Deciding I wanted to start shipping my cookies nationwide was easy.
Actually making shipping live was a different story.
Suddenly, one seemingly simple idea turned into a very long list of little decisions.
What boxes am I going to use? How am I packaging each cookie? Do I need inserts for the boxes? What should those say? Do I need labels? What should the shipping page look like? Do I have photos of every cookie? What needs to go in each product description? What’s my shipping schedule? What happens if it’s hot outside? What policies do I need? How do I make the website feel inviting and easy to shop?
And that’s before actually baking, packing and shipping anything.
Meanwhile, I’m running my existing microbakery, baking for a weekly farmers market and renovating a new 2,400-square-foot space that I’m also trying to fund.
My time is limited.
My money is limited.
And then there was another layer I was adding entirely on my own: comparing what I was building to cookie companies that have already been shipping thousands of boxes around the country.
Their websites are beautiful. Their packaging is completely branded. Their product photography is perfect. They’ve already figured out systems that I’m just starting to think about.
I have a tendency to do this in a lot of areas of my life. I can picture exactly how I eventually want something to look, and if I can’t make that version right now, I can get stuck trying to perfect it instead of just finishing it.
I didn’t want that to happen with shipping.
So I decided I wasn’t building my perfect nationwide shipping operation.
I was building version one.
The version that’s perfect for where my business is right now.
Then I can learn from it, adjust it and let the shipping side of the business evolve as the rest of the business grows.
Why shipping — and why now?
This year, I decided I wanted more out of my bakery.
Right now, most of my sales happen one day a week at the farmers market. At the same time, I’m working on growing my social media, building my personal brand and turning that new 2,400-square-foot space into CeCe’s House.
And somewhere in the middle of all of that, I had a realization:
If growing my audience actually works…then what?
What happens when someone discovers one of my cookies on Instagram on a Wednesday?
What happens if they live three states away?
What am I actually sending all of these new people to?
I don’t want to put all this effort into building an audience only to realize that most of that audience can’t actually experience what I’m making.
So instead of waiting until I have a bigger following to build something for that following, I’m trying to do it backward.
Act as if they’re already here.
If I’m expanding the physical footprint of my bakery, it feels like the perfect time to start expanding its online footprint too.
And yes, I know I’m entering an incredibly saturated market.
There are a lot of businesses shipping cookies.
But I also genuinely believe the cookies I’ve spent years creating are worthy of sharing outside of my local area.
For years I’ve been learning what people come back for at my tiny bakery and at the farmers market. Now that I’m finally taking the leap from a microbakery into a real, much larger space, one of my goals is to see if I can take those same products beyond my local customers.
I’m looking at that saturated market as a challenge.
Can I learn how to create a brand and product experience that stands out when someone isn’t already walking past my booth at the farmers market?
Can I make someone hundreds of miles away care about what I’m building here?
Because if I can learn to stand out in a giant online market, I have a feeling those skills are only going to make the brand stronger locally, too.
I also started thinking about shipping as my own version of Kickstarter
There was another reason the timing made sense.
Turning an empty commercial space into the business you have pictured in your head costs money.
A lot of it.
For a minute, I considered whether I should do something like Kickstarter to help fund the build.
Then I started wondering if I could accomplish something similar through my own business.
Instead of asking someone to contribute money toward the new space, I could give them something in return.
Buy my cookies. I ship you the cookies. The sale helps me continue building what’s coming next.
It also accomplishes something I need just as much as funding: it introduces more people to the brands I’m trying to build.
So shipping stopped feeling like a random ecommerce project and started feeling like another piece of the larger business strategy.
Now I just needed to get it live without turning it into another six-month project.
I started with what I already had
I already use Square for my bakery website, which made the technical starting point much less intimidating.
My website itself has been pretty simple — basic information about the bakery rather than a full online shopping experience.
So for this first version, I added the online store back to the website specifically for the cookies I wanted to make available for shipping.
I’m not going to walk through every button you need to click inside Square. If you need instructions for physically setting up an item or enabling shipping, there are resources that can walk you through that part much better than I can.
What I found more useful to think about were all the pieces surrounding the technical setup.
Because turning on shipping isn’t really the hard part.
Creating something that people actually feel comfortable ordering from is where my list started growing.
My version-one website checklist
Once I stopped thinking about creating the perfect shipping website and started thinking about creating the smallest complete version, the project became much easier to organize.
