Hacker Paradise Review: Surprises (and Setbacks) I Had With This Work and Travel Program

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During my recent month-long stay in Tallinn, Estonia, I had the privilege of living and working alongside 22 peeps in the digital nomad community. I did it with Hacker Paradise, a program tailored for remote workers and digital nomads like myself.

Spoiler alert: it was amazing. 

But it wasn’t without challenges. 

Even with my extensive 17 years of digital nomad experience, I had a learning curve in making the most of this month of coliving and coworking. So much so, that I actually rearranged the entire rest of my year of planned travel to compensate. 

In this article, I’ll provide a detailed account of life at Hacker Paradise, I’ll touch on how it compares to similar co-living and co-working programs, and I’ll share the top lessons I learned. 

Want to see the video accompaniment to this article? Click here to watch!

Hacker Paradise review

What is Hacker Paradise?

For starters, Hacker Paradise isn’t an exclusive club for hackers, despite the name. It’s not about breaking into computer systems; it’s about breaking free from the traditional office cubicle. 

Hacker Paradise is a program designed to facilitate the lifestyles of digital nomads; it’s what I refer to as a co-living co-working program. I wrote about Hacker Paradise along with other similar co-living co-working initiatives in this article: Best Coliving Coworking Programs for Remote Workers and Digital Nomads.

If you’re a digital nomad already, you know the struggles – the constant planning and movement, the logistics, the uncertainty about where you’ll work and live next, the fleeting social scene, and sometimes feeling isolated and ungrounded. 

If you’re not a digital nomad, then, take my word for it. (Or watch this video I made, which outlines the pros and cons of digital nomad life). 

Hacker Paradise simplifies all of that. You no longer need to stress over finding accommodation (in a good part of town for exploring, with good internet, etc), suitable places to work, or coordinating activities in a new destination. 

But even more so, Hacker Paradise isn’t just about convenience and logistics; it’s also about community. It’s about spending time with like-minded individuals who share your passion for remote work and travel. 

Having dinner with fellow Hacker Paradise digital nomads in Tallinn Estonia

As much as we digital nomads cherish our freedom, it can get a bit lonely out there on the digital nomad road. I would know; after 12 years of full-time travel and living locally around the world, I lost all sense of belonging in the world and totally burned out of the lifestyle. I returned to my hometown of Toronto Canada to get a home base, thinking I was missing a cultural connection. 

It took me a few years to realize the sense of belonging I was searching for was in other people who have similar lifestyles; people who understand the nuances of work-life balance and the pace of travel when it is done in conjunction with full-time remote work. People who have the same thirst for slow travel and living around the world. 

This is what inspired me to experiment with coliving and coworking in 2023, in my 17th year of career travel. I dipped my toe in the world of co-living in Madeira Portugal in January, and then I went all-in with Hacker Paradise in Tallinn Estonia in August. 

Here is what I learned. 

Wanna cut to the chase? Check out Hacker Paradise here, and use PROHOBO100 for $100 off. 

This and other links to Hacker Paradise in this article are affiliate links, which means I’ll earn a commission if you click through and end up going on a program. My enthusiasm for Hacker Paradise is genuine! Thank you for your support.

Beautiful Medieval Tallinn Estonia where I spent a month on a work and travel program

Benefits of Hacker Paradise for Remote Work and Travel

Here are some key advantages of choosing this program for your remote work and travel needs.

Outsourcing Travel Logistics

Hacker Paradise is a powerful antidote to the endless tedium of travel planning. If you’ve been on the digital nomad path for a while, you know how exhausting travel logistics can be. Picking a destination, finding suitable accommodation, ensuring it’s conducive for remote work, and planning activities – it’s a lot to handle, when travel is a lifestyle and not just a vacation once or twice a year. 

