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The Marriage System: Transforming Family Life With Caitlin Theobald


December 14, 2023


What emerges from this interview is a firsthand exploration of what it truly means to implement a marriage system that not only transforms your individual experience but also profoundly influences your husband within the context of your marriage. It stands out as one of the most cherished and longest used systems crafted by Blaine and me. 

In the earlier stages of my entrepreneurial journey, I developed a course named “Systemize Your Productivity,” initially focused on time management. However, as inquiries about my business practices increased, I expanded the course to include relevant business elements. 

Despite my desire to incorporate marriage-related content, I grappled with the challenge of seamlessly integrating it into the existing framework. This dilemma led to the evolution of the “Systemize Your Life Academy,” incorporating various components. Although I recognized the importance of the current structure, I remained determined to find a space within the academy to address marriage-related aspects, acknowledging their significance in the overall journey to success.

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

Caitlin Theobald: Unveiling The Success Of The Marriage System Journey

In a compelling demonstration of mindful intent and dedicated effort, Caitlin Theobald has not only implemented but also generously shared the insights of a marriage system. What unfolded was an unforeseen and remarkable journey, as she absorbed systems from podcasts, leading to a spontaneous, fully committed decision that culminated in genuinely inspiring outcomes over the past six months.

As a married mother of three, Caitlin navigates the significant responsibility of homeschooling her two older children while her husband frequently works overseas. Embracing a dynamic family life, the Theobalds have adopted a travel lifestyle, uniting with Caitlin’s husband in safe countries whenever possible. Amid the constant flux of packing and unpacking, Caitlin ensures her children’s education remains uninterrupted on the road through homeschooling.

Harmonizing Family And Passion: Caitlin’s Journey With ‘Systemize Your Life’

In a family deeply immersed in music, Caitlin and her husband share their passion with their musically inclined children. Since Caitlin initiated the “Systemize Your Life” program, there has been a noticeable enhancement in various aspects of her life. While in the past, she effortlessly guided her children in their musical activities, encouraging piano practice or driving them to lessons.

However, as a musician with a profound desire to study and emotionally connect through worship, Caitlin found it increasingly challenging to carve out time for her own musical pursuits. The realization struck that several years had passed without her truly sitting down to play, despite music holding a top spot in her values. The program has proven instrumental in allowing Caitlin to reclaim her passion by introducing effective systems into her life.

Recognizing The Need For A Marriage System

Engaging in thoughtful discussions, Caitlin and her husband explored the idea of a couples’ retreat, inspired by positive transformations observed in a friend’s marriage. They weighed the unique benefits of an intimate retreat against conventional group experiences like church marriage retreats. Despite familiarity with the concept, the actual experience remained mysterious, and Caitlin aimed not just for a getaway but a purposeful and enriching retreat.

As they planned a trip to Costa Rica, where Caitlin’s husband was stationed for work, a unique idea emerged. Recognizing the extended period her husband would spend there, Caitlin proposed dropping off the kids and flying to meet him. Simultaneously, she delved into binge-listening to the “Systemize Your Life” podcast, attempting to implement various systems independently.

Initially, Caitlin embraced the idea of systemizing her life independently, confident in her ability to achieve it without a specific program. However, learning that becoming a VIP student granted access to the marriage retreat system as a bonus, Caitlin immediately perceived its value. Taking a leap, she purchased Systemize Your Life, obtained the workbook, and committed wholeheartedly, going all-in on the journey while on her way to see her husband.

Caitlin’s Strategic Dive Into Systemize Your Life

In the Costa Rican airport, Caitlin immersed herself in the marriage system course, navigating through the content on her phone amidst Spanish-speaking surroundings. Hoping to familiarize herself with the system, Caitlin aimed to engage her husband in the process, persuading him to buy into the concept and potentially work through the workbook, despite his rebellious streak.

Reflecting on the course content, every aspect resonated with Caitlin, establishing a profound connection with the structure and format. She believed it was precisely what she and her husband needed. Despite acknowledging the value of a restful trip, Caitlin was determined to ensure their retreat went beyond a mere break.

Unlocking Transformation: The Marriage System Retreat Decision And The Battle For Connection

The thought of leaving her children weighed heavily on Caitlin, leading to restless nights and numerous messages to mentors, seeking reassurance and affirmation about the decision’s worthiness. Deciding to go on a marriage retreat involves a significant degree of trust, especially when entrusting the care of one’s children to someone else. The financial and logistical aspects can be challenging, acting as deterrents for many individuals. However, Caitlin and I both talked about the transformative benefits that emerge from allowing oneself the opportunity to experience such a retreat at least once.

