How I Sold 41 Cookie Boxes (Without Losing My Mind)

Valentine’s Day fell on a Saturday this year. And normally? The day before Valentine’s Day is prime time for a pop-up sale.

But this year, I was leaving town Friday morning for our annual “Cousins’ Weekend,” and there was absolutely no way I was going to host a pop-up or do an honor system bakery right before a trip. It would have taken too much time, too much prep, and honestly… too much stress.

So I decided I was skipping Valentine’s Day altogether. And then… I changed my mind.

A couple weeks before Valentine’s Day, I started thinking about it again. I didn’t really want to miss the holiday. I just knew I needed to do it in a way that worked with my schedule and my boundaries.

So instead of a pop-up, I decided to do pre-ordered cookie boxes.

And honestly? It ended up being one of the most fun baking weeks I’ve had in a long time.

Finding a Pickup Location (A Win-Win Situation)

I normally host my pop-ups outside a local plant shop, and what a lot of people don’t know is that they also have a small indoor store.

So I asked my friend who owns the shop if customers could pick up their cookie boxes there.

She immediately said yes! Winter is slower for her, and this brought customers into her store who might not normally stop in. So it helped her. It helped me. And it made things easy for customers. Total win-win.

If you’re a home baker thinking about offering holiday boxes, don’t overlook partnerships like this, especially if you don’t want people picking up at your house.

Prepping the Cookies (And Taking “Pretty” Pictures)

Because this was a little last minute, I jumped into action pretty quickly.

First, I made all the cookie dough and froze the portioned scoops. Freezing ahead gave me flexibility and kept the week manageable.

I also needed photos for social media, so I baked one of each cookie and decorated them just for pictures. And let me tell you something… Those cookies might have looked perfect in the photos. In reality, they were not!

The pop tart cookie? Not filled.
The caramel marshmallow? Not filled.
The chocolate icing? Not even the recipe I was planning to use.

There was absolutely no reason to fully assemble everything just for pictures!

They looked right. That was enough!

Home bakers, hear me: you do not have to waste ingredients just to get pretty photos.

The Flavors I Chose

Each box included six cookies:

• Chocolate Chip Cookie Sandwich (with vanilla buttercream filling)
• Strawberry Shortcake (Tammy’s Cookie Co.)
• Strawberry Pop Tart (Tammy’s Cookie Co.) I made a heart on top.
• Double Chocolate (Cooking with Karli)
• Cloud Nine (Tammy’s Cookie Co.) I added pink sprinkles.
• Pink Vanilla (Tammy’s Cookie Co. base, buttercream tinted light pink)

For my chocolate chip sandwiches, I used my go-to chocolate chip recipe and filled them with a simple vanilla buttercream:

2 sticks salted butter
4 cups powdered sugar
2 tablespoons milk
1 teaspoon vanilla

Beat on high for 4–5 minutes.

I added Valentine’s Day M&Ms to the dough, and here’s something I forgot: sometimes when you freeze dough with M&Ms mixed in, they discolor or crack.

That has happened to me before…I just forgot. Thankfully, it didn’t this time. But next time, I’ll probably press them in right before baking. Experience is a great teacher. Even after 16+ years.

Why I Chose Pre-Orders Instead of a Pop-Up

Since I was leaving town, everything had to be pre-ordered.

I used to do pre-orders all the time, but in recent years I’ve leaned more toward pop-ups. It’s simpler for me to bake what I can, sell it, and be done.

But this situation called for pre-orders—and it worked perfectly.

I used HotPlate for the ordering platform, and I love it. It’s easy to use, sends text reminders, lets me set quantities, and allows me to pass on fees.

I do pass the fees on, and my customers have never complained.

If you’re curious about it, click here for my referral link:

Let’s Talk Pricing

Each box had six cookies and sold for $30. Normally, I charge $4 per cookie, so that would’ve been $24. But these weren’t just cookies sitting in a bakery case.

I also paid for:

-Boxes
-Paper shred
-Matte bags
-Heat sealing
-Labels on every cookie
-Ribbon
-Full-color logo stickers
-Credit card fees
-Sales tax

All of that adds up.

So I added $5 and charged $30. And yes, I was nervous. I always get nervous when I raise prices.

But here’s what happened:

First drop: 16 boxes—sold out in 3 minutes
Second drop: 16 boxes—sold out in 1 minute
Third drop: 5 extra boxes—sold out in 5 minutes

Total: 41 boxes.

The demand was there.
And I’m really glad I didn’t underprice them!

My Actual Baking Schedule

Here’s how the week broke down:

Monday
I mixed and portioned the dough. I already had some in the freezer from when I thought I was only doing 18 boxes, but once I decided to make more, I had to make more dough.

Tuesday
Finished the dough and made all the icings, fillings, and toppings.

Wednesday
Baked all the cookies. Finished any glazes. Started icing and topping.

Thursday
Finished decorating. Packaged cookies. Added ingredient labels. Packed everything into boxes and tied ribbons. 

And here’s the funny part… I had ordered the wrong size boxes the week before.

Yep.

The correct ones arrived at 6:30 PM Thursday night but thankfully, I was ready. When they showed up, we put our heads down and got to work. About an hour and a half later, everything was done, and I wasn’t up all night! That’s a win.

Pickup Day

For pickup, I left a list with my friend at the shop—names and how many boxes each person ordered.

Everyone was prepaid.
Everyone picked up.
No confusion.

And she even got a box from my “just in case” extras.

The One Part That Stressed Me Out

If I’m being honest… The paper shred and ribbon stressed me out.

It made a mess.
It was everywhere.
All over the floor.

It was dark.
It was late.

That part made me a little anxious.

Nothing terrible happened.
It was just one of those “okay, breathe” moments.

The Thing I Didn’t Think About

I didn’t think about transporting the cookies when the car was full of our luggages.

So we put the cookie boxes in the market van and our luggage in our car. Dropped the boxes off, left the van at my son’s house, and headed out.

Easy solution.
No big deal.

But I’ll plan for that next time.

The Part I’m Most Proud Of

In the past, I probably would’ve pushed harder.

Made more.
Sold more.
Stayed up later.

But I didn’t.

I stayed within my limits, enjoyed the week, wasn’t overwhelmed and I had fun. And that matters!

Supplies I Used

Here are the main supplies I used. I’m sharing these because I’m always getting asked what works for me.

Boxes
BRP Boxshop
Item #3337 (11 ½ x 8 ¼ x 2 ½)

Paper Shred
Diamond White
Pink
Red

Matte Bags

Heat Sealer

Ribbon
I buy most of my ribbon from Sam’s Club. The pink gingham I used was actually an Easter print.

Label Printer

If You’re Thinking About Doing Holiday Cookie Boxes…

Here’s my honest advice:

-Keep it manageable.
-Price for packaging and fees.
-Use pre-orders if they fit your life.
-Partner with another business if you can.
-Stay within your boundaries.

You don’t have to do the biggest drop. You don’t have to meet every ounce of demand. You just have to do what works for your season of life.

This was one of the most enjoyable baking weeks I’ve had in a long time! And that’s the kind of bakery I want to keep running.

-Michelle