The Working Weekend: How a Creative Retreat Can Change Your Business
Storytelling Communications

The Working Weekend: How a Creative Retreat Can Change Your Business

8 Minute Read

As a work-at-home mom, I spend much of my time working in fits and starts. I research while making my children breakfast. When outlining a post, I’m also keeping my daughter busy with her toys. “Can you get me all the yellow blocks? How about the blue ones?” I write during nap time and when everyone’s asleep at night. I wouldn’t change my work situation for anything, but I also don’t have the brain space I took for granted before working at home with a child. When someone in my mastermind group pitched the idea of a working weekend creative retreat, I was sold. Finally—a chance to have uninterrupted time to work on my business and strategize future plans with other like-minded professionals.

But where does one even start turning this idea into a reality?

How to Plan a Working Weekend

When my mastermind group mulled over the idea of planning a creative retreat, the first thing we focused on was time and place. First, how long did we want the retreat to be? Since we all have little children, we knew we wouldn’t be able to get away for much longer than a weekend, so we decided a Friday through Sunday would work best for our current schedules. Then, we all looked at our family calendars for the rest of the year and chose a weekend that worked for all of us that wasn’t already booked with birthday parties, cookouts, holidays, or other obligations.

Next, it was time to choose a location. Since we’re all located across the United States (representing Massachusetts, West Virginia, Minnesota, and Wisconsin), we wanted to make traveling for everyone as easy as possible, so we looked for deals around major airports.

Once the date and location were decided, it was time to think specifics. Where would we stay? What were we looking for in a hotel? What did we need to bring to make sure we’d actually do everything we planned? Those details may vary for every group that takes a working weekend, but here is what worked for us.

“Space is your friend,” says mindset coach Jessica Eley, “so make sure wherever you go has tables or desks for everyone to work at, as well as rooms with doors so that everyone can be on their own or together, depending on what they’re working on and how they’re feeling. Ideally, you’ll also be able to eat at least a couple meals wherever you’re staying so that you’re not constantly interrupting yourself or skipping meals.”

We wanted a hotel that offered suites, so if any of us wanted to record video content we could simply close the door and talk to the camera while someone else did computer work in the next room. We also looked for hotels that offered continental breakfast, located within driving distance of a grocery store where we could buy lunch and snacks and a downtown area to grab dinner. We were all working so hard on Saturday night that we skipped a nice meal out and ordered Thai delivery instead.

Who to Invite

There are two things you need to know about the gals in my mastermind retreat. First, we’re all work-at-home moms. Second, we’re also all solopreneurs with businesses in different industries. There is a website designer, a mindset coach, and a Facebook ads strategist. We work well together because we all can empathize with the struggles of raising a family while building a business. Because we work in different industries, and because we all could be potential customers for each other’s businesses, we’re able to give each other an outsider’s perspective on our current projects and the goals we set for the future.

working weekend with mastermind group

Image credit: Allie Bjerk (left to right: Katie O’Brien, Allie Bjerk, Erin Ollila, Jessica Eley)

That doesn’t mean you need to look for different types of professionals to plan an event like this. Reaching out to peers in your own industry can be just as rewarding. You’ll understand each other’s pain points and problems intimately, and you’ll all grow by absorbing what works well in each other’s businesses.

Website designer Katie O’Brien says, “I feel it’s so important and super vital to find people in similar stages of life and business because as an entrepreneur it’s not just one or the other. There’s always a blend and a give and a take in life depending on the day and having a mastermind of like-minded entrepreneurs who just ‘get it’ is priceless.”

But what if you’d like to plan a weekend away with other business professionals, but you’re not part of a mastermind group? First, look to the people you talk about your business with often. Who do you talk through any problems with? Who helps spark ideas out of an ordinary conversation? These are your people. It doesn’t matter if you live close or far or are at completely different points in life. You aren’t auditioning for future bridesmaids. You’re looking for working colleagues who feel just as passionate about growing their businesses and supporting your growth, too.

