Travel Hacking for Adults

The internet runneth over with travel advice written by vagabonding bloggers that makes a ton of sense if you’re also a vagabonding blogger. It’s simple, they say. Put your merino wool shirts and exoficcio boxers in a neon backpack, find a hostel, and churn out that paid content, brah. For the rest of us, who travel for work as well as play, and limit our stays in Southeast Asia to weeks not months, it takes more than packing cubes and flip flops to get the job done.

While prepping some 2018 tax documents, I noticed I was outside of NYC for 210 nights last year. I’ve travelled as a properly funded road warrior at McKinsey, visited clients on a budget for Brandt, and embarked on thrifty adventures with Holly and friends. So I figured I’d coronate myself to write down some hard-won tips to make life on the modern road a bit easier. Given the breadth of this topic (from airline loyalty to the fine art of booking flights), let’s focus this Letter on packing and tackle the rest some other time if you’re sufficiently interested.

A quick note before we dive in: Many of you have asked where you can see Urbach Letter back-issues. They’re available here along with other writing I don’t deem important enough for your inbox.


Why is this a mess?

Packing should be simple. It’s something we learn as kids, getting ready for school trips or weekends at grandma’s. But packing for extended time on the road is anything but straightforward. The time-tested strategy of filling a black Samsonite rollaboard with suits, shirts, dress shoes, workout gear, jeans, and business essentials works fine when everything goes perfectly.

How often does this happen for you? Plenty of room overhead, no long walks where you can’t roll, security doesn’t rifle through your entire bag for 50 ml of sunscreen you forgot about 10years ago, meetings or weather don’t require clothing you didn’t bring.

The problem with the black Samsonite rollaboard is that the whole system doesn’t fail gracefully. Time is your only nonrenewable resource, and it gets robbed every time your bag gets gate-checked. Things change and you need to carry the heavy beast. Security gets randy, and your careful packing becomes a swampy mess because it’s a black hole in there. You need to go direct to Europe and find out that American carry-on rules are the Wild West compared to the ship they’re running in the Old Country. Suddenly you are paying to check the world’s smallest valise.

Packing should enable you, not hinder you. Look professional in your meetings. Minimize airport and in-flight frustration. Be unencumbered in your time off. Be uncompelled to return unnecessarily home to re-pack between work and pleasure travel. Be as productive, presentable, and well-rested on the road as you are at home.


7 Not-So-Radical Travel Hacks

Travel bloggers shouldn’t have all the fun. Here are some hacks to upgrade your next trip, even if it’s to Cleveland instead of Hanoi.

