TMBA 202 : 14 Advanced Travel Techniques

TMBA 202 : 14 Advanced Travel Techniques post image

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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,



Published on 06.12.11
  • Gotta admit, I LOVE #11 after paying for a phantom flight to Malaysia to get into the country, will have to give that one a shot next time.

  • Cash…is king.

    Seriously, best piece of travel advice I ever got.

  • Dan

    At your own risk sir! They might just throw you out anyway… :)

  • Dan

    haha yeah still teaching Ian this one– “dude they won’t let me use the AMEX!” this is true of doing business in general in the developing world– cash has such a huge value because credit systems are still a bit…. lets say, sharkey :D

  • Brother, I am at risk of being thrown out of every country I am in every single day of my life!

  • Dan

    Tell me about it! :D

  • seb

    What I learned in 3 months of HK, Bali, Thailand:

    When asking for directions or places, ask tourists not locals, they often know better, where and what is, and also are not afraid to admit when they’ve got no idea. I got this advice from a indonesian girl living in bali. 

    When haggling know who you’re talking to. It doesn’t make sense to haggle with the receptionist who isn’t allowed to negotiate. ask if you can talk to the manager.

    2 weeks before I get to a place where I stay longer, I go on dating sites, change my location and get in contact with a few girls that have something going. I met a lot of great people like that. Just be honest with what you want. When arriving at airports (especially bali) I usually walk to the departure gate and catch a taxi that just arrived to avoid the rip-offs. They tend to be more honest and less likely to rip you off.I have an (imaginary) budget for rip-offs, like 100$/month. This way I feel less bothered when having overpayed for stuff.
    To make aggressive touts shut up, there is actually a hand sign which works especially well in Thailand. Is there a way to upload a video?

  • seb

    uff. the 3rd paragraph should actually be split into 3 paragraphs

  • seb

    Regarding 11: You can also just book an outbound flight with airasia/jetstar/tiger far ahead in the future and then reschedule your flight. You spend a few bucks extra for rescheduling. I actually have been refused my boarding pass at checkin without a travel document. So i did exactly that. 

  • Yep yep, solid advice there.  I also like two bags.  I really like the typical two wheel semi-rigid carryon and a swiss army laptop backpack. The backback can ride on top of the carryon leaving one hand free for digging for paperwork or corralling rowdy kids.  Although more than not it ends up being three bags and a giant suitcase or two because I have the wife & kids along.  But I’ll give my wife props – she can usually make it all work with one big bag and a couple carryons. 

    And you’re right on about being ripped off.  It’s not worth getting your blood pressure up over a buck or two.  It will happen periodically, especially when you are in a new place.  Learn what to avoid next time, move on.

    As for touts, I figure they are like telemarketers.  They will never give up as long as you continue to interact with them.  Save your time and theirs – ignore them and keep moving.  Also avoid eye contact as much as possible.  The same goes for the knick-knack sellers that crowd around taxis at intersections.  I should say same for the beggars, but I’m a bit of a sucker, especially for the blind ones.  If they are really blind.  But I generally give them the benefit of the doubt and a few pesos. 

    Last, a Philippines specific tip – if you’re trying to find something, it’s a safe bet to ask a security guard.  It seems to me like they are happy for something to break up the monotony of their day.  And they generally know the immediate area around their post very well.

  • haha. shower with your clothes on…brilliant!!!

    I wish I would have thought of that when I was backpacking through Europe. That would have been much easier than doing laundry in the sinks. Damn.

  • Hey Dan, another great post. I have something that you may find useful regarding that last bit on frequent flyer programs. The local Hackerspace asked me to give a presentation on earning and burning miles which led to me create a 5 page outline of everything I’ve learned since getting into the game a few months ago. It’s US focused but maybe you’ll find some useful information in it and I’m going to try and keep it updated as the information changes. You can find it at

  • 1- i love convertible wheeled backpacks such as the 25″ rei stratocruiser, + a smaller padded backpack for my laptop and kindle etc which can double as a day bag. just not feelin the briefcase
    4 – yeah great point, every motorboat trip i’ve taken in s. america has led to most on board getting soaked
    5- black comfy sneakers (great for walking the cit + can wear to the club), + a pair of hq sandals 
    7- thanks for the reminder :) 
    8- i like to bring a simple black t-shirt and one pair of jeans, yes jeans are heavy but worth it if you wear em enough 
    13- haha i’m not that hardcore, would rather have a slightly larger bag and a couple changes of clothes, one you’re wearing, one for tomorrow, and one hanging up drying, 
    14-great idea, hadn’t thought of this 

    extra – don’t forget about ex-officio underwear & icebreaker merino wool shirts – couldnt live without 

  • after taking a look around my room, some more gear that comes to mind..  under armour athletic socks and a baselayer shirt, sierra designs super lightweight rain jacket, unlocked iphone  (use as a camera, downloads apps w/ city/subway maps, language translation, etc etc) microfiber quick dry towel, extra laptop power cord, kindle, thats all for now..

