest #1.

First things first: If I’ve learned anything from the other four e-comm shops I’ve launched, it’s that product choice is crucial — that probably seems pretty obvious, but what I mean is that different types of products come with their own built-in downsides.

Crucial detail: Considering I am on the other side of the world right now, I will be using Printify2 to stock this shop — but all products will have my own original artwork.

Now, Printify offers a lot of downright weird shit (chicken-wing shaped pillows, for one) as well as things that people would never buy — nobody needs a mousepad in the year of our lord, 2025. And it’s been an easy process of elimination for most of the remaining ideas that were originally on the shortlist.

Apparel: T-shirts, hoodies, tank tops, etc. immediately invoke sizing issues — offering XS-XL makes inventory 5x bigger (and 5x more tedious) right off the bat. Also people are super picky with clothes and often want returns. Pass.

Greeting Cards: Have you seen the greeting card aisle at Target lately? Millions. The market is pretty saturated, so to stand out, I’d need a LOT of witty, cute, original designs. I’d love3 to do this, but t'd be super time-intensive, and each sale would only net a couple bucks, max.

Posters: I’m already selling posters/artwork in one of my other shops, Backstory Map Co., so I want to try something different.

Notebooks/Journals: I’m a stationery snob aficionado, so this idea originally spoke to me, but the quality of notebooks/journals available from print-on-demand stores is honestly very mehhh. I’ve personally bought millions of blank journals, but never once online (I like to touch and feel the cover/pages first) — so I’m nixing this idea too.

So that leaves us with two final ideas:

Candles: Besides the fact that trying to describe a scent over the internet is like trying to describe what a schnozzberry tastes like, this is actually a viable option. I briefly stocked candles in one of my former (now-closed) e-comm shops, and they were high quality and surprisingly decent sellers.

Tote Bags: Not the most groundbreaking idea, but I think I can have fun with it. Plus, I personally use canvas tote bags all the time. And as far as e-comm logistics go: one size fits all, lightweight (cheap) to ship, could hit the [affordable retail price] vs. [profit margin] sweet spot. And I know from experience that the print quality + quality of the bag itself are solid (often a challenge with PoD products).

‣ Day #2: Hypothesis = People Love Buying Dumb Shit

[June 26, 2025]

I mean that in the nicest way possible.

But it’s true: The dumber, funnier, and/or more unhinged an item is, the more likely someone will impulsively buy it, gift it, or share it (which worst case, is free marketing!)

Plus, when it comes to silly, borderline gag-gift products, people aren’t expecting luxury. Not because you’re selling junk — but because no one is buying a ~$20 tote bag with a sarcastic saying and expecting Louis Vuitton craftsmanship. The vibe is more “this made me laugh, I need it” than “I demand a refund.” A customer base of sarcastic Gen Zer’s and meme-loving Millennials tend to roll with it.

I’ve done the normal, serious e-comm product route before, and this time I want to try something more playful (borderline ridiculous4). So today I’m going to come up with a list of 100+ humorous phrases/sarcastic sayings that could be printed on each product, which should help me choose which of the two ideas to move forward with.

‣ Day #3: Day of BIG Decisions

[June 27, 2025]

Yesterday’s brainstorming session made it obvious, and this morning I officially decided on my product: Tote Bags 👜 ✨

Last night I even shared some rough draft mock-ups hoping to get some feedback, but tbh, the Substack algorithm doesn’t really do instant gratification (I’m learning how to do this whole build-in-public thing as I go, too) — but I sent the silly tote bag idea around to some friends and received rave reviews, and in the interest of time I’m going full speed ahead with minimal upfront validation of concept. Is this foreshadowing? Perhaps. But I’ve got six other projects up coming down the pike this summer, so I don’t expect everything to go perfectly smooth this first go-around.

Anyway, here are some of the mock-ups:

I’ve also officially decided on a name: Totebrag ✨ 🎉

Choosing the name happened fast, here’s a note with the story behind what happened.

And thanks to some feedback that did eventually come my way, I’ve made my last big decision of the day: Here’s the logo I’ll be going with!

‣ Day #4: Less Brainstorming, More Bricklaying

[June 28, 2025]

Today I’m finally starting to build out the Totebrag.com storefront 🎉

I bought the domain yesterday, but otherwise, I’m starting from SCRATCH scratch. In fact, looking at the totally empty, totally blank Shopify site is pretty jarring… I’ve got my work cut out for me this weekend.

I guess I’ve never realized how much incremental work I’ve done over the years on Tidy Plans & Backstory Map Co. — little edits and improvements every couple of weeks really adds up. My goal is just to get to an M.V.S. — Minimum Viable Storefront — before launch day on July 8th, just ten days away, eeeek ⏳

I’m using a new, more modern Shopify theme, so there’s a slight learning curve. But I’m excited to figure it out, because there are a lot more built-in bells and whistles, and I probably won’t need to hack into the code as much compared to my other stores.

Good thing I’m not really loving my time in Singapore — so much so that I’ve decided to cut my losses, scrap most of my Saturday exploration plans, and camp out in a variety of bookstores and coffee shops all day to build. I haven’t really given this city a fair shot, but tbh, I’d rather be working on Totebrag — that’s a promising sign, no?

‣ Day #5: Letting Things Marinate

[June 29, 2025]

Today wasn’t very productive because it was a travel day. I left Singapore midday and didn’t arrive to my hotel in Bali until past 10pm — y’all weren’t JOKING about the traffic here, getting from the airport to Canggu took almost as long as the flight.

But I made it, and honestly, it was good timing to take a half-step back and let things marinate for 24 hours before diving into actually building out the shop. A few ideas suddenly came to mind while WiFi-less/screen-less on my 2.5 hour flight.

Proof that constant consumption is the arch nemesis of creative output ⚡️🧠

Words I would like to have etched into my skull.

‣ Day #6: A Fresh Starting Line

[June 30, 2025]

GOD it felt good to wake up and not be in that cursed hotel in Singapore, and it felt even better to wake up and be in Bali (the dog + rooster + moto alarm clock teleported me right back to Puerto Escondido).

As much as I was eager to immediately head to one of the ten million cute cafés here and get to work, I started off the day (and the trip) by joining a gym a block from my hotel.

This is off the Totebrag topic, but working out is always the first domino that knocks over everything else. Once I lace up my sneakers, everything else falls into place — I eat better, I'm more focused, and the rest of the day is full of momentum, not resistance 💪🏼👟

Anyway, I only ran 2km today (speaking of resistance, I guess my stubborn adoption of the metric system is finally underway because the treadmills here don’t do miles), but it felt great to start things off on the right foot. Now I’m deciding between joining a coworking space, or if I should just spent the monthly fee at those aforementioned ten million cute cafés, since Canggu is basically the only place on earth where I won’t feel laptop-in-public guilt.

‣ Day #7: Deep in the Shopify Trenches

[July 1, 2025]

Holy July, and holy first week of Quest #1 already gone.

Right now I’m knee-deep in finalizing the product list (the funny phrases that will be printed on the tote bags), setting up the artwork for each, and then loading them into the Printify↔Shopify integration.

This part is a time-consuming grind (because there is 80+ phrases!!) and I likely won’t have any exciting updates until I’m done — but I’m hoping to crank it out in the next 24 hours 🏗️👷🏼‍♀️

‣ Day #8: Customer Support Hell

[July 2, 2025]

The grind to create 80+ product listings continues, along with a handful of pesky logistical bugs that needed squashing:

Last week when I registered Totebrag as a new Shopify storefront, I was in Singapore and I forgot to put my VPN on, and all of my Shopify charges were coming through in $SGD. Soooo I just wasted a several hours on live chat support getting that sorted 🤡

But at least I spent the morning at a cute café down the street from my hotel — which, hilariously, turned out to be a café for LIFE COACHES. Bali, I truly cannot5 with you.

‣ Day #9: No Room for Perfectionism

[July 3, 2025]

Today I took a break from product creation and started messing around with hero images for the website home page — which was surprisingly tedious. I’m using Midjourney with some heavy Photoshopping to create original mock-ups, and the perfectionist in me is really coming out. This is the vibe I’m going for, but I still think these photos look super AI-generated (which, well duh, they are).

I’m going to tinker with it a bit more and try to get it to look more realistic, but I need to remember that this is just Totebrag v.1 — obviously the website is going to evolve and improve, and I can’t expect to nail everything on the first go, in just fourteen days.

‣ Day #10: Blehhhhh….

[July 4, 2025]

Full transparency, I’m writing this a date late because I’ve lost some steam 🫠

I’m not totally sure why — perhaps because I’m not used to focusing on just one specific project for this many days straight. Which is a good sign for later into the summer when I have multiple things to work on simultaneously (even after I launch each project, there will obviously still be regular upkeep and ongoing maintenance needed).

