TMBA 202 : 14 Advanced Travel Techniques

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Have you seen Tammi’s “Travel the World Like James Bond” article? It inspired this one.

I’ve been semi-nomadic entrepreneur for over 3 years now. In this post I’ll attempt to inventory some of the approaches I take to traveling that I might be taking for granted, and that might be useful or interesting to other travelers and prospective TMBAers.

One disclaimer: a lot of my clothing advice applies only to tropical climates. I’m not an expert on how to travel in winter climates. My general approach is to find the nearest airport. :)

1. Travel with one day bag and one business bag.

Traveling with one bag makes for a good blog, but not a good travel experience. You’ll want your work stuff to be 100% separated from your clothing. For a long while I traveled with only my North Face surge pack. It has a padded laptop compartment and plenty of space for all my stuff. I found it was a pain to always be taking out my clothing when I arrived in a location and wanted to head out to a WIFI cafe.

I’ve found there are tons of upsides to having a supplemental bag and almost no downsides.

Many people disagree with using such a small day bag, and instead opt for a medium sized backpack or a rolling pilot’s bag.

In general the pilot’s bag is a much better option, but it fails to pass my “bikes and bonka boat” certification. They make it impossible to travel on motorcycles and difficult to travel on native boats– both deal breakers. You also look (and feel) like you are in transit with these larger packs. It might be a small thing, but it’s nice to show up to a place and walk around and hang out at places and not feel like a sherpa. You won’t feel like you’ve got a tourists’ traget on your back.

2. Write the price down and pay in advance to avoid over-paying for local goods.

A common scene. You walk up to a vendor. You have the “how much” conversation. He quotes you a price and you say “okay.” They deliver the goods and when you are ready to pay they pull a totally unexpected price on you. Many times there is a legit reason, but in a lot of places they could just be straight ripping you off. You can avoid this awkward situation by paying before you receive the service. Most vendors will think this is weird but will go for it anyway. You’ll lock your price in and avoid the awkward fall out that can happen when you are hungry, tired, and feel like you’ve been ripped off.

A general philosophy about pricing and negotiations: stop complaining about it. You are an entrepreneur. Find a way to get the information advantage. See these situations as a challenge to get the best value for your money. When you are beat (like the way you get beat by the sandwich stands at JFK airport) say “good game vendor, good game.” I’m sick of travelers belly-aching about getting ripped off. Do your homework and have some fun with it. If some vendor is taking you for a ride I’d hate to see what your business looks like.

3. Keep 20% minimum of your bag empty.

It sucks to use a 100% full bag. Imagine opening a bag that has plenty of extra space in there. That feels better! You’ll also be able to pack your stuff up much faster. You won’t have to perfectly fold every dirty piece of underwear to be on your way. You’ll also have a little extra space for anything you pick up along the way.

4. Travel with a dry bag.

This is something I knew about for years but for one reason or another never got around to. I ended up picking up a small dry bag at Eastern Mountain Sports over the Christmas holiday. This thing has turned out to be incredibly useful. I’m always around the water so it’s got a lot of obvious benefits for beach trips and boating. It’s fantastic for dirty and wet items you want to put in your pack. It can also work as a separator in your pack for your dirty shoes (if you got them). These things are cheap, don’t take up any space, and are super useful.

5. Bring 1 pair of shoes.

You don’t need your hiking boots. You don’t need your italian leather knock-em dead at the club kicks. Those things will collect dust and take up a ton of your pack space. Shoes easily fall in to the “high cost, low use” travel gear items, which should be rooted out from your kit entirely (e.g.,  shoes, tuxedoes, tennis rackets). For these types of items I always get it there. If I’m living next to a tennis court for a few months, I’ll borrow a racquet or pick one up at a local shop.

6. IGNORE touts.

This is a tactic I started to flesh out in my article about Bali. Your attempts to shoo away touts by saying “no thanks” in English are pathetic. Make like an expat and stay stone cold focused on what you are doing. Eventually, you’ll be able to do it without giving it a thought or any amount of energy, which is where you want to be on this stuff.

7. Don’t wish away your travel days.

One of the greatest things about being an entrepreneur is that you don’t wish away your days. I remember when I had and old fashioned job I used to hope the weekend would come faster. What a sad state of affairs. Same deal with long travel itineraries.

Gonna spend the next 30 hours on a combination of planes, traines, and boats? I use it as an opportunity to catch up on some of my favorite podcasts, learn about something new, read on my kindle, and reflect on my life. Traveling is good for this– you are floating above the surface of your life. It’s very difficult to “keep things moving” on the ground when you are up in the air. Use it as a mental vacation and a chance to take an inventory of where you are at, and where you want to go. Incidentally– packing extremely light makes it easier and to enjoy stress free travel over long distances.

