How to Plan a Solo Business Planning Retreat
Last year I decided to start doing an annual business retreat and I cannot tell you how big of a game-changer it was for me. Setting aside time to work on your own business when you’re busy running one every day can be tough! Trust me… I get it! It’s incredible what you can accomplish when you have a few days to yourself to really reflect, review and plan for the next year ahead though!
So what do I actually do on a solo business retreat? This was the top question I got when I shared about it on social media. Especially because when people think about business retreats often it’s for companies that have employees or ones that are being hosted by someone else. So what’s my answer? Pretty much whatever you want! The beauty of going on your own business retreat is you do the planning and make the rules for what will be most beneficial for you. That being said, I know that can also be an overwhelming idea so today I’m breaking down a step-by-step guide for how I plan and prep for my retreats as well as a detailed guide of every reflection and goal-planning exercise I do.
Buckle up or pin this post for later because it’s going to get detailed!
The Prep:
Planning the when and where
The first step is… getting it on the calendar! That may sound obvious but being a business owner… time flies by so this year I got it on my calendar well in advance (4 months out). For me, I decided to do mine mid-November because I like to do it towards the end of the year but also before the holiday madness — you really can do this whenever you want though. This year I did a 2-day trip from Wednesday evening to Friday. You could do more or less time but that seems to be the perfect amount of time for me. It is a lot of mental work so I would just be conscious of that! I also decided I wanted to do it mid-week because while it can be fun — it’s still work so I wanted to treat it as such.
For me, the location was also important. You could really go all out and travel somewhere cool, but I like to do more of a staycation. Somewhere nearby so I don’t have a lot of travel time, but also in an inspiring space outside of my office. Last year, I booked a room at a nice hotel downtown with an incredible view of the city. Then this year, I had actually planned to go to the same hotel but about a month before decided I wanted more chill energy so I booked a hotel right on the waterfront. Typically, I’m spending most of my time inside working so I’m just looking for a spot with a nice view that I could also maybe pop outside for a nice walk. Having the option for room service and being able to pack some meals, snacks and drinks is nice too.
Of course, all of this is a personal preference and you don’t actually have to go somewhere if you don’t want. You could do all the exercises I share at home too. Getting away from distractions and being in an inspiring space is just something that has been helpful for me.
What to Pack
Notebook - I love putting pen to paper, especially for reflections, so I have a notebook specifically for my retreats
Sticky notes
Pens and sharpies
Highlighter
Laptop
Comfy clothes and ones that make you happy!
Food and drinks! I like having my room stocked so I don’t have to run out for every meal - perk of a hotel there’s also room service!
Other optional options - posterboard or bulletin board
Day 1:
Setting Intentions
Once you’ve actually made it to your retreat the first thing I do is set intentions for the trip. On my trips, because I’m staying at hotels, usually I can check in late afternoon/early evening-ish so the first evening is focused on prep, intentions, and getting in the right mindset. My first task is doing a short journaling session.
Here are the questions I ask myself:
What do I want to accomplish during this retreat?
Are there any specific things I want to give extra attention to?
How do I want to feel when I’m done?
After that, I then make a to-do list of all of the tasks I want to do that will support my intentions.
Here are some of the things I had on my list:
Journaling session reflecting on the last year of business
Review numbers for where I will land financially in business this year
Reflecting on schedule and lifestyle
Brainstorm session on what I want to do more or less of
Long-term vision planning/check-in
Aligning and setting goals with lifestyle/vision
Review systems and offerings
Map out project start dates/launches for next year
Review internal tasks and priorities to finish by EOY
Relax a little!
After I do my intentions and to-do list. I relax some! I pack a LOT into my full day, so the first evening is dedicated to getting organized and then some R&R to get ready for that. This year, I unpacked and got organized. Then I watched the sunset, had a nice dinner, a glass of wine, took a bath, did a face mask, and headed to bed at a decent hour!
Day 2:
Reflection of the Last Year
After a nice breakfast and walk by the water, it was time to get to work! This first task is a TASK that takes a while but it’s one of my favorite parts. It’s all about reflecting on the last year and journaling it out. Personally, I’m a pen-and-paper kind of girl for this stuff but you could totally type it too.
Here are the key prompts I go through and reflect on:
Reflection on my word of the year for current year - what was it and how did that go?
What worked well in my business in the last year?
What were my top 5 accomplishments I’m proud of from the last year?
What didn’t work so well over the last year that could use improvements?
Checking in with Financials and all of the Numbers
I’m pretty on top of these anyways so there are not really any big surprises — my accountant will be proud of that, ha! One thing I like to do on retreats though is dive in a little deeper and go through my income categories — since I offer multiple types of services. Then I compare those numbers to the previous year. Here are some of the key things I evaluate when going through my financials:
Where will I land financially this year? (Gross, net income, and project categories) how do these measure up against my goals and how did it feel to be at these levels?
Reviewing annual/monthly expenses - Are there any costs that I could skip next year? Any investments or new software or expenses I want to budget for in the new year?
