How I Planned A Solo Business Retreat — And Why Other Entrepreneurs Should Too

Amanda Holliday
4 min readNov 20, 2020
Image credit: Owen Wassell via Unsplash

I recently took myself on a solo business retreat. When I started sharing my plans with other entrepreneurs, I was shocked with how excited they all were about the concept. I was equally surprised that most of them hadn’t considered ever doing the same thing.

Do you think that corporate retreats are just for big businesses? Since you work by yourself or with a small team, do you really need a retreat to set goals, recharge and plan?

Yes!

As entrepreneurs and solopreneurs, how can we carve out time for looking at how far our business has come, where it is going, and how to get there?

Here’s the deal…When you are grinding away on the day-to-day of running a business, it is hard to take time to look at the big picture and to plan and dream about the future.

By planning time away from the distractions of everyday life, you give yourself the time and space to set goals, dream big, and also give yourself some time to relax. Yes, relax!

Photo by Maddi Bazzocco on Unsplash

Best Practices For Planning A Solo Retreat

Plan 1–2 nights away from home

Yes, you need to leave home. The change of scenery and lack of distractions will help you focus and recharge. Book a hotel or AirBnB.

Write down a flexible agenda

Don’t wing it. Give your retreat some structure, just like a larger retreat would have. This will help you stay on task and focused on your goals for the retreat.

Don’t over pack your schedule

Be realistic about how much time you have. Don’t over promise and under deliver for yourself. You don’t have to do everything in one day. If you only have 1 day to get away, do some of the work before you leave. Give yourself flexibility so that if those creative juices start flowing, you don’t have to cut yourself off before you are done.

Plan time for rest and relaxation

This retreat is not just about planning and getting down to business, it is also about recharging those batteries. This can include taking yourself out to dinner, taking a bath, applying a face mask, enjoying a glass of wine or cocktail.

Plan time for movement

Most of your time is going to be spent sitting, planning and dreaming. Be intentional about setting time aside to move your body. Do a yoga video, schedule a class at a local fitness studio, research a local hike or walking trail. Plan this time so you can reset mentally and physically and stay focused and present.

What To Pack

Not sure what to bring with you? Here is your packing list:

  • Comfy clothes
  • Notepad
  • Pens
  • Calendar
  • Entrepreneur Retreat Workbook
  • Your favorite snacks and beverages
  • Computer and chargers
  • Self care items: facemasks, candles, bubble bath, etc.

What planning should you do?

This will depend on your business and your goals, but on my retreat I worked through the following areas:

  • How Did You Get Here? Before getting into the state of your business and where it is going, spend some time reflecting on where you’ve been and how far you’ve come.
  • Where Are You Now? Take stock of where you are right now in your business. Being in your business every day, it can be hard to step back and analyze what is working and not. Take this time to do that.
  • Drains & Fills: What parts of your business fill you up? Which ones drain you? Think about how different projects, tasks, and people make you feel. Are there things in your business you dread doing? Things you put off as long as possible? What about the tasks and clients that light you up?
  • Strengths & Weaknesses: Be honest about your personal strengths and weaknesses when it comes to your business. Are your strengths being utilized? Are there people or services that can help compensate for your weaknesses?
  • Audit: Calendar, Client, Projects, Tasks: Take a look back at the last year. What projects, clients, events added value, were highly profitable or brought joy. Which felt like headaches?
  • Core Values: Have you identified and written down your core values? If not, ask yourself some questions to help determine what your core values are.
  • Dreams & Vision Board: What do you dream your business will look like in one year? 5 years? Bonus activity: take time to create a vision board with these dreams in mind.
  • Goal Setting: Translate your dreams into goals. Map out your goals for the coming year. Aim for setting 5–7 annual goals and then focus on a couple each quarter.
  • Idea Mapping: Ideas drive a creative business. But having an idea isn’t enough. The idea needs legs to go anywhere. The idea is the starting line. Spend time mapping out the idea, who it is for, why they want or need it, why you are excited to create it, and how you will launch it.
  • Investment Plan: How will you invest your time, energy and money in your business this year?

Are you ready to start planning your retreat? I put together worksheets that will walk you through all the categories above. You can download it here.

Happy planning & dreaming!

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Amanda Holliday

One-woman digital agency. I help small businesses develop digital marketing strategies that convert