Behind The Scenes Of My Solo CEO Retreat

I’m sitting in bed in my hotel room during the last hour of my CEO retreat writing this post. It has been such a transformational 36 hours and I’m so glad I made the time and space for myself to do something like this.

Before I left on this retreat I asked on Instagram and you guys made it super clear that you wanted both a behind the scenes look there and a detailed blog post, so here we are! In this post we’ll go over my original inspiration for the retreat, how I prepared, what I did each day, the outcome, and what I’ll do the same or differently next time! (All of the stories are saved under the CEO Retreat highlight if you want to take a closer look behind the scenes on Instagram.)

First, for anyone reading this who has no idea what I’m talking about, over the past couple days I took myself on a solo creative business retreat…thing. I booked a hotel room about 1.5 hours from home, packed up my car, and holed up to work *on* my business. And I’ll say now that I highly recommend it to anyone reading this post with a business – especially if you have kiddos at home.

The original inspiration for my retreat

I originally decided to do something like this about a month ago. I was feeling bogged down with client work and all of my mom-related responsibilities at home. It was to the point where I was keeping up with client work, but that was about it. I didn’t have the time or space to do anything else. I did my client work for the day, took care of some tasks that probably didn’t matter all that much, and went straight back to mom duty. It was time for a break, a few steps back, and some big picture planning!

My plan was to ask a few business friends to find an Airbnb, meet up, and throw our own little retreat for a couple of days. But the first person I asked couldn’t make it happen for a couple of months. Right away I knew that I couldn’t wait for a couple months, so my solo retreat was born!

I chose a date a couple weeks out and started planning.

How I prepared for the retreat

There were a few pieces that went into my planning process:

• When and where
• Supplies
• What I was going to work on and accomplish

Deciding when and where

The “when” was pretty easy for me. My husband was more than happy (actually, pretty darn excited for me) to do something like this so he was on board to make it happen any time. From there, I coordinated with my mom so I was gone during a time she’d be able to help with Tahlia. Lucky for me, it worked out to be 3 weeks from when I originally had the idea. Not long to wait!

As for where, that took me a bit longer. I knew I needed to be away from my home and even my hometown. I originally tried to find a nice Airbnb, but it turns out those are hard to find in small town, midwest Wisconsin. Who knew?

From there, I started looking at nice hotels. I knew I didn’t want a little one bedroom hotel for $80, I was going to treat myself. I ended up finding an amazing resort, Beacon Pointe, in Duluth, MN. I knew right away that’s where I was headed. There were multiple places for me to work, an AMAZING view of Lake Superior, a fireplace, a jacuzzi, and it was the perfect distance from home (about 1.5 hours).

Packing list

I’m a total organizational and planning nerd so next up came my packing list. I listed out everything from food to office supplies to goodies to help me have fun and relax.

My favorite things included:

• Big post-it pad, markers, and tape
• Post-it notes (lots of colors!)
• Markers
• Big Monthly Planner
• Echo Dot
• Manicure supplies (actually just Color Street nail strips)
• Snacks and drinks
• Ingredients for spaghetti for one less meal out
• Podcast episodes to listen to on the drive

What I planned to accomplish

And last (it probably should have been first), I figured out what I wanted to work on and accomplish. I knew up front that I would work on my business only. I also knew that I wanted it to be tasks I had a hard time completing at home – so bigger-picture planning.

To help, I got inspiration from:

• Reina Pomeroy – I went on a retreat as a part of an accelerator group she hosted in November 2017 and it was incredible. I thought back to what she did and pulled some amazing ideas from it for Day 1. A lot of it is outlined in her Set Better Goals course!
• Racheal Cook – A friend sent me a link to this podcast episode from Racheal and I totally went down the bunny trail (like here) about 2 days before my retreat. And I’m so glad I did! So much of what I did on Day 2 came directly from Racheal’s content.
• Courage & Clarity – And last, on my way to the resort, I listened to Steph’s episode about her business staycation and got some amazing inspiration as well as encouragement to spoil myself and relax!

