Remote Work Interviews

Owl Labs (OL): How'd you get to where you are today in your career, and what are you doing now?

Spencer Jentzsch (SJ): Twisted roads. I'm not at all where I thought I'd be, and I think many people who work remotely have jumped between different careers and disciplines as well. I was a Korean linguist working at a university, then I worked in project management at a software company, and then I started working at Hacker Paradise, first as a trip facilitator, and now as its CEO.

OL: What's the mission of Hacker Paradise, and how would you describe the digital nomad movement?

SJ: The digital nomad movement is for people who don't want to subscribe to the lifestyle of the traditional 9-5 office job, where they work for 40 years, and then retire and enjoy themselves. The way digital nomads look at work is, if there are things you want to do now, you should go out and live your life, working wherever you want to do them. Digital nomads take remote jobs, or take their current job and work remotely for a certain period of time, and they move where they want to go and experience life the way that they want to, instead of being tied to an office in one specific location. It's something people do full-time, for one year, or sometimes for a month or two at a time, so there are many different ways to work remotely as a digital nomad.

At Hacker Paradise, we believe that digital nomadism and working remotely is a direction the world is moving toward. The problem we seek to solve is, when you decide to book travel and live and work abroad on your own, you can book things on Airbnb and find places to go by doing research and reading blog posts on your own, but the thing you miss when you do that is people and community. Traveling on your own can be alienating if you're doing it for a long time without your friends or a network, and that's the service Hacker Paradise provides.

On top of that, we handle the logistics of being a digital nomad for the people who want to travel the world but don't want to do the planning. We plan trip itineraries in different countries for four to eight weeks at a time, set up housing and coworking spaces, and organize educational and social programming for trip participants so they can work remotely and travel with an amazing group of people.

OL: What prompted your transition from trip facilitator to CEO of Hacker Paradise for you?

I was facilitating trips for a long time, and then the person who was in charge of the company decided to move onto other projects. It's not that I wanted to be CEO per se, and for a year after I officially became the CEO, I refused to refer to myself by that title because it felt weird to me. (Impostor syndrome at work.) But then, I grew into the role and took on management of the organization, and now I'm happy to report I've changed my title on LinkedIn.

OL: What do you like about being CEO, and what do you miss about being a full-time trip facilitator?

SJ: I like the autonomy of being in charge and being able to make decisions, but I miss the day-to-day interactions with trip participants. As a facilitator for Hacker Paradise, you spend every day with cool people from all over the world and they become your family, so I miss that level of interaction with the amazing people who travel with us.

OL: Are you on a trip right now, or are you working remotely for Hacker Paradise on your own?

SJ: I do both right now. I used to do more direct facilitation, but now, our team has grown enough to the point that I can pop in and out of the hands-on work. For the last several months, I've been traveling on my own and working remotely for Hacker Paradise. Right now, I'm in Rio de Janeiro, where we're preparing for a Carnival trip that starts in a couple of days. We have about 30 people coming, and we're in charge of keeping everyone safe, hydrated and happy during the celebration. This isn't a standard working trip with Hacker Paradise -- this is strictly five days of vacation. After that, we're heading down to an island called Florianópolis in the southern part of Brazil, and Hacker Paradise will be there for the following seven weeks for a standard remote working trip.

OL: You got into project management so you'd be able to work remotely. What are some of the most common career paths that you see among participants on your trips?

SJ: I tend to think tech companies are a bit more advanced when it comes to their remote working policies, so we see a lot of people working at tech companies in a variety of different roles, such as engineering, design, and even HR and marketing. We're also now seeing a lot of creatives working remotely in design or writing. We also have a lot of people that come traveling with us that have jobs that you would never think you could do remotely. We have real estate agents who have an assistant back home who does the showings and tours to prospective buyers, and they handle the rest of the work remotely. Even if you think your job would be impossible to do remotely, we've probably had someone do it on one of our trips.