In fact, this could be the very first time you all meet, which is what happened in our case. However, if you’ve never met in person, it is important to vet the other members before flying to spend time with them. Before our trip, we met for weekly video mastermind calls for many months. We already knew that we vibed well, and we were all serious about our businesses. You want to make sure you feel comfortable with everyone so you can get right to work when you’re together.

Look for people who are motivated to grow in their own business, but make sure they’re also willing to brainstorm and strategize on yours too. The reason a creative retreat with a small group works so well is that each person is able to get feedback from each other. You could book a hotel anywhere for a solo weekend work session, but you’d be missing the camaraderie and insight other professionals bring to the event.

Allie Bjerk, a Facebook ads specialist, says, “I would absolutely recommend to most online entrepreneurs to make an effort to find their people online and plan an event like this. There’s just something to be said for getting out of your comfort zone (and your house) and changing your scenery. It honestly gave my business an energy that it hasn’t had in a while. Just the element of brainstorming, chit-chatting, feeling real and important in your business . . . you can’t get the same connection online.”

Outline Your Goals

You can’t just fly away for a work retreat with no idea what you’ll do when you get there. Before flying down, we talked about group goals we wanted to accomplish. In our case, taking head shots was a priority, so we booked time on the first night to take pictures of each other in the picturesque downtown. With four people, two could work together at once. Just remember to plan your photo shoot around the sun. Toward the end of our picture taking it was getting dark, forcing us to stop a little earlier than planned.

Erin Ollila

Image attribution: Jessica Eley

We also knew we wanted to learn from each other, so we prepped ahead of time by discussing business pain points and what we’d love to learn from each other when we were finally together in person. But as much as we could benefit from each other’s skills, it was also vital we set personal goals for the weekend. Since this was our first time planning and attending a mastermind retreat, it was important to know those objectives before attending the event so we could measure the outcomes and determine if this was practical and worth doing again.

“To figure out my goals,” says O’Brien, “I took a look back at all the things I’ve been avoiding the last six to twelve months. Things that I wanted to do at home, but couldn’t because I would get distracted and wanted to have enough time to sit down and do them in one swing. I added those to my list first. I also made sure to complete all client work before the weekend came to make sure that the entire weekend was focused on my own business growth.”

Eley agrees, “Focus on finishing tasks while you’re away and have a plan for how you’re going to implement, execute, or share the work you’ve done when you return. Trips like this are an excellent opportunity to batch work, but you don’t want to get a lot done only to have it live on a hard drive!” She continues, “It’s also important to reflect on the time you just took to evaluate what worked, what didn’t, and how you can take components of what you just did and apply them to your life more frequently. For example, can you stay in a hotel on your own a couple days each quarter? Can you participate in virtual group co-working with the same group of people, or can you give yourself one day each week that has a long span of uninterrupted work time?”

I asked Bjerk if there was anything about the trip she wished she could change. “It wasn’t long enough,” she replied. “The experience was really rewarding and one of the most validating steps I’ve taken for myself in my business. Just knowing that it was worth flying halfway across the country to meet three of my best online friends for the first time and that my business was worthy of working on for three, beautiful, uninterrupted days was immeasurable,” says Bjerk.

I’d have to agree.

For more stories like this, subscribe to the Content Standard newsletter.

Subscribe to the Content Standard

Featured image attribution: Andrew Neel

Erin Ollila graduated from Fairfield University with an M.F.A. in Creative Writing. After a 12+ year career in human resources – specializing in employee health and dental benefits, as well as wellness programs– she's jumped headfirst into digital strategy and content creation. Erin believes in the power of words and how a message can inform – and even transform – its intended audience. Her writing can be found all over the internet and in print, and includes interviews, ghostwriting, blog posts, and creative nonfiction. Erin is a geek for SEO and all things social media. She lives in Southeastern Massachusetts, neighboring Providence, Rhode Island, one of her favorite small cities. Learn more about her at

Recommended for you