8. You don’t need nice clothes to go to nice places.

Application specific clothing– like your clubbing gear– is squarely in the “high cost, low usage” category. Don’t bring it. 99% of clubs will let you in anyway, and if they don’t, have your date take you shopping. It’s fun.

9. Choose travel destinations based on contacts.

If you are deciding between a world class travel destination that you are really excited about, and one that you see as a secondary option but you know somebody there…. go to the place where you know somebody. Provided the person you know is a good host and has been in the destination for a little while, having them as a guide will give you a depth that’s difficult to achieve on your own. This lesson has been borne out time and time again for me.

It also defends against ‘non-sequitor’ traveling. By going places where you’ve got people you care about your a building important relationships and building things that could be meaningful for your life and business. Seeing new places is a wonderful experience, but I find it even more enjoyable to build stuff when I go to a new places.

Whereas two weeks for me in Tokyo be just that– two weeks in Tokyo, a two week romp in Ubon Thailand would almost certainly result in many new friendships, a high falutin’ business idea or two, and plenty of in-depth local knowledge.

10. Fly in to hubs, go further afield on budget airlines.

This is a simple point but many people aren’t hip to it because flight search engines like Hipmunk don’t have budget airline inventory. Buy your round trip ticket in to places like Singapore, Bangkok, and the like. Use airlines like Jetstar, Air Asia, and Tiger Air to get to your island getaway.

11. Create your outbound tickets.

Many countries offer visa on arrival to travelers who are in possession of an outbound ticket. You often have to show this ticket to an airline representative at origin. It’s rare, but sometimes customs agents at destination will want to take a look at your ticket. This is some risk in this advice, and some very real potentially catastrophic downside– so do your own research– but it’s very common for expats in the region to do a little photoshop magic on an Air Asia or Tiger Air ticket.

If you do do this, you could consider using real flight information and using a different airline than the one you are flying on (so if you are flying on Tiger, use Air Asia ticket for your outbound). I do not understand the liabilities to doing this, I can say the chances of you getting caught are relatively low. If you land your ass in jail, don’t email me.

12. Set up your Skype-in phone number for family and customers back home.

Skype-in is a fantastic service. You pay 30 bucks a year. You pick a phone number in your home country and state (for me that’s California). In your Skype profile, you put in your current local phone number. People who dial your USA local number will be forwarded to your local phone. Skype will also record voice mails if you don’t pick up the phone.

13. Consider showering with your clothes on.

I think I have a draft blog post called “the one shirt shower.” I have a mini-obsession with doing laundry on a daily basis. It’s part of my routine to find a place to hang up my clothes wherever I’m staying. It might seem a little weird– but why not clear out your pockets and walk right in to the shower at the end of the day? Wash those clothes up good and hang them out. They’ll be ready to go the next day! :D

14. Search Twitter for interesting people when you get on the ground.

I’ve found twitter to be the best way to network with people when you are on the ground in a new place. This is especially true if you are actively blogging. Even if you aren’t planning on meeting people on the ground, you can get some great information by asking locals and expats you find on twitter. The TMBA guys have also been using couch surfing as a way to meet interesting people on the ground.

When you do contact people on twitter– consider asking for their specific advice or inviting them to a pre-planned event. For example, “my friend and me (both have similar interests) are meeting at 8PM tonight for dinner, here’s the address if you can make it!” That kind of thing will succeed much more often then “can I buy you a cup of coffee.”


Here’s some bonus tips from my hyper jet-set and high-end traveling buddy:

  • Sneak into airport lounges. “If there isn’t a lounge for my airline alliance, I simply use another. If you are dressed decently and just walk in like you own the place, you will own it. If you get slack, you say, oh shit, I forgot my card. Flash a nice smile. It’s on, 9/10.”
  • Load up on the toiletries if/when you stay at a nice hotel. Even if you aren’t staying there, you can simply ask at the front desk or the concierge for whatever you need. If necessary, just take the elevator up to the rooms area and you can raid the maid’s carts. (Of course, this is somewhat classless, but I’ve done it!)

My friend also berated me for not taking advantage of miles bonuses and frequent flyer programs. I suck at “lifestyle overhead” stuff and I see managing premium accounts for stuff like that as a pain the butt. @AnythingIan and I are racking up some bonuses on our business, so I think thats a personal weakness I’d like the business to be set up to help me out with. Anyway, always something to learn and improve!

I would love to hear your advanced travel tips!

Cheers from Bali,