How to Plan a Solo Biz Retreat

Here’s the library I went to last year for my solo biz retreat. I reserved a room full of whiteboards and windows! I’ll probably do it again this year . . .

Here’s the library I went to last year for my solo biz retreat. I reserved a room full of whiteboards and windows! I’ll probably do it again this year . . .


It’s a new year, and if you’re a freelancer or self-employed (or you plan to launch your business this year!), it’s time to start planning now. Entrepreneurs have to make sure they’re regularly casting a vision—one, three, or five years down the road.

Last January was the first time I had an official “solo business retreat,” and even though many things changed for me throughout 2018, it was still the best decision I ever made for intentional planning.

Before jumping in, I want to say that I modeled my entire solo biz retreat weekend after the resources provided by fellow editor, @MelEdits. I highly recommend checking out her blog post on how to create a goal-setting retreat that works for you.

What is a solo business retreat?

This is a time every freelancer or entrepreneur should set apart every six or twelve months or so to reevaluate business goals. It’s a time to reflect on what’s working, what’s not, and what areas you want to grow and expand.

You can hold a “company retreat” in your own home office, but I suggest going somewhere new, fresh, and free of distractions.

For a successful solo biz retreat, you should do the following:

  • Evaluate previous goals (what worked and what didn’t

  • Create newer goals (dream big, people!)

  • Map out a marketing plan based on new goals

  • Flesh out a client list to inform what kinds of clients you want to work with in the future

  • Refocus priorities and figure out how to stay motivated in the day-to-day

To help you brainstorm for your own business evaluation retreat, here are some questions to ponder:

  • When are you most productive?

  • When are you most creative?

  • When do you crash?

Considering your peak productivity hours should 100 percent play a part in narrowing down your 2019 goals.

  • Which clients did you love and why?

  • Which clients made you want to pull your hair out and why?

  • Which clients brought you the most $$?

  • Which clients did you enjoy working with, but financially, it didn’t really pay off?

Mel suggests rating your clients on a scale of 1–10 in different categories and then adding the number and ranking your clients from best to worse. This felt kind of weird to do, to be honest, but when I did this last year, it was like a million lightbulbs went off in my brain.

Once I figured out who the best clients were for me (for all of the reasons), I could then brainstorm how I could potentially work with them more in the upcoming months. I also gave myself permission to “cut out” the clients or types of clients that weren’t working for my business.

  • How can I replenish my resources?

  • Where and how should I invest in new resources?

  • What resources did I invest in that I can now say goodbye to?

Making a resources wishlist—whether it’s certain courses or associations you want to join or conferences you want to attend—will help you create attainable goals for the year.

Continual professional developmental is key when you’re a freelancer. Don’t forget to stay curious and always make learning a priority. Plus, you don’t know the work opportunities that could come from these learning projects!

  • What are the strengths of my business?

  • What are the weaknesses?

  • What are the opportunities?

  • What are the threats?

Mel also encourages freelancers to conduct a SWOT analysis during a solo biz retreat, and I have to say, this is simple, but SO necessary.

After evaluating the strengths and weaknesses of my business, I created measurable goals one month, six months, one year, three years, and five years out. The three- to five-year goals were not as specific obviously as the one-year goals, but this was such a helpful exercise for me—even if some of them ended up changing throughout the year and evolving into something else.

As freelancers, it’s really easy to keep your head down in current projects you have or simply try to get work for the next month. But we have to be able to be in the present details and planning for the future, which is why a two-day retreat can be incredibly helpful.

If you’re a freelancer planning to make yearly goals and strategically evaluate your business, let me know what works for you and what doesn’t. I’m always looking for new ways to grow!