  1. Two-Bag Strategy. I generally travel with a single bag now (see the Cool Thing below), but I advocate a 2-bag system for serious business travel. First things first: ditch your ten pound rollaboard, which becomes an unruly anchor as soon as road conditions deny efficient wheeling. Instead, pack your clothing in a soft-sided suitor (suit supply or Brioni are best) and put your travel essentials and toiletries in the briefcase you’ll be using for meetings at your destination. Nothing you need in flight goes in the main bag — it can get shoved in the first overhead slot you find, including under the hinge where rollaboards don’t fit. Your briefcase comes to the seat with you, and is now your office.
  2. Single Extra Pair of Shoes. The biggest force-multiplier in packing light is footwear reduction. Nothing is heavier, harder to pack, or bulkier than shoes. They need to be sequestered from clean whites, they’re oddly shaped, and they add pounds not ounces. You should be able to go out after work in your dress shoes (see capsule wardrobe below). For my current weeks-long expedition seeing clients, working remotely, and sailing around the Greek isles, I’ve opted for versatile suede boat shoes. I can do my yoga and pushups barefoot, thank you very much. However, I’ve missed out on impromptu hikes too many times to travel without gym shoes now. Choose a pair of light zero-drop trail runners from NB or Altra that can dry quickly and won’t take up too much space in your bag.
  3. Capsule Wardrobe. This concept is better explained by an expert, like Dan Trepanier of AOS. TL; DR? Don’t bring any two items of clothing which cannot be used together to form a differentiated look. Instead of thinking about each day and planning an “outfit,” bring a selection of your home wardrobe which will be able to pinch-hit for anything you might run into. This system is more resilient to inevitabilities like stubborn wrinkles or tomato stains, and will reduce your stress levels.
  4. Edit your toiletries. Dopp kits around the world are disastrous toxic dumping grounds of spilled liquids and unloved safety pins. Start by engendering pride of place with a new bag. I prefer this one from Patagonia which protects the rest of my kit from errant toothpaste. Then, take a zero-based-budgeting approach to what you add into your pristine new bathroom-on-the-go. I like a spare toothbrush, moisturizer, and cloth tape. Your idiosyncrasies are welcome here, as long as they’re thoughtful and compact.
  5. Foul Weather. True rain jackets can now fit into their own pockets, as can warm puffy layers. Unless I’m going somewhere with obvious weather, like Thailand, both come with me as a matter of policy. It’s no fun being cold or wet, especially when they keep you from staying healthy, saying yes to adventure, or performing at your best.
  6. Stuff Sacks. Throwing everything in your bag loose is lazy, and is the number one cause of the impenetrable swamp-bag. Even if you refuse to ditch your rimowa for a soft bag as I’ve implored, I insist you store your like items in stuff sacks or packing cubes like these from Eagle Creek. Try one cube of underwear/socks and one of casualwear. Or fill one with outerwear and another with gym clothes. Either way, they’ll be right where you left when you get to your destination, making unpacking and repacking a much less daunting endeavor. Pro tip: designate a big one for laundry, it weighs nothing and your clean clothes will thank you.
  7. Bring Adventure Enablers. A tiny crushable backpack like my preferred ReFactor Tactical SSE bag (or cheap clones on Amazon) takes up no room in your bag. Yet, when the group decides to go for a hike, you’re suddenly the hero who can bring water, sunscreen, snacks, and a fleece. Holly and I learned this the hard way when we had full hands and empty bellies up an unexpected climb of the spectacular El Teide in Tenerife. Other things in this category include micro headlampsbuffs, and choosing workout sneakers with some tread on them.

Cool Thing of the Week:

Cotopaxi Nazca

If you are ready to jump into the deep end and start traveling with a single bag, the underappreciated Cotopaxi Nazca is a great place to start. The Nazca belongs to a class of backpacks which open up to a split-sided suitcase arrangement. The entire concept is interesting, and there are other good but less business-appropriate options in the Cotopaxi lineup and by Letter-approved brand Fjallraven (in 3 sizes). The core value here is that your stuff is inherently more organized (and more accessible to grubby TSA fingers) when it’s not stacked deeply. Tuck the backpack straps away, and it’s a decently presentable briefcase for your meetings.

Here’s how I set mine up. Get on the plane in your suit and shoes — you’ll get treated better anyway. Extra dress shirts and two packing cubes go on the empty left zipped side. Workout gear and sneakers go on the right side, where space is lost to the outside pocket. The outside pocket gets your sunglasses, headphones, battery bank, and kit o’cables, while the laptop pocket gets …your laptop. Your old rollaboard weighs between 8 and 12 pounds empty. The Nazca weighs 2.4lb, and fits under the seat in front of you to foil the budget airlines’ profit drivers. Bonus: locking zippers.

Get /Giphy With it:

Useful JPEG to send to colleagues:

Mandatory Self-Promotion

After years building startups in NYC, and a stint helping McKinsey & Co. develop their startup accelerator, I’m now leading the charge @ Brandt & Co., a boutique consultancy serving investors and founders in the early-stage ecosystem.

If you like the Urbach Letter, the best way to give back is emailing me copious atta-boys to print out and stick on my fridge.

The second best way is connecting me to your friends at family offices, VCs, and terrific startups. For investors, Brandt & Co. focuses on a class-leading diligence product to shine light on technically complex early-stage investment targets. For founders, we aim to prepare them for institutional scrutiny and provide the tools to help their companies grow and scale.

Get the Urbach Letter in your inbox.

  • This field is for validation purposes and should be left unchanged.