Co-Living and Co-Working, Harmonized

The living and working setup with Hacker Paradise varies by location. In some destinations, everybody is together in a large home or repurposed boutique hotel (or even a castle!). In Tallinn, we were all staying in an environmentally sustainable container hotel; an old railway depot filled with repurposed sea containers (each container being a room). It was suuuuuuper funky! 

Hektor Container Hotel, where we stayed for a month
Hektor Container Hotel, where we stayed for a month

Some accommodation naturally has co-working space built in, and in other destinations Hacker Paradise arranges memberships for everybody at a nearby co-working space. In Tallinn, the container hotel had space for co-working on-site, making for a super easy (as in, non-existent) commute. 

Either way, all you have to do is choose the destination (and in some cases, certain accommodation options). Hacker Paradise takes care of the rest. 

coworking at our accommodation in Estonia
coworking at our accommodation in Estonia

Explore in New Ways 

I saw and did things in Tallinn that I wouldn’t normally have done on my own; sometimes because of a higher cost or other challenges to doing it solo, sometimes because it’s not something I’d have thought to do, and sometimes because I simply wouldn’t have had the energy to coordinate it all on my own. 

In all cases, I appreciated the opportunity to discover Estonia in new ways that significantly enhanced my experience of the place, and made me feel like I got much more out of my month there than I would have gotten if I weren’t with Hacker Paradise. (I’ll admit this is a bit of a double-edged sword, which I’ll get to later). 

Road trip! I would never have rented a car to visit this waterfall or national parks of Estonia on my own
Road trip! I would never have rented a car to visit this waterfall or national parks of Estonia on my own

Easier to Get Out (Especially for Introverts) 

While you might think that a group travel experience like Hacker Paradise would be an introvert’s worst nightmare, on the contrary – as an introvert myself, I found it to be a much easier way to get out and explore! 

Picture this: there’s an event/museum/whatever you might like to visit. But you’re a little tired, and you’re in a new destination that you aren’t familiar with, which means you inherently need to be alert and attentive so you can get where you’re going and have your experience safely and smoothly. And once you get there, it’s a whole other kind of energy output. And sometimes….it’s just easier to stay home and eat potato chips. 

But when there is another person (or people) headed out to where you want to go anyway, it’s much easier to tag along; there’s safety in numbers (when you’re in a destination where safety is an issue), and it’s fun to explore new things with different people who are viewing the same thing through their own specific cultural lens. 

Hiking in Estonia with Hacker Paradise friends


Hacker Paradise is like a family. It is run by a small welcoming team, and once you have participated in a Hacker Paradise program, you are a permanent family member with access to a Slack channel with all HP alumni (currently over 1,000 people). 

A large percentage of the people on my trip in Tallinn had done Hacker Paradise trips before. I get it: I plan to be a “repeat offender” myself. 

This is because of the beautiful community spirit on each trip. It is incredibly inclusive, and the facilitators work hard to make sure it isn’t clique-y or segmented in the way that groups can often get. This is quite impressive too, because the range of ages and nationalities on a trip can be vast – from early 20’s to mid-70s, and while most participants tend to be North American or European, on my trip we also had members from Brazil, Argentina, and Taiwan. 

The community spirit is even more enhanced by Hacker Paradise’s schedule of activities; read on. 


Looking for monthly accommodation? Here are some digital nomad-friendly options that are fantastic alternatives to AirBnB

Want to focus just on co-living? Here’s a collection of coliving spaces around the world to check out 

Hacker Paradise Activities and Schedule

This is what sets Hacker Paradise apart from other co-living and co-working programs; the facilitators create a schedule of events that help to connect and elevate everybody’s experiences across the board. 

Every week there are lunches at local restaurants (and HP picks up the tab), potluck dinners, skill-share sessions, “deep meaningful conversations” (which sound a bit odd as a formalized thing, but were real highlights!), and social evening events that pave the way for everybody to connect, to grow personally and professionally, and get to know one another on a deeper level. 

Hacker Paradise is more than just a travel agency; it’s an experience. 