OL: Some people take their job and start doing it remotely and some people get a new remote job in order to become a digital nomad. What advice do you have for somebody who loves their job and doesn't want to give it up, but they want to be able to take advantage of remote work by traveling?

SJ: My advice is to never do what the blogs tell you to, because they usually tell you to quit your job, buy a one-way ticket, and you'll figure it out in Bali. That's terrible advice.

If you have a job and a career you love, there's a way to talk to your employer about trying it out, first. I recommend our program for people in this position because we're a professional organization made up of people who work remotely full-time, so you can go to your employer and say, "Hey, I want to try this out for a month, and I'm going to be working and traveling with this organization that's full of people like me who I can network with." That's a better proposal than just saying, "Hey, I want to move to Thailand for a month." That's a big ask of an employer.

Instead, if you want to try being a digital nomad and keep your job, you can explain that you're traveling work an organization, discuss the pros and cons, and try it out for as little as two weeks. Then, if it doesn't work out, you can fly back to the office, but if it works well, maybe you can start working remotely for a small amount of time.

We've had people take this approach while traveling with Hacker Paradise, and then after the trial period, their employer usually says something along the lines of, "I saw no dips in your productivity, you seem happy, and everyone on the team is happy for you." By trying it out in a structured way, employers that usually start out thinking remote work isn't viable eventually come around. If you want to keep your job and work remotely, whether you're traveling or just working from home full-time, build a business case so it's easier for your employer to say yes.

OL: It's a great idea to try fully-remote work on a short-term basis before deciding if you want to adopt the digital nomad lifestyle, because it may or may not work for you.

SJ: Some people don't like being uprooted, which is another aspect of digital nomadism that blogs don't tell you. Some people try it out and absolutely hate it, because they miss their family, their friends, and the comforts of home and their city. And that's perfectly fine. Just because Instagram popularizes this lifestyle doesn't mean it's for everybody.

OL: At first blush, digital nomadism sounds idyllic. What's the knowledge gap between remote work adoption and wider digital nomad adoption?

SJ: Many people think it's incredibly expensive to be a digital nomad, which always shocks me because it's people who live in San Francisco and New York who think my lifestyle is expensive. The cost of living in most countries around the world is half the price of what San Francisco costs, or even less than that, so the myth of digital nomadism being too expensive is generally untrue if you live in a big city in the United States.

For many others, there's a barrier in their head that makes them think remote work isn't possible with their career or employer or industry. And in those cases, I tell people they need to start a conversation to figure out ways to make it happen if you want to do it. A lot of people are emotionally tied to things at home as well -- such as relationships, puppies, intramural basketball leagues, etc.  People have lives at home that they don't want to give up, but what I try to impress on people is there are many different flavors of working remotely. You can come on a trip with us for a month, and then go back to your life at home. Some people travel with us for six months out of the year, and they spend the rest of the year at home, so they can maintain dual lives and "families" at home and abroad. The great thing about the freedom and flexibility of remote work is you can adapt it to your preferences and your lifestyle in whatever way works for you.

OL: Do you have a place you call your permanent residence, or are you 100% globetrotting?

SJ: I don't. I've been working and traveling with Hacker Paradise for three years now, so I don't have many material belongings anymore. I've sold my car, my apartment, and all of my stuff in it. I have three boxes in storage at my parents' house, and I have my suitcase and backpack that travel with me.

OL: What does the Hacker Paradise team look like today? Where are they working from, and how do you collaborate successfully with all of you working in different locations around the world?

SJ: It's been a learning experience. Possibly the biggest thing I've learned since moving into the CEO role is that scaling a business and a team is more difficult than you think. When I started, there were only three of us -- two of us were facilitating trips, and one person was working remotely. It was a small team based in only two locations, and now we have 12 people that work for us in seven different locations. Growing to a team of 12 doesn't sound like a big number, but we've actually quadrupled in size over the last couple of years, and a lot of growing pains have come with that.