It’s also been a bit overcast and gray in Bali for the past few days (which, I realize sounds ridiculous because I’m literally in a tropical paradise, but I’m wholly convinced that the sun affects my mood more than any other human on earth — hence why I’m always chasing summer + dry season).

Anyway, instead of forcing myself to work, I gave into the resistance and took a break from Totebrag (I had a lot of regular freelance work to do anyway). And hey, it was the Fourth of July, which I ended up spending super patriotically 🇮🇩🫡

‣ Day #11: Release Quick + Iterate

[July 5, 2025]

Okay, it’s a new day and with it comes fresh eyes and renewed motivation 💪🏼

And after several iterations, I’ve finalized the phrases/designs that will go on the first round of tote bags — there’s 90 (!!!)

Some of them are better than others, and I’m going to run the list of 90 by a few trusted friends that each have a very specific niche of weird humor (and which is why they are my friends) and ask them to each pick their ten least favorites, and replace accordingly.

The list was surprisingly easy to come up with, which means it can definitely be improved if I spend more time brainstorming new phrases. But at the bare minimum, I now have a base of products to launch. Here’s a few of my favorites (along with a slightly tweaked color palette I’ve decided to go with for the product mockups):

‣ Day #12: Sunday Rainy Funday

[July 6, 2025]

After being in the monotonous Printify↔Shopify trenches for a few days, my “minimum viable product offering” is finally loaded into the shop.

I can see the light at the end of the Quest #1 tunnel, but I still have a TON of work to do, mostly to get the website layout/homepage design ready. Good thing I just ordered a(nother) latte and cold coconut — gonna spend this overcast Sunday powering through the loooong pre-grand opening to-do list.

Evening Update: Holy MONSOON, that wasn’t just overcast skies — but gosh do I love a good tropical downpour. I spent the evening working in the common area of my hotel listening to the rain that eventually overflowed the pool, while getting done a slew of things:

• Configuring all of the checkout options and improving the cart design ✅

• Fixing customer communication emails (so they aren’t Shopify’s hideous default) ✅

• Setting up privacy, shipping and return policies (snoooooze fest) ✅

• Setting up the Contact and About Us pages (loose placeholders for now) ✅

‣ Day #13: Eeeeeeeek

[July 7, 2025]

In the Grand Opening home stretch! Today was too chaotic to really give a good meaty update, but basically, my day went a little something like this:

• Spent the morning at a coworking space building out the shop homepage design

• Went home and took a 30-minute nap, woke up and hated how it looked lols

• Spent the evening re-doing the entire thing, casual 16-hour work day

I also added an accordion to the product page template that I’m obsessed with, because of it’s buttery transitions (this new, more modern Shopify theme is 🔥) and also because I injected a tiny bit of personality — which then inspired me to write unique, witty product descriptions for ALL EIGHTY ONE PRODUCTS.

It’s going to be worth it, but WHYYYY did I decide to undertake this at the eleventh hour?

‣ Day #14: It’s happening!!!

[July 8, 2025]

Wahooooo! Target grand opening date achieved:

Let this serve as a formal marker that Totebrag is now officially live, launched and open for business! 🎉

She barely skidded over the finish line at the buzzer, but she’s here: Totebrag.com 👶🏼 🎀 ✨

Visit the Totebrag Storefront

🏁 The Epilogue

Since officially launching on July 8, I’ve already made a few big improvements:

• Finished adding funny product descriptions6 for all 81 products ✅

• Added four extra product photos7 to each listing ✅

• Improved image file names + alt text for SEO ✅

• Set up an alias email to avoid paying $8/month to the Google gods for email hosting ✅

• Add alphabetical sorting options on the “Shop All” page ✅

• Like fifteen other small things I forget, lol sry 🤷🏼‍♀️

There’s obviously still a ton to improve, most notably, adding *literally hundreds* of more bags (and in more design styles) — I’m really gonna go for a volume play with this shop.

But that will come with time, and for now, I’m just happy that I actually launched the damn thing — and that v.1 is good enough to brag about 😉

Thanks for following along (tbh, I’ll be surprised if anyone actually made it this far), and keep an eye out for Side Quest #2, coming soon!

XOXO,
-Em

I’ve had enough.

After allowing it to gather dust for far too long, I’ve officially declared war on my “someday” list. Not because the timing is perfect, but because I’m tired of waiting around for it to be.

Armed with a pen, a large coffee, and the napkin that it came with, this morning I wrote down all of the creative projects and hobbies that I’ve been itching to build and explore — and it looks like I’m going to need some more caffeine.

The list is… eclectic, to say the least: I quickly came up with a dozen ideas for micro-businesses and side hustles — and that was before I flipped the napkin over and started listing all of the personal challenges and lifestyle experiments I want to tinker with.

Some ideas are delightfully ambitious, some ideas are half-baked at best, and some ideas are ready to give my imposter syndrome a run for its money. But none of that matters unless I stop daydreaming and start doing, so I’ve picked the most enticing ideas and I’m diving in head first.

Here’s the plan: Seven projects. Three months. A new launch every 10 to 14 days. Minimal planning ahead, maximum figuring it out as I go.

And as I mentioned earlier this week, since sharing in public is often where the magic happens, I’ll be providing a behind-the-scenes look at the raw, unfiltered process as I tackle each challenge — sharing the wins, losses and learnings as I go. Figuring out how to build in public on Substack is absolutely part of the chaos.

Welcome to ✨Side Quest Summer✨

Now, you might be thinking: “Seven new projects? Won’t you be spreading yourself too thin?” Yeah, probably, but I’m choosing to interpret that as: “With enough throws of the dart, I’ll eventually hit the bullseye.”

Plus (1.) I’m going to have a lot of free time on my hands the next few weeks, and (2.) I hope this becomes a lesson in overcoming perfectionism and just launching the damn thing already — an obstacle notorious for tripping me up in the past.

Important sidebar: I have plenty of thoughts on the totally valid “don’t monetize your hobbies” argument, and I plan to talk more about that next week. But in my defense (and hear me out, because this is a bit meta), I’ve realized that launching niche micro-businesses is, in fact, one of my hobbies. Some people knit or go on hikes. I apparently find joy in vibe coding and hunting down the perfect domain name.

Anyway, thanks in advance for following along — by reading this here post, you’ll be able to one day say “I knew about Emily’s weird little projects before they were famous.”

Happy Summer Solstice, Happy Side Quest Summer, and Happy Birthday to me.

Now, someone pass me the screwdriver.

Some housekeeping…

I will be posting a lot of ‘notes’ going forwards, which in case you are unfamiliar, is the Substack version of tweets — now with 99% less toxicity! You can follow along with those bite-sized updates here.

It must be a good sign that how I wanted to spend my birthday morning was to wake up early, go to my favorite coffee shop and finish writing this post, right? Cheers to 36!

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 nature …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: my little corner of the internet to think out loud, explore my creative whims, and follow the detours that would eventually reroute the original plan.

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 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.

What Goes Up Must Come Down

Two suitcases, an overweight backpack, and a tote bag bursting at the seams.

Three flights, two long layovers, and an eight-hour time zone jump.

Needless to say, after twenty-eight hours in transit, I was beyond relieved to finally step into my apartment and put my bags down — but this time, unpacking made everything feel heavier.

After spending the last five years without a fixed address, I’ve finally landed in Valencia, Spain — the city that, if the visa gods are kind enough, I plan to officially call home going forwards.

This decision has been a long time coming: When my original plan to spend the summer and fall of 2020 in Europe blew up into socially-distanced smithereens, I decided to embrace the awkward (and apartment-less) limbo phase I suddenly found myself in. After waiting things out for a bit, I eventually packed my entire life into a few bags and set off for Mexico with a one-way ticket in hand, my only real plan being to wing it. I certainly never imagined that I’d stick to this transient travel lifestyle for five whole years. But thirty countries, five continents, and dozens of cities later — well, here we are.

Traveling has been amazing for all of the reasons you might expect, but the best accidental side effect is that nomading provides the opportunity to test-drive what life in other cities, countries, and cultures could be like. Over time, hopping from city to city began to feel less like aimless wandering and more like intentional research. The past two years in particular, I’ve been increasingly focused on mapping out my future: the kind of life I want to build, the version of myself I want to evolve into, and the rhythm I want my days to take. And at the heart of all of this careful self-reflection remains one lingering question: once this whole travel phase runs its course, where do I want to plant roots and build a life?

Choosing to permanently move to a new city — especially one that’s in a foreign country, with a different language, on another continent — should probably feel pretty monumental. Yet somehow, things have felt surprisingly natural so far. I’ve already spent the past two summers in Valencia, and showing up to a place where there was a friend waiting for me at the airport, where I don’t need to rely on Google Maps, and where I can mostly speak the language has put me miles kilometers ahead of where I probably should be at this point.