My Take On The Importance Of Marriage Retreats

While acknowledging the challenges that may arise when deciding to go on a marriage retreat, Blaine and I, who co-teach the course, emphasize the importance of taking time away without children. Despite facing obstacles, such as conducting the retreat at home or adapting by hiring a sitter to join us in a hotel, we consistently prioritize and facilitate our yearly retreats. This yearly struggle underscores the commitment required to prioritize one’s relationship.

Navigating a marriage retreat during a phase of intense separation anxiety and grappling with overwhelming feelings of mom guilt can be a challenging experience. There are emotional challenges and internal struggles that can make parents feel like they are falling short.

However, despite the difficulty, we firmly stand by the decision to implement the marriage system, emphasizing the transformative outcomes that can emerge on the other side. The enduring benefits and positive impact on the relationship serve as a testament to the value of overcoming the initial hurdles and navigating through the challenges.

The Spiritual Battle For Marriage And The Transformative Power Of Retreats

Marriage holds profound significance, particularly for women of faith, as it involves navigating the spiritual battle surrounding family and marital bonds. The pressure to make decisions fostering fruitfulness in these relationships is intense. While it may initially seem like taking time away from children, the truth is that what benefits the marriage ultimately benefits the children.

Marriage retreats are the cornerstone of my relationship with Blaine; without these retreats, navigating the challenges we faced might have been insurmountable. The shared system cultivated through these retreats serves as a crucial anchor, holding us together during the most challenging times.

The ongoing battle for family and marriage is universal, challenging the belief that one will never face disconnection in matrimony. Everyone is susceptible to relationship challenges, and no one is exempt from this reality. Retreats become a proactive means of fortifying your relationship against the unpredictable challenges that may arise, providing a strong foundation for navigating the uncertainties of life.

Navigating Family Values And Foundations Through A Transformative Retreat in Costa Rica

In the heart of the Costa Rican jungle, Caitlin and her husband embarked on a transformative retreat, setting the stage for a journey of intentional living. Upon arrival at their beach resort, Caitlin, eager to fully immerse herself in the marriage system, requested the resort staff to print her workbook.

With a spontaneous and flexible approach, the couple delved into their creed and legacy statement, shaping a vision for their family. This retreat became a pivotal time for aligning family values, addressing schedules, logistics, and the need to reconnect after seven months of her husband’s extensive travels.

Through intentional conversations, Caitlin and her husband made significant decisions for the upcoming summer, not just planning activities for the kids but also enrolling them in schools. Instead of a lengthy to-do list, they focused on identifying their values, confidently saying “yes” to aligned opportunities and purposefully saying “no” to those incongruent with their highest values, deferring some discussions for a later, more opportune time.

The Role of Marriage Retreats In Nurturing Meaningful Conversations And Clarity In Relationships

Often, people may not realize that these discussions aren’t merely about superficial preferences. Instead, they delve into the deeper values that shape one’s identity as a parent and influence desired outcomes for their children. These conversations go beyond the surface level and explore the significance and meaning behind various choices. These include financial expenditures or personal indulgences, uncovering the underlying motivations that contribute to conflicts.

Blaine and I embraced the idea of marriage retreats because we were advised that aligning ourselves from the start reduces year-long conflicts. While occasional disagreements still occur, having our agreements documented provides a clear reference point. Even if we don’t do it perfectly, the clarity gained from the marriage retreat is obvious.

We manage to do an okay job, recognizing that there’s room for improvement in the years ahead. The ongoing practice is part of the journey. The beauty lies in the clarity gained—no more questioning why certain activities matter to each of us. It’s about understanding and respecting the priorities we’ve established through open conversations, free from distractions like burning dinner or children’s needs. The marriage retreat provides dedicated time and space for uninterrupted connection and meaningful discussions.

Navigating Life’s Challenges: How Systems Provide Support Amid Loss And Transition

Navigating the challenges of dealing with Caitlin’s father’s early onset Alzheimer’s and his passing in June, the Systemize Your Life course emerged as a grounding force, offering a sense of hope amidst the pain. Discussing potential needs for the marriage retreat was crucial during this emotionally charged period. While Caitlin’s husband was wonderfully supportive, expressing expectations and the desire for his presence during challenging times made a significant difference, transforming him into her hero and a pillar of support through one of the most significant losses in her life.

Upon returning home to a house in progress, with not everything fully sorted, completing the Systemize Your Life course in November provided clarity on their direction and actionable steps. The knowledge gained from the course has been invaluable, ensuring Caitlin doesn’t feel isolated in navigating these challenging moments. It acknowledges that, in times of grief, even seemingly mundane tasks can unexpectedly weigh heavily on one’s spirits. This comprehensive approach highlights the importance of the Systemize Your Life program in providing support during life’s most difficult seasons.