  • Dan

    Great stuff Nandrin! Absolutely could go without my ex-officio underwear. I’m not so hot on the icebreaker shirts.IPHONE is probably the most important thing I carry outside of my laptop.

  • Dan

    Yo Arnaud thanks for the linke and the shout! Damn looks like you know your stuff, that’s a bit daunting! I think that’s exactly why I don’t get in to it. Party of me still feels I can make more money if I focus on my business, but I know that is just the lazy part of me talking. I’m working on setting up business systems to take care of this kind of thinking for me.

  • Dan

    haha. you risk becoming  a social outcast if you talk about it publicly :D

  • Dan

    Like your approach here with touts and the security guard trick– I like engaging locals that have spare time… it’s great for playing with the language and learning a bit. I think a lot of people feel like they owe something to touts because of “cultural respect” issues or some kind of mis-placed western guilt. I think westerners have such a hard time with it and it sucks to see people constantly loose their focus/attention. That’s why I come down so hard on the point. No surprise to me you’ve thought of this one as well.

  • Dan

    This is interesting: one of the points I was toying with but couldn’t articulate was “don’t assume that locals know what they are talking about.” It can often be the case that locals know very little about things in the expat/traveler scope of concern. Also getting bad directions from locals seems to be pretty common… 

    Love the haggling point– I’ve got a draft article about saving on hotel room rates by going right to the manager at the beginning.

    There is a similar hand sign in the Philippines that I’ve picked up and now I seem to be using it everywhere (with diminishing returns!) you can link out to stuff in the comments….

  • jet

    I reckon a low-key backpack (no brand, no bright colors, not too big) is essential in avoiding scammers and thieves. On the road I stick my laptop sleeve in a drybag, then that inside a very worn ‘thai monk shoulder bag’. That’s the ‘2nd bag’, keeps your laptop guaranteed dry, and hides it from looking like an obvious target. You then have a bonus beach bag for when you get to wherever you’re going!

  • Dan

    haha nice tip, worth nothing that north face also makes water proof satchel and day bags, my buddy here in the Philippines rocks them– a little pricey but could be worth it.

  • I would absolutely automate as much as possible. Take an hour or two and sign up for all the major programs in one afternoon. Then your number will be ready when you need it. Someone with a business selling products could probably earn a significant number of Membership Reward points using a corporate Amex. Then use a free service like AwardWallet to track the miles and have it send you monthly updates. I’ve just gotten in the habit of each time I spend any money asking myself “Could I be earning points on this?”. Slowly it adds up and now you’re flying business class instead of coach. Let me know if you have any questions I can help with.

  • I completely agree on #9. There’s nothing better than to go somewhere cool where you “know” someone – even if it’s someone you’ve never “met” in person, only online. I love to bridge online with offline. Another great way is to connect with people based on common interests. Go to Buenos Aires and sign up for tango school. Go to the Philippines and hang out with a scuba school. Instantaneous friendship right there.

    And manoman – the DRY BAG! Srsly a must have. I have always used plastic bags, but this time I am upgrading to a dry bag for my trip to the Brazilian Amazon next month. Dry bags – great for camera gear. In humid locations like the jungle, carry a sock with a cup of rice so camera & lenses don’t fog up on the inside. And if you are going deep into the bush but still need Internet – try and which also allows you to plot your adventure here:

  • Dan

    Word…. I’m going to be taking this advice. 

  • Dan

    haha those are some serious internet tools! love the dry bag i’m finding i use it all the time. also totally agree on the interest based approach. i think when i first started traveling i would go to places and “see the sites” or whatever and that ends up being unsatisfying… going in with an agenda about what you like and are interested in isn’t a revolutionary idea, but its one i didn’t always have. i think part of that is also confidence… when you’ve been around the block a few times you tend to ‘exoticize’ places less.

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  • I have been using Chris Guillebea’s Travel Hacking Cartel ( and it is well worth the $15 a month to simplify the whole process.

  • i love ex-officio shirts and underwear. I can’t wait to get another pair when I’m back stateside.

  • This is awesome!! I plan on doing a world trip at the beginning of next year so it helps to get some advice. I came over from Andrew’s blog becasue the showering with your clothes on intrigued me. I will have to try this method out. I shower with my yoga mat and yoga towel so I guess it’s a similar idea.  I am also on couch surfing. I have met a lot of really cool people. Actually have one staying with me tonight. :) I am glad I came across your blog. I need some travel inspiration. Thanks!

  • Dan

    Hey Meg thanks :D! We are going to have a bunch of weirdos showing in their clothes! :D

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  • Great Post!

    I have personal experience regarding #11. I was
    flying to Thailand assuming that I would be able to get visa on arrival.
    However I didn’t realise that I needed to have an ongoing flight. I was
    panicking when the jetstar staff wouldn’t let me check in, and I ended
    up buying a ticket from Phuket to Singapore at the last minute to be
    allowed on. The thing is, I bought a 1st class ticket, which was fully
    refundable, so I simply cancelled the ticket straight away and got all
    my money back.

  • Dan

    UGH. Nighmare man. Did the same on a trip to China one time. Huge bummer.

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