From Long Distance Relationship to Full Time Travel with Remote Work – Becca & Dan

A website that really started from a long distance relationship, travel enthusiasts Becca and Dan shares how their stories came together and gave birth to Half Half Travel. In this episode, we talk about the transition to remote work, maintaining relationships across the world and the business of blogging.

We explore solo vs couple travel, the mindset differences between tourists and nomads, as well as balancing work, blogging and travel. Don’t miss this episode as Becca and Dan shares their most important travel and remote work tips.

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The following is an extremely summarized version extracted from the transcript of the full conversation. I strongly recommend listening to the podcast for all the valuable insights. You will also hear more detailed and contextualized stories from the guest(s), as well as pointers from me in a two-way conversation.

Please give a brief introduction of you guys and website.

Becca: We met in New York during the winter of 2015. We talked about a budding love of travel between us. I had already spent time studying abroad in Hong Kong when I was in college. Then I took some time after university to work in Shanghai at a school. I spent two years in China traveling Asia, and then I came back to New York. I was working a corporate job when I met Dan. He said on our first date that he wanted to travel and work remotely for a year, which back then was a really new idea. I didn’t know anyone else who worked remotely, and people didn’t think it was possible.

Dan went on a program called Remote Year, which is for people who work remotely and can travel with a group of people working remotely. The program is run so that everybody is exploring the world together and taking time in international cities where they’re set up in coworking spaces to work remotely successfully. So Dan went to Morocco, Spain, Portugal, Serbia, England, Mexico, Peru, Argentina, Colombia, and somewhere in the Czech Republic.

Dan: I went to 12 cities and ten countries. Every four or five weeks, the whole group would travel from one city to another city, and it was an excellent way to focus on work. Some people used it as a perfect excuse to eat out at many local restaurants, meet locals, learn a new language, try new things and meet new friends. I got a lot of value in transitioning from working full-time to freelancing. It came at a perfect time because I could carve out some more time to work on Half Half Travel. It was only an Instagram at first, and we had three posts, six posts, nine posts, something pretty insignificant. I thought that our story was interesting, so I submitted it to a bunch of press outlets, and it got picked up. Then the Instagram gained a lot of followers pretty quickly. My background is in Web Development. I realized we’re getting all these press mentions, and we should have them linked to a website because I knew it would be valuable in the future. So very early on, before we even wrote any blog content, we had backlinks from some pretty major news outlets covering our story. I think it was pretty beneficial to our growth once we started writing content and growing the website. We started focusing primarily on the website in 2018.

Becca: We started this Instagram because we were long-distance dating. I was living and working in New York, and Dan was traveling the world for 12 months. I visited him every three months; we would go to Barcelona, Colombia, Lisbon, and Argentina. I stayed for two weeks, and we made these photos that were half what I was doing and half what he was doing; they’re match up perfectly. Half Half Half Traveled website said thanks for visiting us; here’s our Instagram. So you were getting to the website, but it was driving you back to Instagram. No one was talking about travel bloggers four years ago.

I took vacations traveling in Latin America and Asia, and I always wrote down what I did and share them with friends. Dan suggested putting these travel guides on our website, but I wanted to polish them and make them better. We went to Hong Kong in the summer of 2017. We went to all those photo spots like the Rainbow building that everyone has seen on Instagram because it’s so fun to look at. One of our first articles was about Hong Kong, and it was popular, so we learned how to do it better.

Dan, was your first trip to try remote working while traveling?

Dan: It’s interesting; I wanted to go on the travel and work program because I had some experience working remotely. The team I was on had a couple of remote engineers, so it was okay; remote working was something that I could do. I got the idea because I went on a trip, and the trip was cut short. It was a seven-day trip, and I was traveling in Colombia. I could have stayed longer if I could work in a hostel or a café. I talked to one of my co-workers, and she said one of her friends was on this program and to check it out. Remote Year is a pretty polished product now, but back in 2016, when I started, there wasn’t much. It was like a Squarespace landing page.

Becca: They had run one trip, and it was a startup. It still is a startup, but the company was so new that they had only run one successful trip and people had okay things to say about it.