That being said, I’ve only just begun to untangle the logistical fine print of staying here long-term. I’m still in a temporary apartment, I’m about to dive headfirst into complicated visa paperwork + notoriously frustrating Spanish bureaucracy, and I still need to leave Spain for a few weeks this summer before I can officially call this wonderful country home.

But despite the messiness ahead, my spirits are high, the sun is out, and the oranges are in season. I’m back in my favorite daily routine, I’ve already made a few new friends, and each day reveals something new about this city. There’s a special kind of fleeting magic in being the new kid on the block — it’s a mix of curiosity, nerves, excitement, a built-in excuse to try new things, and a suspicious awareness that most of what I still don’t know will only reveal itself with time.

Fortunately, time is on my side. Because rather than just passing through yet another city, this arrival came with a heaviness that I haven’t felt on any of my other trips. Heavy in the best way possible — for once, not like lugging around bulky overweight luggage, but more like there’s a gravitational force tugging me to stay.

April 30, 2025: Writing online already feels like baring my soul to the world, so today I figured I’d lean into that diary-level honesty and share an embarrassing little secret: My highly unscientific, wildly inconsistent, held-together-with-duct-tape writing process that I’ve painstakingly curated over the past few years.

It currently consists of the following:

• A 78,000-word Google doc sorted into 22 tabs of vaguely themed word vomit

• Sixteen raw, unfinished, embarrassingly rough first drafts

• Over a dozen stream-of-conscious voice-to-text blurbs in the notes app of my phone

• A stack of coffee-stained journals filled with impossible-to-decipher penmanship

Given this chaos, perhaps it’s no surprise that so far in 2025, I’ve fallen off the consistent publishing train. I’m trying to be more patient with myself, as I’ve realized there’s a fine line between pushing through a creative block and forcing something that just isn’t there. Sometimes, the wisest move is to stop chasing words that aren't ready to be caught — though I must admit, there was one particularly frustrating day last week when I nearly lit all of my non-idea-yielding journals on fire.

But instead of hitting [PERMANENTLY DELETE] on all of my dysfunctional drafts, or worse, feeding them to ChatGPT and asking it to “find a good angle” as several people kindly suggested (advice I ignored, because I refuse to believe that the 86 billion neurons in my human brain aren’t sufficiently creative enough on their own) — I’ve decided to grease the wheels by putting together a list of some of the half-baked essays that have been sitting in my drafts for a while.

If any of these topics resonate and/or leave you wanting more, let me know in the comments, and maybe I’ll write a full post about them. 🙂

⭐️ On Life Transitions

Sometimes, life changes so subtly that it goes unnoticed for months, and only in hindsight does a distinct, well-defined phase become apparent.

But other transitions — graduations, career changes, breakups, moves — arrive with great fanfare and an obvious punctuation mark. It’s always a strange feeling to be acutely aware that a major life chapter is coming to and end, and as we speak, I can see the pages in my book beginning to turn.

In a few days, I’m leaving Mexico to fly back across the pond, and for the first time, I don’t have plans to return to Puerto Escondido long-term. Five winters here feels like the perfect accidental round number to close this chapter on — I still love this place and will definitely return for shorter stints here and there, but the version of me that once fit like a puzzle piece here has evolved, and I’m ready to plant more permanent roots elsewhere.

As I count down the single-digit days that remain, I’m already nostalgically mourning the life I've built here, while wrestling with a mix of eagerness and apprehension for what’s ahead. So if I seem a bit unhinged these next few days, that’s just the emotional rollercoaster talking (please fasten your seatbelt).

⭐️ On Cutting Back on Booze

I’ve never worried about having a problem with alcohol. I tend to be on the responsible end of the spectrum among my friend group, I never drink alone and I don’t feel a compulsion for the booze itself — it’s purely a social thing.

That being said, at the tender age of 35 and 11/12ths, even just a few beers will absolutely wreck my sleep, make my heart race, and turn me into a shell of a human the next day(s). Shouldn’t that be enough to set off alarm bells? And if it’s ‘purely a social thing’ why is it that I never go out sober?

After spending the past 15+ years poisoning myself at least once a week, last month, I significantly cut back on my alcohol consumption, almost to zero. And I felt fantastic. As it turns out, waking up without a headache is actually what I find to be kind of addictive.

⭐️ On the American Dream

Perhaps unsurprisingly, immigration has been weighing on me lately.

This is obviously a hefty topic, and one that I want to approach thoughtfully rather than with knee-jerk reactions. But it’s hard to stay quiet when $200 million worth of racist, anti-immigrant propaganda keeps interrupting dinner.1

Beyond the clown show that is the Trump administration, I come at this topic from an interesting perspective, given that I’m currently living in Mexico, and because I’m a few months out from navigating another country’s immigration process.

So yeah, deportations without due process, ICE detaining folks during scheduled immigration appointments, threatening to send U.S. citizens to foreign prisons, and the rise of nationalism/xenophobic rhetoric in general tend to keep me up at night.

Sidenote: I have a hunch that many Americans don’t realize this (or perhaps even know who she is), so I want to point out that Claudia Sheinbaum, the first female president of Mexico who took office just over six months ago, is absolutely killing it. Not only does she have record-high approval ratings, but she’s even more popular among men than women.

It’s kind of wild timing — the juxtaposition of Mexico's progress with the simultaneous unraveling of things in the United States has been interesting, to say the least.

A well-spoken, steadfast, effective female president? What a concept.

⭐️ On Biological Clocks

Babies. A topic that I don’t feel ready to write about yet, but one that feels increasingly urgent to confront with each passing day (as mentioned, I’m 35 and 11/12ths years old). Here’s what else I’m working with:

• I genuinely still don’t know if I want children, or if it’s just another societal expectation that I feel compelled to fulfill.

• Several of my friends, including some younger than me, have already struggled to get pregnant.

• Given that I am undecided if I even want children, I am uninterested in putting my body through the chemical-induced torture of freezing my eggs.

• Does any of this even matter because maybe I’ve already missed my chance?

I’ve read tons of eloquently written pieces by women who have made the conscious, empowered decision to NOT have children (this one by , I particularly loved). I support Lane wholeheartedly and deeply admire her conviction — in fact, I can only hope to reach that same level of clarity one day. For now, it’s still a mental game of ping pong — mostly because I struggle to see the “yes, I want children” path as a real possibility.

That’s because any time someone asks me if I want kids, my mind doesn’t go to a pink nursery or a list of cute names. It goes straight to the question: with who? How can I envision a life with a child if I don’t know who my partner in raising it would be?

Yeah, yeah. I can already hear the well-meaning advice rolling in: “But Em, you have to have kids, I can’t imagine my life without mine!” The thing is, I can envision my life without children, and it’s wonderful. Or perhaps, “But Em, it’s 2025, you don’t need a man to have a baby!” As it turns out, there are a few things that I am already 100% sure about.

⭐️ One Last Thought

I saw this one-line zinger somewhere on the internet a few weeks ago and I haven’t stopped thinking about it since: There is a version of you 10 years in the future that is begging you to enjoy life a little more right now.

Plain Croissants and Missed Opportunities

Last Friday morning, I sat down at my favorite table at one of my favorite bakeries, excited for a catch-up with an old friend that I hadn’t seen in a while. The waiter approached, and before I could mention that I was waiting for my friend to arrive, he asked, “Your usual?”

It caught me totally off guard — sure, I do stop by this spot often, and this particular waiter always greets me with a smile. But I didn’t think I had achieved the status of being “one of the regulars” quite yet.

Perhaps my go-to order — a latte and a plain croissant — is a bit uninspired and easy to recall. But sheeeesh, for as much as I take pride in my sense of adventure, rejecting the status quo, and claiming to be allergic to monotony, when did I become so…. predictable?

Now, I guess it’s not totally my fault. Humans are hardwired to seek familiarity. We gravitate toward routines and we’re creatures of habit for a reason. Repetition creates rhythm, and our rituals provide us with a sense of control in a world otherwise full of an overwhelming amount of choice. It’s often just a matter of preference or practicality: That Friday lunch spot with the tasty B.L.T., that drive-thru coffee shop that’s conveniently on the way to work, that well-trodden running route that strategically dodges the big hill on the north side of the park. We get our hair cut at the same salon, take our car to the same mechanic, and shop at the same grocery store because we know what to expect — that the same brand of peanut butter that we’ve been buying for two decades will be on the left-hand side of aisle nine.

On a biological level, this helps us conserve cognitive energy and move through life with minimal friction. After all, why reinvent the wheel when our wheels are already parked in that same shady corner spot, just where we like them? Why risk rolling the dice on the unfamiliar and untested? Comfort zones are just that — comfortable. The boats shall remain unrocked, apple carts undisturbed, thank you very much.

