Pineapple upside-down cupcakes: a parable

We threw a birthday luau for a close friend today, and one of my responsibilities was to make pineapple upside-down cupcakes — her favorite Hawaiian dessert. I was happy to oblige.

I spent at least a week thinking about pineapple upside-down cupcakes. I had never made them before. In fact, I’m pretty sure I had never eaten one before (the big version, either). So I poked around in the world’s largest cookbook (Google) and found two recipes that were popular in the blogosphere: one from scratch and one using a box of cake mix as the base. Naturally, because I am an aspiring foodie, I chose to make the scratch recipe.

I swear, those cupcakes were cursed. First, a giant jar of maraschino cherries jumped to its death in the parking lot right outside the doors of Cash ‘n Carry. Then, it was discovered that I bought a can of pineapple chunks and not the crushed pineapple called for in the recipe. No big deal, except that my husband was standing next to me when I made the discovery, grabbed them from me, and pureed the heck out of them with our hand mixer before I could stop him. It was sweet of him to try to help, but he turned the pineapple chunks into pineapple baby food (try draining that!). Can you believe that after the pineapple baby food incident, I then discovered that our teenager went through a dozen eggs in less than 24 hours… and I didn’t have the six eggs I needed? So the score thus far is: one jar of dead cherries (but kindly replaced by the store), 16 ounces of pineapple baby food, and a midnight run to Safeway for eggs. Once the eggs are mixed into the batter, these cupcakes should be smooth sailing…


These cupcakes were an absolute mess! They rose too far above the pan and melded together, they were stuck to the inside of the pan, and they seemed to look much more “cakey” than the photo in the recipe looked. It was already after 1:00 am at this point, so I decided to throw in the towel and go to bed. I would have to buy a store-made cake on the way to the party, and chances are the cake would NOT be pineapple (we are in Seattle, after all).

I woke up this morning feeling disappointed in myself that I couldn’t deliver the much longed-for pineapple upside-down cupcakes my friend craved. I decided to take one more look at the cake mix recipe and go for it. It wasn’t effortless, though: this still required another trip to the grocery store for the cake mix and more pineapple, and clean up the muffin tins that were disasters from the night before. However, the traditional boxed cake mix cupcakes turned out beautiful!

good cupcakes


I’m so glad I decided to try the pineapple cupcakes again after sleeping off my earlier failed cupcakes. The second time was easier, faster, less messy, and they turned out great. I also learned from my mistakes of the night before and tweaked many of the steps (though the second process was not perfect; I bought the incorrect pineapple the second time around, too).

(Editor’s note: Despite their appearance and the fact that they were falling apart when picked up, the party guests loved the taste of the first batch. See the post-script here.)

This is a site about nonprofit development/communications, not a cooking blog … so why did I share this story? It is a parable and therefore the analogy means something personally or professionally to you. I know what lesson I took from it regarding development and fundraising.

Happy birthday, dear Brook!

Twenty-six years of friendship and counting.


4 thoughts on “Pineapple upside-down cupcakes: a parable

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s