Mastering Growth: A Deep Dive Into The CEO Retreat Experience


December 19, 2023

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I’ve returned and officially settled in after my significant event, what I fondly refer to as my CEO retreat. This can also be called a leadership retreat because, in today’s context, it very much encompasses both roles. I’m thrilled to spill the details because I’ve received numerous inquiries. 

Fresh off this year’s retreat, the insights are still vivid in my mind, akin to that post-birth moment when you’re encouraged to capture the birth story before details fade away. So, even though my suitcase remains unpacked, I’m diving into sharing the recent experience while it’s still crystal clear.

Honestly, my CEO retreat is no walk in the park. It involves a substantial amount of work, to the extent that it can be quite exhausting. I’m here to provide a recap of my CEO retreat—why I undertake it and its significant benefits. I also want to take you through the honest details: the preparation, the actual event, and the aftermath. It’s crucial to understand the entire process, not just what happens during the retreat. By sharing these insights, I aim to give you a comprehensive understanding and help you assess its relevance to you.

Listen below for the entire episode on The Systemize Your Life Podcast

The Evolution Of The CEO Retreat

This retreat is a unique creation born out of collaboration between myself and my good friend Stefanie Gass. Stefanie is a successful online business CEO, specializing in teaching people how to generate income through podcasting, coaching, and courses. If you’ve been following my podcast, you’ve likely heard her on previous episodes, and if not, I highly recommend checking her out.

This retreat, which we unintentionally started four years ago, has evolved into a well-crafted process. Stefanie has been a significant influence on my entrepreneurial journey, and this retreat encapsulates principles that have been integral to my business for a long time.

From The Dreamer Summit To Essential CEO Retreat

Over the last four years, this retreat has undergone significant evolution. Stefanie and I have integrated it into our mastermind, which now also involves our friend Polly Payne and our respective teams. The genesis of this initiative traces back to our joint participation in the Dreamer Summit, an online event Polly Payne used to organize. Stefanie and I were both invited to speak at this summit, and the idea to collaborate on an online event sparked during that time.

In a nutshell, our initial CEO retreat happened during the Dreamer Summit, and from that point, it has organically transformed into something I now consider absolutely essential. While elements of this process are covered in my teachings within Systemize to Scale, a significant part, especially in terms of planning and preparation, is something I’ve always incorporated into my business and now share extensively.

Why You Need A CEO Retreat Every Year For Clarity And Focus

The burning question you might have right now is, “Do I need a CEO retreat in my business every year?” The emphatic answer is yes, you absolutely should. Now, it might not resemble mine, and that’s perfectly fine.

What I’m practicing in my CEO retreats today isn’t a carbon copy of my initial experience or even the ones I did with different entrepreneurs in the past. However, it has consistently provided me with the clarity and focus essential for navigating the upcoming year. It’s akin to the annual marriage retreat I undertake with Blaine, both serving as crucial pillars in maintaining clarity and alignment in different aspects of life.

How To Kickstart Your CEO Retreat

Before you charge ahead in any direction, it’s crucial to address any lingering questions in your mind. It’s about having concrete, provable data—facts, written plans, measurable objectives. Without this, you risk spinning your wheels on tasks that may not matter at all. If doing this for an entire year seems daunting, break it down into quarters. Stay hyper-focused on the present and the immediate future, gradually building trust in yourself and the process to set and achieve goals further down the line as your business evolves.

This commitment to planning and following steps stems from my experiences in junior high and high school, where leadership roles and meticulous planning were integral to my growth. I’ve witnessed the consequences for those who neglect this process, experiencing short-term success followed by inevitable struggles. So, the resounding answer is yes. Yet, the key is understanding what this process might entail for you and your business, delving into why it’s a necessary affirmative.

Navigating the complexities of business ownership and motherhood while striving for growth demands a clear target, a vision, and a well-defined path. If strategic planning isn’t your strong suit, that’s likely why you’re here. And that’s perfectly fine. Let’s dive in and figure out how to get started on this journey together.

Breaking Down The Process

Grab a piece of paper and get ready to take notes. This is going to be a casual, anecdotal chat where I’m breaking down the recap of my CEO retreat. Imagine we’re sitting down for coffee, and I’m sharing the details as you asked. If you have more questions or want to discuss further, feel free to drop them in the group or send me a DM. I’m here to share insights and details about anything I might not cover in this conversation.

Speaking from a place of vulnerability, I want to lay out all the details of my CEO retreat experience—from the initial preparations to the event itself, and now the wrap-up, which I’m currently seven days out from completing. It’s essential to note that every person’s perspective and outcomes from an event like this are unique, and that’s what makes it so fascinating.