I basically needed to make sure I had:
- The cookies I wanted to ship created as products in Square
- A clear product photo for each cookie
- A useful description for each product
- Pricing and ordering options
- Shipping enabled and configured
- A clear shipping schedule
- Care and storage information
- Basic shipping and order policies
- A page that felt intentional and easy to shop
- A strong image at the top that made the page feel connected to my brand
- A way to test the entire experience before telling people it existed
None of those things individually are particularly overwhelming.
It’s seeing all of them at once — while also thinking about packaging, fulfillment, marketing and everything else — that can make “I’m going to start shipping cookies” suddenly feel like a much bigger project.
So I started working my way through the list one decision at a time.
I didn’t wait until I had time for the perfect photos
One of the first places my perfectionism could have delayed everything was the website photography.
I had product photos of my actual cookies.
What I didn’t have was the lifestyle image I pictured for the top of the new online store.
I wanted something warm and natural that made the page feel like an actual extension of the brand rather than a collection of products I had just uploaded to a website.
Eventually, I want to photograph that image myself.
But I didn’t have time to plan another photoshoot before launching.
So this became one of the places where I used ChatGPT to help me get version one done.
I uploaded photos of my actual cookies and used them as references to generate a temporary lifestyle-style hero image for the website.
Does it look a little AI?
Yes.
Would I rather eventually replace it with my own photography?
Absolutely.
But that doesn’t mean it wasn’t useful.
It allowed me to get much closer to the website I had pictured without making a photoshoot another requirement standing between me and launching shipping.
When I have time, I can replace it.
That’s becoming one of my favorite ways to think about using AI in my business: not necessarily as the final product, but as a way to get past a bottleneck.
I used ChatGPT for the tiny decisions that normally eat up my time
The website image wasn’t actually where ChatGPT saved me the most time.
It was all the little decisions.
Once I started working through my shipping checklist, one question would constantly create three more.
I needed product descriptions.
Care and storage instructions.
A shipping schedule.
Shipping policies.
Packaging.
Box inserts.
Copy for the inserts.
A QR code.
And then somewhere for that QR code to actually go.
None of these tasks are particularly difficult.
They’re just the kinds of things that can somehow consume an entire afternoon when you’re trying to figure them out one at a time.
So rather than staring at a blank page every time I needed to write something or wondering what I might be forgetting, I started using ChatGPT almost like a brainstorming partner while I worked.
I’d explain what I was building and my particular situation, have it help me identify the next decisions I needed to make, brainstorm options, and then work through those options until I landed on something that made sense for my business.
And I think that’s an important distinction.
I wasn’t asking AI to build my business for me.
I still had to know what I wanted. I still had to decide what made sense. I still rejected plenty of suggestions because they didn’t sound like me or didn’t fit the brand.
What it removed was a lot of the blank-page time.
When I only have a few hours available to work on something, I’d much rather spend those hours making decisions than trying to figure out what decision I need to make next.
I chose one shipping day instead of trying to operate like a giant ecommerce company
Once the website started coming together, I needed to figure out what actually happens when someone places an order.
Again, I tried to build the system around the business I have today.
I don’t have a fulfillment department.
I have farmers market production, a bakery to run, a new space to renovate and all the other jobs that come with owning a small business.
I didn’t want nationwide shipping to accidentally create another seven-day-a-week job.
So I chose one shipping day.
Orders close Sunday at 11:59 p.m., and those orders ship Tuesday.
That’s it.
That means I can batch the work.
I know how many orders came in. I can plan production accordingly, package everything together and ship everything together.
Would a giant cookie company operate like that?
Probably not.
But I’m not a giant cookie company.
I’m building the version of shipping that works for my business right now.
If someday the volume requires multiple shipping days, I’ll add more.
That’s a future problem I’d be very happy to have.
I simplified the packaging instead of trying to custom-brand everything
Packaging was another place where I could feel myself starting to go down a rabbit hole.
Custom boxes.
Custom printed cards.
Custom everything.
Huge minimum quantities.
Weeks of waiting for things to arrive.
I love branding, so this is exactly the kind of project I could happily overcomplicate.
Instead, I went back to version one.
What actually needs to happen for a cookie to arrive safely and for opening the box to still feel thoughtful?
