traveling workcation tips

8 Workcation Tips For Running Your Business While Traveling

Exactly a year ago this month, I set off on a long time dream-come-true that would change my life (and the way I ran my business!) in so many ways: I took Crafted by Carly on the road for a 4 month trip through Latin America alongside 25+ other digital nomads.

This trip was incredible in so many ways, but one of the biggest lessons it taught me as an entrepreneur was how inspired and fulfilled I felt while traveling, and how I really could grow my business from anywhere in the world. 

When the 4 months was up, I returned home to NYC—I had a fiancé holding down the fort & a wedding to finish planning, after all—but since then, I’ve continued to take shorter working trips any chance I can get.

So whether you’re looking to head to a tropical beach, a big city, or to work from a totally different time zone – here are my top 8 tips for your next workcation: 

1. Plan ahead

The most Type A advice I can give you is to plan ahead!

While it’s always good to leave room for some spontaneity while traveling, your working trip will go a lot smoother if you plan a few things out. This includes looking at any deadlines you may have during that time, planning and scheduling content ahead of time, and reworking your call scheduler to fit in with your travel schedule and potential new time zone.

I also recommend looking into what sort of activities you want to do while you’re there. If there’s a day trip or a morning tour, for example, you’re going to want to make sure you get ahead of any deadlines and avoid scheduling calls that day.

2. Choose the right accommodation 

Where you decide to stay is going to have a huge impact on how comfortable and enjoyable your time working is. For me, hotels are not ideal for traveling when I plan to work, because it may mean being holed up in a small room for several hours a day or working from a bed.

Instead, I usually opt for an Airbnb that has good natural light, fast wifi, and a kitchen table or desk for working. Coworking and coliving accommodations are also popping up more now, such as Selina, which is a hostel with private or shared rooms and coworking space for an extra fee. 

3. Find other cute spots to work 

While I usually work from my Airbnb if I have lots of calls, I also like to make sure I’m getting out & about during the day. And for me, checking out cafés and restaurants is one of my favorite parts about traveling and experiencing local life in a new city.

So naturally, it’s a win-win to find laptop-friendly cafés and restaurants to work from! I usually do some research ahead of time and flag any places that look good to me in Google Maps. 

4. Sort out your cell phone plan 

If I’m traveling out of the country for a full-on vacation, I may be inclined to skip the international data plan, instead opting to utilize only wifi to save some money. But when working, I find it really important to have a data plan—even if it costs a bit of extra money.

This makes it easier to keep up with emails and client correspondence if I’m on a tour, or connect to a hotspot if I’m trying to work on the go (such as in an airport or on a train).

For shorter trips, I typically use the “AT&T Passport” plan which allows me to have unlimited data out of the country for $10/day, but you can also explore options like Google Fi or a local SIM card.

5. Schedule dedicated work time 

After you have a loose plan of the activities you want to do—which may include a morning tour or a day trip out of the city—fill in the blocks of time that you can dedicate to working.

Unlike when you’re at home and in your usual routines, this may mean working nights, weekends, or while you’re in the air. The important thing is to have an idea of when this “work time” will be – it will help you know when you have to be plugged in and focused, which will make it all the easier to fully unplug and be present when you’re on that tour or checking out that famous landmark. 

6. Hold onto any routines or non-negotiables 

Sometimes when traveling it can be easy to abandon our usual routines because we’re in a new setting or just in “vacation mode.” But when workcationing, it’s more important than ever to maintain balance and prioritize your wellbeing—and a key way to do that is through the routines that help us stay grounded at home!

Keep it simple: such as taking your morning walk, journaling, doing a 10-minute meditation, or drinking enough water. I guarantee these practices—whatever they are for you—will help you feel your best so that you can be extra focused for your “work time” and extra present for the new things you experience!

7. Put yourself out there

I recently started working with a client that I met on none other than a food tour in Lisbon, Portugal last month. And I still can’t get over how cool that is!

Whether you’re traveling solo, with a partner, or with friends, be open to striking up conversations with new people. And not just because they might turn into future clients—that’s certainly not what I was expecting in this case—but because human connection fosters understanding, empathy, and is just, simply put, fun!

Some of my favorite ways to meet people (especially when I travel solo) is through free walking tours and Airbnb Experiences.

8. Go with the flow & enjoy

Last but certainly not least, enjoy it! This past April, I took a working trip to Europe where my client work happened to slow down and I only had to work a couple of hours a day to keep up.

One month later, I took a trip to Mexico City and my workload was insane. The cool lesson? Both trips were amazing in their own way, and it was a good reminder that I can live this lifestyle no matter what comes up with work.

Ready to plan your next workcation? I recently started a travel blog as a fun way to help show my friends, family, and fellow #bizbesties that traveling more often is well within reach. Check it out to help you choose your next destination! 

Up next: What It’s Like Working As A Digital Entrepreneur in the Dominican Republic