For me, how and what I pack has always been a very personal thing, and I have been somewhat embarrassed by my overpacking ways, particularly when someone with whom I spend a lot of time finds out. The embarrassment, I would discover, was even worse when it was my colleagues (rather than my friends) who found out abut my packing habits.

After a few awkward airport encounters where my colleagues carried everything on the plane, and I had to check + carry on, I decided to try curbing my overpacking ways.

What a freaking nightmare that turned out to be.

The Story:
I was heading to a three-day conference in Vegas. By that point, I had been to a few different conferences of this type, so I thought I knew the drill and was determined to not overpack. So, I packed three business outfits, travelled in jeans, packed one pair of flats, one pair of heels, one purse and a messenger bag that was only big enough to hold my laptop and a notebook. I walked through the airport with my smallest rolling suitcase and my messenger bag, holding my head high.

As soon as I got to our booth, I knew I was in trouble. A girl in my department asked, “What are you wearing to the reception?” All conferences have receptions, mind you, so I planned to wear whatever I had on that day. But this one was different, apparently. It was cocktail attire.

After working 8 hours at the show, I spent my only free time that day frantically scouring the shops at Caesar’s, searching for something that could pass as cocktail. $300 later, I barely made it to the event.

To add insult to injury that trip, we went out every night. Everyone else looked so cute while I felt like Frumpy McFrumperston trying to piece together passable outfits with the little that I took. Even worse, it’s nearly impossible to re-wear clothes in Vegas, as they all end up smelling like a mix of smoke, liquor and desperation. I was miserable.

On that trip, I swore: NEVER AGAIN.

Frolicking through the airport with as little as possible just isn’t worth it to me.

Since then, I have put my packing energy into being more strategic without having to be without things I might need, or want. And I’m much happier for it.

Do you have a packing horror story? Share yours below!