I found shipping boxes that worked for what I needed.
I chose clear matte bags that I could heat seal individually.
And when I needed printed inserts, I found a way to make those feel nice without immediately ordering hundreds of custom postcards.
I chose a higher-quality paper, uploaded the design as a regular document to Staples, had a small quantity printed locally and cut the pages in half.
I could pick them up the same day.
It was dramatically cheaper.
And I wasn’t committing to hundreds of version-one inserts that I might want to redesign two months from now.
That’s exactly the kind of solution I’m looking for at this stage.
Good enough that I’m proud to send it to a customer. Simple enough that it doesn’t stop me from launching.
I’m putting together a separate post with the actual boxes, bags, heat sealer and other supplies I’m using because I think the practical side deserves its own resource rather than turning this post into an enormous shopping list.
One little box insert accidentally became an entire part of my marketing system
This was one of my favorite unexpected parts of the process.
Once someone orders cookies from me, I don’t want the relationship to end when they finish the last cookie.
So I started thinking about what should actually be inside the box.
Obviously, someone needs to know how to store and enjoy the cookies. But I also wanted them to understand a little bit about the bigger story they had just become part of.
That led to a branded insert.
Then I thought the insert should have a QR code.
Which created another question:
Where should the QR code go?
I decided to create a special page on my website where I could give customers additional information without trying to cram everything onto a small card.
And then I realized the page I was building would also make a really useful landing page for social media.
Suddenly, something I created because I needed a piece of paper inside a shipping box had turned into a central place where someone could find important links, learn what’s happening and go deeper into the brand.
That’s one of the things I’ve enjoyed about building this.
I’m not necessarily sitting down and designing some enormous marketing funnel.
I’m solving the next logical problem.
And sometimes solving one small problem creates something useful somewhere else in the business.
I tried to build the smallest complete customer experience
This might be the biggest shift in how I thought about the project.
Shipping isn’t really one task.
It’s a chain:
Someone discovers the brand → lands on the website → understands what I’m selling → places an order → knows when it will ship → receives a package that feels connected to the brand → knows how to enjoy the product → has somewhere to go afterward.
Once I started looking at the project that way, I stopped asking whether every individual piece was perfect.
Instead, I asked whether there were any major holes in that chain.
The website image doesn’t have to be my forever image.
The packaging doesn’t have to be my forever packaging.
The shipping schedule doesn’t have to be my forever schedule.
The inserts don’t have to be my forever inserts.
But someone should be able to move through the entire experience without feeling like they’re participating in my experiment.
It can be version one behind the scenes without feeling unfinished to the customer.
I think that’s the balance I was really looking for.
Version one doesn’t mean I don’t care how it looks
I also don’t think simplifying something means throwing it together.
I still care a lot about the details.
I want the website to feel inviting. I want the cookies to look good when someone opens the box. I want the insert to feel intentional. I want someone ordering from another state to have the same feeling about the brand that I want someone to have when they eventually walk into CeCe’s House.
The difference is that I’m learning to separate thoughtful from perfect.
Thoughtful is achievable right now.
Perfect will keep moving every time I get closer to it anyway.
The goal isn’t to build my forever shipping system
If you’re another small bakery owner who has been thinking about adding shipping, I think this is the biggest thing I’ve taken away from the process so far:
You don’t have to figure out the shipping operation your business might need two years from now.
Start with the business you have.
Choose what you’re comfortable shipping.
Decide when you can realistically ship it.
Create a simple place for people to order.
Make sure they understand what they’re buying and what to expect.
Figure out how you’re going to package it.
Think about what happens after the box arrives.
And then get version one out into the world.
Maybe I’ll discover I hate the boxes I chose.
Maybe customers will want something I haven’t thought about yet.
Maybe one shipping day becomes two.
Maybe I’ll completely change the website photography.
Maybe I’ll redesign the inserts ten times.
Maybe the way I’m shipping cookies a year from now will look nothing like the way I’m doing it today.
That’s okay.
I’d rather make those decisions after shipping real orders than spend months trying to predict every possible problem before I’ve sent the first one.
I’m finally expanding my tiny bakery into the kind of physical space I’ve imagined for years.
It feels like the right time to challenge myself to expand what I’m building online, too.
I don’t need version ten yet.
I just need a version one I’m proud enough to put out into the world — and enough room to let it grow from there.