Deep Meaningful Conversations and other weekly activities with Hacker Paradise 
Deep Meaningful Conversations and other weekly activities with Hacker Paradise 

During my first week in Tallinn, we sat down as a group and brainstormed what things we wanted to do throughout the month. By the end we had a staggering range of ideas, from exploring local restaurants to planning excursions, day trips, weekend trips, visiting museums, galleries, and even a list of movies we could watch “at home” on impromptu movie nights. This list (along with relevant links) went into our group Slack channel (Slack being where the magic happens on a Hacker Paradise trip). 

Although the facilitators do coordinate some events (such as those on the weekly agenda and a few others as well), ultimately everyone pitches in. Hacker Paradise is best viewed as a collaborative effort, and this is what helps create the strong community spirit. 

For example, shortly before we arrived in Tallinn, one of the participants (Didier) chimed in on the Slack channel, saying how he likes to visit Michelin-starred restaurants wherever he goes, and he asked if anybody would like to join. Because of his initiative, a group of eight of us had a remarkable dinner that will go down as one of the best meals of my life. 

Eating at a Michelin restaurant in Tallinn with fellow Hacker Paradise foodies 
Eating at a Michelin restaurant in Tallinn with fellow Hacker Paradise foodies 

What surprised me was how much these collective experiences shaped my time in Tallinn. I might not have ventured to a Michelin-starred restaurant on my own, nor would I have rented a car to explore a national park in another part of the country. I discovered incredible museums and galleries, that I wouldn’t have explored if not for the fellow participants spearheading these activities. 

This is also where the double-edged sword comes in……

Balancing Work and Life 

In planning for this trip, I made two incorrect assumptions about what my Hacker Paradise experience would be like. 

Here’s the first (I’ll highlight my second mistake in the next section): 

I thought co-working with other remote workers would be a great way to hold myself accountable to getting work done. In fact, a part of me hoped I would be even more productive co-working than I am when left to my own devices. 

Things didn’t quite work out that way (at least, not initially). 

coworking with Hacker Paradise in Estonia at Hektor Container hotel lobby 

Maintaining a healthy work-life balance is a fundamental skill for digital nomads, and it’s something I thought I had down to a science. In fact, I even created a whole video on the topic. But my month with Hacker Paradise taught me that sometimes, even the most seasoned nomads need to relearn some things.

Before you officially join Hacker Paradise, you’ll hop on a call with one of the program’s representatives. They want to ensure that you have a remote career or at least an ongoing project because, let’s be clear, Hacker Paradise is not a vacation. It’s all about living, traveling, and working together. 

Here’s what I didn’t account for: everyone has a different work schedule. Many participants on my program were remote employees working for various companies, and they had specific hours to adhere to. Those working for North American companies often kept hours that ranged from 4 PM to midnight, while those connected to European companies worked during the day. 

And regardless of work schedules, when people weren’t working, they were off doing cool stuff, to which everyone was invited.

I’d frequently see messages pop up on Slack: 

“Hey, gang! At 2 PM, I’m going to check out [this café] or visit [this museum]. If you want to join, let’s meet in the lobby at 1:30.” 

Goofing around on an excursion I wouldn't have done if not for the ease of tagging along with the group
Goofing around on an excursion I wouldn’t have done if not for the ease of tagging along with the group

These messages were a constant, an everyday occurrence; a tantalizing reminder that there was always something exciting happening. The challenge for someone like me, who makes their own hours, was that I could pick and choose what I wanted to do – and when, and with whom. And when there was always something cool going on, my work-life equilibrium lost its…equilibrium. 

Not only that, but as an introvert, it’s important for me to schedule down time on my own to recharge. That too, along with many of my work tasks, initially fell by the wayside as I cherry-picked from the buffet of amazing experiences, restaurants, and more to join people and enjoy. 