Breaking down income by the number of projects I did in each service category and the profit each produced
Income/project comparison of this vs last year
Provide any additional observations I noticed or changes I made that would provide more context for this year’s numbers
Checking in with my Schedule/Lifestyle
My next journaling and brainstorming prompt is focused on reflecting on my schedule and how that is supporting the lifestyle I want. This year, this was a bigger point because I definitely had some seasons I was working a lot more than I would like and I knew I wanted to make some changes to avoid that in the new year. Here are some of the things I went through:
What would my ideal daily schedule look like? Timing for work hours, when do I get up and go to bed?
What does my daily work schedule look like? Only taking calls on certain days? Prioritizing certain tasks on certain days?
What do my months look like? Would I like to have some half days in the mix? Are there things in my personal life I would like to prioritize? (Visits with family/date nights, etc.)
What does my year look like? How much time do I want to set aside for vacation/and taking days off? Are there certain months I want to take on fewer projects?
What are things that would overall improve my happiness?
Sticky Note Brainstorm — More or Less
After reflecting on numbers and my lifestyle I then move into a brainstorm of things I want to do more or less of in the new year in my business. You don’t have to do this on sticky notes... you could just bullet it out but I like to do sticky notes so I can move things around if I want.
Examples:
I want to create more passive income streams
I want to work less late nights
This exercise helps lay the groundwork for some of the goals I’ll be setting.
Sticky Note Brainstorm — Long-term Vision/Planning
I also use sticky notes for this and like to put key things I would like to achieve in my business and life in the next 1, 3, and 5 years. This is an exercise I do ongoing so I also like to check in with my previous visions. Are those still aligned with where I’d like to go?
I like to do these reflection exercises on how I’m feeling overall in life and where I’m going before setting my goals for the next year for a few reasons. Hitting income goals and growing your business is great, but making sure you feel good about it and are living your life is also super important! The longer I’m a business owner, the more I have shifted my goals to not just hit vanity numbers but to also make sure things are really aligned. It’s something I put even more emphasis on in this year’s retreat too.
Setting Annual Business and Personal Goals
After I’ve really reflected on my vision, the next step is to evaluate the workload I’d like to take on for the next year. Do I want to take on the same amount of work? More/less? Then I set my income projections and goals off those amounts and evaluate if I need to make any changes to my offerings or pricing to also hit the income goals I would like.
Here is the process I go through to set my goals:
What is the max amount of projects I want to take on each month in each category to support the lifestyle I’m after? How many projects of each category or what income range would I like to hit for each?
What do those numbers amount to annually? Do I need to adjust my pricing at all? Or adjust the number of projects I want to take on? (more or less)
How does that break down to monthly income for cash flow. What is the min and max I could make each month based on my project capacity? Do I need to adjust pricing/offerings based on this?
Are there any new income sources I would like to focus more on or launch in the next year? What goals would I like to attach to those?
What word of the year would I like to guide me?
What other non-financial goals would I like to set for the year? What will my check-ins be for those?
What personal goals would I like to set?
Review Systems and Offerings
This kind of piggybacks off the last section. For this, I take things a step further to really look at my offerings and see if there are any adjustments I want to make to things. Do I need to adjust timelines? How I manage my projects? The software I’m using? Are there any other investments I want to make in the new year that could help me? Are there new products/offerings I want to launch? This is all about evaluating the backend of my business, how things are running, and brainstorming on any changes I’d like to make.
Map out Project Start Dates/Launches for next Year
From here I map out all of my available project start dates for the year as well as make launch plans. Because I’ve already set a goal for the number of projects I want to offer, I can then space out projects accordingly and add my availability into Click-up (my project management software). For this I break down when I will offer website or branding start-dates, social media projects, and collateral. This also allows me to adjust start dates based on trips I have planned or time I’ll be taking off. Then the other exciting part is mapping out any launches I’ll be doing and getting dates and tasks on my calendar. Getting things on my calendar ahead of time is KEY for me!
Day 3:
Review Internal Tasks and Priorities
To cap things off, the lastttt thing I do is reflect on any tasks I identified need work and I set priorities for them. Usually I’ll do an “end of year” priority list and make note of all of the things I want to be completed before the new year. Usually that includes some business tasks like website updates, updating case studies, adjusting agreements, etc.
Then if there are other tasks, like new product/offering launches, I’ll usually break down key tasks and milestones and add them to my calendar. Then I’ll also add dates into my calendar for goal and business check-ins, education days, and days dedicated to internal business tasks to help set myself up for success for everything I planned throughout my retreat!
Phew, I knew I did a lot on my retreats but typing it all out really shows I do A LOT! Like I mentioned, the great thing about planning a retreat is the itinerary is up to you, but I hope having a guide for how I’ve done them will help you get some ideas! If you have any questions or other ideas feel free to leave a comment or shoot me an email because clearly, I live for this kind of stuff!
Want to plan your own business planning retreat? We’re making your life even easier with our goal planning workbook
The workbook includes 35+ pages of journal prompts, reflection questions, and fill-in-the-blank sections — Including the exercises we went through in this blog post!
Anna Osgoodby
Founder of Going Bold Studio, Anna Osgoodby is an award-winning designer and social media marketing expert. With over a decade of experience, she specializes in helping small businesses with their social media, branding and Squarespace website design.
