How to work remotely from anywhere

Last December, on the day after I turned 29, I had a light bulb moment: In less than a year I would be entering my thirties and I hadn’t come nearly close to crossing off the big things on my bucket list.

What had I been doing these past 10 years?

Oh, working my ass off to live out my dream career (which wasn’t bad—after all, as the founder of a creative agency, I was working with some seriously authentic and inspirational wellness practitioners).

But still, I wanted to be living a freer, deeper, and richer existence. I wanted moments that I could keep with me forever. I wanted to spend my time doing more than sitting in traffic between the 101 and the PCH. Things like surf in Hawaii, take a solo road trip, have a beer in Santa Fe, spend days on the beaches in Mexico, actually do those touristy things.

So, I promised myself that at least once a month for an entire year I would get out of LA, see the world…and continue to get my work done.

And I’ve made it happen: In the months since I’ve been to New York City, Maryland, Ojai, Oahu, Cayman Islands, Joshua Tree, Tulum, Cabo San Lucas, Australia, and Palm Springs, all while keeping up with work.

Throughout these 10 months, I’ve experimented with how to best hack my travels for both pleasure and work (whether I’m just a few hours from my apartment or in the middle of the Pacific Ocean). Here’s what I’ve learned about what you have to do before, during, and after your trip to make it happen.

Part 1: Plan ahead

This is where you strategically set yourself up for success. The goal is to make sure that your travels are prepped in such a way that everything you need to get your work done—whether it’s strong wifi or an OOO—is lined up and ready to go. I try to get to a place where my upcoming travels won’t inconvenience me, my work, or anyone else.

Travel smart

Book your travel for “off-hours”, such as red-eye flights or on weekends, so that you’re less likely to be MIA during normal work hours.

Find that wifi

It goes without saying that you’ll want to make sure you’re staying somewhere with reliable wifi—or, worst case scenario, able to create a wifi hotspot. Find places that have a strong, consistent internet connection (contact your hotel or Airbnb hosts to confirm if you’re not sure). Relying on an internet cafe you found on Google? Map out where it is and how you’ll get there so you don’t have any issues once you land.

Get ahead on your work

It’s not just about the work you’ll be doing while you’re gone; traveling while working means you’ll also want to be strategic about the work you do before you leave. My tip: Try to get as much of the hard-to-do-remotely work from home while you’ve still got your office.

Set up an international data plan

Got a big conference call with your client? Consider scheduling your trip around it—or making sure that you’ll have reliable phone service when you’re away. Check in with your cell phone service provider beforehand so you’re ready to hit the ground calling (or texting).

Ready, get tech, go

Technological issues are not cute when you’re in a beautiful location and everyone else is at their desk. Beyond the usual packing list necessities, make sure you bring a portable hard drive, external mouse, and all the chargers. Also: Check that your iCloud files are all up to date and synced. Same goes with your Zoom, Skype, and Google Hangout accounts (and don’t forget to bring the logins with you).

Manage expectations

Make sure that your clients/co-workers/employees are clear on what your availability will look like. Same goes with hours: If you’re going to be in, say, Australia, you’ll be sleeping when everyone else is working—so let them know you might be delayed in responding to their messages.

Part 2: While you travel

The key here is to really maximize your time, energy and efforts while traveling. Because you want to be crossing things off your bucket list…while also crossing things off your to-do list.

Schedule your day

Answer emails, conduct meetings, and do your work in three-to-four hour blocks, either in the a.m. or p.m. If you work in the morning, schedule your adventures in the afternoon—and, if you can, wake up early so that you can explore before you get some work done (even if that just means trying the cute breakfast spot you’ve been eyeing).

If you work in the afternoon, wake up early to spend an hour in the morning answering a couple quick emails (put out the fires I like to say), get clear on your to-do list for the day, and then schedule all your meetings and “heavy” work in the later part of the afternoon/evening. Pro tip: Alternate your days so you can have a good mix of the two.

Check in regularly

If you manage employees, send them an email with to-do lists (due dates included) and have check-ins to track status on all projects—this ensures things are getting done while you’re traveling.

Say hi

If you’ve been open with your clients about where you’ll be working from, send them (or your employees/managers) a postcard. Also always appreciated: picking up a cute souvenir for everyone back at home.

Part 3: When you get back to reality

It’s sometimes the hardest part of traveling, but try to jump right back into the swing of things, so that it’s almost as if you never left. It’ll make it all the easier to leave for your next trip, promise.

All about those zzz’s

Sleep on the plane/car ride home, so you’re not tired when you’re back home. (Easier said than done, I know.)

Get unpacking

Unpack your bag and toiletries as quickly as possible. (I know, I know.) But save the laundry for a day or two after you’ve gotten back and done a bit of work.

Return to your routine

Whatever your home timezone is, bite the bullet and get back into it ASAP. Don’t try easing into your usual routine, either. “I was in Mexico” isn’t a great excuse for being unreliable once you’re back at the office. (Same goes for “Sorry I slept through our call, I’m just feeling sooo jet-lagged.”) It’s a sacrifice you gotta make if you want to do the whole travel-while-working thing.

Put in the time

If you spent a bit more time on the beach than you anticipated (hey, it happens), make up for it by spending a few extra hours at the office when you get back. Again, it’s all about sacrifice. You’ll feel really good as you cross off things from your to-do list.

Plan your next trip

You successfully worked remotely—time to figure out your next far-flung office location!

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