But by refusing to roll said dice, we also run the risk of getting stuck in a cycle of stagnancy. Familiarity may keep us sane and settled to a degree, but it’s also why we stay in jobs we dislike, relationships we’re unhappy in, and places we’ve outgrown. It’s a fine line, but it’s crucial to recognize when we are clinging to familiarity simply because of the sense of security it provides. Oftentimes, the fear of the unknown seems worse than any discomfort that comes with staying put.

Now, this is a major Emily, practice what you f@#king preach moment, because as evidenced by my bland-ass croissant above, I’m a sucker for playing it safe. Sure, I realize that my whole “life without a fixed address” thing might seem pretty adventurous to most people, but here’s the irony: With the inherent potential for chaos that comes with living abroad, I’ve often found myself clinging even tighter to the routines I am able to recreate no matter what country I’m in.

It’s a strange paradox — choosing a lifestyle that constantly forces me outside of my comfort zone while simultaneously seeking the refuge of predictability. I mean, what’s even the point of traveling 4,000 miles halfway around the globe if I’m just going to try to recreate my life from back home?

And how many experiences have I missed out on because, instead, I chose to do [that thing I do at the same time every day]? How many opportunities have knocked, only to be ignored because I resisted change? How many chance encounters have slipped right past me that, if I weren’t plagued by my morning routine tunnel vision, could have shifted the trajectory of my day? Probably more than I’d like to admit.

But change is hard, and humans are stubborn. In fact, right now, as I’m finishing typing up this essay, guess what — I’m back at that same bakery, and like a complete and utter hypocrite, I just ordered that same latte and same god damn plain croissant from that same friendly waiter.

This time, however, I was served up a minor plot twist:

“Sorry — we just ran out of plain croissants. Can I get you something else?” he apologetically asked.

Laughing at the universe’s not-so-subtle hint to spice things up, the decision felt easy:

“Surprise me.”

Recommended related posts:

• Follow Me to Weird Places — An invitation to throw your rigid itinerary in the trash before your next trip (even if that means leaving your comfort zone).

• A New City Every Month: An Experiment in Change — How changing up our surroundings can lead to unexpected shifts in personality, energy, and perspectives.

• Celestial Enlightenment — Why not do more things simply because they make us feel a zest for life?

The Nail in My American Coffin

It was the first and only time I’ve ever time-traveled — we took off at 4:30pm on Monday, October 16th and landed at 10:30am on Monday, October 16th. After ten hours in DeloreanAir ZipAir economy class, I stepped outside of the airport terminal and was met with blinding Californian sunshine, the scent of salty asphalt and a loud, familiar accent.

Maybe flying in directly from Japan — a place that reprogrammed the operating system of my mind — was a bad idea. The surreal precision of Tokyo, including everything from its immaculate streets to its impeccably orchestrated subway system, was still fresh in my mind and had set an impossibly high bar. Not to mention, how could San Diego prove itself as a place worth moving to when most of this trip would be spent in a jetlagged blur? Was five days, four nights even enough time to make a life-changing decision of this magnitude?

On the other hand, I was ready to fall in love and was convinced that San Diego was the one. In fact, I had re-routed my entire travel itinerary 7,000 miles around the other side of the globe in order to make this pitstop. If that’s not the setup for a romantic meet-cute, I don’t know what is. And it wasn’t entirely a blind date — I had lived in California for the two years leading up to the pandemic. But this was my first time in San Diego, and I was hopeful that being a bit further south would allow me to escape the (imo) depressing San Francisco fog and provide a more relaxed rhythm to life. I was entering year three of living without a permanent home base, and the itch to finally settle back down was now un-ignorable.

On paper, San Diego checks most of my boxes: solid weather year-round, a smaller city surrounded by nature, an active beach volleyball community, some semblance of diversity, and direct flights to my side chick, Mexico. I even had a head start in the friends department, thanks to the pandemic-induced SF exodus and the uncanny number of San Diegans I’d met during my international travels. Hours of research made it clear that Ocean Beach would be my neighborhood of choice, so I rented a quaint little studio and made myself at home, eager to experience things through the eyes of a local.

Day one1 was promising, although still on Tokyo time, I was wide awake at 5am. Fortunately, the cute coffee stand on Voltaire Street was open, so I grabbed an egg sandwich for “dinner” and got my long overdue pumpkin spice latte fix (you can take the basic white girl out of the states, yada yada). Twenty-three crisp American dollars later, I was floored. Sure, I had expected some sticker shock being back in the states, but this was beyond what I had imagined (several $11 IPAs and one $27 gallon of laundry detergent would later confirm2 that this was not a fluke).

Nevertheless, with my pricey PSL in hand, I carried on to Dog Beach for some prime early-morning people watching. It was alive with surfers, joggers, dog-walkers, and a group of retirees who, with their friendly smiles and pop-up volleyball net, quickly drew me in for a chat and a few pick-up games. It was like taking a peek into my potential 65-year-old future, and I couldn’t resist picking their brains about life in San Diego. A bit older than I’d imagined, but hey, new friends! The rest of the day I spent getting the lay of the land, nourishing myself with some Baja-style fish tacos and chatting up a pair of bartender locals that, at first, seemed hesitant about hyping OB up to yet another east coast transplant, but later let down their guard and admitted how much they adored living there.

Still, after a few more days of exploration, something wasn’t quite clicking. While many things in my “pros” list were validated, the “cons” column seemed much con-ier than I had hoped.

I’m not sure if it was the aggressively gray morning marine layer, the variety of holistically-blessed yet capitalism-fueled "wellness" products for sale at the Wednesday night farmers market, or seeing the brutal reality of this country’s homelessness and addiction crisis up close — probably a combination of all three. But I just couldn’t shake the feeling that I was slipping back into my old American life, facing the same daily frustrations that I had once left behind. Oh, and where the heck were the bike lanes?!

To be clear, this post isn’t a dunk on you, San Diego. You’re a fantastic city, and my criticisms aside, I still had a great time. I just didn’t feel the chemistry — please consider this my apology for ghosting you. Maybe it’s a weak consolation prize, but if I did have to choose a place in the U.S. to settle back down, you’d still be on my short list.

Cliché breakup justifications aside, the thing is — and this is something that this trip helped me realize — is that no one is forcing me to settle back down in the states. Nearly 18 months have passed since this October 2023 jetlagged adventure, and in that time, my perspective on things has shifted significantly. I used to assume that leaving my home country meant losing my sense of security. But today, the idea of putting down permanent roots abroad no longer intimidates me. The world feels smaller, my comfort zone bigger, and my desire for a picket fence non-existent. Consider this yet another step in my ongoing pursuit towards achieving societal pressure escape velocity.

Yes, settling down abroad will require a complicated visa process, lots of paperwork, challenging logistics, overcoming cultural barriers, and sometimes feeling like an unwelcome outsider (or worse — assault by water gun). But rather than settling for a U.S. city that’s the lesser of fifteen evils, the potential for a more expansive, more fulfilling life that allows me to be my best, happiest self is a prize that I’m willing to work for — let’s just hope that I remember to send a few postcards.

Recommended related posts:

• On Passport Privilege — A friendly reminder that the opportunity to voluntarily immigrate to a new country that I’ve hand-picked is not something I take lightly.

• Stacking the Happiness Odds in Your Favor — My thoughts on the domino effect that results from the decision of where we choose to live.

• Societal Pressure Escape Velocity — A must read for those also considering the idea of an unconventional lifestyle.

No Subtitles Necessary

Despite living in a surf town full of barefoot hippies and woo-woo free spirits, I’ve never dabbled in psychedelics. Not mushrooms, not ecstasy, not LSD, not a sip of ayahuasca. So I suppose I don’t know this for sure — but I can’t imagine that even the finest concoction of chemically engineered hallucinogenic giggle dust sold by a wizard could come close to the rush of dopamine I felt upon receiving this compliment from my Mexican friend the other day:

“Emi, no mames — no puedo creerlo, tu español ha mejorado un chingo!” which loosely translates to: “Wow, Emily, your Spanish has improved a shit ton!”

After 1,900+ days of Duolingo, 350+ podcast1 episodes, 120 hours of formal one-on-one classes, and two years of brute-forcing myself though conversations in which I was in over my head, I’m proud to claim that I finally feel conversational in Spanish.

I no longer translate from English in my head before speaking, I use sarcasm and crack (sometimes funny) jokes, and I usually only need to ask for the definition of a word when it's a Mexican slang deep cut. Sure, I still make errors in every third-ish sentence, there’s advanced grammar that still trips me up, and I still have a very thick (cute??2) accent. But I can now generally let things run on autopilot and hope for the best.

It’s pretty wild that much of my social life now happens in a foreign language — several of my closest friends here don’t speak much English at all. The impact this has had on my experience living in Mexico has been unsurprisingly enormous: Comparing my first two years here (when successfully communicating with a taxi driver felt like an achievement) vs. the past two years is night and day (the latter being a heck of a lot more fun). I’ve gone from being a silent spectator of Mexican culture to fully embracing and participating in it — and in turn, I've developed a deep appreciation and love for this country that no words in either language could do justice.