Navigating Loss, Intentional Living, and Transformative Day-to-Day Shifts Through The Marriage System

The loss of Caitlin’s dad prompted deep reflections on legacy and the significance of day-to-day living. His remarkable ability to make everyone in his life feel like a priority, despite having a large family, left a lasting impact. Losing him underscored the importance of living life with intention and a focus on meaningful connections. It evoked a sense of readiness to shed unnecessary burdens and embrace a humble receptivity to life’s experiences, reminiscent of the biblical verse encouraging the casting off of entanglements and running the race with purpose.

Caitlin was determined to follow Chelsi Jo’s advice and pour her heart into every aspect of it. With a commitment to humility and a willingness to take advice, she’s already witnessing significant fruit. The transformation is profound, emphasizing the idea that altering day-to-day routines has a cumulative effect on the trajectory of her legacy.

Empowering Women To Navigate Life’s Complexity With Purpose

“The essence of my mission is rooted in the belief that magic emerges from the mundane moments of life.”

The essence of my mission is rooted in the belief that magic emerges from the mundane moments of life. The intricate stage where our entire life unfolds is composed of those seemingly insignificant details that often go unnoticed, particularly by many women due to challenges like time management and a lack of organizational skills. 

I consider myself fortunate to have had a mother who prioritized these aspects, even as she juggled work responsibilities. Witnessing her sacrifices fueled my determination to redefine the narrative. My mission is to empower women to manage both their personal and professional lives without losing themselves in the process, navigating the complexity with dedicated attention to patterns and details.

The challenges some women face in managing the intricacies of life can stem from various factors, including upbringing, personal wiring, and thought processes. While holding admirable ideals, the gap often lies in translating these aspirations into real-life practices. 

The ability to implement such ideals is crucial in becoming the present, intentional mother one desires to be, especially during the crucial years when children are young. I love the unique calling and gift in bridging this gap, enabling women to navigate the complexities of life with practical and transformative guidance.

Even Husbands Appreciate The Marriage System!

Caitlin’s husband, a strategic thinker and Marine Corps special operator, wholeheartedly values the Systemize Your Life program. Recognizing the importance of effective systems in managing the dynamic nature of family life, especially with his military background, he considers the investment in the program among the best decisions made. This acknowledgment not only reassures Caitlin but also underscores that the program’s principles extend beyond motherhood, impacting various aspects of their lives.

The positive changes witnessed during the holidays, such as hosting stress-free Thanksgiving and organizing a peaceful birthday party, demonstrate the tangible benefits of implementing systems. The newfound sense of calm in their home has generated excitement for the coming year. Armed with tools acquired from the program, they anticipate enhancing their future marriage retreats. Caitlin’s husband appreciates the lasting positive impact of Systemize Your Life on their daily lives and looks forward to its continued influence in the future.

Investing In Transformation

This strongly underscores the value of financial investments in programs like Systemize Your Life. It transcends mere trends, offering concrete benefits that significantly enhance daily life. When Caitlin discussed the program with her husband, it wasn’t about following a trend but embracing a genuine transformation with practical advantages in their family’s day-to-day activities.

Conveying the value of investments, especially in personal development programs, poses challenges, often rooted in past experiences of unmet expectations. Despite uncertainties, there’s a shared understanding of the transformative power of Systemize Your Life, even when precise outcomes aren’t guaranteed upfront. It’s a substantial investment in oneself, demanding trust and belief in the program’s distinctive approach.

Empowering Mothers: Caitlin’s Journey With The Marriage System

Acknowledging and valuing the often unseen and private work of mothers is a significant aspect of the Systemize Your Life program. Caitlin emphasized the importance of the program’s community aspect, where participants can share their experiences, receive encouragement, and be recognized for their efforts. 

This communal support serves as a game-changer, helping moms overcome their inner critics and appreciate the value of their work as homemakers. In a society where such contributions are sometimes overlooked, this shift in perspective becomes empowering and transformative.

I want to take a moment to acknowledge and appreciate the tremendous effort and resilience Caitlin has demonstrated in implementing the Systemize Your Life program. Her commitment to consistency during challenging times, such as dealing with the loss of her father, is truly commendable. 

It’s evident that her dedication has not only impacted her home, bringing light to her family, but has also resonated within our community. Her openness and the sharing of her experiences today have been inspiring and deeply moving. Thank you, Caitlin, for being a source of strength and encouragement for others.

Resources To Get You Started

If you’re inspired by Caitlin’s story and want to explore the Systemize Your Life program, head over to chelsijo.co/syl for more information. Whether you choose the DIY option or the comprehensive VIP experience, there’s an opportunity for you to enhance your life and create meaningful changes. Your journey awaits! Don’t forget to look into our other blog posts where I highlight marriage like How Creating A Legacy Statement For Your Marriage Can Impact Future Generations.

Thanks again for being a part of this conversation.


Frequently Asked Questions

My husband and I need the marriage system! How do I get started?

First, check out our free Facebook group, where you can find help and support as you jump into this system. Or jump right into our program where the marriage system is held: Systemize Your Life.


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