How Does a Minimalist Pack? A Quick Retrospective on a 1-Day Business Trip

Anything I do more than once I expect to get better at. Traveling is one of those things. My job has me traveling a fair amount and each trip is an opportunity to perfect the way I do it. I also like challenging myself to pack as lightly as possible.

This trip was for a quick 1-day sojourn to Chicago from New York City. It would have me leaving Wednesday evening and coming back to NYC Thursday evening. I spent the vast majority of Thursday at the client’s office delivering a workshop.


The first gathering of stuff.

Let’s take a look at my first stab at packing for the trip:

  • Slacks, undershirt, grey button up shirt, socks, underwear, athletic shorts

  • Mittens & scarf

  • 12” MacBook Retina & power cord

  • iPad Air 2 w/ charging brick and cord

  • Apple Watch series 1 (not pictured) and its ridiculously long charging cord

  • iPhone 7 Plus (not pictured) and Lightning EarPods

  • Medium size Moleskine notebook & pen

  • Toothbrush, toothpaste, deodorant, pomade, contacts, comb, NightGuard (dentist’s orders…), glasses & case, sunglasses & case, dopp kit

  • Wallet

  • 15 The Ready Vol. 1 magazines (not pictured)

  • A stack of post-it notes (not pictured)

  • A handful of sharpies (not pictured)

  • 100 ping pong balls (not pictured)

Not being happy with my first attempt at anything I took a look at everything laid out on the table and decided to see if I could make another attempt at removing the nonessential.


Didn’t make the 2nd cut.

I decided to not bring:

  • Mittens & scarf (I was only going to be there for a day and would spend most of it indoors anyway)

  • Sunglasses (landing at night, spending the whole day inside, and then flying out again in the dark)

  • Comb (I don’t actually have a hair style that requires a comb — I dunno why I grabbed it in the first place)

  • iPad (since I was bringing my computer and my phone and the flight was short I figured I didn’t have much use for a third device)

  • Athletic shorts (realized I wasn’t going to have time to workout)

After removing those things, this is what was left to go into the bag:


A couple things to note:

  • I decided to only bring the iPad charging brick (as opposed to my iPhone brick and/or Apple Watch brick) because it would super charge my phone and watch and I didn’t necessarily need to charge both of those things at the same time.

  • At the last second I decided to bring my Beats noise cancelling headphones but not the charger and cord. My reasoning was that the flight was short and that I should be able to get there and back without needing to charge them. I was right.

  • I definitely could have worn the same pants on the plane and then to the workshop the next day and it wouldn’t have been a big deal. Although, I guess I’d really be rolling the dice on keeping them stain-free for two days in a row (I have a magic ability to somehow always get food on myself).

  • I regret not bringing my scarf and mittens. It was 19 degrees at one point and I walked from the hotel to the client’s office (roughly half a mile).

  • I forgot to grab an adapter (USB-C to VGA) at the office before I left so I had to buy one when I got there.

  • If I didn’t have to bring workshop material (magazines, ping pong balls, post-its, and sharpies) I probably could have just brought my backpack and not needed my carry on as well.

Overall, pretty solid attempt. Didn’t really bring anything that wasn’t used and didn’t leave much behind that I really wish I had with me — which is generally my metric for determining whether I did a good job packing.

Travel as a Skill

Today’s snippet comes to you from 35,000 feet.

I love to travel. I’ve been fortunate in that I’ve been able to do it more than most. Quebec City, Anchorage, Ireland, London, Berlin, Prague, Doha and back and forth across the United States. Part of the reason I love it, other than the obvious result of being somewhere new and exciting at the end, is that I view it as a game. It’s not just a thing to be endured — it’s part of the fun itself.

I enjoy getting to the airport or train station early and sitting near my gate with a good book, a podcast, or some music close at hand. Like a racing video game that only continues if you hit certain checkpoints by a certain time, I know there are certain checkpoints I need to hit to keep my day going. A day of traveling is a day of using my skills to hit checkpoints as swiftly and skillfully as possible. Packing lightly, responding to my environment, keeping an even emotional keel, making a plan — these are my skills that have been honed over years of travel (but are nowhere near an elite level yet).

It may seem strange to view travel this way but packing precisely the amount I need to successfully conduct a trip, going through security as smoothly as possible, walking through the terminal as calmly and collectedly as possible, getting onto and off the plane without exerting myself or causing delays for those around me — these are just a few of the things that can go a long way to making travel a more pleasurable experience.

If I do each of these well then I am swept up in the well-honed (well, usually) process of modern travel. I hit each checkpoint with plenty of time to spare and then shift my attention to the next one. One after another with as little stress and discomfort. With as much skill as possible I move through my day. Like nearly everything I do, it’s something I try to get better at without over complicating or over burdening it with meaning.

The other option is to be stressed and annoyed and view it as an unpleasant barrier between me and my ultimate goal. The nice thing is that it’s really up to me.