How to Fit 8 Pairs of Shoes in a Carry-On

This was one of those weeks where there was no such thing as a “weekend”…as I spent last Friday evening preparing for a Saturday morning flight, I saved one of my most daunting projects for last (not necessarily advisable): Packing. Now I’m not one of those women who allow myself the luxury of that checked-bag – mostly for fear that I’ll one-day repeat my Milwaukee experience from years ago when my luggage never showed up. I figure since I’d have to carry all of my shoes in my carry-on anyway (to avoid separation anxiety), I might as well just shove everything in (besides, your carry-on bag can’t be “overweight”). Needless to say, packing is always a very strategic yet often a very stressful operation in the Hogan house.

So what’s my solution? The Brigg’s & Riley Baseline 21” upright rolling bag (with built-in garment bag). Yes, surprise, surprise, I’ve found myself the largest legal carry-on approved by TSA. And believe me, I use every inch of it!

As I left home this weekend, I knew I was going to be in at least three, but most likely four different cities over the following five to seven days (that’s right, I hadn’t even booked my final flight home). Of course, as any other normal person in the accounting industry, I live and die by the rule that I am only allowed to wear a pair of shoes once during a trip, so do the math – I’m traveling with eight pairs (make that nine, counting the ones I flew in).

Packing my bag is a bit like Tetris – somehow trying to wedge every stitch of clothing in between those heels. I’m actually considering a patent for my genius stuffing skills, but for now, I’ll share the love with a few trade secrets:

  1. Don’t be a stacker – you’ll waste valuable space! I admit that there was a day when I would neatly organize shirts, pants, socks, etc. each in their own “stack” – and simply place them in the suitcase. This technique simply doesn’t work when attempting to include five pairs of 4” heels in a bag. You’ll be out of room before you can say stiletto!
  2. Double stuff! If I can roll it, squish it, fold it, or squeeze it – it’s most likely going to be stuffed inside shoes. All those little things add up, so when you can repurpose the empty space inside all those heels, you’ll find that you can make 21” go a lot further! Just beware, this enables you to pack small, but I assure you it won’t be packing light.
  3. Think outside the bag! Believe it or not, I don’t clean my house, go to the gym, or like flying in high heels (a few trips running through SFO in 5” platforms has cured me of that desire). Unfortunately, that means that all the heels need to be packed. Never fear, just be creative – I’ll often pack some of my small-but-heavy items that I don’t need immediate access to while en-route (my laptop power cord, phone charger, & ScanSnap), which frees up space in my infamous Orange Bag for that extra fragile pair of glass slippers.

 Since a picture’s worth a thousand words, I’ve included a shot of my bag packed for a 7-day trip. And in case you’re wondering, yes, I wore every pair!

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What’s in My (Orange) Bag?

This past weekend was one of those weekends – spent packing up for a week in Boston for the XCM Quarterly Sales Meeting and our Summer team outing in Cape Cod. Now I’ve always prided myself with my ability to “pack small” – trust me, my carry-on bag is NOT light – but one thing that packing small requires is something I learned last year from one of my highly-respected fellow road warriors, Darren Root: “Everything needs to have a place”. While the inside of my Orange tote might look a tad different than Darren’s Tumi backpack, I’ve found that sticking to this system enables me to stay on top of things and ensures that I never leave anything behind.

So as I prepared to hit the road this week, I decided to give you a glimpse into my world by showing off what’s inside my bag – and, more importantly, why it’s in there…

A – A is for Apple, so naturally, I always keep my iPad handy. From in-flight reading & pod casts (like the THRIVEcast), to email access, it’s a must-have whenever I’m on the go!

B – Bye bye big laptops! My new Ultrabook is TSA friendly and doesn’t break my back while we globe trot together.

C – Can’t live without my ScanSnap S1100 mobile scanner…I guess this falls into the “once you’ve had it, you don’t know what you’d do without it” category.

D – Disaster Recovery Bag: You never know when you’ll need it, but you sure don’t want to be without things like hand cream, B vitamins (for those early mornings after late nights), EmergenC, wet wipes, and back-up travel toothbrushes.

E – Education Creation Bag: While I tend to use my iPhone camera more, I still keep my digital with me to capture plenty of Facebook photo content. I also always carry my Flip with me since you never know when that moment will arise where you can score a great impromptu interview (keep your eyes out for more of these from CloudSolutions Alliance this year). **Lesson learned from experience: always bring extra batteries, even if it is fully charged**

F – Fabulous Foldable FLATS! Not just any flats, these would be my authentic Tieks (thanks for the recommendation, Michelle Golden!). Not even sure where to start with these beloved “Just Shoot Me Heels” recovery shoes, but if you don’t have a pair – what are you waiting for??? **Bonus points: They’re actually cute enough to sport in public – not that Dave Cieslak would have a photo of me in mine or anything…..**

G – Gone are the days of lanyards or clip-on name badges…I travel with my ITA badge holder with a magnet back, so no more planning my wardrobe around those pesky nametags. PS – That’s my flash drive there too, which often saves the day itself.

H – How convenient is this? My tote bag came with this strapped-in pouch which is perfect for the few things I’m constantly accessing: business cards, a pen, and gum.

I – I might get hungry. I’ve learned my lesson to always travel with snacks. The only thing worse than going all day without eating, is trying to stomach airplane food. I’ve been caught too many times without time to grab something at an airport (or, even worse, landing in an airport after-hours when nothing is open). Protein bars, dried fruit, nuts, and these homemade energy bites (thanks, Pinterest) are my travel staples.

J – Juice it up. This is my power pouch. Going back to Darren’s “everything needs a place” – when I keep them all together, it’s easy to do a quick cord-count when I’m dashing out of a hotel room to catch a flight.

K – Kim’s favorite item: Mophie Juice Pack Air. This external iPhone battery functions as a case while charging your phone. This thing has saved me more times than I can count (including that night in San Francisco – right, Kara Haas?)!

L – Life line. When all is said and done, there’s nothing I use more in this bag than my iPhone. It’s the last thing I power down on the plane and first thing to power up when we land. Whether it’s to call home, pay my bills while I’m gone, or get directions to where I’m going, I’d be lost without it (literally).

There you have it – that’s what’s in my bag. Check back again soon and I might even show you how to pack 8 pairs of shoes into a TSA approved carry-on!