10 Questions to Ask before Signing Up for a Work & Travel Program
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10 Questions to Ask Before Signing Up for a Remote Work & Travel Program

Signing up for a remote work program can be a big commitment and there are a lot of options out there these days. How are you supposed to know which one is right for you?

Hacker Paradise has been around since 2014. We love it. It’s an incredible group of people from all over the world and all walks of life.

Many participants who have joined us have also experienced other remote work programs, and have recanted not-great stories where the reality of things ended up being quite different to what they were expecting.

Here are just a few examples:

  • Some were placed in housing over one hour away, by public transport, from the coworking space.
  • Others described co-participants breaking the code of conduct, and not facing any consequences.
  • We’ve also heard of moments when people realized that they where the only ones on the program who were actually working.
  • And then, imagine being checked in by trip leaders and then never seeing or hearing from them again.

That’s messed up.

Let’s make sure this doesn’t happen to you. Here are some questions you can and should ask before committing to a program. For full transparency, we’ve included answers to these for Hacker Paradise.

Disclaimer: Our program is not perfect and may not be the right fit for everyone. There are a bunch of mistakes we’ve made throughout the years, and we’ve tried to be honest in highlighting those below.

1. “Do people actually work?”

If you are a serious remote worker, this is the first question you should ask. Remote work programs have become popular not only among the remote working community but among those taking a gap year or those who simply want to travel.

Being the only one in the group who is serious about working can be distracting and alienating. Before you sign up, it’s always good to ask who your peers will be.

Hacker Paradise: Yes, all of our people work. We would argue that we have the most serious remote workers of any program out there.

Whether full-time remote employees, freelancers, entrepreneurs, or those finally dedicating time to focus on their side projects — all of our participants have a job or a project they’re working on. In fact, it’s a requirement to come on one of our trips.

2. “What do you mean when you say ‘like-minded’ people?”

This phrase is so overused that it has become trite. We admit that we’re guilty of it as well.


What does that really mean? It’s totally ok to ask for examples of these people and their commonalities.

Hacker Paradise: For us, we mean ambitious, curious, open-minded, and all-around lovely people. We don’t care about your industry, age, gender, sexual orientation, ethnicity, nationality — in fact, we like to have a diverse group of all of those things.

3. “Where is my housing in relation to everything else?”

An hour train ride to get to the coworking space isn’t very fun. Ditching the commute is one of the best reasons to leave home and come out on the road.

Try to get an idea as to where your housing is in relation to the coworking space. If all participants aren’t on the same property, it’s also good to get a sense of where you’ll be in relation to the rest of the group. Do a little homework on the neighborhood you’d be in, and make sure it has access to the things you will need every day like grocery stores, restaurants, coffee shops, etc.

Hacker Paradise: Our housing is within a 10–15 minute walk to the coworking space. We try to make sure that all the things you might need are in that radius so you don’t have worry about public transportation. You will be in close physical proximity to our community and see other participants every day.

We might not always be in the central tourist areas as often the surrounding areas are safer and more authentic.

4. “Can you give me specifics regarding your recent professional development activities?”

Most programs do some sort of professional development but the type, frequency, and quality can vary greatly.

In order to learn more about the professional development activities, ask for specific examples of what they have held in the last couple of weeks. Check their social media as well to see what type of events they focus on.

Hacker Paradise: We usually hold two talks every week and a networking event monthly in each location. We generally have around four workshops or classes a month. There are events geared at setting goals, receiving help/advice from others in the group as well as sharing your own expertise. And that’s not to mention a bunch of social activities that are organized by either you facilitators or led by the community itself.

No events are mandatory so you attend what you are interested in.

Now for some specifics. An example of what two weeks of typical programming on one of our recent Medellin trips looked like:

  • One orientation session
  • Four presentations including acting with Dragos, understanding frameworks with AJ, optical illusions with Noémi, and decoding why we are so stubborn with Renata.
  • Two potluck dinners plus two official Monday group lunches
  • One casual rooftop BBQ networking event with the coworking space, a meetup with another remote program here currently, and a crypto party
  • Recurring Spanish classes and salsa classes
  • One goals setting session and one event to ask for help. We set 33 goals for the next two week period and created a list of 25 things people needed help on with an average of three people volunteering to assist in each request.
  • Two writing group sessions
  • Some pretty awful karaoke renditions that were only saved by some incredible dancing, kayaking and ziplining in Guatapé, and hiking with people from the coworking space

5. “What else are you going to ask me to pay for?”

