The lessons we have learned from our first workation

Since the opening of the shared workspace in Cape Town in 2016, CoworKite has hosted two three-month remote work programs from the United States. In January 2018, we started our first workation in Cape Town for location-independent professionals. Being kitesurfers ourselves, our package and value proposition was focused on attracting people that share passion, not only for remote work, but also for an outdoorsy, beach lifestyle, and water sports. We’ve learned a lot from the remote work programs that we’ve hosted, and from events that we’ve personally attended. Now it’s our turn to share our experience. There are lessons here for those who plan to organize and run their own remote work and travel program, coworking-coliving retreat, or workation, whatever you want to call it.

Lesson 1: Community is everything, and less can be more.

Coworking and coliving is all about the community. Even though it was our first workation, we wanted to have 20 people and a fully-booked event, at least at some stage. Now we know that was a mistake. If only eight people signed up for our coworking retreat, that would be eight right people. Instead of focusing on the number of participants, it’s more important to have a tight-knit community, because participants will become future ambassadors telling others that it was an experience of a lifetime, and they’ve met fantastic like-minded people. We didn’t start CoworKite with intention of making money and building scalable business, but to bring together unique kitesurfing coworking community and surround ourselves with these people. So we have also chosen to invest in less people and to build meaningful relationships with them.

Lesson 2: Even if bookings are above expectations, you’ll probably lose money on the first workation.

We’ve allowed some people to book and pay after arrival, and if they cancelled at the last minute we didn’t have the heart to ask for payment. We’ve given 100% refunds to those who’ve paid in advance, but couldn’t make it in the end. We paid vendors for events where only a few people showed up because the wind was blowing and they decided to go kitesurfing. We’ve lost money on the currency exchange rate because we paid for the accommodation in Rand, which firmed 10%, literally overnight, while we were charging people in Euros. Our marketing costs were three times higher than what we planned.

You need to think of yourself as running a business. Your event might seem profitable if you aren’t paying yourself a salary and you don’t count your endless hours as a business cost, because you organize everything on your own and you personally work as a community manager; or if you own apartments and a coworking office, and you don’t count that as a cost. But remember your time is valuable and you could’ve rented your properties to someone else. The bottom line and the hard truth is that, if you hire an experienced person as a community manager, pay them a decent salary and offer return flights, outsource kitesurfing events, rent apartments and office, and pay a marketing company, then on the first workation you’ll either lose money, or you’ll earn like an intern.

Lesson 3: Be flexible and offer great value, but know when you have to say no.

It was our first workation, so we decided to be super-flexible to attract more people. The event window lasted three months, we had flexible packages with or without accommodation, bookings could be from one week up to three months, and payment could even be made after arrival. The coworking office and check-in were available 24/7, and apartments were on the beachfront, a short walk from the office. All rooms were private, and on arrival everyone got a SIM card with 3GB of data. In addition to the full time community manager, local host was around to provide a “live like a local” experience and to advise people about the best restaurants and kitesurfing spots. As an organizer, you’ll be expected to go above and beyond in coordinating the program and handling different requests. Having said that, setting boundaries and knowing when to say NO to some requests is important, as you can’t always please everyone.

Lesson 4: You will learn a lot about yourself and create long-lasting friendships

The main benefit of coworking retreats is long-lasting friendships, both for organizers and participants. Working, living and kitesurfing for 2 – 3 months with smart, successful and adventurous entrepreneurs and freelancers from different parts of the world is an invaluable experience. It’s an opportunity to learn a lot about business, life, kitesurfing, and also about yourself.

Lesson 5: Every remote work program is not for everyone.

There’ll always be some people that won’t be super-happy with everything, whether it’s the coworking office, apartment, roommate, events or something else. What is important is to manage people’s expectations by communicating everything on the web page and during the interview. Explain what is included in the price, what is not, and what the rules are for guests, the accommodation and the office. Your coworking retreat may be an amazing life-changing experience for some people, but it won’t meet the expectations of others. The coworking and coliving program is not a one-week vacation, and your program will not be perfect for everyone. Most participants on our program were happy, but a few will probably not return to our future remote work&travel programs, no matter how hard we’ve tried to satisfy them. It’s just not their thing.

Lesson 6: How to price the coworking retreat? Inexpensive side trips are better than free.

