[CEO Friday] How to take your whole company overseas, and live to tell the tale.

Expensify is unusual in many ways.  But one of our most well documented oddities is our habit of taking the whole company overseas for a month.  There are a huge range of reasons to do this: to work, to play, to finish off the year before, and to get inspired for the year ahead.  But regardless of your reason, here are some hard-learned tips for making the habit work for you: 

• Choose someplace far away, in every sense.  Aim for someplace on the other side of the planet, with a different culture, different climate, speaking a different language, with a lot of timezones and water between you.  The more “foreign” it feels, the closer it’ll push you together.
• Try to achieve the triumvirate: power, internet, beach.  It’s easy to find any two, but getting all three can be tricky.
• Pick someplace cheap.  It’s a great luxury to eat well, stay in nice places, and know you can buy your way out of any serious problem without breaking the bank.  Also, rent out your apartment (or even your office) on AirBNB to defray the costs.
• Maintain a very light grip.  If you try to plan every last detail, you’ll go crazy.  Instead, just say “Meet at this cafe, in this city, in this country, at 10am on X date.  Figure it out.”  Some people will decide to come early, others at the last minute, but everybody will get there one way or another — and you don’t need to stress over the details.
• Cover the flights, if you can afford it.  Have everybody book their flights and submit an expense report; it’s the single biggest expense of the trip, but people don’t have very strong airline preferences, so it’s a good candidate to pay for.
• Leave the rest up to them.  The other major expenses are food and lodging, and though not big, they do add up.  But people have extremely strong preferences for what they eat and where they sleep, so this is best left up to them to pay for.
• Take a whole month.  Less than that is too short to justify the expensive flight and jet lag.  More than that and people get antsy.  A month is just long enough to get sick of it, which is the perfect time to come home.  A good itinerary is 1 week in the capital city, 2 weeks on the beach, last week back in the capital.
• Pack light.  Start with whatever you are currently wearing at this moment, but swap out your pants for shorts, your shoes for sandals (no socks).  Add a toothbrush and passport to whatever is currently in your backpack.  Buy a silk “sleep sack” at REI.  (It’s like a sleeping bag, but for hot weather — it keeps mosquitos away when sleeping.  You won’t need it most of the time, but when you do, you’ll be grateful.)  You literally don’t need more than that; anything more than that is just weighing you down.
• Don’t pack anything in crinkly plastic bags.  They don’t sound so loud when packing them, but they are truly deafening when unpacked in a quiet dorm full of sleeping (or now, rudely awoken) people.
• When your team is small (4 people) just do everything together.  Stay in the same hotel, eat the same restaurants, work in the same cafes, and go to the same clubs.
• Accept that you’ll split up as the team grows.  Don’t fight it — just have a morning 10am standup meeting that pulls everyone together every day and sets the tone.  After that, just have everyone stay online and shout out where they are working that day, and they’ll cluster organically.  Create a shared Google Map where everybody marks good spots with outdoor power and wifi, hotels, good restaurants, etc.
• Prepare to work offline, possibly a lot.  That means get a local copy of your servers running on every developer’s laptops so they can develop on localhost.  Set up Gmail/GDocs offline.  Download documentation for the languages and systems you use – PHP, JS, Underscore, etc.
• Bring an extra laptop battery if you can.  (This is a major downside of having a MacBook Air.)  The best places to work aren’t always next to an outlet.  Alternatively (or additionally), bring a US extension cord.  Walgreens currently carries a nice white one with thee, three-prong plugs, that is pretty compact and rolls up nice.
• Unlock your GSM phone ahead of time.  Get an unlimited data plan on arrival (usually surprisingly cheap) and tether.  Lacking that, you can likely get some kind of USB GSM modem, or even just a portable wifi hotspot.
• Pick some large goal that involves a substantial majority of the team.  Ideally something you’ve wanted to do for a while but haven’t ever made the time.  Set a goal to have it done before you leave.  (Ideally you can release it before you leave, but better to do it when you return as it’s generally bad practice to ship major new features before hopping on a flight for 20 hours.)
• Plan a group activity every weekend.  Scuba, hiking, rent some scooters.  Something outside.  The week is for working, but the weekend should be for playing.  It’s best if the company can cover this (because it’s a decision made on their behalf), but not critical.
• Have a big finale dinner.  Find the nicest restaurant in town and get an unnecessary amount of food and alcohol.  You deserve it (but the company should pay).
• Don’t tell your investors until it’s over.  Better to beg forgiveness than ask permission.
• And the official term isn’t “workation” or “retreat” — it’s “offshoring yourself”.  At least, that’s what we’ve called it for the past 8 year’s we’ve been doing it (my last company and this).

Good luck to you, and please drop me a line to let me know how it goes!