Part of me wonders if this is why I’ve leaned into writing (in English) recently. It’s almost as if this blog has become an outlet for all of the complex emotions and nuanced opinions that I struggle to express with exact clarity in Spanish. Maybe not, but the timing is certainly suspicious — or perhaps my brain just needs a place where the por/para dilemma doesn’t exist.

Either way, my love for words, semantics and etymology has taken on a life of its own, making the past few years a fun challenge. But don’t get me wrong, it’s also taken plenty of hard work — despite what many gringos seem to think, you won’t learn a foreign language simply through osmosis when living in a different country (and certainly not if you only use your Spanish to order at restaurants). “You’ve lived there for five years, you must be fluent by now!” — if I had dollar every time I’ve heard that.

I say this because even with all of the progress I’ve made, there’s still a looong way to go. Each time I think I’m getting the hang of it, an irregular verb or funky grammar rule always pops up, reminding me that language learning is a marathon and I’m running it in chanclas.

Fortunately, I don’t plan on stopping anytime soon. In fact, when I head back to Valencia in May, I’m planning to enroll in three months of intensive classes — this is partially a scheme to stay in Spain longer than my allotted 90 days, partially so that I can finally learn how the heck to conjugate vosotros, and partially (okay, mostly) because I’m FOR SURE throwing myself a graduation party upon completion. Oh, and don’t worry — todos ustedes están invitados.

Recommended related posts:

• In Pesos We Trust: At first, living life in pesos was jarring, but I’ve learned to appreciate how a currency can carry the personality of a place.

• No Hay Luz — No power, no WiFi, no cell service. Bienvenidos a Puerto Escondido!

Before the World Needs Me

The coffee is always prepped the night before: beans ground, water poured, travel mug patiently set on the counter. A quick flick of the [ON] switch is all it takes when my 6am alarm goes off, as there’s no time to waste — in Mexico, the sunrise is the only thing that’s ever on time.

The ocean is just a seven-minute walk from my front door, so by the time those first peachy streaks of morning appear, my feet are already in the sand. I always bring a notebook and pen, though more often than not, I let my thoughts ebb and flow impermanently along with the waves.

As peaceful as it is, I’m never alone. The beach is dotted with dog walkers, ambitious joggers, and occasionally, a crew of rowdy vampires stumbling home, eager to escape the dawn light that will expose their recklessness. A few local fishermen battle the pelicans for the first lucky catch of the day, and of course, there’s a handful of surfers paddling out before rush hour, their youthful energy and weathered boards promising a solid people-watching opportunity whether there’s a swell or not.

Everyone knows the sunsets here are magic — with a due-west-facing beach and a hot, arid winter climate, the evening golden hour show is not only breathtakingly spectacular but remarkably consistent. It’s the main event, free admission, seven days a week, no alarm clock needed. But the real payoff comes from waking up with the roosters — there's a subtle satisfaction in getting a head start on the day while everyone else is still snoozing that makes overcoming any groggy reluctance to leave my warm bed worth it every time.

I don’t catch the sunrise often, but I should — because with it comes a calm sense of freedom that quickly evaporates once the town begins to buzz. And if there’s one thing I’ve learned from this occasional addition to my morning routine, it’s that stealing a few quiet hours from the day’s demands, deadlines, and distractions feels like the world’s most obvious, worst-kept secret — but still, sunrises belong only to those who are willing to wake up and claim them.

Recommended related posts:

• In Pesos We Trust: At first, living life in pesos was jarring, but I’ve learned to appreciate how a currency can carry the personality of a place.

• Jetlag Diaries — The beauty of inviting chaos, rejecting comfort zones and blindly putting your trust in strangers.

• No Hay Luz — No power, no WiFi, no cell service. Bienvenidos a Puerto Escondido!

Accommodation Roulette

December 20, 2024: Greetings from Puerto Escondido, where the holiday crowds have begun to pour in, just in time to celebrate the town’s shiny new designation as one of Airbnb’s Top Trending Destinations for 2025.

Ugh. Maybe we should start calling it Puerto not-so-Escondido?

Now, I’m painfully aware that my navy blue passport and I have contributed to the rapid, unsustainable growth that’s taken place here over the past few years — but as someone who longs to protect the spirit of this formerly sleepy surf town, the sight of international chain restaurants putting up 'Coming Soon!' signs in La Punta still stings.

Despite all of the recent development and expansion, Puerto remains a special place. There’s an intangible yet undeniable magnetism here that lures many people in (myself included, as it’s been my winter home for the past five years). If you’re curious what life here is like, I posted a photo dump on Instagram the other night — but please keep in mind that as social media often goes, these cherry-picked moments leave out much of the messy reality.

I feel obligated to add that among the spectacular sunsets and lounge-chair coconuts are a slew of lowlights that never quite seem to make the photo carousel: the constant power outages, the 4am rooster wake up calls, the mosquito bites that carry the risk of Dengue Fever, and the fact that last Tuesday, I spent the entire night vomiting my brains out (Food poisoning? Bad water? Wait, was that Dengue?!)

Living here means you must roll with the punches that this paradise often throws — a skill I’ve honed through many years of sacrificing personal comforts for the sake of ticking things off my bucket list. In fact, dealing with fowl-mouthed neighbors1 feels like a walk in the park compared to some of the other chaotic moments I’ve faced during my travels.

In the wise words of my friend Sharon, who has had a front row seat to countless such moments, “everyone loves a good disaster story.” So in the spirit of keeping things real (and because I’ve somehow accumulated an unfortunate amount of material for this topic), I thought I’d share some of my best worst travel mishaps:

• Last summer while in Rome, Sharon and I locked ourselves out of our Airbnb (our fault!) and didn’t realize it until 3:30am (still our fault!) — the owner surprisingly came to our rescue, but after a few failed attempts with the spare key, she stormed off in a fit of stereotypical Italian hand gestures, and we didn’t hear from her again for twelve hours (kind of not our fault!) It was a weekend during peak tourist season, and at that hour, the only option for sleep was an overpriced bunk bed in a 20-person hostel dorm across town.

• Ignoring the scorpions, tarantulas and snakes for a moment (hey, that’s just classic Central American charm), the oceanfront villa that a group of friends and I rented for a month in San Juan del Sur, Nicaragua was pretty incredible. Sunset views, an infinity pool, a private chef on call — the works! Well, that was until the power went out, the faulty generator began filling the villa with fumes, and we all almost died from carbon monoxide poisoning. Hey, does anyone else have an excruciating headache?

• This past summer, I decided to switch things up and stay in a different neighborhood of Valencia — one closer to the beach, as I was eager to soak in more of the Spanish sun. While making coffee on the very first morning, a mouse darted across the kitchen floor. And he wasn’t alone — I’d soon discover that the entire building was infested. Just like that, I was packing up yet again, scrambling to find a pricey, last-minute place to stay as my carefully laid plans for the next three months fell apart.

• After clocking about 20k steps around the Acropolis in Athens a few years back, my ex-boyfriend and I returned to our apartment to relax. I decided to do some light stretching on my yoga mat in the kitchen, when mid-Pigeon Pose, I began to hear the faint trickle of water from under the sink. Hmmmm, that’s weird, nobody’s in the bathro—BANG!! A shoddy pipe suddenly exploded, and a flood of scalding hot water began filling the kitchen. We scrambled to figure out how to shut off the valve in this unfamiliar apartment while burning ourselves in the process. Fortunately we happened to be home when the pipe decided to give way — a massive stroke of luck given that both of our passports were in a backpack sitting on the floor just a few feet away. But now that I think about it, maybe we would have been better off with ruined passports? Because just a few days later, we boarded another flight and my ultimate travel nightmare became a reality…

• Bedbugs. Yep, bedbugs. And no, we weren’t slumming it in some sketchy hostel, we were staying in a fancy, highly-rated guesthouse that seemed immaculate at first glance. We didn’t even notice until the third day when the bites began to appear. And GOD DAMN do those bites hurt. Though for me, the psychological toll was worse — for the next few months, I couldn’t sleep through the night due to a phantom feeling that something was crawling on me, and every time I saw an ant in the house, I’d spiral into a full-blown panic attack that they were back. I’m not exaggerating here — it’s taken me over two years to just be able to write about this.

Needless to say, these “travel hiccups” (putting it lightly) are a big reason why I’ve essentially stopped nomading this past year, and why I finally plan to put down roots in Spain in 2025.