Dan: I got inspired by that, and then I decided that in 2016 I was going to travel to one place on my own. In January, I went to Columbia, February I went to Austin, Texas, with a friend work from a cafe for a couple of days. Then I went to DC, and then I went to Utah; it was nice because you can be somewhere and work. You could work Monday through Thursday and take a day off in a superb location. You’re able to have a weekend trip that isn’t in your typical neighborhood. I got the feeling for it, and then I ended up getting into Remote Year. That was the kick-start to diving headfirst into remote work and travel.

Becca: In 2018, we both decided to sublet our apartment in Brooklyn. I quit my job and then got rehired to work remotely part-time, and Dan did the same thing. We went to Europe on a one-way ticket, planning to work remotely and travel with no plans. Because of some of the connections and opportunities that arose, we wound up doing Remote Year’s new four-month program as a couple from September to December in 2018. We did a mini Remote Year bite-size program in South America and Mexico, working remotely and traveling.

Did you find Remote Years valuable and necessary to jump into a remote work model?

Dan: I got a lot of value in it because, looking back, I didn’t have that much travel experience before going on the program. It’s not like I hadn’t left the country before, but I hadn’t had that much experience traveling. It wasn’t like I didn’t think I needed it, but things were very convenient. It worked out well because I was able to have some things set up ready to go. It ended up saving a lot of time.

Becca: I had a lot more travel experience, but I had much less remote work experience. By the time we took our trip, I was happy to arrange, plan flights, logistics, and reservations. The difference was I realized how much time I was spending making our itineraries, finding out logistics, doing research, making bookings, and negotiating Airbnb. Doing something like Remote Year costs money, but it saves you time doing all that legwork on your own. Then we also were able to travel with people who are doing the same thing more or less on the same schedule. It is an incredible networking opportunity to meet people from all over the world. They are very different from people you would meet in your close circle of friends at home. I think that has been one of the more eye-opening things in travel, meeting someone very different from you but sharing a common interest. Spending time with people in a travel community, you learn more about yourself and other people and professionalism.

Do you think the digital nomad mindset is different from that of other travelers?

Dan: It helps to travel with a group when you’re in places that don’t have a strong community of people working remotely and traveling. So in Mexico City, you’re pretty much guaranteed to find either ex-pats or people that are doing the same thing on their own. But suppose you’re in a place like Belgrade, Serbia, or even the Czech Republic. In that case, it’s sometimes harder to find that community. Having a group of people that you’re familiar with and connected with. I feel like everybody always gets along super easily. If you can’t find a community of people, it can sometimes get lonely in those more obscure cities.

Becca: Another thing interesting for us was that we traveled independently, working in our Airbnbs and some hostels in Europe. We went to Czech Republic, Portugal, Estonia, Latvia, Lithuania, and Ireland. We were on our own; we didn’t have any community during that time. We didn’t meet any other nomads, and then we did Remote Year for four months. Then we went to Vietnam for a month and then to Taiwan for three weeks. We didn’t have the opportunity to have that community feeling because we were working US hours from East Asia. It’s a fantastic place to be; it’s beautiful, and the people are amazing, and the food is excellent. But in terms of having a community, it was a lot harder to find that entirely on our own. In Taiwan, we didn’t meet anyone because of that strange work schedule.

How did you find working from Taipei, Taiwan?

Becca: We wrote an article on our website called The Best Cafes in Taipei to Work At. We took all these notes about the cafe culture there. We found that the coffees are very expensive; the coffee itself came out to five US dollars. Because coffee was a commodity, they knew that you would sit there for four hours, and they were taxing you for that.

Dan: I think it was pretty affordable, but the first coffee was more expensive. You’re paying for your seat, I imagine.

What tips do you have for maintaining a long distance relationship and what are some challenges you faced?

Becca: I would say some of them were figuring out when we would see each other next, but we always knew that there would be a time when we would see each other. I think the hardest thing was not seeing each other for almost four months when Dan left for the first time. When they think about long-distance relationships, people don’t realize that you get to visit each other. When you visit, it’s so much fun. I still think our Portugal trip was one of our best trips ever. We were very excited to see each other and remember that our relationship was real. If people are in long-distance relationships, we suggest planning trips and getting excited about them. Never act like you’re never going to see each other because that’s not the point. The point is to have good visits and make special memories that you can use to keep you afloat and positive.