It’s a business retreat where community is the biggest value and price determines who can join. If the price is too low then everyone can afford it, and you won’t be able to provide private rooms in great apartments, an experienced trip leader or other value. Mature remote workers will never return to future retreats if they are not able to meet like-minded people who are at the same stage of their business and/or personal life. Having said that, a high price tag may still result in turning some people away, no matter how much value you include in your package.

Planning a weekend or an after-work trip for a group of kitesurfers is time consuming and not an easy task. The side trips we’ve planned were either paid for by us or charged at cost. The lesson we’ve learned is that inexpensive is better than free. Placing a price tag for each side trip brings responsibility and shows that what we are offering has a value.

Lesson 7: Be open to change and take time to listen.

Doing something for the first time is never easy, but nobody said it would be. When things don’t work out quite the way you thought they would, being open to new ideas is critical. Our mistake was that often we focused too much on solving issues and making everything work, instead on empathy and listening, which is key to making the participants happier. Sometimes it is more important to show people that you care about them as a person, and listen to their problem, rather than trying to solve it.

Lesson 8: Enjoy it and have fun as the organizer – and don’t take things too seriously.

There is not much more to add to the statement above. Problems during the event shouldn’t prevent us from having fun, being positive and enjoying meeting new, interesting and like-minded people. There were more than a few times we forgot that these were the reasons we started CoworKite workation in the first place.

Lesson 9: Find the right balance of entrepreneurs and remote workers.

While most of the participants were in their mid-30s, with a 50/50 male-female ratio, the first CoworKite trip taught us that this is not the most important balance that we should focus on. This isn’t a two-day networking event. For a remote work program that lasts a month or even a few months, like ours, finding the right balance of entrepreneurs and remote workers is crucial. Ideally, the percentage of entrepreneurs should be somewhere between 20 – 40%.

Before the start, we were proud that almost 70% of participants were entrepreneurs and investors, some very successful. This wasn’t planned; we simply promoted the program in our network, which consists mainly of entrepreneurs. The energy, knowledge and skills they brought to the group was amazing. Since they are used to leading and making the decisions, following is not easy for them. While the digital nomad lifestyle generally means a lot of freedom, entrepreneurs tend to do their own thing even more, especially those addicted to kitesurfing.

To build an inclusive community with a relaxed vibe, it’s more important that the majority of participants have more to offer to the group than just business experience; they also need to be nice, kind and down-to-earth people who will participate in most of the events, instead of being just super-successful entrepreneurs.

For shorter coworking-coliving retreats up to two weeks, this balance can be very different.

Lesson 10: Organize events and workshops that have cool speakers and industry experts.

People love going to cool events, and it’s a perfect opportunity for industry experts to gain followers, and to showcase their new product or service. We’ve put in a lot of effort to have interesting local and international guest speakers and presenters. We’ve had fun and educational evening presentations with successful bloggers as guests, like Miriam from Wake Up Stoked, and Melanie and Juergen from Lifetravellerz.

Watersport events and courses were held by Infinite Lines, a specialised kiteboarding school, and Pure Apnea, the best freediving school in Cape Town. In terms of professional development activities, we had a dozen different workshops, talks, presentations and goal setting sessions. Apart from that, we had many casual get-together dinners and rooftop braais (BBQs).

Lesson 11: Have a code of conduct and guest policy.

Some participants asked if they could invite their friends to CoworKite events, or their spouse joined them in apartment. We didn’t have an official guest policy, or exact rules, which was a mistake. Once we allowed the first participant to bring a guest without paying, others wanted to do the same. To keep things organized and respectful for other participants, having a guest policy with associated fees is a must, both for attending events and for accommodation.

Secondly, a code of conduct ensures that all retreat participants are on the same page and follow the same rules.

Lesson 12: Ask people for feedback.

Collecting feedback, both during and after the first workation, is very important. Ask attendees for feedback a few days after the remote work&travel program has ended, while the experience is still fresh in their minds. For us at CoworKite people who have extended their Cape Town workation are the best proof that we are on the right track as well as returning participants.


The lessons we have learned will be applied to our future remote work&travel programs, starting from workation on Mauritius, which lasts from June to August 2018. Hopefully our experience will be helpful to everyone who organizes coworking retreats, and that you’ll learn from our mistakes.

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