Nobody likes add-ons. Once you have committed to a price, it’s frustrating to see the price continue to go up due to things you weren’t expecting to pay for.

Ask what’s included and what you might be asked to pay for in the future. Here are some common things you might not be aware of:

  • Are you being charged a membership fee or deposit?
  • Are you responsible for electricity, water, or wifi bills?
  • Do you need to pay more to have your own room or your own bathroom?
  • Are you going to be sold a side trip at double the market price?

Hacker Paradise: We don’t require you to pay anything beyond the standard price.

All the money you send to us is going towards paying for your trip directly. There is no separate deposit or membership fee.

If we plan a side trip, we do it because we want people to go, not because we want to make money. The side trips we’ve planned in the past, we’ve charged at cost.

You’ll always have your own room with us unless you opt to share with someone in order to share cost.

The one add-on option we have: you can opt to pay a bit more (usually 150-400 USD a month) if you want to upgrade housing. Generally, this means either having the master bedroom with ensuite bathroom in an apartment you share with other Hacker Paradise members or getting a 1-bedroom apartment all to yourself. No secret fees here.

6. “Do people come back?”

There is no better way to gauge the customer satisfaction of a program than to see if they have returning customers. Is this a scenario where people are excited to come back for more or where people are excited for it to be over? Are people trying to extend their trip or are people trying to leave early?

Hacker Paradise: People come back to us in droves. On our current trips, 45% – 60% of our participants are returning.

7. “Where can I see unfiltered reviews of you?”

It’s easy for anyone to cherry pick or manufacture quotes to put up on their website. Do some research outside the info that the company itself will provide for you.

Hacker Paradise: Take a look for yourself — our Trustpilot reviews here.

8. “Who is on the ground and what is their involvement?”

Let’s just say it — one of the reasons why you choose to go on a program like this is because you are hoping someone else will be there to solve the problems you don’t want to deal with. You’re not alone. And that’s totally respectable.

The question is whether the group you are looking at is on the same page as you in terms of their involvement on the ground.

Find out how often you’ll see them. Are they working alongside you or even living with in the same building as you? Do they have other jobs they’ll be busy with? Do they have experience doing this type of thing?

If you’re paying for a community manager, a trip leader, a facilitator — whatever their job title is — you should check that they’re going to fill the role that you’re envisioning.

Hacker Paradise: We are there before the program starts and will be there until the last day. There are two facilitators on every trip and this is our full time job. You will see us every day.

We have a wide-array of life experiences and have been doing facilitation and community management for a long time. This is not our first rodeo.

We keep everything running smoothly so that you can focus on your work and enjoying the location instead of having to deal with all the other minutiae.

9. “What’s the process to report or resolve an issue?”

Shit happens. It’s just part of traveling.

The real question is: how are problems handled when they arise? Do you talk directly to someone on a trip with you or get sent to a corporate representative to complain?

Hacker Paradise: It’s simple. You come and talk to us. We will be working at the table next to you.

10. “How flexible is it?”

Some programs require a one year contract. Others lock you into a set itinerary. Some charge a large deposit that you pay upfront and won’t get back, even if you have an emergency and don’t end up traveling with them at all.

Know what you are getting in to.

Hacker Paradise: We’re flexible. Once you’re accepted in the program, you can choose to come on any trip. Come for as little as two weeks, as long as a year, or choose to pop in and out throughout the year.

You build your own itinerary so you can choose to start on one continent and switch over to the next. You just need to give us enough heads up so we can make sure we have a spot for you there.

Need to take a break? Not a problem. Again, just give us enough heads up so we can plan ahead for it.

If you need to cancel before the trip starts, we most likely won’t be able to give you a 100% refund. We keep enough back to cover the costs we have already paid for (housing, coworking fees, etc.) and refund the rest. This usually ends up being around half. We try to fill your spot with another participant so we can push back more money your way.

Have an emergency while on trip? Come talk to us. We’re understanding people that care about you as a person more than making profits.

We hope these questions will help you pick the program that is right for you. If you feel like that could be us, schedule a call with our people so that we can get to know each other a little better. And fun fact: you’ll chat with one of our Community Facilitators — the super heroes that run our trips, not sales-people. That means you’ll get to ask your questions to an authentic human, with real life Hacker Paradise experience, that will later be your on-trip buddy!

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