How (And Why) Remote Workers Should Take Mini Retreats Together

Part “workacation,” part business trip, spending some time with fellow solopreneurs or freelancers can help you all recharge–and find ways to collaborate.

How (And Why) Remote Workers Should Take Mini Retreats Together
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I spend most of my time working alone from home. While this makes for an extremely productive environment, the truth is that it can get lonely. Most of my communication with clients and peers happens through a screen or over the phone, and while I embrace technology to stay hyperconnected, I’ve realized there’s no substitute for the real thing. When all of your work and communication is virtual, things can start to feel pretty isolated.


Remote workers, freelancers, and solopreneurs shoulder a lot of stress  as they navigate the ups and downs of working alone–more, on balance, than their in-office counterparts, according to one report last year. Those strains can be even more difficult if, like me, you live in a fairly rural area. It’s one thing to ride your bike a few blocks and fire up your laptop at a coworking space, surrounded by dozens of other people who are doing the same. But when you’re based someplace where those opportunities aren’t available, I’ve found the only solution is to create them yourself.

So I reached out to a fellow solopreneur, and we made plans to meet up for a four-day mini retreat in Palm Springs, California. That may sound like just a vacation, but we actually got a lot done–and banked some much-needed human interaction in the process.

Related:  What My Team Discovered When We All Worked Remotely For A Week

Why Retreats Matter

Aside from overcoming the feelings of loneliness associated with solo work, we realized there were a few other key reasons a retreat could be helpful.

My retreat partner is a like-minded solopreneur who works in a similar space and understands my business model. This was key. We’d hoped our retreat would open the door to collaboration–and it did. Meeting in person with a person or small group of people who are already familiar with your work can naturally lead to conversations around potential ways to work together. And spending a few days working side by side lets ideas percolate slowly, in a way that just grabbing a coffee (or scheduling a Skype call) and chatting for an hour might not.

Experiences like these can also help remote workers create a solid support system. When you run your own business but do it alone, there’s sometimes a shortage of people you can turn to for troubleshooting help or even just encouragement. Planning mini retreats a few times a year can create a space for those bonds to form or grow–and you can build upon those relationships after the retreat ends.


Related: How To Plan A Corporate Retreat That Doesn’t Suck (The Life Out Of Your Team)

How To Plan A Mini Retreat

You don’t want your retreat to feel like a high-stress business trip, but a thinly disguised vacation isn’t what you’re going for, either. Here are a few tips to strike the right balance between kicking back and being productive.

Select your small group of attendees. In my experience, small groups of three or fewer are ideal for mini retreats. Also keep in mind that those joining you don’t all need to do the exact same type of work. If there are areas of overlap or a shared business niche that you each serve in different ways, you’ll still have plenty of ways to collaborate.

Agree on a budget. Again, this isn’t a vacation. Setting a budget for your retreat (before you start booking) helps make sure everyone you’re meeting up with is comfortable with the amount they’re investing in the trip.

Set a loose agenda. You don’t need to plan each day minute-by-minute (this isn’t a trade conference), but a rough outline of your daily plan will help keep your working hours productive. During our retreat, we broke each day down into time for individual work and collaborative work–and at night, we planned an activity that helped us get out and explore the area together.

Pick a place with amenities onsite. Look for a place that has a lot to offer on location or within easy walking distance. We booked a stay at the Ace Hotel in Palm Springs for our retreat–and found that we hardly left the grounds since almost everything we needed was a few steps away: nooks for coworking, restaurants for when we needed a lunch break, and a relaxing pool area for our daily wind-down. This minimized the planning we had to do while we were there (and cut down on the temptation for sightseeing when we should’ve been working).


Look for opportunities to take in-person meetings. If you’re traveling to an area you don’t normally visit, find out if there are nearby connections or clients you can meet up with while you’re there. This is a great way to get one-on-one time with people you’ve known or worked with for a while but have never had a chance to meet in-person.

Working on your own from someplace out-of-the-way has its benefits, but the experience can feel isolating after a while. If you’re intentional about shaking up those rhythms–no matter how much you might thrive on solo work–you’ll come back feeling refreshed and, hopefully, with a stronger network than ever.

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