With the advice of fellow HP participants and also a friend from afar (who I’ll introduce in a minute), I learned to accept FOMO. Even with a whole month (which can seem like a long time at the outset), I wouldn’t be able to do everything I wanted to do, with everybody I wanted to do it with. And that’s okay. 

(It may also be part of the reason many Hacker Paradise participants enjoy reuniting on subsequent trips…to keep the fun alive and further deepen connections). 

My Biggest Challenge with Hacker Paradise (and any Work and Travel Program)

While the work-life balance mistake was a rookie lesson I had to re-learn, this next mistake really took me by surprise: I dramatically underestimated the energetic output a program like Hacker Paradise would require.

Just to clarify – there’s no problem doing a month with Hacker Paradise. Even two or three months, back-to-back: that could work just fine. 

But in the name of my Great 2023 Experiment with co-living and co-working, my month with Hacker Paradise was the third month in a 10-month trip I had orchestrated, with me moving approximately once a month. 

I know better than to travel this quickly. I’ve made this mistake before. 

But I assumed that with the outsourcing of all the logistics of travel planning that Hacker Paradise and similar remote work programs do, I could quicken my pace of travel because I wouldn’t have to worry about finding and booking accommodation etc. 

The problem was, I don’t have a lot of experience living and working with a group of people, and as you already read earlier, my work-life balance got out of whack while I struggled to find a groove. And getting to know 20 or so people while living and working with them is amazing! – but it takes energy, and it wasn’t energy I had budgeted for

Even something as simple as having lunch or dinner out with new friends, takes energy I hadn't budgeted for
Even something as simple as having lunch or dinner out with new friends, takes energy I hadn’t budgeted for

Thankfully, I learned that this challenge wasn’t mine alone to endure; I spoke to several Hacker Paradise alumni, and many of them mentioned that after a Hacker Paradise trip, they like to take a couple of months to decompress and recharge. They use that time to travel on their own, or in a smaller group, or even to return to their home base (for those who have home bases). 

It’s a sentiment I now fully understand and resonate with. 

The pace of travel/life with a group like Hacker Paradise, while exhilarating, can also be a bit relentless. If you’ve already been on the move for a while, it’s essential to acknowledge your own needs and establish a balance that suits you best. 

After my experience, I chose to restructure my remaining travel plans for the year, creating more time to just live and work in a slower, more intentional manner.

This pace of travel with Hacker Paradise isn’t a downside; it’s simply a characteristic of a program like this, and it’s what makes it unique.

Curious to learn more? Check out Hacker Paradise here, and use PROHOBO100 for $100 off. 

An impromptu late-night dance video game session - so much fun!
An impromptu late-night dance video game session – so much fun!

The People of Hacker Paradise: Community-Based Travel 

Hacker Paradise is not just about the places you visit; it’s equally about the people you meet and the connections you build. I can’t emphasize enough how amazing it was to spend a month with 22 incredible people from around the world.

Before I joined Hacker Paradise in Estonia, I got some confused looks from friends and acquaintances. They wondered why, after over a decade as a digital nomad, I would choose to participate in a program seemingly tailored for beginners or those new to the digital nomad lifestyle. 

In fact, many of the people on my program were very experienced digital nomads. While I won the prize for tenure in the lifestyle, there were people with up to 10 years of digital nomad lifestyle experience. 

Some were itinerant nomads, and others had home bases and traveled at will for large chunks of the year. There were also remote workers who are very much rooted in their home countries/towns, but who enjoy traveling with Hacker Paradise once or twice a year. 

And yes, there were a few newbies to the lifestyle as well, who were welcomed with open arms and were able to glean all kinds of travel wisdom from more experienced nomads. 

But Hacker Paradise isn’t about teaching you how to be a digital nomad; it’s about who you do it with.

The real value lies in the connections you forge. For me, this is where the Hacker Paradise experience truly shines. 

