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

Spencer Jentzsch
Hacker Paradise
Published in
9 min readFeb 5, 2018
Things can seem the same. How do you choose?

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?

I’ve been running Hacker Paradise for the last two years. I love it. We have an incredible group of people join us from all over the world and all walks of life.

Many participants who have joined us have been on other remote work programs and have told me stories where things were quite different than what they had expected.

Here are just a few examples:

  • Placed in housing over one hour away by public transportation from the coworking space
  • Several people breaking the code of conduct without any consequences
  • Realizing you’re the only one on the program who is actually working
  • Checked in by trip leaders and then never seeing or hearing from them again

That’s fucked up.

Let’s make sure this doesn’t happen to you. Here are some areas you should dig into before committing to a program like this. For full transparency, I’ve included my answers for Hacker Paradise as well.

Disclaimer: Our program is not perfect for everyone either and there are a bunch of mistakes we’ve made throughout the years as well. I tried to be honest in highlighting those below as well

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. Know before you go who your peers will be.

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

Whether they are a full-time remote worker, freelance, an entrepreneur, or finally dedicating time to focus on their side projects, all of our participants have a job or a project they are working on. In fact, it’s a requirement to come on one of our trips.

What do you mean when you say like-minded people?

This phrase is so overused that it has become trite. I admit that we are guilty of it as well.

¯\_(ツ)_/¯

What does that really mean? Give me some examples of these people and why you think we’re like-minded?

Hacker Paradise: We mean ambitious, creative, 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.

Check out our Instagram. We highlight one of our participants ever third post so you can see and read about the types of people that come on our trips.

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 dig into where your housing is compared to the coworking space and also to the rest of the participants in the group. Make sure the neighborhood you are in has good 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 physically close to our community and see other participants every day.

We might not always be in the central tourist areas as, many times, the surrounding areas are safer, cheaper, and more authentic.

Make sure you know where everything is located in relation to you

Can you give me specifics about 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 a group does, 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 hold two talks every week and a networking event generally every month in each location. We generally have around four workshops or classes a month. There are events for setting goals and getting help from the group every week, not to mention a bunch of social activities that are both organized by facilitators and also self-organized by the group.

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

Now for some specifics. So far in our two weeks in Medellin, we’ve done the following:

  • One orientation session
  • Four presentations including acting with Dragos, understanding frameworks with AJ, optical illusions with Noémi, and why we are so stubborn in changing our mind with Renata. See more of talks and workshops we’ve done in the past here, here, and here. Watch some of our past talks on our YouTube channel.
  • 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

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 didn’t know you were going to be expected to pay for.

Ask what is 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 actual 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 75–150 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. Totally up to you to opt in if you are interested.

Are people ready to go home or ready to sign up for their next trip?

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. Currently in Medellin, 60% of our participants are returning participants and in Bali, 45% are returning.

We had 68 people join us over the course of the three months we were in Cape Town last fall. 37 of those (54%) were returning Hacker Paradise members.

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.

Take a look at Coworkations to find some solid, unfiltered reviews. Think of it as a Yelp for remote working programs.

Hacker Paradise: Take a look for yourself here.

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. It’s totally why I signed up for my first one as well.

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. Do they work alongside you or even live 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 are 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 minutia.

What’s the process when I have a problem?

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.

Choose your own adventure. You pick where you go.

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.

Originally published at www.hackerparadise.org on February 5, 2018.

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Spencer Jentzsch
Hacker Paradise

COO of Hacker Paradise. Korean linguist. Appreciator of shitty rosé.