Preparing for my CEO retreat this year was quite challenging, as we aimed to engage in more meaningful work during the event. Anytime you seek success, preparation is key. Managing hectic schedules and attending to a handful of non-school-age children at home for five days requires thorough preparation—it’s the name of the game.

From Detailed Plans To Photoshoot Perfection

After analyzing a significant amount of data, Stefanie and I assessed what we did last year and set goals for this year. We meticulously created an entire workbook to outline how each day would seamlessly lead into the next. A considerable portion of our preparation involved organizing this detailed plan. Given my approach to task management and business workflows, I tracked every aspect of our preparation, and it amounted to approximately 15 hours. We conducted around five three-hour sessions, focusing on completing the workbook and preparing for our photoshoot.

During my CEO retreat, I choose to conduct my yearly branding photoshoot, and it requires thorough preparation. We enlist the talents of an exceptional brand photographer, Denise Karis, based in Arizona, whose work I truly admire. Her patience and energy are remarkable, and I initially connected with her during my time running an event-based wedding business. Our collaboration has spanned over eight years, and I highly recommend investing in a high-quality brand photographer, whether or not you incorporate it into your CEO retreat. Consistency with a skilled photographer contributes immensely to elevating your brand and online presence. 

The Details Of The Photoshoot

For the branding photoshoot during the CEO retreat, meticulous preparation was key. I acquired a guidebook from Etsy and adapted it in Canva to align with our goals. Planning each outfit was a deliberate process, involving a thorough closet try-on session. In prior sessions, Stephanie and I reviewed our past images, creating lists of what we loved, what we didn’t, and what we wanted more of. This critical analysis informed our decision-making, ensuring we repeated successful elements and avoided what didn’t align with our brand vision.

This year marked a significant enhancement in our CEO retreat with team members assisting during the photoshoot—a true luxury. Their support included steaming our outfits and ensuring a smooth process of changing between shoots. The meticulous organization was evident, with each outfit meticulously arranged on labeled hangers. This level of preparation, even without additional assistance, proved highly effective, resulting in an abundance of diverse images from a single shoot.

The Comprehensive Prep For A CEO Retreat

The preparation extended to readying my home for guests and ensuring my children were well taken care of in my absence. This involved completing their laundry, stocking the fridge, and organizing the living space. Despite the exhaustion, the excitement for the upcoming event overshadowed the extensive pre-event preparations.

The meticulous planning extended to the event itself, covering details such as meals, daily schedules, and special activities. Every aspect, from dining locations to the timing of events, was thoughtfully arranged. Polly Payne played a significant role, guiding us through a session where we could dream and fill out planners, reinforcing the idea that much of the groundwork was laid before the actual event to ensure a seamless and productive experience.

Navigating Unforeseen Challenges

Despite meticulous pre-event communication about everyone’s health and safety, an unexpected challenge arose as one participant fell ill shortly after everyone arrived. This led to the individual being quarantined in their room. Additionally, there was another case of mild illness, requiring adjustments such as virtual participation for those affected. The situation, although unforeseen, highlighted the resilience and adaptability of the participants, turning an unexpected hurdle into a manageable aspect of the event.

Despite unexpected challenges, the event continued with some adjustments to the schedule to accommodate the health-related hiccups. The team demonstrated flexibility by starting slightly later each day, ensuring the well-being and happiness of all participants. Fortunately, the impact on the content delivery was minimal, and the team even found they had more time for various aspects of the event. Now, let’s delve into how each day of the event was structured.

Kickstarting Our CEO Retreat

For day one, it’s highly recommended to incorporate something enjoyable and dream-focused. A pleasant dinner is also advised. The use of binders is strongly recommended for its practicality, as it allows participants to keep track of worksheets and notes throughout the entire year. This involves hole-punching the relevant materials and organizing them in a three-ring binder for easy access and reference.

Ensure to bring your planner to the event. On the first afternoon or night, consider doing a photo shoot right away. This allows you to get it done and over with, providing a super satisfying start to the event.

Setting The Stage For Success

After the photo shoot, the vital focus of the CEO retreat is addressing what didn’t work in the previous year. This reflection can be done at the end of the year, whether in January, late November, or any time in December. The timing is flexible; the key is establishing a rhythm that works for you. Really, it can start in the middle of the year, if that’s what works. Personally, I appreciate knowing my plan for the entire year from January, particularly for accounting and the start of a new calendar year. This process helps create a clear roadmap for the next 12 months.

During the CEO retreat, a crucial aspect is sharing and analyzing numbers. Participants discuss the sources of leads, income streams, and identify areas where people may encounter obstacles. This thorough review provides insights into what’s effective and what needs improvement. For those who may be new or lack extensive data, it’s acceptable to make informed estimations or express aspirations. Any input contributes value to the discussion.