Thanks to those resources and some of my own ideas, here’s what I had outlined to work on during my time away:

• Set goals and intentions
• Brainstorm what’s working and what’s not
• Financial planning and projections
• Review expenses
• Launch calendar for remainder of year
• 90 day plan
• Marketing and content plan for this website
• Marketing and content plan for Summit In A Box
• 6 months of content mapped out for each business

Behind the scenes of each day

After 3 weeks of dreaming and planning, I was SO ready to dive in once I got to my hotel room. I took the time to settle in, actually unpack my bags into drawers and cabinets, and eat dinner. And from there it was go time!

Day 1: The big picture

I was intentional with what I planned for my first day. I knew I’d only have a couple hours to work since hotel check-in wasn’t until 4 and I’d still need time for dinner. I also kept in mind that I’m pretty useless creativity-wise after 8pm. With that being said, I used that time to get an idea of where I was at overall.

List of everything I’m doing

I started with a big list of everything I’m currently doing and offering in my business. Things like:

• Products
• Services
• Social media channels
• Marketing methods
• Team members
• Tasks

I took about 20 minutes to do this to ensure I wasn’t missing anything important.

What’s working and what’s not

Next, I grabbed some colorful markers and used them to identify:

• What was working
• What wasn’t working
• What needed to go
• What needed to be outsourced
• What needed to be revisited, reworked, or get more attention

I was pleasantly surprised with what I found with this exercise. In the past, I’ve had a ton of extra stuff going on in my business but since last year was a year of simplifying for me, there wasn’t anything I decided wasn’t serving me well and only a couple things I found that I needed to take off my own plate and put on someone else’s.

Evaluate expenses

After I took some time to reflect and make quick notes of tasks I’d need to complete and assign based on my findings, I moved onto reviewing my recurring expenses. I decided to move on to this, since at this point in the evening (like…8:00 lol) I was tired and needed something easy and systematic, rather than something that required a whole lot of brain power.

This is something I like to do at least a couple of times per year to make sure I’m not paying for something I don’t need. Again, I did a big purge last year, but I did find one $200/year subscription that I wouldn’t have cancelled in time without doing this.

Financial projections

And I wrapped up the day with financial projections for the remainder of 2019. If you’re not familiar with doing this, you basically make a spreadsheet with all of the income and expenses you anticipate each month. I broke out the different types of products and services I offer and estimated what I’d make from them each month and broke down expense categories and estimated the money I’d be paying out.

The goal of this is to see where you’re sitting profit-wise. When I did this exercise for 2018, it was scary. If I remember correctly I was going to lose $5-10k throughout the year with the initial plan I had. So from there I planned different launches, raised prices, and adjusted expenses to make at least a little profit.

This time though, I was pleasantly surprised. Without having to make any changes I had a projected profit for 2019. Yay!

From there, you have a spreadsheet that looks exactly the same with actual income expenses. I filled out the actual income and expenses for January and February and called it a night!

For more information on financial projections and an awesome spreadsheet tracker, be sure to check out Reina’s Set Better Goals course. She’s the reason I even know this is a thing!

Day 1 wins

I kept track of my wins for each day (and I totally recommend that you do too!). They were:

• A lot of stuff is working
• No big commitments that I need to stop
• In the green for the first round of financial projections

Day 2: 90 day plan, marketing, and content planning

The second day, and my only full day, was when I planned to tackle the big ticket items. And I did!

I did some launch planning, set 90 days goals and broke them down, reworked my marketing, and mapped out 6 months of content for this blog and Summit In A Box. I also hit a hardcore midday slump…but we’ll save that for the “what I’ll do differently” section later on in this post.

Launch calendar

I started the day (after getting distracted by a Facebook ad and hiring a Pinterest manager) by mapping out my launch/promo calendar for the rest of the year. I grabbed a big post-it and marker, broke it into 12 sections, and started by adding the things I already knew were coming up like next month’s summit and a launch for Summit In A Box.

