It’s Either a Great Time or a Great Story
Every experience adds up to something—even the bad ones. A mantra I come back to time and time again is: “it’s either a great time or a great story.”
Easier said than done, of course. In the moment, disappointment and fear can be overwhelming. But with enough time and perspective, even the experiences that shake you or break your heart soften into stories you’ll laugh about, lessons you’ll cherish, or turning points you’ll be grateful for.
Here are a few of mine:
The High-Speed Horse Carriage Crash
On our very first anniversary, Ronnie surprised me with a romantic evening out, starting with a horse carriage ride on Michigan Avenue in downtown Chicago, under the Christmas lights.
As the ride drew to its romantic end, the horse suddenly bolted—tearing through downtown traffic, smacking into cars, and ripping off rearview mirrors along its path of destruction. It took a hard left turn, but the carriage didn’t follow. Ronnie, the driver, and I were violently ejected into the middle of the street when the horse slammed into two poles, abruptly halting and tipping the carriage onto its side.
By some miracle, Ronnie and I landed on our feet completely unscathed. Terrified and shaking harder than I ever had in my life, I thought for sure the night—and romance—was ruined.
But now? We laugh about it. What should have been a sweet, storybook date night has become one of our wildest, funniest memories. When we recount it with friends, we can’t help but co-tell the story, each time adding more flair to the retelling. And yes—we even have a photo of the aftermath to prove it.
The Engagement Photo Fiasco
Fast forward about five years from the carriage crash, and Ronnie and I were on the path to getting married. He planned a magical proposal at the Enchantment Resort in Sedona, Arizona, a place that has since become special to us. Everything was perfect…until the photographer showed up.
The photos look like we’re awkwardly superimposed on a bad green screen of the Sedona canyons. The poses resemble middle school dance pictures. And to this day we joke that every time she snapped a shot, the flash bulb exploded—because her equipment looked like it belonged in a museum.
Ronnie had found her through the resort, which assured him she’d photographed countless weddings there. Looking back, I’m not so sure.
Regardless, I was ecstatic to get the photos back—until I opened them. I was crushed. I wanted to treasure those images forever, and not a single one from her professional camera was usable. Thankfully, she had taken a few shots on my iPhone, which I still keep.
Now, however, those god-awful engagement photos are one of our favorite jokes. Anytime a friend gets engaged, we whip them out. Without fail, they get a big laugh. What felt like bitter disappointment at the time has turned into one of our most reliable icebreakers—and a reminder that perfect is never the point.
The Layoff + Pregnancy
A few years later, I took the biggest job of my career—building a division from scratch at a high-pressure Series D startup. I poured everything into it: strategy, execution, hiring, sales, marketing, and landing marquee customers. It was a “hail Mary” attempt to help the company turn things around.
But when we couldn’t raise more money and revenue wasn’t enough to keep funding the dream, it all came crashing down. Just days after finding out I was pregnant with my first daughter, Charlie, I was told I’d be laid off. Even harder, I had to lay off a team of incredible people I admired and cared deeply about.
I was devastated. Vulnerable. It felt like the rug had been ripped out from under me.
But with distance, I see it as a blessing. That layoff gave me precious time to rest in my first trimester, space to reset my priorities, and clarity about the work I wanted moving forward. It opened the door to the best professional experience of my career. Even more meaningful, I was later able to hire back one of the teammates impacted by those layoffs—a moment that felt full-circle and healing in ways I never could have imagined at the time.
The Takeaway
Whether in life or in your career, time has a way of turning traumas into treasures. What feels devastating today might become tomorrow’s funniest story, your most important lesson, or the blessing you never expected. Sometimes, if you let it, the outcome is even better than the original plan.
Recipe for Turning Traumas into Treasures
What you’ll need: A little bit of courage, an emphatic yes, some gratitude, willingness to have a sense of humor about it, time.
How to make:
Give yourself space to process the disappointment or fear.
Let time do its work.
Revisit the story with fresh perspective.
How to enjoy: Tell the story out loud. Laugh about it with friends. Even better, co-tell it with the person who lived it with you, I promise it will get better (and funnier) every time you retell it.