Still, I’d be lying if I said that — uninvited critters and property maintenance fiascos aside — I didn’t sometimes worry about whether I’m really ready to give up the freedom of this incredible lifestyle. I still haven’t been to South Africa or Argentina or Australia or anywhere in Southeast Asia. Instead of subjecting myself to expensive, complicated visa paperwork and the limitations that come with owning a doormat, why not just escape to Chiang Mai2 this summer when I inevitably run out of Schengen days? Why buy a couch when I could buy a plane ticket to Peru? How could I walk away from my annual love affair with Puerto Escondido?

Recounting all of these horror stories serves as a good reminder that (1.) no, bucket list destinations are of course not always what they’re cracked up to be regardless of what Airbnb thinks, and that (2.) yes, I am ready for a less frustrating life. There’s no doubt that these past few years have been unforgettable, but the wanderlust pendulum has begun to swing back, and I’m finally ready for four walls that I can call my own again — I just hope that my next spin of the accommodation roulette wheel proves to be a winner.

Recommended related posts:

• To All of the Places I Will Never Visit: More likely than not, a portion of our bucket lists will remain untouched forever — and that's okay.

• Follow Me to Weird Places: Why you should leave some room in your next trip’s itinerary for a bit of spontaneity.

• On Passport Privilege: Sometimes it seems that I simply jet-off to whatever corner of the world my little heart desires, so this is a reminder that I don’t take that privilege lightly.

The Seasoning That Makes Life Extra Tasty

December 10, 2024: Last month, I wrapped up my second cohort of an online writing bootcamp called Write of Passage.

Like my first go-around this past spring, it was five jam-packed, high-energy weeks of idea sharing, peer editing, and connecting with internet strangers (who always seemed to have way more in common than you’d expect).

Enrolling in Write of Passage back in April was a leap of faith, but it has already paid off with several cool, random opportunities that have come my way directly from it. Most significantly, WoP hired me as an official editor this second go-around — proof of the good that comes from following your curiosities, and the magic of side quests on full display.

In fact, side quests — also known as hobbies, passion projects, short-term obsessions and creativity-fueled personal experiments — have been an important part of my life in recent years, as I’ve broadened my definition of success to encompass more than just traditional work. Now, instead of a 9-5 salary, I’m focused on an Octopus-style1 portfolio career. I have client-based freelance work, I run three eCommerce online shops (more on those below), and even scrape together a few pennies from this here blog (shameless plug to support my writing here).

Any free time left over is filled with a rotation of improving my Spanish, improving at beach volleyball, and long morning runs — all personal hobbies that obviously generate $0, but which, if I’m being honest, get near-equal priority to work because they bring me more joy than a few extra billable hours ever could.

Now, whether living in a small Mexican beach town has allowed me to realize the perks of living unconventionally, or if it's my own independent spirit that led me here in the first place — well, that’s a bit of a chicken-or-egg situation. But either way, I find myself constantly surrounded by other people doing interesting shit:

Take Leslie, a new friend I’ve made since I’ve been back in Puerto Escondido. We’ve gotten to know each other pretty well over the past two months, which is mostly a factor of unintentionally seeing each other every day (consider this a spoiler for another essay I’m cooking up…)

A few weeks ago, Leslie competed in the Reto Puerto Escondido 2024, a 2.5 kilometer open water swim off the coast of Playa Zicatela, the famous Mexican surf pipeline with huge waves and intense currents. She finished second in her division, a massive personal accomplishment that was later celebrated with a pool party (us) and a long nap (her). Up until that day, I had NO idea Leslie swam competitively — turns out, neither did she:

“I love swimming so when I heard about the competition, I just decided to sign-up.”

She also takes salsa lessons, is a regular at morning fitness classes, and is part of the beach volleyball community here, which is how we initially met. To be fair, like many others in this youthful-leaning beach town, she has a bit of 27-year old energy to help fuel all of these hobbies. But blaming a lack of motivation on age (or work, or busy schedules, or kids, or whatever) is an easy excuse — the reality is that most of the time, it’s a matter of saying yes, showing up and getting involved.

You don’t need to wait for permission, an invitation, or a red carpet to be rolled out in front of you. I’ve said it before, and with each new online bootcamp, each new creative endeavor and each new hobby, I only find more truth in the idea that side quests are the seasoning that makes life extra tasty.

Another Shameless Plug…

This time, for one of my OG side quests that I basically never talk about, but totally should.2

A few years back, I launched what I like to call ✨ Emily’s Ecomm Empire ✨ — a collection of Shopify stores that sell things I’ve designed. To be fair, the term “empire” might be a bit of a stretch, as I just recently broke even with one of the three stores. But the opportunity to mix my left-brain entrepreneurial spirit with my right-brain creativity has made this become my most beloved project. And who knows, maybe one day it’ll eventually pay the bills.

Today I want to introduce my first online shop, Backstory Map Co: Posters, maps and artwork inspired by my years of travel, weird obsession with vexillology, and love for nerding-out over a good map. All 400+ designs have been hand-doodled by yours truly!

In Pesos We Trust

For the past few weeks, I’ve had 60 Mexican pesos — a gold-rimmed $10 coin and a vibrant purple $50 banknote — sitting loose on a bookshelf near my front door, patiently waiting to be returned to its rightful owner. For my fellow Americans keeping score at home, that’s just under $3 USD. Though the real value behind this little pile of pesos goes far beyond its monetary worth.

One morning last month while on my way home from the lavandería, a water delivery truck serendipitously crossed my path. “Compro tres!” I yelled to flag the driver down, knowing that the large blue garrafón jugs in my apartment were running dangerously low. Wow — clean undies and a full supply of water? I was cruising through my morning to-do list.

It was only after the nice man had lugged each extremely heavy jug all the way into my apartment that I panicked, realizing that I had just spent every last bit of small change on my laundry. All I had left was a stack of $500 bills straight from the ATM — notoriously difficult to break, particularly in this cash-forward, locally-run little beach town where I live. Imagine stopping into your local NYC bodega and trying to pay for a $1 bottle of water with a crisp Benjamin — that’s essentially what I was trying to pull off.

“Hiiiiijole… pues, vives aquí? Vuelvo mañana. Tranqui,” the man muttered, which roughly translates to “Enjoy your water silly gringa. I’ll come back tomorrow, just pay me then.”

This large-denomination dilemma is a familiar problem in Puerto Escondido. In fact, on my very first ever morning here a few years back, I decided to take a stroll around town to check out my new digs. Naturally, I stopped for coffee, this time armed with an easier-but-still-kind-of-a-bitch-to-break $200 bill. The friendly barista who was on shift at 7am laughed, and handed me back the $200 bill in-tact along with my latte. “I’ll see you around, just pay me next time.”

Was it my trusting face? A stroke of beginner's luck? Hold on — was he flirting with me?! (He was not.)

As it turns out, it’s just a neighborly mindset of “I have faith that this complete stranger will eventually pay me back,” a sentiment that’s more prevalent in Mexico than anywhere else I’ve traveled. It’s a big part of what makes the culture here feel so warm and welcoming, and a shining example of how a tight-knit community should function. No contracts, no IOUs, no slinging the same twenty bucks back and forth on Venmo. Just mutual respect and a quiet reassurance that even if no one is specifically keeping track, the favor will always come back around — generosity is the default setting. It’s a refreshing contrast to the often tip-driven, pay-upfront, transactional relationships back in the States. After all, I guess it’s pretty hard to nickel and dime someone when nickels and dimes don’t exist.

Initially, living life in a different currency was jarring, especially the first time the ATM spat out Monopoly money instead of legal tender. But I’ve learned to appreciate how a currency can carry the personality of a place. That’s why in the shoebox full of funky coins and misshapen bills I’ve collected from nearly all of the three dozen countries I’ve visited — neon Hong Kong dollars, volcanic Nicaraguan córdoba and lucky Japanese 5-yen coins included — the Mexican peso remains my favorite.

It’s the informal running tab I often rely on at my corner fruit and veggie stand. It’s the friends who would rather go out to dinner a second time than be paid back. It’s the owner of my guesthouse asking for payment only after I’ve stayed a few nights to make sure everything is to my liking. And most importantly, it’s the unspoken agreement that, even though it’s been over a month and the water delivery man still hasn’t come back, those 60 pesos will remain sitting on my bookshelf and won’t be spent on anything else.

Random tangent disguised as a footnote:

*The latest version of the $50 MXN bill features the beloved ajolote, a salamander-like endangered species native to Mexico and symbol of the country’s biodiversity. When the bill first entered circulation in 2021, it was so popular that many people began hoarding them as souvenirs. It won the International Bank Note Society’s annual Banknote of the Year award and even inspired “50 ajolopesos” merch. The ajolote is also known as the Aztec god of fire, lightning, and the underworld, which I find absolutely hilarious because it looks like this.

Recommended related posts:

• No Hay Luz — No power, no WiFi, no cell service. Bienvenidos a Puerto Escondido.