Dan: I think the thing that we always say about long-distance relationships is that for us, we talked more than couples speak when they’re in person. We spoke every day on the phone, and we texted almost all the time.

Becca: We were emailing all day long; we probably didn’t work for a year because we were just always talking.

Dan: I think we got to know each other more apart than we did when we were together in New York with everyday busy lives. The other thing is it made sense; I had something to look forward to when she would come to visit. It kept me grounded to have something versus wandering and traveling. It is valuable to plan trips together and then value the time you have together once you meet for a certain amount of time.

What are the pros and cons of couples’ travel compared to solo travel?

Dan: I only really did solo travel for two weeks, so I haven’t done much. I think traveling as a couple I can speak a lot to. The pros would be that you always have someone to travel with; you can split costs, so that was nice. You’re never really lonely, and you’ll probably have a better time, as long as you like the person you’re traveling with. I think the cons would be it’s easy not to meet other people and stay in your comfort zone. So it’s a lot harder to feel motivated to step outside of your comfort zone to try new things. Suppose that’s meeting new people, trying new experiences, or going to a restaurant; it is a lot harder if you’re traveling with someone else versus traveling solo. So the pros and cons of solo trips are you meet a lot of people when traveling solo. I always tried to find a travel companion.

In Iceland, I went alone, but I met some guy in a hostel and decided to drive around Iceland together. It was nice to appreciate some insights and talk about how cool it is or take some pictures together. The experience is much more valuable; I pushed myself to try new experiences because it’s pretty uncomfortable. I’m not a very social person on my own, so it takes a lot for me to go and do these things.

Becca: I think you did a great job traveling independently, and I’ve traveled alone in China, Costa Rica, Thailand, Japan, Hong Kong. I like that I have traveled alone. I don’t know if I would take a solo trip nowadays, but I’m happy that I traveled alone and threw myself into that in my early 20s. One of the biggest feelings you get from traveling alone is that I’ve written about this on our website. When you get something right or have success, you get all the pride, and you get to pat yourself on the back. That success and that victory are all yours. Those are small wins; when you travel alone is an extraordinary feeling. I think traveling as a couple, you can always be safe, and I’ve never felt unsafe. The fact that you’re not alone becomes the benefit of being with someone else.

How do you decide where to go or for how long? Are there days whereby you take a break from each other and do your own things?

Becca: We know couples who have been on big trips for a year. Then at some point, they decide to do their solo travel for two weeks. That’s cool and fine.

Dan: We’ve never done that. We do a very similar travel style and budgeting expectations. We both prefer to cook wherever we are; there are rare cases where it was cheaper to eat tacos and street foods than it was to make food in Mexico. I think Vietnam was similar where it ended up being more affordable to go out to eat most of the time; instead of buying groceries. The markets and grocery stores were farther away, and no one went there; it was more expensive. So we have very similar budget expectations and very similar travel styles. We’ll both suggest something and talk about it together.

Becca: It’s a shared thought process, and Dan lets me do the research. Then he lets me convince him that it’s a good idea. When we went to Myanmar in Fall 2019, we searched for flights, and we somehow found $540 round trip tickets from New York to Yangon. I feel like we’d never see this price again in our life. Dan asked if it was safe and fun, which it is. So we went to Myanmar for two weeks, and it was awesome. I feel terrible that they’re having some tough times, and I hope they recover. It’s a beautiful country.

Is Myanmar easy to work from remotely?

Becca: I remember trying to get an email, but my internet was too slow. I had to pull up my laptop a few times to do something for work. So I wouldn’t recommend it as a digital nomad destination, but neighboring Thailand is very popular.

