Confessions of an Over-Planner

How compulsive organization nearly derailed my wedding

There I stood before my groom, while the priest mapped out the protocol for the Big Day. I tried to focus on what he was saying, but my mind stayed fixed on its current obsession: How was it that my groom to be, to whom I professed love everlasting, was somehow unable to show up to our rehearsal on time?

My thoughts leap-frogged to how certain members of our wedding party, my nearest and dearest friends and relatives, still required verbal directions to the rehearsal dinner – even after I’d taken care to print, collate and distribute these details. A week in advance.

Then, something pierced my consciousness, halting the circular pattern of my thoughts. No, it wasn’t my husband-to-be’s sweet smile, nor was it a spiritual epiphany. It was an itch. An insistent itch, emanating from the red welts that were emerging across my skin, spreading in swaths down my back.

My hives represented an inconvenient truth, betraying the unease roiling beneath the surface. Their appearance marked not only my skin but the first deviation from my grandiose wedding vision, every moment of which was planned out with a precision worthy of a military offensive, using a tool called “The Wedding Packet.”

Photo by Jennifer Shaffer

Originally discovered floating around the dark wedding blogosphere (like the dark web, but for compulsive-curious brides), the document ostensibly endeavors to keep a bride cool and calm by organizing each detail of her “special day.” But its true purpose is turning what should be the most celebratory of occasions into a joyless logistics exercise. My version opens with its own table of contents and comprises contact information for “key wedding day” individuals, descriptions of each event – from Bridesmaid Sleepover and Night of (mandatory) Fun to the choreographed sparkler exit – and a minute-by-minute wedding day agenda. I itemized each person’s role down to the smallest minutiae: My father’s list, for example, included a reminder of his responsibility to lift my veil after our walk down the aisle. (Consequently, my maid of honor’s list also included this line item: “Fix veil after father of the bride lifts it, if he screws it up.”) With no spontaneous moment left unplanned, what could go wrong?

Those in receipt of The Packet noted with sarcastic disdain its close resemblance to a legal brief, not only for its matching failure of brevity. And they weren’t even privy to my other planning tools: a 25-tab Google Sheet, a separate master timeline of tasks broken down by month (inexplicably, my beribboned napkin rings were due for completion 11 months before the big day), a dedicated email account with correspondences filed by vendor type, and Pinterest.

Oh, Pinterest. My acquaintance with the visual bookmarking platform, the launch of which fortuitously coincided with my engagement, was about as much a religious experience for me as was the sacrament of holy matrimony. With each scroll of my mouse, Pinterest delivered a fresh row of inspirational photography, promptly “repinned” with ecclesiastical fervor. Pinterest boards begot lists, which begot Google Sheet tabs, in what I believed to be a virtuous circle of hyper-organization. I was the nervous pitcher, and my spreadsheets were the encouraging coach, slapping my back after a conference on the mound.

The following items were added to my list of wedding necessities forthwith: “out of town” bags; a candy buffet, for which I spelunked the complexities of the bulk candy supply chain; a menu of signature cocktails, including the “something old” fashioned; and an emergency kit, just in case (fingers crossed) there might be a corresponding emergency worthy of its deployment.

Photo by Jennifer Shaffer

Instead of easing my mind, The Packet, Pinterest and all my other tools only fueled the stress fire. Each decision inspired new worries: Was this the right cake topper, the right first dance song, the right font for our “wedding signage”? A yes to one was a no to everything else. And the collection of no’s became a bushel of missed opportunities, carbonated with the pressure to choose correctly from a glut of arguably viable options.

Even the emotional resonance of the day became an item “to do” – and every candid photo of a groom overwhelmed with emotion as he beheld his bride for the first time became a bullet point on my List of Candid Photos I Need.

On the morning of my wedding, I pre-empted the romantic “first look” with a panicked phone call to the groom about a certain missing limousine. (My fiancé, who originally captured my heart in part because of his unwavering composure, had earlier in our engagement ended a similarly furious phone conversation with “I DON’T HAVE AN OPINION ON POMANDERS.”) As I stood waiting in the hotel parking lot, veil down, flowers up, I cursed myself, my fiancé and my spreadsheets at the logistical failure.

En route to the church via my father’s pickup truck, I felt the joy from the Bridesmaid Sleepover and Night of (mandatory) Fun evaporate. And I blinked back tears as I thought about my failure to adhere to The Packet’s prescribed bride-groom sequestration and added it to the growing list of failures of The Plan.

There exist no photos of me smiling at my wedding ceremony.

Looking back, I can see that the fear of missing out – on photo booth props and table runners and gobo uplighting – caused me to miss out on the moments themselves.

Yes, there are some moments I’m glad to have orchestrated: I had aspirations of a giant, drunken circle-sway for our last dance, for instance, and I’m glad not to have trusted its organic formation. And there are other details that went awry despite my best attempts at control (our sparkler exit, for one, was about as drunken as our last dance circle-sway). I now wear these mishaps as a badge of honor; I can relay them with little regret.

But it is the missed moments that I continue to lament, the failure to really be in the present as my months of planning finally came to fruition. You can see it on my face in our wedding video. You can see it in the hives that returned for our first dance.

That weddings are so exalted in our culture is another topic, but their import derives in part from their ephemerality and finitude. By design, the aim is to have only one.

As with any decision in life, potentially better alternatives abound.

And though I look back on my blotchy-skinned photos with a twinge of wistfulness, I also see the earnest look in my husband’s eyes – the same man who was late to the rehearsal and neglected to remind the limo of the itinerary change – and I can only conclude that I have made at least one choice correctly. ◆

‘Confessions of an Over-Planner’ appears in Milwaukee Weddings 2018.

Find it on newsstands beginning January 1, or buy a copy at

Be the first to get every new issue. Subscribe.




Karisa Langlo is the Digital Editor for Milwaukee Magazine.