• Deep Chats with Strangers in Airport Bars — A front-row seat to the comedic chaos of humanity in transit. Pull up a chair!

• Jetlag Diaries — The beauty of inviting chaos, rejecting comfort zones and blindly putting your trust in strangers.

Jetlag Diaries

Picture this: You’ve just touched down in a new country after a long, restless overnight flight. You hurriedly gather your things and sleepwalk off the plane, unsure of what time zone you’re in, what year it is, or what planet you’re on.

An electrifying flood of unfamiliar sights, smells and sounds greets you: neon signs pulsating in a language you can't read, unidentifiable aromas invading from all angles, the symphony of human chaos harmonized in a key you’ve never heard — and you haven’t even left the airport terminal yet.

The nerves build as you wait in the immigration line, unsure of what lies ahead: Will the people be friendly? Will you be able to find an ATM? Has a few weeks of Duolingo practice really taught you enough to get by? All of your research and planning is finally about to be put to the test, yet those dogeared guidebook tips suddenly feel insufficient.

Your body clings to the rhythm of home — circadian and otherwise — as the sharp mechanical ‘clamp’ of your new passport stamp yanks you from liminality. You’ve officially been welcomed into this foreign land, no safety net or chaperone provided. As you step out into your new surroundings, a fusion of anxiety and exhilaration courses through you, and the hunt for your suitcase and a sense of direction finally begins.

Each passerby offers a glimpse into the cadence of everyday life, though it feels like you’re watching a movie without subtitles. You catch snippets of conversations that you don’t understand, but surprisingly, there are some that you do — as it turns out, everyone laughs in the same language.

Your 3am eyelids struggle against the piercing sun, and the world unfolding before you is washed in a dreamlike, surreal haze. The architecture, the landscape, the vehicles, the storefronts — it all feels so fascinatingly…different. Yet an inexplicable magnetic curiosity invites you in, as if to remind you that your comfort zone will never expand unless it’s purposely stretched.

After a few minutes of clumsy charades, the shopkeeper finally understands your gesture towards an unpronounceable chocolate pastry — or is that sausage? Either way, you dig out a handful of heavy coins and allow them to be plucked directly from your palm, hoping that no ‘tourist tax’ was also collected. Sometimes, you simply behave no choice but to roll the dice on strangers being good people.

In fact, with each small win and gesture of hospitality — the welcoming smiles, the nods of approval, the friendly exchanges — you begin to feel more at ease. Though the specific execution of habits and customs here are approached differently, you can’t help but notice the similarities that defy borders. Maybe this place isn’t as foreign as you thought?

Still, you’ve accepted that at some point, things will go wrong: a missed train connection here, a wrong turn there. But even the most frustrating travel mishaps and misunderstandings evolve into funny stories with enough time. So why not lean into the chaos? When negotiating with the unknown, sometimes it’s better to simply toss your map in the trash and put your faith in the magic of detours. After all, the whole reason you came here was to get a little lost.

Recommended related posts:

• Follow Me to Weird Places — Encouragement to step off the beaten tourist path and get lost in unpronounceable places.

• Deep Chats with Strangers in Airport Bars — A front-row seat to the comedic chaos of humanity in transit. Pull up a chair!

• Schlepping It — Reality check: The full-time travel lifestyle isn’t always so glamorous.

An Antidote for the Sunday Scaries

Congratulations! We are delighted to inform you that you have been selected for the position of [inflated job title] with [soul-sucking corporate overlord]! We’re thrilled to offer you a generous starting salary of [$X, non-negotiable — much like your hours].

The scope of your role will range from monotonous busywork to crisis management, with no real distinction between the two. We promise to mask our lack of personal life boundaries (company policy) with a cushy corner cubicle and unlimited plastic silverware so that you can eat dinner at your desk anytime you’d like!

Last but not least, you’ll receive three full weeks of paid-time off that you must first accrue and will later never feel quite comfortable using. We’re confident that this position will provide just enough financial stability to keep you handcuffed to a cycle of existential dread, and too little time to reflect on what you actually want out of life.

Best,
-Management

It’s been six years since I hopped off the corporate ladder, and while I’ve certainly found joy in working on my own terms, I’d be lying if I said that I don’t sometimes feel the temptation of a stable, traditional career.

Last Friday around 5pm, when all of my friends met up for a drink to kick off the weekend, I stayed home to kick off the search for new freelance projects. I’ve forgotten what it means to unplug on vacation, and more weekends than not, my laptop and email inbox accompany my morning coffee. I’ve had to reel in my personal budget, navigate private health insurance and I’ve put several personal aspirations — like homeownership and motherhood — on the back burner.

But the thing is, even with all of these sacrifices, struggles and scrambles — I’m never going back. Without fail, every time I casually log onto LinkedIn to browse full-time roles “just to see what’s out there,” I end up slamming my laptop shut 20 minutes later with a renewed appreciation for my independent lifestyle. 

Surprisingly, it’s not the actual freelance work itself that’s made a difference in my overall job satisfaction — I still have deadlines, clients to answer to, tedious tasks and the occasional late-night emergency project. What has made a massive difference however, is having autonomy over when and how much I work, which in turn, has provided the flexibility and time to be able to pursue a number of other personal interests: extended travel, learning a new language, writing online, launching a few indie projects, and picking up a couple of other new hobbies.

For me, having freedom over my daily routine is more valuable than any annual raise or hefty bonus that I ever received in my former corporate life. Sure, I’m not the proud owner of a four-bedroom rancher nor do I have a shiny new Lexus in its driveway, but I also haven’t had a case of the Sunday Scaries in six years — and I plan to keep it that way.

Now, contrary to what you might expect, I actually believe that money does in fact buy happiness. Obviously, there’s a minimum threshold that we all must earn in order to cover basic needs and maintain a comfortable enough lifestyle. But there comes a tipping point when we should also evaluate the psychological costs and emotional toll of devoting our lives to a job — because even the most lucrative, prestigious careers can be overshadowed by an unbearable schedule or an unfulfilling daily grind.

I so wish that we were able to easily quantify happiness1 just like we can quantify a salary, because I bet many people would reshuffle their priorities:

“Yeah, Harry raked in $220k last year, but his Occupational Contentment Quotient (OCQ)™ was a meager 14 out of 100… bleak.”

Perhaps Harry would reconsider things if he realized the incredible irony in working a job, to pay for a car, that he only uses to drive to work.

Okay, okay. In all seriousness, part of me does get it — shit is expensive and we adults need to pay for it all somehow! But the thing is, the more time we spend grinding to pay for our lives, the less opportunity we have to pursue things that actually make us feel alive. It’s the missed moments with our families, the hobbies that gather dust, the dreams that get postponed, and the wondering where all the years went. And for what? More money in the bank, but less life actually lived?

I’m not recommending that anyone abruptly quit their job George Costanza style, but it’s important to thoughtfully consider how we allocate our time in order to avoid falling into the eat, sleep, spreadsheet, repeat abyss.

In fact, I believe that the best antidote for the Sunday Scaries is just that: breaking up the monotony of any regular old week with things outside of work that light you up and bring you joy. You could join a book club! Enroll in vocal lessons! Start a community garden! Volunteer at an animal shelter! Learn to meditate! Take an improv class! Write poetry! Jump on the pickleball bandwagon! Wander around your local Michael’s Craft Store and see what you are inexplicably drawn to! This antidote is available without a prescription and the recommended dosage is completely your choice.

Importantly, this can be done while still working a full-time job — I’ve obviously taken it to the extreme with my sometimes “intentionally underemployed” freelance schedule, but it was only in doing so that I realized just how profoundly fulfilling and soul-enriching my new hobbies and creative projects are. By making a conscious effort to prioritize personal time, pursue our passions, and emphasize play, we are bound to rediscover an energy and enthusiasm for the everyday — these side quests are the seasoning that make life even more delicious.

“But Emily, I also have two young kids at home, I don’t have time for a shower, much less a new hobby!” Look, clearly I have no standing in this arena, but after chatting with so many of my mom-friends, I’d argue that it might actually be even more crucial for parents to carve out at least an hour or two each week for themselves, and themselves only. Everyone should have something that helps them crawl out of bed when their morning alarm goes off, and for most people, conference call marathons and inbox tsunami surfing ain’t it.

I realize that I probably put a higher value on free time than most people — everyone’s threshold is different when it comes to the income vs. hours matrix. And while there’s nothing wrong with being career focused, it’s important to keep in mind that work is a bottomless game, with the only finish line being retirement — and I don’t know about you, but I’m not willing to wait until I’m 65 to begin savoring life.

Have I earned less and taken on more risk than had I kept working my corporate finance job I left back in 2018? Yes. But has designating time to embark on side quests, new hobbies and passion projects brought me more happiness and fulfillment in the long run? No question.

Recommended related posts:

• Finding My “Next Thing” — Get in loser, we’re going to find new adult hobbies!

