How (and Why) to Plan a Quarterly Solo Business Retreat

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As a small business owner, it can be so overwhelming to juggle #allthethings. In seasons of abundance, while the cash flow might be sweet, the workload can be debilitating. In fallow seasons, while you may have a surplus of time, the fear and doubt can be all-consuming.

Regardless of what season you are in, there are always a multitude of things to do, and if the past seven years of business have taught me anything, it’s that so many of my fellow business owners (myself included!) can often feel like we are merely treading water.

It feels akin to the myth (or perhaps the truth!) about the sophomore slump. An artist has a lifetime to work on their debut album. If after however long of trying it is finally met with critical acclaim, then the pressure begins for the artist to create something fresh and new. With the added pressure of touring and management and expectations, the second album has a tendency to not be as masterful.

I see this play out in business as well.

While you can spend years dreaming up your business plan, once you officially launch, the day-to-day pressures begin to mount. There are so many decisions to make in a day to keep everything afloat and one of the mistakes that I see business owners making is that they are moving too fast. They believe that they must keep treading water and that it’s the only way to survive. They keep doing and pushing and striving, without regard for their own well-being or their original intent.

This was me, too.

After a couple of years in business, I realized how my weekends and holidays were morphing into time to “catch up” and work on my own business rather than to rest. I had these ideas for how to move my business forward, but I felt like I never had the time to sink into the deep thinking required for some of those big visioning tasks.

I was caught up in the tide of doing. Treading water. Not making any real progress despite all the efforting.

Eventually, I decided to take myself on a 2-day business retreat to finally dedicate the time to work on my business and stop leaving myself the scraps. After that first time away, I knew this was a structure that I needed to maintain. It soon evolved into a quarterly business retreat, and I’ve been doing some version of this for the past five years.

Since I’ve maintained this ritual for myself, I don’t feel as though I am merely calling the shots out of exhaustion or haphazardly reacting to opportunities that are presented to me. My decisions and direction feel more purposeful because I remind myself regularly of where I want to go and how I’d like to get there based on my present circumstances and capacity.

Quarterly retreats have become my way of ensuring that I am taking the time to be the CEO of my own company.

They are dedicated time when I can envision the future I want for myself and my biz and create a plan for that growth. It’s when I can finally take a look at what’s been simmering on that back burner and bring one of those projects to the front to give it the attention for which I have just not had the capacity. (I like to call these my “back burner projects.”)

If you read the title of this blog and maybe you started reading skeptically thinking, “OK, Mags. Sounds real nice, but HOW do I actually make this happen?” Buckle up, dear ones!

Let’s break down how you can make this work for you.

How to Plan Your Solo Business Retreat

Step 1: Make the time.

In my experience, this is the most challenging part!

You have to protect your time. Do whatever it takes and whatever you need to make that so.

For me, it’s critical that I not only block the time on my calendar, but I also have to state my intention and let others know that I am taking this time intentionally off.

At the beginning of each year, I block these days on my calendar. That’s all that is needed to ensure that nobody can accidentally book a call with me via my scheduling link, but if your calendar is not integrated—be sure to block off the time in both places!

This next step has been the game changer for me—I have to tell my clients. If I keep it quiet, then I am more likely to abandon myself and acquiesce to the needs of the day rather than dedicate that time for myself. By sharing with my clients that I’ll be out at that time, I can then make plans around those off days. I treat it as any other OOO day, and this has been the thing that has helped a ton.

I also communicate with my family. Over the years of doing these quarterly business retreats, I have been married, single, and now in a relationship again, so who I need to communicate with in my personal life has changed. However, I always make sure I let the people in my life know that I won’t be as available on those days, especially if I’m planning to be out of town or out of the house.

Step 2: Assemble Your Ideal Retreat Ingredients

Once you’ve identified the dates, then comes the fun part of allowing yourself to be a scientist. Between now and your first retreat, begin to observe the elements you crave in order to create the most desirable environment for you.

Get curious about what makes you feel most alive, creative, and focused, and take note! Pay attention to what sounds, food, clothes, movement, or sense of place allows you to tap into that expansive head and heart space. Whether you are tracking this in a physical paper planner or within your notes app of choice, begin observing, taking notes, and discovering patterns.

The goal with this is to have the information so that you can create the conditions for you to feel your most open and creative.