The Strategic Approach At Your CEO Retreat

For those at the initial stages of their business journey, projections for the upcoming year can be centered around achievable goals. Whether it’s the number of podcast downloads, building an email list, or initiating new projects, setting realistic projections becomes a focal point. Even for those launching and establishing their presence, these initial goals serve as stepping stones towards future accomplishments. 

Establishing monetary goals, even if they initially feel arbitrary, provides a tangible target to strive for in your business. In the early stages, like the example of aiming for $10,000 in a year, it creates a framework for your efforts. These goals may have variations throughout the year due to different sales periods or initiatives. The key is having a clear aim that motivates and guides your actions.

Collecting and analyzing data from the previous year is integral to refining your business strategy. It allows you to identify what worked and what didn’t, offering insights for more informed projections. Having well-established workflows and systems in place aids in systematically gathering this crucial information. The collaborative aspect of a mastermind, combining various perspectives and insights, enhances the effectiveness of the analysis and the formulation of a comprehensive strategy.

From Modest Beginnings

The evolution of your CEO retreat over the years highlights the organic growth and transformation of your approach to strategic planning. The initial simplicity of a co-working space and a small conference room has blossomed into a well-structured and impactful annual event. This journey underscores the importance of starting with what you have and gradually refining the process based on experience and insights gained along the way. The essence lies in the collaborative and enjoyable nature of the gathering, fostering both professional development and a sense of camaraderie.

“Meaningful and impactful endeavors often begin with a simple see of an idea.”

The emphasis on starting small and gradually nurturing the growth of your CEO retreat is a powerful reminder of the importance of taking that initial step, no matter how modest.  Meaningful and impactful endeavors often begin with a simple seed of an idea. Your journey from a small conference room to the grandeur of an Airbnb showcases the evolution fueled by commitment, learning, and continuous improvement. Encouraging others to initiate their process, regardless of the current scale, reinforces the notion that every significant journey starts with that first, often modest, step.

The Power Of The Focus Statement

So here I am, reflecting on the crucial moments of our CEO retreat, and one thing stands out – the power of having a clear focus statement. Last year, I poured my heart and soul into helping fellow CEOs reshape their businesses, guided by my operating system. It was a fulfilling journey, witnessing their transformations, but amidst it all, I neglected having a focus statement for myself.

This year, we were resolute that each of us would walk away with a crystal-clear focus statement. Day two was dedicated to distilling our aspirations into actionable plans. Month by month, we mapped out what we’re doing, what we’re selling, when and to whom. Hard numbers became our allies – sales targets, conversion rates, the whole nine yards. It’s a game-changer. This focus statement is not just a wish list; it’s a roadmap for the year ahead.

Focus Statements Lead To Implementation

For those of you contemplating this process, start now. Whether your focus statement has concrete numbers or general goals, it doesn’t matter. What matters is putting it down, taking that first step. This is a journey that evolves over time. Your focus statement today might look different a year from now, and that’s perfectly okay. The key is to begin and refine as you go. Trust the process, embrace the journey.

Moving on to day three, our focus statements took center stage as we delved into strategic planning. It was the time to chart out the “when” of our objectives. When are we executing this? When are we launching that? These conversations are crucial because, let’s face it, as CEOs, we sometimes find ourselves in silos. The temptation to shift or pivot arises, and having these discussions with peers is invaluable.

Being in that room allowed us to iron out the details, ensuring our plans aligned with the focus statements we crafted. It’s easy to get carried away in the lone wolf mentality once you step out of that retreat environment. Random whims and stray actions can jeopardize the goals we set. So, setting up these plans served as a compass, guiding us through the year, making sure we stay true to our commitments. It’s about avoiding the pitfalls of inconsistency and maintaining the integrity of our strategic vision.

Turning Strategies Into Actionable Workflows

Day Four was like stepping into my wheelhouse—it was all about implementation planning. This is where the rubber meets the road. We took those high-level plans, those big strategies, and translated them into actionable workflows. It’s not just a vague idea of what needs to be done; it’s a clear roadmap of tasks, events, and projects.

The key here is meticulous scheduling. We not only identify what we’re going to do but also what we’re consciously choosing not to do. Every commitment, event, and project gets a designated spot on the calendar. We build them into our workflows and project columns, and they find a home in our Google Calendar. Now, there’s crystal-clear clarity on when family vacations are a no-go because, well, there’s a business event on the horizon. It’s the beauty of having a well-organized, structured plan that leaves no room for ambiguity.

Prioritizing Family And Business

I’ve reached a point where I no longer want to find myself juggling significant business endeavors while my family requires my attention. It’s a luxury I am fortunate to have, and I’m making the conscious choice to avoid it. I’ve been there before, especially in the past year, and it was a challenging experience. While I appreciate the lessons it brought, I’m determined not to repeat it. I want to be fully present for my family when they need me, without feeling torn in different directions. This aversion to feeling pulled in multiple directions is precisely why I’ve invested time in creating the systems that now guide my business and life. It’s about finding harmony and balance, ensuring that I can dedicate focused time to both my work and my family without compromising either.

