Wednesday, March 4, 2026

Why It's So Hard To Pack Less

I hear from a lot of people that they always check a bag and they're always shocked when they find out I rarely check a bag. If I do, it's only on my way home from a trip and nothing I've purchased there gets checked. Why? Because if my clothes go missing, that's one thing, but if things I just bought go missing, I'm going to be really upset.

Do you struggle to pack less, but can't figure out how to actually take less? This is why it's so hard for you.

When I ask why people don't just do carry-on, I get a lot of responses, but here are some of the most popular reasons they decide that they'd rather check a bag:

  • They don't want to drag their bag through the airport
  • They need too many things
  • They want to bring 6 pair of shoes
  • They won't carry their coat on
People are more than free to their opinions and travel styles, but when they complain about baggage fees and want me to give them tips, but then hate every suggestion I have, then the problem is definitely them. If you don't want to pay baggage fees, then you need to take fewer things and downsize your suitcase. You don't need to check a bag that is also oversize and/or overweight, unless you are packing to move across the country, need a bunch of camera equipment, or have medical items that take up a lot of space, but you can't live without.

So, why is it so hard to pack less? As a former overpacker, I get it. I had no strategy and just took a bunch of things and figured I'd decide what went with things when I got there. I wanted options. I love shoes. I never knew what I needed and often still brought things I didn't need and didn't wear or use. 


My whole outlook changed in October 2006. We were on our honeymoon and we arrived in London with two big bags, but because also didn't know where we were going or how to get there until we showed up, we spent hours riding the Underground, going up and down escalators and stairs, and walking over cobblestones. My ankles were swollen from the long plane ride (because did we really know about compression socks in 2006?) and I was tired and hungry. 

My bags weighed too much and I could barely even pick up my larger bag, which was horrible going up and down stairs when stations didn't have escalators, and I cursed myself for bringing anything at all. When we were near our hotel, I said if we weren't there soon, I was going to toss my bag into the street and just live without it. I didn't. We got to our hotel, where we were given the smallest room I had ever seen, and we dumped our bags, changed our clothes, and went around the corner to eat, at probably the worst restaurant I'd eaten at on a vacation. It was food though, so I didn't die of starvation.

I learned a lot on that trip. I wore the same pair of shoes the entire 2 weeks we were gone, because my legs were so swollen from the plane and I couldn't get them into the boots I packed. That's when I realized I didn't need a bunch of different shoes, just two very good pair of shoes. 

I packed too many heavy items of clothing. Not only did I end up having to lug those around, but I also didn't wear most of them, because the weather wasn't as cold as I expected. 

I started changing the way I traveled after that trip. I didn't always get it right, but I tried, and the more I tried, the better I got at it. We've gone from two big suitcases and carry-ons to two large carry-ons and personal items, to one large carry-on and personal items, and sometimes 1 small carry-on and personal items. 


I stopped packing things just because I might wear them. We joked about the "fear-based lifestyle" making you overpack because:

  • What if I want woolly socks?
  • What if I want to wear a Hawaiian shirt?
  • What if I need extra boots?
  • What if I need more pajamas?
  • What if I'm asked to a gala and I don't have a tuxedo?
  • What if I go sailing and don't have the proper shoes?
  • What if I want to go spelunking and I don't have ropes?
  • Will people know where I'm from? Better pack four or five more Oregon shirts!

You get scared you won't have everything you need, but you need way less than you think and you can always buy things if you do need them (we had to buy jackets one year when we went to Disney and it was much colder than expected, when a few years before that we were wearing t-shirts and shorts at the same time of year).

If you need everything from home when you travel, then you're not really traveling that well. You might as well stay home where all your things already live. You want options, but don't realize you're leaving yourself open to too many options when you have too many things and it makes it harder to make a decision each day to get to the point that you can leave the room.


What you need is to make a packing list before you go, but a good packing list that gives you mix-and-match options and not too many of them. You can make a ton of outfits from just 8-10 pieces of clothing, and even that is sometimes too many pieces.

Use your energy and decision-making before you go to plan your actual trip, not every outfit you plan to wear each day, because you're going to get there and then realize that it's impractical or uncomfortable or something you don't actually like now that you brought it with you. Plan your trip, watch the weather, make a layering plan, and go have fun. 

What are some of your biggest struggles when packing less?