In 2018, after 12 years of full-time travel and immersing myself in local cultures, I had a pretty significant episode of burnout. It took me years to understand that the root cause was a lack of a social network – a group of like-minded individuals who understood the digital nomad lifestyle and shared the same wanderlust while also balancing a remote career.

Hacker Paradise brings together individuals with not only the same mindset but also a wealth of experience in the digital nomad world. During your time in the program, you’re bound to connect on a deeper level with at least a few of your fellow participants. And the beauty of it is that these connections often endure well after the program ends.

Over time, you can develop your own social network of friends who are also living and traveling around the world. It’s a network of kindred spirits who understand the nuances of remote work and the itch for adventure.

My friend Matt is a multiple Hacker Paradise alumni, and has also done Remote Year and other co-living co-working programs…a few times. He has been a digital nomad for over 10 years, and his most recent co-living co-working program was less than a year ago. So he sure ain’t doing it to learn about the lifestyle. 

In the next section I’ll explain why he still does these programs, and the net result of his efforts. 

The connections you make with people on remote work programs transcend time and borders
The connections you make with people on remote work programs transcend time and borders

Building a Global Social Network of Friends 

Shortly after I met Matt online (he reached out to me to be on his podcast), we circumnavigated the US by train together. This was a crazy stunt that only two experienced nomads like ourselves thought was a good idea at the time – crazy for many reasons, including that we had never even met in person before! 

But we both knew something our naysayers didn’t: as digital nomads, we could navigate living with one another and balancing the thrills of discovering new places with the routine of work. And given that most intrepid travelers are inherently pretty flexible, we figured we would get along fine. 

We did! And along the way, I met a dozen or so other digital nomads who Matt was friends with as well. This blew my mind. 

These were all people he had met over the years of doing Hacker Paradise and other co-living co-working programs. Matt had a massive global network of like-minded friends who he met up with regularly. 

With his experience in these programs, he can now literally put a message out to the ether saying “I’m going to X for two months: who’s in?” And before he knows it he has a group of five people to rent a villa with in the south of France. 

Just have a listen to his podcast The Maverick Show, and you’ll meet a bunch of these amazing people that he is friends with, and who he met through programs like these. 


Interested in digital nomad communities? Here are the best places to connect with other digital nomads (online and IRL). 

Not sure how much the digital nomad lifestyle costs? Join the club. Here’s a guide to budgeting for long-term travel

Hacker Paradise for Couples: Exploring Co-living as a Duo

It’s now time to debunk any ideas you have of Hacker Paradise being only for swinging singles. It’s not. And in fact, I got into some particularly deep chats with one of the couples on my trip, and they said Hacker Paradise is instrumental for their relationship. 

First up let’s look at the cost aspect. Because as a couple you’re sharing one room, the cost per person to participate as a couple is much less than two singles. You each still pay a program fee, but then you share the room cost. 

Beyond the inherent financial advantages of traveling as a couple, Hacker Paradise makes it easy for couples to spend time together and apart, as they wish. 

Life as a digital nomad couple is not always peachy. You are together 24-7; living, working, and traveling together. Even if you’re soulmates, this can wear thin after a while. 

This becomes especially challenging while together in a foreign place, where opportunities to have significant experiences and connections with others outside of your couple-bubble can be difficult manifest. 

Hacker Parardise makes this much easier. Within the group you may each find yourselves befriending different people, and you can foster these friendships over coffee or on excursions that your partner may not be interested in doing. 

Or perhaps one day one of you doesn’t want to go out while the other one does. Whoever wishes to go out and have a travel adventure won’t have any shortage of people to do it with. 

When you reunite at the end of the day, you’ve collected individual experiences and new ideas to bring back to your partnership and incorporate into the fold. Keepin’ it spicy, in a sense. 

On our trip (with 22 people) there were three couples. 

But also, there were many participants who were in serious relationships and were doing Hacker Paradise on their own. This is because coliving and coworking programs are a very easy way to travel solo; the built-in community is nurturing without being overbearing. 

