7 Essentials For The Entrepreneur On The Go

I have been on the road for 6 months now, more or less. My luggage consists of a carry on backpack and a messenger bag. I like to think that I keep it light for a first time, long-term traveller.

My style of travel is slow and (relatively) cheap. I’ve spent most of the past 6 months in 3 significant locations: the island of Bali in Indonesia, the tropical paradise of Puerto Galera on Mindoro, Philippines and the mellow student city of Dumaguete, PH.

A lot of my time is spent geeking out on my laptop. I make my living online through e-commerce marketing and development so I rely on my tech heavily. Over the past few months I’ve taken mental notes on the essential items that someone who travels like I do needs. This is more out of necessity then anything else.

The thing about combining travel and work is that your living costs become intertwined with your ‘business expenses.’ If my laptop crashes and wont restart, I’m in trouble! (good thing I saw the Apple light and got away from Winowze eh… eh ;-D) And when you’re on a tight budget and something goes wrong with the vehicle that pretty much generates your income, you better believe I’m forfeiting a few days worth of solid meals to get it fixed, all while cursing myself for not being prepared.

So to save you the hassles.. and missed dinners.. that I’ve experienced as a ‘digital nomad’, here’s my list of travel essentials for the online worker on the go:

A Spare Charger Cable For Your Laptop

This is one of those “aw maaaaan… do I have to?” items that you shouldn’t think twice about making room for in your luggage. The other day the mag-safe connection for my Macbook committed suicide and stopped working due to being bent at strange angles over a couple of years.

The one Apple reseller in Dumaguete (I was lucky that there even was one in my city) had a replacement charger unit for $100+ (5500 pesos) but was out of stock. My friend Damian came to the rescue, lending me his spare charger to keep me going for the time being. Save yourself the hassle and stress, buy yourself a cheap spare charger for $20 on eBay or Amazon before hitting the road!

An External Hard Drive

A once a week backup (the pre-installed Time Machine mac facility works well for this) will stop you from waking up sweating every few days from that nightmare where you had a hard drive failure.

I have lost data before and had no backup, the most annoying part was looking for a PSD file or document a few months later and remembering that it was on your old computer that self-destructed and left you heart-broken.

A Messenger Bag

I know that they’re hipster flags, and you haven’t worn one since your college days; but a messenger bag has been the best compromise for me between a laptop bag that can stick out while traveling and a normal backpack that can be a bit clunky for day-to-day use, hopping on and off your scooter and taking impromptu walks with your laptop in toe.

You will need a decent laptop sleeve to protect your laptop from other loose items in the bag. I suggest having one of these anyways, regardless of how you carry your laptop, for an extra level of protection.

As Much Underwear As You Can Fit In Your Luggage

Not tech related, doesn’t increase productivity and in no way relates to working online, but packing as close to 7 pairs of decent underwear as you can will save you a bunch of hassle.

Case in point: you go for a mid afternoon walk, perhaps trying to shake off the hangover from the night before ;-D. You get lost and end up walking 3k in clear skies, mid afternoon heat. You WILL need a shower once you find your way home, and I promise you will not want to put those soaking wet boxers back on once your done. If you’re Tynan style minimalist and don’t mind the hassle of washing your clothes in the shower everyday, go ahead and bring 3 pairs of those tighty whities. I prefer to take my showers starkers (that’s naked for the non-cockneys), have my laundry done once a week and pack a few extra pairs of undies instead.

I know ex-officio underwear is highly regarded by many long-term travelers. If you’re in the UK I highly recommend Rohan underwear @ http://www.rohan.co.uk/ (in fact all of their clothing is awesome: durable but still maintains a small element of style).

A Quality Notepad

I bought two moleskine notepads, one ruled and one plain, with me and I can’t recommend them enough. When you are sitting on a bus or plane and want to jot down a note or idea without whooping out the laptop and starting up evernote, notepads are invaluable.

My friend David Hehenberger uses a pocket-sized notepad to track his expenses and Damian Thompson has a nice leather-covered journalist pad that he uses to note down pretty much everything – ideas, names & phone numbers, to-do’s, etc – tying into his Getting Things Done (GTD) system.

Tip for the Scrooges: combine a notepad with a webcam and you will never have to buy another birthday card again:

Good Sounding Headphones

I had a decent sounding pair of headphones that blew up on me just the other day, and I spent a day or so   walking around the shopping mall looking for a pair of noise canceling headphones, with no success. While you might be able to pick up some ‘beats by Dre’ or similar form-over-function headphones if you are in a major city, finding a quality pair of noise canceling headphones can be a difficult task while on the road.

It’s amazing how much use my headphones get, come to think of it. I wear them when I go out for a walk, when I hit the gym (aka once a decade), when working, browsing and even when I go to sleep to block out the sound of crowing Filipino roosters (trust me… there’s always roosters).

Take advantage of your local Richer Sounds or Circuit City and invest in some quality headphones.

Multi-Use Trainers (‘Sneakers’ If You’re Nasty)

If you’re into the whole Vibram thing and have figured out a way to keep the stank off them, I hear they are a good trainer for travelers. The invisible shoes are recommended as a good mix between trainer and sandals as well.

I recently bought a pair of black FILA running trainers that are inconspicuous enough to wear on a night out (then again so are my $2 sandals here in the Philippines), but sporty and functional enough to wear for a run or to the gym if you’re into all that ‘keeping healthy’ malarkey stuff.

I had a pair of Converse Chuck Taylor’s before with a big superman ‘S’ on the side. While I got a lot of “cool trainers bro” comments walking down the street, the laughing and blatant name-calling in tagalog that followed was just not worth the embarrassment of wearing them.

Overall Thoughts:

When you’re packing to leave on a big trip, you can spend hours going over every last item, trying to find the best deal on a backpack or the smallest packing towel. The best litmus test for any item you pack is whether it’s still around after a month on the road. After unpacking and repacking that headlamp that you never use a few times, it will find its way into the nearest trash can.

If you plan to work while you travel, save yourself much hassle and splurge on the items above, even if it means skimping on other items. They will come in handy and there is a good chance that they will become your most used/useful items.

If you have any other suggestions for travel essentials for the ‘entrepreneur on the go’ please leave them in the comments below – I’d love to hear your thoughts!