I filled in a couple more months with potential promo ideas, left a couple blank, and called it good!

This was a pretty quick and simple exercise, but the point was for me to have a visual to reference and make sure I wasn’t over-committing in the rest of my planning.

90 day plan + task breakdown

Using the launch calendar, I worked up my 90 day plan. This and the rest of what I’ll tell you here came from Racheal Cook so head over there to get all the details and some amazing worksheets.

With my 90 day plan, I let myself have 3 focuses per month:

• One was always client work
• One was something I was promoting or launching
• And the last was something I was creating

I’m one to schedule #allthethings at once, so limiting myself to three was really important.

From there, I assigned 5 goals to each month based on those focuses.

I grabbed my colorful sticky notes, used one color per goal, and broke each one down into smaller tasks. Then, the sticky notes went onto my Big Monthly Planner.

This setup was perfect for me because I could move tasks around easily when I had too much going on in a week.

As I was doing this, I was also writing down what my top 3 focuses would be per week, with one of those always being client work.

Aaaand after that I hit a wall and did just about nothing for 4 hours 😉 #winning

Updated marketing strategy

Once I regained my focus, I moved onto my marketing strategy for this brand and Summit In A Box. I used this amazing blog post by Wandering Aimfully  to map out a customer’s journey through my brand.

I didn’t discover anything ground-breaking, but did decide that I need to:

• Focus on getting more new traffic for both businesses
• Try different opt-ins for Summit In A Box
• Get more from my content (better plan for the content itself + method of promotion)
• Continue showing up on Instagram stories
• Keep making real connections with people

6 months of content planned

After revisiting my marketing strategy I felt more excited about the type of content I could create and the purpose of that content than I had in a while so I moved on to planning content for both of my websites. Going into this retreat I was hoping to have 6 months planned, but by the end I ended up with 8!

I used my launch calendar to make sure I was writing on relevant topics leading up to launches or promotions. Other than that, I included some ideas directly related to what I do as well as a wider variety of topics that would attract new audience members.

For example, on Summit In A Box, rather than making every single post specifically about summits, I included some related to attracting new audience members, collaborating with other business owners, etc.

New content creation + promotion workflow

This wasn’t on my list for the weekend, but just sorta happened. After realizing that I needed to do a better job of sharing my content and mapping out so many new topics, I ended up in Asana reworking my content creation and promotion workflow for my team.

Overall, it’s more streamlined, requires less from me, takes advantage of team members’ strengths, and will make more use of the initial creation effort.

Outlining content

To end the day I started outlining this post. Again, this wasn’t something that I’d necessarily planned to do, but since I was feeling inspired I went with it!

Day 2 wins

Day 2 wins included:

• Outsourcing Pinterest management
• Shifting team member responsibilities to suit their strengths
• 8 months of content planned

Day 3: Putting it all in motion + a new idea

Day 3 was a shorter day, having to be out of my hotel room by 11. But I was good with that and ready to get home to my sweet girl and husband! The initial plan was to load all of the tasks mapped out in Day 2 into Asana and outline as much content as possible. Things didn’t quite go that way, but for good reason! More on that in a second.

Added blog posts to Asana

Since all of my content planning happened on paper or a random text editor, I took the time to add them to my editorial calendar in Asana. I used the new task template I created at the end of Day 2 and assigned each post a due date (aka publish date). From there, one of my VAs will go through each one and assign dates to the tasks of each team member

A new idea + adding tasks to Asana

In launch calendar I mapped out at the beginning of Day 2, there were two promotions that I wasn’t super excited about. They were promotions of existing products I have for this business that either don’t sell super well or that I don’t feel excited about anymore. However, I added them to the calendar anyways because I think it’s important to give audience members the opportunity to get their hands on what I offer, I didn’t want to go 6+ months without selling anything, I wanted to bring in some money apart from my services, and I was determined not to launch anything new.