You wanna do couple time on your own? Go on. Take that romantic bike ride.  

You wanna build personal friendships outside of your relationship? Have at ‘er. 

You wanna socialize together as the power-couple that you are? Power to you. 

You wanna divide and conquer? No need to be attached at the hip. 

Anything is possible.

Cultural Diversity and Cross-Cultural Exploration: Surprise! 

While a significant portion of participants tend to be North American or European, Hacker Paradise thrives on its cultural mishmash, creating an environment where everyone is collectively out of their element in a new destination. 

I was pleasantly surprised how this cultural diversity played out. When you explore a new place, you’re viewing it through your own cultural lens (often unconsciously so); when you’re alongside others who have their own cultural backgrounds that affect how they see things, interesting conversations happen as people share their perspectives. 

In a sense I was not only discovering Tallinn and Estonian culture and food, but I was also discovering cultural nuances and viewpoints of my fellow participants as we traveled and lived together. It’s a fascinating exploration that adds depth and nuance to the month. 

During my time with Hacker Paradise, there were people from North America, Europe, South America, and Asia. Conversations were a cultural exchange in themselves, an opportunity to learn about different customs, traditions, and worldviews. 

If you watch my video about Hacker Paradise, you’ll hear from multiple participants who share how this held surprises for them as well. 

How Igor realized that alone time isn’t a bad thing, despite his cultural upbringing of constantly being surrounded by family. 

How Renee realized that certain ideas and concepts that she thought were universal, were strictly American. 

How Didier realized that cultural sensitivities vary dramatically. 

With representation from over 10 countries, my month in Estonia with Hacker Paradise allowed me to proverbially travel much further. 

At a medieval restaurant in Tallinn Estonia
Cheers to cultural diversity and exploration! This is what travel is ultimately about 

Is Hacker Paradise Worth It?

One of the reasons why I haven’t done any coliving coworking programs over the years, was because I knew that I could do it myself for less money. I could find my own accommodation and activities in the same destination for way less – so why would I do the program? 

There were two things that I wasn’t taking into consideration. 

One, was the value of outsourcing the travel planning and logistics, and to know that I can show up and the accommodation is going to be great, in a good neighbourhood, and there will be good Internet, and a coworking space will be nearby, etc.  

It’s a significant amount of time – and mental energy – saved. And sometimes that’s worth paying for. 

The second and equally important component is the social element. This is the X-factor that can make a significant difference in your digital nomad experience. The burnout I had in 2018 stemmed from the absence of a social network of people who understood my lifestyle, shared the same sense of wanderlust, and balanced a remote career along the way. Hacker Paradise fills this gap beautifully.

And because it’s not a lifestyle that you would do every month of the year, spending a little extra for the month that you DO do an HP trip, is a totally justifiable investment in my opinion.

Although I would advise attending for a full month and booking the accommodation where everybody is staying to get the most from the experience, you can also join a program for just two weeks instead of a month, and in some cases you can get your own accommodation and just pay for the program activities. 

Here’s the cherry on top: once you have done a Hacker Paradise trip, you also get a discount on future experiences. 

Speaking of discounts, PROHOBO100 will get you $100 off Hacker Paradise. 

Visit Hacker Paradise here, and use PROHOBO100 for $100 off. Maybe I’ll see you on a trip. 


Watch this video I made about the experience, featuring five people from four countries spanning four decades in age. Lots of interesting perspectives!

Nora Dunn of The Professional Hobo looking out over Tallinn Estonia

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2 thoughts on “Hacker Paradise Review: Surprises (and Setbacks) I Had With This Work and Travel Program”

  1. I had never heard of this before and it sounds like a great experience. Will definitely check it out though I am not quite sure if it isn’t a bit too much “together time” for my taste…

    • Hey Kitty,
      It’s up to you how much time you spend with others or not! Though you ARE paying to be a part of a community, so if you’re in a “lone wolf” frame of mind, you won’t get much value.

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