Previously, we were mostly co-located, and I could talk to people face-to-face and we'd make decisions quickly and easily. We all knew what was going on in each others' worlds, and we were all close friends from traveling together for so long. Now, there are people on my team whom I've never met in person, and that's been a new challenge to overcome. We've had to put in place a lot of processes and structures around HR, standards of communication using Slack, email, WhatsApp, Zoom, and other collaboration tools we didn't need when we were all working in the same place. So we've had to implement a lot of structure.

One thing we're good at that is traditionally challenging for remote and distributed teams is how you still get people to be friends and bond with each other without in-person connection.

When I first started at Hacker Paradise, my colleagues and I would spend time together every day in the same location. We'd go to cafes together and talk about how to help people get more out of their remote work experiences. We always did a lot of things together, and now, we have team members I've never met. To replace that, we try to put systems in place that we can still get to know each other. We're not big enough now, nor do we have the resources, to plan two retreats every year that the whole team attends to mingle in-person, which is what a lot of remote companies do once they grow large enough.

That's not a reality for us yet, so we have to do other things to build connections remotely. We use the Donut Slack app that matches teammates together every two weeks, at which point you have a Skype call together that's purely social over a cup of coffee or a donut, if you prefer. We have an all-hands meeting every two weeks that everyone attends that's a nice mix of business and socializing. We've been trying a lot of initiatives to help replace the water cooler talk you'd have in an office so people still feel close-knit, even though they might never have met in person.

OL: One challenge we hear about from distributed teams is time zone management. Do you have any specific guidance for not sending Slack notifications or email alerts that might disturb people during offline hours?

SJ: The hardest thing for us is finding a time for all of us to join a virtual meeting together because we're all traveling and the time zones are constantly shifting. We have to be very flexible and check and double-check schedules when setting up meetings, which our team is great about doing. We try to limit those meetings that everyone needs to attend to biweekly, so even if you have to wake up at 5 a.m. for the meeting, you don't have to do it very often.

Most of us will like mute Slack or turn it off during certain hours every day. We use WhatsApp for urgent and emergency communication so people can get in touch no matter what time it is. It's also about proactively communicating your schedule with the team. For example, I tell people that if they message me after a certain time on Slack, I'm won't get to it until the next work day. If they need something urgently, they can call me or WhatsApp message me.

One challenge that comes with working remotely is that, if you aren't careful, the ability to work anywhere, anytime, can result in you working all the time. When your team is distributed, people can message you about work at midnight your time, and if you're up and not putting limits on yourself, you will inevitably end up doing work at midnight because you think it's pressing. We try to set a culture and tell people to get their work done, spend time in the evenings with their friends and family, and leave work until the next day.

The double-edged sword of remote work is that the same freedom that lets you work anywhere means you can also work at any time if you're not careful.

OL: For those companies that are remote-only, or hybrid teams where some people are remote or some people are co-located, what would be your advice for helping implement more productive remote work policies for those companies that haven't adopted it universally yet?

SJ: It's so interesting because more traditional companies often think the way we work is challenging, but I look at hybrid teams, where some people work remotely and some people work together in an office, and think that's the more challenging prospect.

At Hacker Paradise, if we want to talk to each other, we have to get on a call or get on Slack, which reduces a lot of side chatter or words lost in translation. I always think that, if I was part of a team where I worked remotely but others worked together in an office, I would feel like I was left out of the loop of so much that would be happening there in-person. People think remote companies are challenging because they're one end of the spectrum, but I believe it's harder to be somewhere in the middle.

That being said, when you move to an all-remote company structure, you need stronger communication and better documentation to ensure that, even if I'm not there right next to you to guide you through things, you can figure out what you need to do and not have to wait eight hours for me to wake up and answer your question. Clear communication and effective documentation are the tools that really help you when you go remote.