Dan: Thailand is great for a beach trip or weekend trip or depending on your work type. If you’re lucky enough, and your work is through email or writing, it’s a good place. But we’ve had a lot of trouble in many places trying to upload photos, almost everywhere. When I got back to New York after traveling for a year, I was so thankful to upload all my pictures to some third-party backup because I was risking having one copy of my photos because I couldn’t upload a spare copy anywhere. So it depends on the type of work you do, but it’s possible.

Did you plan on seeking out remote work, or did the opportunity just arise?

Becca: We were both working in offices in New York, Manhattan; we happened to be working only seven blocks from each other, which is very close to each other. Dan was working for a contract client, and I was working full-time for a company. We decided that we were going to make the big remote digital nomad trip. We bought the flights and two weeks before we gave our notice. When I put in my notice to the company, they asked if they could keep me longer. When I said no because I had a flight to the Netherlands booked. Still, I suggested that I could work remotely for them, especially if you couldn’t find anyone to replace me. So within about five days, they sent me a new offer that was a part-time remote gig. Dan luckily wound up with the same type of thing. So we did have to try to get our jobs to be remote. Our goal was also to work on the website while we were away, so we were pretty busy.

Was your original plan to quit everything and focus on the website?

Dan: There’s more nuance to my side of the story. I wasn’t a full-time employee anywhere. I was contracting for a company, 35 hours a week. It was almost a full-time commitment in terms of a contract, but I wasn’t committed. It was pretty straightforward for me to work that contract remotely. Then in August 2018, the agreement wasn’t renewed because the company laid off all of its contractors. At that point, because that work was a significant part of my freelance portfolio, I didn’t have anything else to do. I had another client that was 10 hours a week. But I thought this would be an excellent time to start working on the website. So then we went on a Remote Year, and that’s when it kick-started.

Becca: During the second Remote Year experience as a couple, we worked for Remote. They asked us to do remote in exchange for creating digital content for their social media and video and photos for their content files and website. We got lucky with that. We were also writing for our website, which at the time we thought was good but looking back, we’re like, what were we thinking? We’ve learned a lot in three years with regards to our website.

Do you think that the Half Half Travel project was a cornerstone pillar in keeping you guys together while in a long-distance relationship?

Becca: I think our relationship would have worked regardless, based on our personalities and how we wanted to come out of long-distance still together. The time felt like it was moving faster because we were busy with the photos. Once we started getting the press attention, that made us feel even busier. It also motivated us to work on the project. It was this giant snowball of making us stronger as a couple brand. We started being Becca and Dan from Half Half Travel, even if we never intended it to be that way.

Dan: It was interesting because people have conversations when they start dating. I feel like you don’t get to have the type of conversations about creative input or decision-making for things that impact the two of you. We share an account on Instagram; we share a voice. If Becca said something that I feel didn’t work with my voice or what I wanted to say, we would talk about it. We had different and unique conversations that younger couples or couples earlier in the relationship might not have.

Becca: Pretty soon, it started becoming a business. It’s not because Instagram turns into a business; it’s more complicated than that. When I was visiting him in Argentina, I was literally on a layover in Jamaica. I got Wi-Fi at the airport lounge. We got an email to our Half Half Travel email from a magazine in France that wanted to buy one of our photos for usage in their magazine. We wound up selling one of our Half Half Travel photos to them, and then they sent us copies of their magazine in French two months later. That was a big moment for us; companies are finding us, and people value our work. It gave us a lot of ambition to keep doing it in some way.

What gave you the confidence to go all-in on the website and make it a full-time thing?

Becca: The decision to leave New York and travel coincided with us getting an email from a hotel in Portugal that invited us to stay with them, do a review on our website and take some photos. We said to each other, if we don’t have a way to accept these opportunities, we might start missing out on other things that come our way. So one of our first stops on our Europe trip was trying out this hotel, meeting the owners, and getting to know their story. They have a fantastic story, and they asked us about ours. We would never have made these relationships with companies worldwide if we sat here and did it all digitally from home. So travel turned out to be an essential aspect of getting the website on the road. We had to get out there and make the best of it. There’s a big difference in the content on our website from June 2018 versus a year later writing about Taiwan in March 2019. We just improved so much based on practice, research, and learning what worked.

