Bootstrapping your stay

Remote work, done while traveling, is ruled by its own set of sojourn laws. Whether you are staying a fortnight or two months, a single truth always prevails: The cost of decisions you will make during the first 48 hours of a visit to your dreamland of choice, can – and probably will – haunt you for the whole stay.

Or would you prefer to bootstrap everything you need in the first 48 hours and enjoy your cocktails and sunsets for the rest of the time?  It is not only  possible, but also the quickest and most comfortable way of dealing with all tough decisions which are made without putting yourself, and your wallet, on the mercy of ‘friendly’ travel agents.

The “Amsterdam Bar” on Koh Phangan island

Why 48 hours?

The 48 hour window fits neatly into weekends. It is the best part of a week for setting up your stay. For most of us, the end of a week is free. And since the brave entrepreneurs who are striving for a startup success don’t recognise the concept of free time, I assume that they are willing to travel during the weekends just like any other day.

The alternative, namely messing your workdays with travel, will result in losing a lot of working hours which will make your contractors very unhappy with you. You don’t want that. I’ve been travelling for months now and working on a plane is still a habit which sometimes eludes me.

The final argument: the people. The weekend is – socially – the most active time of a week. Getting your local networking will be the easiest when there are a lot of travelers: backpackers and nomads   willing to share their reflections concerning the place.

48hThe Bedstation Hostel in Bangkok – a great place to bootstrap your weekend and meet a lot of travelers

Let’s talk information

Acquiring quality information is key to planning a stress-free stay. I’m talking real quality. Skip all tourist agency promo stuff as it is generic and it will harm both your wallet and your experience. We need to know what is the situation in the place you are planning to go.

What kind of information do we need? We will look for:

  • place to stay during the first weekend
  • safe heaven for the rest of the stay
  • source for cheap & quality meals
  • spot to build some personal space work
  • finally – a place to workout

In other words, you will need to gather information needed to build an environment for your daily routines.

First, people who are already there know best. Any inquiries should start with finding local Facebook groups (e.g. Koh Tao Community) or joining one of the nomad communities.  Secondly, there is a fair chance that one of your friends or friend of your friends has already been to the place you are planning to visit. Therefore, a small beer-interrogation wouldn’t be amiss, just ask away and watch the information flow. Lastly, fallback to tripadvisor forums and nomad blogs  [ like this one  😉 ]

“Before you leave the airport” checklist

Before we will get to selecting a good place for your first 48 hours, let’s talk about the airport. There are three things you ought to have before leaving the baggage pickup and lobby. Without them you are prone to losing both time and money. Information and items listed below are  a small fortune on their own:

SIM card

  • Double-check which operator is recommended by other travellers in a given area; use nomad communities and forums

List of local scams

  • This one is crucial; many scams are targeting travelers and even though  some of them take advantage of a victim’s greed, you could be caught by them if you are unlucky enough. In this case skimming through travel blogs, tripadvisor and uncle google should be sufficient.

Price of a taxi to your hostel

  • Contact the hostel for the price of taxi you should pay from the airport. Haggle as hell, during my last trip to  Bali I was asked for a triple price as a “hello to Bali”. Usually it makes sense to stick to a trusted, popular cab corporation.

The only thing left to know is where to stay during your first weekend.

Early commitment is a sin, your 48 hours outpost

Remember, you can always go easy on yourself. Book a hotel for the whole stay and cry yourself to sleep over the state of your wallet and ask yourself some morbid questions each day: why there is a construction next to my place; why do I have salt water under my shower (don’t laugh, it happened to me, I mean the salt water part, not the crying one).

The alternative is to book a place for the first 48h just to scout the terrain. I usually pick up one of the backpacker hostels in the area which are always overflowing with people going through the whole country. That is to say, an abundance of knowledge at the tip of your beer bottle each day. Meeting awesome people is a bonus. But also be picky, try finding a true backpackers haven (good example would be the bed station in Bangkok). Huge lobby, quality breakfast and great communication with the rest of the city.

Believe in building your own experience

Your best remote work experience should be something you can pin on a map. I usually go with 4-5 pins, all not far from the place I will pick as a living area. Or rather, the place I will pick for my long stay base will always be close to the pins. All the information below could be gathered from the above mentioned places or just by talking with fellow backpackers.


Depending on your dietary restrictions, budget and taste for the local cuisine, you will have to decide between the local restaurants, food markets, and and cooking on your own (I’m skipping pricey tourist bars and restaurants on purpose). While the latter may seem the cheaper way, you might still get surprised at the prices on local food markets.

In Thailand, I was paying about $7 for 4 healthy meals per day – you couldn’t hope for a cheaper price at the local supermarket. Another argument is: don’t waste one of the best travel experiences – rich local flavours and culinary curiosities you wouldn’t dream of putting on a frying pan.

Screen Shot 2015-04-28 at 11.36.41Fresh coconuts from the local market


Since taxi prices usually skyrocket somewhere between 3rd beer and 2am, the city center is something you would prefer to have in the walking distance from your place. Having it closer might be an option for a weekend visit, but not for a couple of weeks with strong attitude towards staying sane. Additionally, it is a good practice to check the place you are going to on tripadvisor – sometimes you may marvel at the creativity of local scammers.

fun“All day all night” (11am – 4am) party at Koh Phangan island


Access to a proper internet connection and keeping your personal space intact are probably the two most difficult things to achieve in the lovelier corners of the world. Working from a local cafe is a possibility, albeit not one you might want to use as a base for your operation. The conditions are simply too fragile. On the other hand, in a paid coworking space you will not only have the stability but also a chance to network with other people working there. Some places [like hubud] are even organizing events how cool is that?

Local cafe in Bangkok -  a perfect workspace for  with one of the finest cold brews to be found.Local cafe in Bangkok – a perfect workspace for with one of the finest cold brews to be found.


Taking care of your trainings during travel is a challenge. Finding a proper workout routine is a separate challenge on its own. Usually you will find a decent place to train around you. Since smaller gyms are not always listed on google maps, I would advise on talking to guys in your hostel. In the unlikely event of gym drought in the region, you might want to check local hotels which often let you use their private gyms for a small fee.

Screen Shot 2015-04-28 at 11.36.02Muay Thai gym in Thailand

Final pin

Deciding on a place to stay is probably the most tricky decision you will face. There are always a couple of equally interesting and affordable options.  In fact, there is such a variety  of them that the topic deserves a separate article.


Bootstrapping a stay is a process one must learn over time. Sadly, there are some steps we could not avoid without paying dearly for cutting corners. While the approach presented in this post is something working for myself, you will probably find your own variation with enough practice.

The most important part is the fact that the greatest experience for longterm stay will always be the one crafted by yourself.