Anne and Meghann.
Photo by Melissa Quaal.
A retreat can be a real turning point in your business—the point where your business dreams turn into achievable goals. As solopreneurs, we lack a team of colleagues with whom to reflect, brainstorm, strategize, and draft annual work plans. A business retreat is a rare opportunity to surround yourself with a small, supportive group of like-minded solopreneurs or colleagues who you trust to take a critical look at your business together with you. You become not only each other’s team but also cheering squad.

I recently planned a business retreat with fellow solopreneurs, Melissa and Anne, where we used a planning tool I developed to dive deep into our creative businesses and identify actionable steps toward our ideal business futures. Here, I share some of the core practicalities and considerations to take if you’d like to plan a retreat of your own. Planning the details beforehand will ensure your investment (of time, money or both!) is effective and will allow you and all the participants to be fully present in the discussions and get the most out of the retreat.

Who to Invite?

It is important that your group is cohesive so that the retreat is a space absent of judgement, where profound discussion can take place openly and honestly, and all participants feel fully supported. Melissa, Anne and I knew that we would have this together based on our experience at Craftcation where we met in 2017.

Meghann, Melissa, and Anne.
While carpooling from Ventura to LAX, something magical happened: we were able to be candid with one another in a manner that rarely occurs, as if in a targeted consulting session. Our businesses all have different offerings and our levels of experience differ as well, but we all blog, we had past careers in non-creative fields, our aesthetics are somewhat similar, two of us sew, two of us offer patterns, two of us have our blog as the main focus, etc. These are qualities that allow us to have a deep understanding for each other’s work, but also enough distance.

Some points you’ll want to consider when identifying who to invite for your retreat are:

  • Focus and stage of business
  • Ability to listen, be candid, and confidential
  • Personal and/or business competition

Managing Expectations

A clear objective and rules of engagement are important to managing the expectations of retreat participants, including yourself. You can either draft these before inviting fellow solopreneurs, or draw them up jointly in the early planning phase. Although it may seem evident, having these objectives written out ensures that everyone arrives prepared, on the same page, and with similar expectations of what they’ll be getting out of the retreat.

Where and How Long?

Location is important, but it doesn’t have to break the bank. This year, we were in a beautiful apartment in Old San Juan. But last year, I held a “retreat” in my dining room. The budget and amount of time that you are able and willing to invest in your retreat will be your parameter. Although I’d say 3 days is ideal, you can do a lot in one full working day!

We chose Puerto Rico because we wanted sun and warmth in January. Since I’d been to Puerto Rico before, I knew that Old San Juan was a colorful area that would allow us to step out the door for pleasant walks, as well as visit restaurants and shops during our down-time. On a conceptual level, I wanted to find a place that was beautiful and creatively inspiring while calm and peaceful.

Some points to consider when choosing your location:

  • Is there Wi-Fi?
  • Is it an inspiring space away from daily routine?
  • Is there good ventilation and/or fresh air?
  • Is the space conducive to group work and smaller break-out groups?
  • Is it located in an area that allows for movement, such as short walks during breaks?
  • Is there a kitchen or space for preparing coffee, tea and other refreshments, as well as a bathroom?

How to Structure Your Retreat?

I suggest drafting a timed agenda, while remaining flexible if some points end up requiring more time. That’s ok! The agenda should help to guide your discussion in logical succession and also have planned down time. For our retreat, we had very structured mornings and unstructured “free” afternoons. The discussions that took place in the casual moments were equally as important as those during structured, scheduled agenda points.

Meghann, Anne, and Melissa. Photo by Melissa Quaal.
Suggested Agenda Points:

  • In the spotlight – each participant talks about the current state of their business, past year challenges, and hopeful direction.
  • Unsolicited advice – one participant sits listening and taking notes while the others talk about their business as if they weren’t in the room. Scary! But SO good!
  • Visioning – what does your ideal business look like? Or, in your wildest dreams, where would you like your business to be in 5 years? Now go there.
  • Identify what is holding you back from getting to the ideal vision.
  • Identify what could get you to the ideal vision.
  • Stop, Start, Continue – what do you need to stop doing in your business, start doing (that you aren’t doing already) and continue doing?
  • Planning – identify “deadlines” and work backward, planning activities in your calendar.
Photo by Melissa Quaal.

Thoughts on My Next Retreat

I can’t think of a better way to start the year than a small business retreat! I returned home so inspired, motivated, and ready to move forward with confidence. The changes I would make for future retreats are minor and mainly in the details. Based on the feedback I received from Melissa and Anne, as well as my own reflections, here are a few tips that may be useful for your retreat too:

  • 3 to 6 participants and three full working days seems ideal.
  • Participants should arrive with key business figures filled out on their “preparation document,” such as income, site visitors, newsletter subscribers, etc.
  • In addition to notepads, provide participants with basic, empty monthly calendars to facilitate planning. Paper & pen are often easier to work with in a group rather than using digital technology.
  • Keep your Day 1 agenda minimal. This is the day when you’re most vulnerable, so it’s important to allow plenty of time.

“YES! That’s it!” we called out several times during our time together in Puerto Rico. It was exhilarating! It never got old or felt repetitive to “talk shop” during our short week together. There was a constant flow of constructive brainstorming between the three of us, and it felt gloriously productive.

Check out these two posts for additional ideas:

A “how to” for a shorter retreat: https://www.paperandoats.com/blog-native/how-to-plan-a-diy-mastermind-retreat

Unsolicited Advice: https://seanwes.com/podcast/209-unsolicited-advice-recap-of-a-mastermind-retreat/

Participant Reactions

Melissa: I cannot over-state the value of traveling to Puerto Rico for a creative business retreat.  The work I did there included systematically reviewing my current business, envisioning the future, and breaking down goals into bite-size pieces. Doing all of that while surrounded by supportive women who ‘get it’ left me feeling ready to tackle a big re-branding and launch a business I believe in.

Anne: How often do you take a break from your business to step back and actually assess how things are going and where you want to go? I loved being with other creative women who could honestly look at my business and brainstorm the possibilities for its trajectory WITH me! As an independent business owner, doing everything myself, I can’t express how valuable this was to me.  Sometimes we are too close to our own work to see what’s there. I experienced some critical breakthroughs around new offerings in the immediate time frame and huge goals for the future. I loved breaking these big goals into little pieces so everything felt more doable. Not to mention, the gorgeous location enhanced everything about the experience. 5 stars!!!

Planning a Business Retreat with Other Entrepreneurs
Meghann Halfmoon

Meghann Halfmoon


Meghann Halfmoon is the designer and creator behind the sewing pattern label halfmoon ATELIER. She believes that simple design and simple choices can have a big impact: on the way we feel, on the way we live and on the world! However, choosing fashionable, socially conscious products is still harder than it should be. Meghann can help make it easier.

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