• The Modern-Day Mission Trip — The origin story of my passion for side quests.

• Celestial Enlightenment — More encouragement to do things simply because they make us feel a zest for life.

September 6, 2024: Hello from the Big Apple! It’s been nearly a year since I’ve been back in the States and the reverse culture shock is hitting hard as expected.

Even though New York is listed as “place of birth” on my passport, it’s never been a city I see myself living long-term — but I love doing short stints here to soak up the electric energy while feeling like a local and a tourist at the same time.

Today I’m publishing a post that I began writing a few weeks ago while I was still in Spain, and I used yesterday’s long travel day as inspiration to get it over the finish line. It’s long, but it’s a fun one. Thanks for reading along!

Deep Chats with Strangers in Airport Bars

Humans are fascinatingly bizarre. When you break it down, we’re really just squishy bundles of nerve endings, former orangutans who now own smartphones, and reality show contestants fueled by existential dread. We act both impulsively and with logical reasoning; we’re habitual yet curious, communal yet territorial. Some of us are good-natured souls full of empathy, while others are downright evil. And at the end of the day, we’re all just acting out in the hopes of receiving a hug.

That’s why people-watching is my favorite sport. And it’s more than just something I enjoy passively — I consider perching myself upon a bench in a high-traffic zone my life’s mission and one true calling. In fact, as we speak, I’m sitting out front of a cute coffeeshop on a busy street corner in Madrid as a nonstop stream of entertainment in the form of raw human behavior passes by.

Most days, I can’t help but wonder: What drives some people to commit random acts of kindness while others act like complete selfish dicks? Why are some people okay with PDA while others cringe at the idea of a public peck on the cheek? Why do some people put on airs in an attempt to seek approval from strangers, while others shamelessly broadcast their domestic spats to a public jury? This woman has passed by five times in both directions, what could she possibly be up to? And why did this man choose to sit on the same bench as me when there are two other perfectly good, wide open benches just a few yards away?! Oh no… oh god… he’s going to strike up a conversation with me, isn’t he?

Now, while observing humans from the safety of the sidelines is my forte, chit-chatting with these same strangers is an entirely different story. I’m happy to extend a routine “buenos días” to a barista or a universal head-nod to a fellow jogger, but beyond micro-pleasantries, I find small talk with strangers hollow and uncomfortable. Admittedly, this is mostly just me projecting as I can be a bit socially awkward when put on the spot, one on one.

Yet there’s one major exception to my anti-small talk stance: As a nervous flier, I usually seek out a pre-flight, nerves-calming, chilled glass of red wine — and without fail, every time I plop down on a barstool at a Vino Volo or a Chili’s Too, I always end up lost in deep conversation with the unfamiliar face sitting next to me.

Quick backstory: I’ve spent the last four years traveling full-time, which means I’ve spent a ton of time in airports, often alone. I’ve come to the conclusion that between the jetlag, the melting pot crowd and the socially acceptable custom of eating Sbarro’s for breakfast, airports are the crown-jewel, Olympic stage, and undisputed Mecca of people-watching. It’s really just one big petri dish of anxiety, as even the newest, most state-of-the-art, calmest terminal food courts with vibey ambient lighting only exist to distract us from thinking about terrorist attacks or that we’re about to be smushed into an aluminum tube next to someone with walking pneumonia for the next six hours. How could people not lose their minds?

Plenty of times, I myself have been the chaotic main character, unintentionally delivering top-notch entertainment in the form of vocally cursing out flight delays or sprawling myself out on the terminal floor for a good night’s sleep. But no shame, because there’s always somebody worse: The guy who hasn’t exercised in a decade but is currently attempting the 200m dash with three suitcases in tow; the disorganized mess in the recombobulation zone hastily stuffing embarrassing toiletries back into a bag that just won’t zip; or my favorite, that one dude who, as he unbuckles his belt at the security checkpoint, habitually pulls down the fly of his jeans next — “hey so uhhh, we have x-ray machines and whatever, so you can actually keep your pants on…”

Can you even imagine mixing a bit of booze into this already wild, wild west of human behavior?

Perhaps that’s why I can’t help myself from diving into conversation with my fellow traveling barflies — the potential for quality content is just too good. Though, it’s not just the alcohol that gets people loose-lipped. In airport bars, there’s an entire concoction of psychological factors at play that cause people to confide in strangers and divulge the juicy stuff (some of these are proven theories, others highly scientific hunches):

Subconscious Safety: Once you’ve finished getting felt up by your assigned TSA agent, a subliminal sense of peace of mind will instead take hold. Yes, we’ve already established that people act bat shit crazy in airports, but still, they are some of the safest public spaces we’ve got. Perhaps this is a uniquely gun-related American phenomenon, or simply a factor of the sheer number of surveillance cameras per square inch. Either way, as a frequent solo female traveler, it's refreshing to be able to let my guard down knowing that the beady-eyed dude across the bar probably isn’t going to follow me out the door with a crowbar.

Incognito Mode: Okay, so there was that one time when a sweet old lady, after two glasses of chardonnay, asked me if I was single and then for my email in order to put me in touch with her grandson (we LOVE a wing-granny) — but generally, the transient nature of airport bar patrons means that there is zero opportunity or expectation to continue the conversation thereafter. One small dash of perceived anonymity, and suddenly the fella next to you is confessing to tax fraud.

FOMA: Not to be confused with fear of missing out, FOMA — or, the fear of masticating alone — is a disorder in which self-conscious humans cannot bear the thought of admitting to the restaurant hostess that they would like a table for one. The good news: Airports offer temporary respite from this chronic condition, as society has deemed it perfectly acceptable to split a family-style-sized fajita platter with your suitcase. The bad news: There’s the unsettling side effect of suddenly being alone with your thoughts that leads these anxious lone wolves to start swapping stories with a random bar mate.

The Tommy Bahama Theory: Think back — have you ever seen a 55-year-old white male in a Hawaiian-print shirt in Logan Airport in the middle of February not blabbering away? Not a chance! Much of the time, people in airports are kicking off their vacations and just in a good ass mood, ready to talk your ear off. And I hate to break it to you, but that first $18 margarita that got him to overshare about his recent trip to the gastroenterologist is only the tip of the iceberg.

Now, while all of the above elements play a part in generating relaxed, free-flowing chit-chat, when it comes to clearing a path towards vulnerability and deep, candid discussion, there’s one ingredient that stands out from the rest:

The Easy Layup Opener: As you pull up a chair in the liminal twilight zone of an airport bar, there’s one clear and obvious conversation starter just begging to be asked by the friendly face seated next to you — “so, where are you headed?”

It’s important to note that as humans, we are wildly unrealistic when envisioning future versions of ourselves. That’s why a future-facing question like “where are you headed” will often elicit a response packed with inflated expectations and romanticized narration. Every un-lived day ahead is still full of possibility, so who wouldn’t fantasize about the best-case scenario? Funnily enough, it’s these same idealistic replies that end up inadvertently revealing our innermost wishes, genuine hopes and unfiltered aspirations — no deep-cutting questions or probing interrogation necessary.

This is why just ten minutes after I ordered a glass of pinot at SFO one time, the woman next to me revealed that she and her new boob job were on their way to Austin to win back her ex. It’s why a gentleman in a suit once confided in me that he was miserable at work and, even though he still hadn’t told his wife, he was planning to quit after this one last business trip. It’s why that single dad I chatted with on a layover at O’Hare told me that he just knew this would be the family vacation that finally ironed out all of the hiccups with his kids.

Call it wishful thinking, but daydreaming about our untapped future potential is much more enjoyable than rehashing the blunt reality of the past — it’s human nature. Let me put it this way: When a coworker asks how your weekend was, sometimes the honest answer is embarrassing! “Well, Deborah, my La-Z-Boy and I morphed into one lifeform, I ordered Domino’s twice and I attempted to disassociate from this hell hole of a job” is not exactly the version of ourselves that we want to put out there for discussion. But talking about our dreams and visions of what one day could be? That’s the good stuff.

So if you’re like me, and have long yearned for a magic solution for what to do when you find yourself yanked from the safety of your people-watching bench and thrown into the uncomfortable cross-fire of small talk, keep this in mind. Rather than mentioning the weather, the score of last night’s Orioles game or asking my biggest pet peeve of a question, “so, where are you from?” instead, consider swapping that out for “so, where are you headed?” Because no matter how the other person chooses to interpret it, by making use of future-facing questions, you’ll bypass any superficial, awkward small talk and instead propel yourself into deeper, more compelling, meatier conversation — no boarding pass required.

Recommended related posts:

• The Best Things in My Life are Free — A perfect encapsulation of why I feel such insane culture shock when I come back to the States.

• Follow Me to Weird Places — Encouragement to step off the beaten tourist path and get lost in unpronounceable places.