Step 3: Decide What to Work On

Now that you’ve created the container, what do you want to work on during your solo business retreat?

I like to use the Eisenhower Matrix to help me determine which one of the back burner projects to work on.

Quarterly business retreats are the time to work on those projects that are important but not urgent and would make a positive impact on your business. You know the ones. These are the projects you tell yourself to do someday, but someday never comes. Or something that needs to get done, but you keep putting it off. Things like outlining your next program or offering, finally creating that lead magnet you’ve been meaning to launch, rewriting your website copy to reflect who you are now, reviewing your mix of offerings and ensuring you have a clear and structured customer journey, creating a relational marketing plan, auditing the current state of your business, etc.

I have found that I like these retreats to be a blend of mundane-but-important tasks and at least one deep work project. Having a task that has a clear start and endpoint helps me to feel like I’ve accomplished something. That energy then propels me into the deep work that might be the larger intention of the retreat. For me, that mundane-but-important task is bookkeeping. I love setting aside time on these quarterly retreats to complete my bookkeeping and reconcile my Quickbooks for the past quarter. It makes me feel accomplished, and Future Maggie is always grateful that Past Maggie has done so when it comes to tax time. What could be that thing for you?

If you’d like support with working through how to prepare for your first retreat, lucky for you, I’ve created a Pre-Retreat Checklist to walk you through the entire process and help you get organized for your next quarterly business retreat.

If having set goals feels too rigid for your system, then consider any questions you want to be with and reflect on during the retreat. I tend to be more anti-goals, so if you’re like me, it might be supportive to set your intention for what you’d like to have and how you’d like to feel at the end of the retreat. Throughout your retreat, check in with yourself to make sure that these things are still aligned for you. You can always edit your questions at any time so that they remain as true to the present moment (and present you!) as possible.

Be realistic about what you can accomplish. It might take a couple of times before you realize what you ultimately want out of this time away.

Step 4: Work Out the Logistics

I like to first determine what I’ll be working on before I begin to create the experience that I believe will be most supportive for me and the back burner project I’m being called to focus on. If I need to get a lot of writing done, then I prefer a change of scenery. That’s when I find a friend who needs house- or petsitting or I might even book a 2-night stay somewhere.

Two months before: Book any accommodations and travel arrangements, including plane, bus, or train tickets, or make sure your car is ready to get you where you need to go.

One month before: Schedule any appointments or reservations.

If one of the things you desire to have as a part of your retreat is a session with a coach, mentor, or bodyworker, then you want to make sure you’re getting on their calendar! Book it now.

Personally, I love to start mine with a session from an energy worker. Then as I wrap up, I love to have a massage.

One month to two weeks before: Gather any supplies you’ll need. Maybe you desire a fresh notebook or a big Post-It board to capture your big ideas. This doesn’t have to be expensive, and shopping secondhand is always recommended.

The week before: Take an hour to finalize your agenda.

A Major Caveat to All of This

You do not need to spend any money to make this happen. If you’re in a season where making an out-of-town trip or even a staycation isn’t possible, you can still create the ideal essence for your solo business retreat right in your own home.

There have been times when my quarterly business retreat looked like a 2-night overnight stay at a tiny house in my own city. Other times it’s been a road trip. And more recently, with my life circumstances changing, it’s looking more like two half-days within a week of each other. It always looks a little different. Sometimes I feel the call to stay at home in my PJs, jamming out to my favorite tunes. Other times, I’ve craved the feeling of being anonymous in a coffee shop, being one amongst many working on our own projects, and feeling an odd sense of camaraderie in the process.

Bottom line: You get to make the rules. Make this work for you—for whatever stage of life and business you’re in.

After Your Retreat: Keep the Momentum Going

Before your retreat concludes, create a container for yourself to keep things moving in whatever way feels most supportive for you. Now that you brought your back burner project to this point, what do you need now?

Is it accountability? Is it a project plan? Or regular meetings with yourself? Whatever it is, create the structure.

Commit to the structure for the next quarter and remember… keep your scientist hat on. If the action plan you created didn’t work, you can always adjust it for the next quarter.

While the structure of these retreats has evolved for me over the years (heck, not one has ever looked the same!), I can indisputably say that they’ve been an indispensable part of my business growth and development.

To help you get started, access this Pre-Retreat Checklist Notion Template as a companion to this post to help you plan out the details of your retreat and get you closer to making it a reality. 