6 things to consider before planning a coworking retreat


There are a many perks of working remotely–like not having to deal with an awful morning commute and being able to work (and take breaks), whenever you want, wherever you want. But it can also get very lonely, especially if most of your communication with people happens over the phone or via a screen. Twenty-one percent of remote workers said that loneliness was the most challenging part of their working arrangement, according to a 2018 survey by Buffer.

That’s why one of the things I look forward to the most every year is getting together with other people for a retreat. In the past, I’ve made it a priority to at least do a mini-retreat with one other freelancer, but this year, I was able to organize my first small group retreat.

Making a small group retreat happen, however, is no small or simple task. It takes some careful planning. From the perfect location to the right activities, there’s a lot to figure out. Here are some lessons I learned in the process.

1. Consider shared lodging

Staying in a large house with multiple bedrooms turned out to be a great option for my small group retreat, as it was a relaxed, cozy environment. I found and booked a home located on Eagle Ridge Resort in Galena, Illinois, but if you’re looking for something a less location-specific, sites like Airbnb or VRBO present endless options for finding a home-based location in almost any city.

Retreats like this can also serve as a networking opportunity to build new professional relationships in a relaxed setting. A large house is perfect for that setup. People can retreat to their own rooms when they need privacy, and have impromptu conversations in the common living space. As I previously wrote for Fast Company, spending a few days side by side lets your ideas percolate slowly. Shared lodging is conducive to those types of interactions.

2. Plan indoor and outdoor activities

The weather didn’t always cooperate during the retreat, so it was helpful to have plenty of onsite activities that didn’t rely on us being outdoors. Sure, it would’ve been nice to play a round of golf or to sit around a fire at night–but it wouldn’t have been as fun in extremely windy weather. We planned plenty of indoor activities to keep the group busy and entertained–like board games, an onsite spa, and multiple indoor fireplaces where we could roast marshmallows.

3. Schedule time for people to be alone

While staying in a house together creates the environment for new deep relationships to form, it can start to feel like close quarters if everyone feels like they have to be together all the time. Remote workers are especially prone to feeling like this, especially if they spend most of their time alone.

Choosing space where each person has a private room and allotting time for self-directed activities allows the group to breathe and reflect throughout the retreat. That way, when they do interact with one another, they’ll be more likely to have productive conversations because they’re not talking to each other out of politeness or obligation.

4. Arrange a time to cook a meal together

Staying in a house or apartment with a full kitchen means you can cook meals as a group, which is a team-building experience in itself. Not only is it a cost-efficient way to cover a few meals during the stay, but it also lets different team members showcase their skills outside the work environment and creates a collaborative experience with–hopefully–tasty results. Just make sure your selected site comes with dishes and cookware, so you don’t have to tote pots and pans along with you. Be mindful of people’s dietary restrictions and allergies, too—you want people to feel included in this activity, not excluded.

5. Pick a spot with ample room for coworking

Community spaces are essential when you have a group of people staying in the same place–especially if you want to spend part of your retreats working with each other. To make that a comfortable experience, make sure that you pick a venue with plenty of shared space (think living rooms, dining rooms, outdoor patio, etc.) where people can work collectively but not feel cramped. When I booked my mini-retreat, we picked a home with five different spaces that can serve as common areas with plenty of seating and electrical outlets.

6. Provide optional outings

Lastly, a mini-retreat is an excellent opportunity to explore a new area. But you shouldn’t make this compulsory for people—no one likes forced fun. It’s also a good idea to arrange a few different options for attendees to choose from. What you consider to be a fun activity might be someone else’s idea of a nightmare. It’s also important to give people the option not to participate. Some people might want to take this opportunity to schedule some time to themselves.

Freelancers, remote workers, and solopreneurs have a lot to gain from hosting (or attending) a mini-retreat. But to make it an enjoyable and productive experience, you need to think about your objective and pick spaces and activities that reflect that. It might take a little more planning, but trust me, you’ll be thankful for the extra time you took to consider these factors.

Kaleigh Moore is a writer and consultant for companies in the SaaS industry.

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