Dan: When we started, I was way ahead of where we were in terms of growth because of my background. I already knew how things worked. I learned a lot about SEO and outreach marketing and all the stuff it takes to run a website, not only the technical aspects. I was always way ahead of where we were in terms of how other people perceive us. We get many inbound inquiries, and we have to say no to many things because we don’t have the capacity. There was an exciting trajectory of where we were and then how far we’ve come.

What advice do you have for anyone starting a blog?

Dan: If anyone wants to start a travel blog, start now, start tomorrow, don’t put it off. I feel like you can always learn and improve. One of the worst things you could do is say; I need to do this before I start. I need to take this course. I don’t know enough about that. Even writing in Google Docs and having ten blog posts in draft is much better than procrastinating and putting it off. So I’d say my number one advice is to start right now. Write an article, see how it goes, publish it, put it out in the world, share it on social media, see how people perceive it, and then continue. Our first posts are pretty terrible. We keep going back to our posts from 2018 to try to improve them, but we wouldn’t have those posts from three years ago if we didn’t start them. So start today.

Becca: My biggest tip is don’t be discouraged if some of your articles don’t perform at all. Our article about Hong Kong was number one or two on Google for a while; I don’t think it gives that ranking anymore. So stay positive; you never know when you might be number one, based on valuable advice you’re offering and how much traction your website gets. You might be surprised.

How do you manage remote work and travel at the same time?

Becca: We have not traveled much at all since the pandemic, but we just returned from a trip to California, where we worked remotely for two weeks. So that counts because we were not home and we were five hours away, which is farther than some countries. One important thing is your setup and Wi-Fi and ensuring that you pack correctly in terms of all the things you need to be successful. It’s something we talk about on our website quite a bit. But Dan and I both have preferences as to how we like to work. Dan took a laptop stand and an external keyboard for our trip, and I took my mouse, which I’m attached to. I have to have a mouse on a mouse pad to the side. We had to make sure we have headphones for meetings and avoid being in the same room simultaneously. I think people should go with a plan and expect some challenges.

Dan: The other thing is, wherever you are, if you could work remotely, you can probably pick up something if you forgot it. We picked up a mouse in a supermarket in Lima because Becca didn’t have one. So wherever you are, you can always get something. If something isn’t working for you, or you want to change your setup, there’s always the option to upgrade or find something that works. We’ve been working remotely for our jobs at home in our small apartment for the past year, so we’re used to it. But I think our website probably has a good history of things we’ve struggled with ourselves and decided to overcome and become more effective. What’s worked well for us is to over-communicate, so share calendars when we have meetings at the exact times and things like that.

Do you work specific hours, or are quite flexible?

Becca: We both have set hours with our companies, but they tend to be a little different. I’ll work from 930 to maybe 630. Sometimes we’ll work until 1030, but some days we’re done at seven.

Dan: It’s generally pretty flexible. Becca and I both work full time, and Half Half Travel is a side project. It is an essential distinction because our hours would be much more flexible if it were our full-time job, and our website would be much more significant. My working day generally starts at 1030 when I have a daily meeting. I’ll usually work till 530 or 630, but it’s typically flexible. I think what’s essential for me is that the company I’m at now has flexible expectations. As long as you’re getting your work done, it’s okay, but you should be online and available if somebody has a question. I think being a responsible remote employee is important. So for anyone traveling and doing it now, the worst thing you could probably do is work from a random country and then not be available. It’s essential to be responsible, and that is an excellent way to make sure you continue to have your job. It’s worked well for us.

Where do you find time to work on your website with all the other businesses?

Becca: We don’t watch TV. People ask us what we do at nighttime when we’re not working. We sit on the couch and build our website.

Dan: Yes, it’s better than TV. The three years we were writing cost us money; we didn’t start making money until 2019. So it’s something that we enjoyed doing; I think that’s important for any side project. We like taking photos, we like editing them, we like creating articles, we like sharing our experiences. We enjoy seeing that people got value out of it. That was the most rewarding thing for us, and then monetization came second. We also have another business. We do family photography in New York.

Becca: We only do a few jobs per year, but we do have another business.

