Two Weeks, One Shop, Zero Chill
Behind the scenes of Totebrag: My newest online store, built in a chaotic and caffeine-fueled fourteen day sprint.
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 micro-businesses 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 Quest Summer projects “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 Project #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 Project #2, you can do that here — things will kick off in about 48 hours 😉
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 Project #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!
Side Quest Summer · Project #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 Project #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 stationerysnobaficionado, 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 Project #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 in Side Quest Summer
[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 new projects 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 Project #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 👶🏼 🎀 ✨
🏁 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 Summer Project #2, coming soon!
XOXO,
-Em
🌟 Side Quest Directory
A constantly evolving directory of all of the micro-businesses I’m building in public as part of Side Quest Summer.
Pssst…take a peek if you’re interested to see what might be in store for Project #2.
Shopify has a great promo for new stores: $1 per month for the first three months. It’s the perfect accidental deadline to push yourself to launch quickly and hopefully get a few sales (and get into the black!) before the regular $39/month fee kicks in.
Printify is a third party print-on-demand partner that directly integrates with my Shopify storefront. Here’s how it works:
I upload an original design and position it on a product (say, a coffee mug, a t-shirt or a tote bag — this is what I’ll be deciding today).
Whenever a customer places an order, Printify prints my design onto that product.
(And this is the best part…) Printify then ships the product with my design on it directly to my customer. I never have to lift a finger.
Obviously, using a print-on-demand partner means lower margins (I’ll earn about 20-40% less per order) because they take a cut for doing the ‘manufacturing’ and shipping legwork. But to me, it’s still worth it because:
It’s a great way to launch a beta version of a brand/product line (if the shop catches on, I would likely take things in-house, end-to-end).
It’s really the only way that I can pull this whole thing off while I’m on the other side of the world.
My dream is to one day create a greeting card line as cute and fun and amazing (and as large as) Bloomwolf Studio’s. Today is not that day.
Perhaps I should seriously circle back to those chicken wing-shaped pillows?! 🍗
My first impression of Bali (well, Canggu at least) is that there’s a ton of bullshit I’ll need to ignore: Shameless influencer photoshoots, bros loudly taking calls to peacock their importance, the sea of plastic faces/chests — but all of that aside, this is going to be a fantastic place to spend the next few weeks and be super focused on launching the rest of my Side Quest Summer projects 👩🏼💻🤓
I beg you to read some of them because they took me forever, they are a bit of an easter egg, and it’s my favorite part of the project 🥹 Here are two of my favorites: [Chicken Nugget Stash] + [Farmers Market Impulse Purchases]
I already know I’m know to re-do some of these, because the dainty flowers poking out of a bag that says “Mozz Stick Stash” doesn’t really hit.
Oh my gosh, Emily. Send me the link and I’m gonna by stuff. I got some birthdays coming up!!!!
Emily! This is fantastic. The energy, inspiration and momentum of both this project and your own personal flow is has got me all lit up. Yay and thank you for sharing your process. One thing though, you've dramatically underplayed the brainstorming session that apparently produced these witty winners of funny statements on the bags. This is not easy to do and you've the humor is a central pillar of what will be the success of this. I'm seriously impressed. Well done! (Hoping to draft behind you on this one.) : )