OL: What do you think are some of the biggest misconceptions or myths about remote work that make employers balk when setting flexible work policies? What's a myth people believe about Hacker Paradise?

SJ: Everyone thinks we're on vacation all the time. Even my mom still doesn't completely grasp what I do every day. People think I'm on vacation all the time, and a big reason for that is social media.

If you look at my Instagram account, I don't post pictures of me working until midnight -- I post pictures of myself hiking and hitting the beach. I understand that's the perception, but as with everybody else's lives, you only put the nicest aspects on Instagram. I'm not showing the sh*tty days that I've had, I'm showing the days where I had the most fun.

People often think we're just hanging out when the truth about our program is, there are a lot of people who put in long, hard days and because they're motivated and inspired sitting with other professionals. We've had people say they're more productive working and traveling with groups like ours than when they're sitting in meetings or listening to Sally in the cubicle next to them talking about her cats at the office. Employers and HR professionals who limit flexible work policies don't tend to see the possible upside of greater productivity outside an office, which is the biggest misconception in my mind.

OL: Where do you think the gap lies that makes it harder for more companies to adopt remote work? What's missing that would make that conversation easier?

SJ: The conversation is influenced by what's in people's minds based on the perceptions about work policies that they have lived. Many members of the baby boomer generation that make up the leaders of big companies today grew up with the mindset that butts in seats and time in the office represent how much work is getting done. That used to be a fair assessment, but now with the technology at our disposal, that's changed. Now, people can work from wherever and fulfill the same responsibilities they would in an office.

Bridging the gap will come down to changing hearts and minds. It takes time for organizations to make huge cultural and policy shifts and adopt new technologies, so remote work adoption will take some time. It's still in like the early adoption stages, where more people and companies don't embrace remote work than those that embrace it 100%.

OL: What do you think the future of work will look like in 10-20 years?

SJ: Work is going to continue evolving until it becomes even more remote work-friendly because people like it so much. We're starting to see now that if companies don't provide flexibility as a perk, they're losing their best talent because they know they can find that perk somewhere else. Many younger professionals especially value these experiences and this lifestyle, sometimes more than a specific salary. There are people like me who are changing jobs, and even careers, specifically so they can work remotely, so I think the workplace is going to catch up soon. As people start to move to more remote lifestyles, in addition to working from home, they'll be looking for more structure and networks to fill the social gaps that come with not working in an office environment, so I predict programs like ours, that help provide community and social structure while working remotely, will continue to grow. You can't go without it. Any services or programs that help people combat loneliness and find connections while working remotely and traveling the world will keep growing.

Social structure and connection are primal needs we all crave, no matter where we go in life. Otherwise, we'd probably devolve as a society entirely.

OL: What do you love about what you do?

SJ: I love talking about remote work to dispel misconceptions, because so many people think the remote work community is made up of only spoiled, privileged millennials and Instagram influencers. That's not who we are. We're people of all ages, from all countries and all socio-economic classes, and what brings us together is our shared mindset that we want to do something different and have adventures sooner, rather than later in life. We're people with jobs, we care about what we do, and we want to make a difference in our own lives and the lives of others.

Key Takeaways

1. Remote and distributed teams need to live and die by clear communication and documentation.

Spencer cites clear communication and consistent documentation as two must-haves for building and scaling remote teams, especially if employees are distributed around the world as Hacker Paradise's are.

2. If you want to keep your job and become a digital nomad, try traveling and working remotely on a trial basis to build a business case for your employer.

Spencer recommends traveling and working remotely on a short-term basis for people who aren't sure if they want to be digital nomads full-time, or for those trying to convince their employers to let them take their office jobs with them around the world.

3. There's no right or wrong career for working remotely.

Contrary to what you might think, Spencer believes there's no right or wrong remote work career. Hacker Paradise sees digital nomads from a variety of different industries and disciplines on its trips, from engineering to marketing and HR to real estate.

To learn more, read our interview with Brian Peters of Buffer next.