The $2,200 Oops: A Lesson in Travel Chaos and Grace
What Happens When You Book the Wrong Date for 16 People (and How to Pivot Like a Pro)
Mistakes are not a matter of if—they are a matter of when. If you’re planning a retreat, a group trip, or even just a casual dinner reservation, at some point, you’re going to screw something up. And guess what? That’s okay. The secret isn’t in being perfect—it’s in how you recover.
I learned this the hard way.
The $2,200 "Oh Sh*t" Moment
Next week, I’m taking a group of 16 people to Vegas. I had this perfect send-off planned: a high-energy, mind-blowing Cirque du Soleil-style show, Awakening at the Wynn. It would have been the ultimate grand finale before we all flew home on Sunday, a perfect last hurrah.
Except… we don’t leave on Sunday.
We leave Saturday morning.
And I? I booked the tickets for Saturday night.
Which means that unless I can work some last-minute magic, I’m about to eat $2,200 worth of show tickets that no one can use.
Cue the panic.
Step 1: Breathe. You Are Not a Failure.
Here’s the thing: you will make mistakes. Everyone does. The bigger the event, the more moving parts, the higher the chance that something will get overlooked, miscalculated, or totally f*cked up.
But what you don’t do is spiral. You breathe, you assess, and you pivot.
So I sat down, choked back the immediate desire to rage-cry, and went into solution mode.
Step 2: The Pivot—Finding a Way Out of the Mess
Turns out, the only available night for Awakening is Tuesday the 4th—four days earlier than planned. Not ideal, but possible.
Now I’m in the process of begging, bargaining, and Jedi mind-tricking the ticketing office into letting me swap those dates.
This is where you learn to be relentless but charming—always ask for what you need. People want to help, especially if you’re polite, persistent, and explain your situation in a way that makes them want to be the hero.
And if that doesn’t work? Backup plan. Always. Maybe we find a different show. Maybe I turn this into some kind of unexpected, last-minute surprise event. The key is not to get stuck on the "perfect plan"—it’s about making the best of the situation you’re in.
Step 3: Give Yourself Grace (And Have a Damn Backup Plan Next Time)
The hardest thing about screwing up isn’t the logistics—it’s the mental beating we give ourselves.
We tell ourselves we should have caught it. We should have double-checked. We should be better.
But perfection isn’t real. And the most seasoned travel planners, retreat leaders, and event organizers all have one thing in common: they know how to roll with the chaos.
So what’s the takeaway?
You will make mistakes. Accept it.
Breathe. Freaking out helps no one.
Pivot like a pro—there’s always a fix if you stay flexible.
Be relentless in problem-solving. Ask for what you need.
Have a backup plan. No, really. Always.
Final Thought: Own Your Mistakes, Then Move On
At the end of the day, no one is going to remember that the show wasn’t on the "perfect" night. What they will remember is the energy, the excitement, and the way you handled the unexpected.
Screwing up doesn’t define you—how you recover does.
Now, excuse me while I go grovel to the Wynn box office.