Several factors contributed to the challenges I faced last year, with one of the most significant being our move, which presented its own set of difficulties. However, upon reflection, I realized that a crucial aspect was my lack of focus and effective implementation. Despite these challenges, we experienced substantial growth, impacting numerous students and engaging a large audience through the podcast. I’m genuinely grateful for these accomplishments, but I’m driven to elevate my performance in 2024. I understand that many entrepreneurs share this aspiration for improvement, and the CEO retreat is a powerful tool to gain clarity and set the course for a more successful year.

Navigating Precision

At this stage, we reached a point where we were crystal clear on our action plan. We not only identified what needed to be done but delved deeper into specific projects, breaking down every task required for completion. For instance, I decided to enhance my podcasting process, addressing some inefficiencies on the backend. With the collaborative support of everyone present, we systematically went through each step, and now, when you access my project cards, you’ll find a comprehensive guide outlining everything necessary to execute the project. The level of detail is immensely valuable and provides me with a clear roadmap for implementation.

Juggling Passion For Home Management And Professional Dreams

One of the most vulnerable things I could share is that I have a hard time focusing when I sit down to do my work. I’d rather vacuum, cook a meal, or engage in home management any day of the week. That’s why I created Systemize your Life—a four-week program that aligns with my passion. I love it so much. So when I get pulled away from that, I always find myself wanting to go back. But I have really incredible dreams, and I have complete and utter certainty that pursuing this is another essential part of my journey.

I just want to ensure that I can show up at both places to the best of my ability. Going to the co-working space helps tremendously, as does having my mastermind. However, being able to sit down and write out everything I need to do and how to do it, especially as the Perfectionist on the Enneagram, helps overcome that initial hump of getting started on something. If I know what to do, it’s done right. It’s the not knowing, the guessing, that always trips me up. Having that clarity was so valuable for me, and at that point, I felt really done.

Post-CEO Retreat Reflections: Unveiling The Exhaustion And Exhilaration Of The Journey

We ended up having a fifth day, and that’s where we focused on some team training, operations, and various aspects for our team specifically. Obviously, that was brand new to us this year—bringing our teams and incorporating that portion into the retreat.

Wrapping up from the actual event, I cannot express to you how unbelievably beneficial this whole thing has been to me. I also wanted to write about what it’s been like wrapping up from the actual event. I had no idea that it was going to be as exhausting as it was.

The event was really hard. It’s deep. It’s hard work; leaving my kids was hard. I missed them so much. The way it ended up with Blaine, we ended up not seeing each other for a week and a half because of his work rotation, then me being gone, and then his work rotation, and then coming home. I missed him sorely. The whole thing was just really hard on me. I didn’t want to touch work for five days. This blog post is the first time I’ve really gotten back into my cockpit or my dashboard where I keep all of my work and felt like, “Okay, I could do this again.”

I’ve been catching up on a lot of sleep lately. Unpacking is still on hold. Instead, I’ve been enjoying downtime with my kids, indulging in Christmas movies, and cherishing moments with my husband. The CEO retreat was intense, especially with all the preparation involved. Looking ahead to next year, I’ll be making adjustments to streamline the process. Reusable elements from this year’s efforts will undoubtedly ease the load.

Lessons Learned With Balancing Business And Life

One key lesson is prioritizing more sleep in the lead-up to such events. Recognizing the importance of rest as we approach any significant undertaking is crucial. Additionally, I’ve decided to extend my time off not just for the five days of the event but for the entire following week as well. This is a commitment I’ll stick to because tackling major initiatives demands my full attention, and I need that extra time to decompress. Instead of immediately diving back into work, I’ll be taking a break to engage in simple joys like roasting carrots and beets to nourish my family. The business aspect of my life often pushes me outside my comfort zone, making this time for family and self-care all the more essential.

For you, it might be the home aspect that feels challenging, and that’s why having systems in place is crucial. These systems aim to make both work and home life more manageable, ensuring you can navigate both without feeling scattered.

Resources To Get You Started

I’ve shared a wealth of information, and my sincere hope is that you take my advice to heart. Between now and the end of January, I encourage you to seek out a partner for this process. Explore our Facebook group, connect with someone in your entrepreneurial circle, or if you’re a current student of mine, reach out within the student community. There are individuals, just like you, eager to embark on this journey together. It requires vulnerability, openness, and a simple ask. I’m anticipating seeing those posts in both of my Facebook groups and witnessing the connections that unfold.


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