But…you know how it is when you have a new idea!

As I was finishing up loading my blog post topics into Asana, one of them gave me an instant idea of something I could launch once April’s summit is over. It would align with the summit’s goal perfectly and help people involved in the summit take even more action. It would also be a way to get an income boost from all of the new audience members I’ll have around.

So instead of outlining blog posts, I talked to a couple business besties about this idea, mapped it out, and added it all to Asana.

And since I was already in Asana, I took all of the sticky note tasks I had in my Big Monthly Calendar from Day 2 and added them to Asana as well.

Started this post

At this point I had about an hour left before I had to be out of my hotel room and I hadn’t showered or started packing up. That time limit made me feel a little resistance so instead of outlining new blog posts I felt inspired to write this one instead! I did as much as I could and called it the end of my solo CEO retreat.

Day 3 wins

Day 3 wins included:

• A fun new idea!

What I’ll do differently next time

Overall, I’m calling this a huge success. I achieved what I wanted to and feel so inspired to take action in my business. The two things I can think of that I’ll do differently next time include:

• Plan an outing on Day 2: I thought I’d be able to work from sunup to sundown on Day 2, but that didn’t happen. I hit a slump around lunch time and couldn’t get myself to dive back in. I tried eating, doing my nails, exercising, eating more, taking a nap, and scrolling social media. I finally snapped out of it about 4 hours later after talking to my mom on the phone for a bit. Next time, I’ll plan to do a little shopping or something else fun outside of my hotel room.
• Bring melatonin: This one sounds silly, but the first night I was up until midnight and awake at 4am. And this is coming from someone who is usually sound asleep by 9:30. After so much good work my brain wouldn’t shut off, even after spending some time in the jacuzzi, and I was having anxiety from being away from Jeremy and Tahlia. I was kicking myself for not brining melatonin along.

What I’ll keep the same next time

There are a lot of things I’ll plan to do similarly next time, but the ones most relevant to share include:

• Length: Two nights was the perfect length for me. I was worried it wouldn’t be long enough, but by the end I was ready for a break from working and more than ready to get some baby snuggles. Making it any longer would have also put me in implementation mode, rather than planning and feeling inspired.
• A nice hotel room: I splurged on my hotel room and I’m glad I did. If I do this more than once per year I won’t spend quite as much, but I do think it’s really important to have more than one spot to work. In my room, there was nice-sized table, a couch, a big kitchen counter, and the bed. I used them all!
• Treat myself: I’m good at talking myself out of things like this, but during my 3 days I got ice cream once and coffee from my favorite coffee shop twice. It was a ton of fun and I didn’t even feel guilty. 10/10 would recommend 😉
• Taking inspired action: And last, I’m glad that I let myself focus on what I was feeling inspired by, even if it meant a little jumping around. It brought up ideas I wouldn’t have had otherwise and kept me focused overall since I didn’t keep having a nagging thought of something I wanted to work on later. I just did it!

The real MVP

And I just have to throw in a little shout out here to my husband, Jeremy. I had a couple people ask me on Instagram how they can convince their husband to let them do something like this and that really made me stop and realize how lucky I am.

There was no “convincing” or “letting” in my situation. My husband was more on board with the idea than I was in the beginning. He realized that after 14 months of being a nursing mommy that I deserved a little break and he very highly values what things like this do for my business. Every time I invest in a program or take time for something like this, my business grows, and he sees that.

So a cheesy little thank you to Jeremy for being so loving and supportive, taking such perfect care of our sweet girl, and not making me question that this was the right call.

Is it time for you to take a CEO retreat?

I know that so many excuses can come up for letting yourself do something like this.

For me, those excuses look like:

• I’m still nursing and it would be a pain for Jeremy to have to give her bottles
• I wouldn’t be a good mom if I left
• It’s selfish

But really, all of those excuses are so silly after seeing how transformational this was.

So, I’m telling you right now that you CAN give yourself permission to do this. Pick a date in your calendar and make it happen!