Now that we work remotely, we can travel for longer and work remotely at the same time. In 2019, I had a contract that ended, and Dan took off from work, so we went away for two weeks. Actually, now that I think about it, I was working that whole time. Somehow I was working from Myanmar, which I don’t recommend; I guess it was slow. I don’t remember; I guess it wasn’t exciting. I was working at night now that I think of it, so not great at all.

Dan: In 2020 and 2021, for the first two months, we haven’t been traveling too much. It’s been a little challenging for us but for no real good reason.

Becca 

We worked remotely in the Dominican Republic in 2020, right before the pandemic when cases were low. We went upstate for a week to the mountain region of New York, near Canada. I remember working remotely in a chair in our hotel room. When you don’t have to be online for a nine to five, your options are a bit wider. Especially if you can do fewer hours a week or manage that expectation with your client or company. We haven’t traveled for a long time, but there is still a pandemic, so I think that’s why.

Is there a lot of work behind running a travel website?

Dan: I realized early on in 2016 when I traveled; I wanted to do this. I was ahead of the curve contacting people to see if they wanted to represent me. I knew the path, but I didn’t know the endpoint. I was trying to figure out my way, and I worked all the time. I worked lots of hours when I was traveling. I think I worked more than when we were stationary. It’s what kept me grounded and motivated. I would spend my weekends relaxing and enjoying places, and going out hiking. It’s a lot of work.

There are no ghostwriters for content and no editors. It’s just the 2 of us.

Becca: We don’t want people writing for us at this stage because our brand is us. For people who have a generic model that’s not about themselves, then, by all means, have people from any country with any name doing the writing and say it’s you. We talk from the heart, and when we give travel advice, we talk about our stories. I don’t think anyone could do that for us.

Dan: Some people have built up their blogs; then, they transition to hire a team and hire contributors. But for us, our website is us, so it feels weird to open it up to other people. We probably could make more with having that growth, but it’s not suitable for us. I think it’s such a personal backstory. Maybe in the future, but it’s not right now.

What’s your favorite travel destination and why?

Becca: I love Hong Kong; it is my number one. It is such an incredible blend of cultures with an urban and natural feeling to it. There’s always a beautiful backdrop to the buildings; it is ideal for spending some time.

Dan: I like the Czech Republic a lot. I feel like the culture is welcoming, although some people don’t feel like that. I’ve had genuine experiences in the Czech Republic. Also, it’s super green; I was able to make a couple of road trips there and spend a lot of time in the middle of the country and around some of the perimeters. It’s a beautiful place. I enjoyed a lot of it, and it’s super old. There’s a lot of history. I feel like it was one of my first experiences seeing some of those super old buildings from the 1600s and 1800s. You don’t see that in the United States. I think it’s pretty cool.

What’s your one best travel tip?

Dan: Mine is to take half of the stuff out of your bag, and that’s what you actually need to travel.

Becca: My tip is, don’t spend all of your budget on something that only lasts a few minutes. Make your budget last longer by staying in hostels, cooking meals, taking a train instead of a taxi, and then doing something cool with your leftover money.

What’s your top remote working tip?

Becca: I think mine is to be communicative and over-communicate meaning. For example, even when we were in California the other week, we were three hours behind New York time. There were many days when I thought I would miss the morning meeting, so I communicated that I plan to miss it, but I would update everyone with everything necessary, and there were no problems. If people can set reminders that they need to over-communicate something that might be assumed by either your team or your boss, then you can be successful at remote work.

Dan: Mine was going to be the same. I do have a smaller tip. If you use Google Calendar, enable multi-time zone settings. There’s a way to allow two time zones, so when we were in LA, I enabled West Coast and East Coast; it was beneficial. I always communicate in their time, and I always made meetings in their time. It’s also helpful to put the timezone time in the meeting.

Becca: I do that too. I make the title of the meeting, 9 am Eastern Time daily meeting. It’s super confusing, mainly because as you work more worldwide, the daylight savings time happens in Europe, usually two weeks earlier than in the US. So there’s a gap when you have to wait for the US to change their clocks, and you only really realize that if you’re working with people in England, France, or Spain.