The Pursuit of Enough

Welcome back to our series from two Millionaire Money Mentors who are living out their retirement dream by sailing around the world.

So far we’ve covered When Is Enough Enough? We Sold Everything to Find Out, It’s Not a Number, and It’s Not a Number, Part 2. If you missed any of those, please read them first as today’s post builds on them.

This post is written by the Admiral and tells her journey to life on a sailboat.

And remember, in the very last post they will answer questions from ESI Money readers about this lifestyle. So please leave your questions in the comments below! 

So I now turn it over to the Admiral…

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By The Admiral

After months of soul searching, sitting on the rocks at Botany Bay, I said it out loud: “I think we should sell the Dallas house.” 

It took me a long time to vocalize what had been emotionally building up for a long time. I knew that Sailor had been ready to sell the house years prior. He was not attached to possessions. He would have been happy to transition to a nomadic life aboard a long time ago. 

For me, our home in Dallas wasn’t just a house, but an expression of everything I had built over decades, creating a true sense of roots. The home was my safe environment, and it felt like my own sanctuary. It represented three decades of treasures and memories, gathered through world travels, international engagements, and long-term friendships.

That fall day on the rocky shoreline of Vancouver Island, I gathered my courage to speak the words. I had been thinking about the implications of this conversation for months, recognizing the complexities of managing two concurrent and very divergent lifestyles. I knew that the straddling was costing me one of the personal values I hold most dear: Presence. I also knew that the minute I said the words out loud, a series of events would begin to unfold that would be hard to reverse. I needed to be sure. 

I asked Sailor to sit down on the black rocks at the edge of the Strait of Juan de Fuca. The dense fog obscured the view of the rocks just on the other side of the shallow bay, which only added to the gravity of the moment. Once I said it out loud, a weight lifted off my shoulders. It felt right. I felt the sense of freedom that would come from this decision. Everything I had built, every piece of my identity, all that I had accomplished – it will always be a part of me without the material attachments. It was time to move forward, jump with both feet into our new life.

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I have been asked so many times, in so many ways, if this life aboard was all Sailor’s idea. Whether I was just coming along for the ride, supporting his dream, being a devoted wife. I am not the type of woman to simply follow out of devotion. I have my own reasons, my own dream, my own ways that this experience is aligned with what rings most true. This lifestyle is taking my commitment to self-discovery to new levels, and awakening new parts of me. I have always been an independent thinker and charted my own course through life – long before I met Sailor.

Coming from a dysfunctional, abusive, and poverty stricken childhood, scarcity and struggle were the only constants. Moving 22 times before graduating from high school, constantly being uprooted, needing to reestablish community and circles of friends multiple times per year. I never experienced the concept of belonging. The need to reinvent myself in a new school every few months taught me about reading people and adapting fast. I developed a survival adeptness that evolved into entrepreneurial skills.

At age ten, I knew I wanted to join a summer camp to learn to ride and care for horses – but only the Girl Scouts whose parents could afford it attended that camp. I read about a statewide contest that set me into action. Right there in the newsletter, the challenge was put forth. The Girl Scout that sells the most cookies in the State of Florida wins a free summer camp stay at Camp Wildwood. Selling door-to-door by foot, setting up a table outside grocery stores every day after school, and walking into retail businesses presenting the delicious treats to the employees — 2,196 boxes of cookies later, my ticket was secured. 

Those three weeks taking care of my beautiful white mare, Lightening, and learning to run the barrel races, was my reward. The blue ribbon Lightening and I earned together was a bonus. I learned young how to create desired outcomes, even if it seemed impossible on the surface. 

Devoid of any role models or mentors to provide direction, and being financially self-supporting by age 14, I learned to be scrappy. An empathetic guidance counselor steered me to get a work permit before the legal working age. Since retail stores thrive in evening hours, working 3-10 pm, 6 days a week, allowed for a full time job to pay the bills. My problem solving abilities and resourcefulness were well developed out of sheer necessity. Survival was my super power.

With no savings of my own, and no ability to apply for financial aid since I had no documentation of parental earnings, the path forward was grim. I found my way to a private university that offered me a full scholarship based on academic performance. I moved halfway across the country to attend a school I never heard of, to a city I had never considered, knew no one, and felt no sense of connection or belonging. What the heck is a Horned Frog anyway? General business and communications seemed like a logical curriculum choice that would give me options, since a deliberate consideration of my career path was never a conversation.

Throughout and after my university years, there was a patchwork of early jobs where I tried to find my niche – music industry promotions, bank clerk, travel agent, horse racing management, investor relations. The transitions made no sense on a resume but made perfect sense to me at the time. The jobs provided me with the financial support I needed. The only objective was again survival – paying my bills and not going into debt. The concept of saving, investing – or even understanding what a credit score was – was outside my financial literacy.

The myriad of jobs also gave me a taste of working with teams and hustling to prove my worth in a variety of environments. The frequent recognition of my ability to identify gaps, increase efficiency, and provide solutions seemed consistent, regardless of the industry. In my role as Director of Investor Relations, I passionately suggested pursuing the glaring opportunity to harness the emergence of new technologies. After receiving a literal pat on the head from my chauvinistic boss, I knew it was time to take a chance on myself.

In 1998, I started an interactive technology company. I was fascinated by the possibilities created to be a pioneer on this new frontier: The Internet. The concepts of maximizing process automation and expanding reach exponentially drew me in. Connecting the dots for others, explaining how businesses could leverage each innovation as they were unveiled, came naturally to me. I was enthusiastically offered a few jobs to put my talents to work for others, but I wanted to see what I was capable of, and what new versions of me would emerge. 

With no entrepreneurial experience or education, I started a company with a laptop, some bartered services, and a couple of credit cards to cover expenses until the first payment from a client came through. Surrounded by many more business-savvy founders, I navigated my way through the start-up years, doing my best to project confidence. My lack of experience and resources kept me focused, and pushed me to work harder than anyone else. 

Soon, the business began to thrive, and my self-taught crash course in financial literacy started without me ever signing up. Seeing 5- and 6-figure contracts come in, wrapping my mind around the number of digits on the payments being received. Obtaining a commercial line of credit to improve the company’s cash flows. Learning about payment terms. Managing payroll and payroll taxes. Being responsible for millions of dollars passing through the company’s bank account each year. The numbers were incomprehensible on a personal level. 

The first year I was able to pay myself a 6-figure salary, I felt like I had finally made it. I was no longer scraping by paycheck to paycheck. Financial scarcity was evolving to financial stability – something I had never experienced before.

The office lobby located in a prominent Dallas business center was decorated with trophies from industry awards. The influx of accolades fed each next big step. For decades, I ran the company confidently. I navigated through the economic impact of the dotcom bust, September 11, the 2008 financial crisis, and the constant technology changes that altered the landscape of the industry. The company grew and the team continued to break barriers of innovation and creativity. 

By year 10, the Dallas Business Journal ran a cover story, recognizing my “Techno Tenacity” as a force to be reckoned with. By year 12, the business had 32 employees, generating more than $3 million in annual revenue. In year 15, I was named among Dallas’ Top Women in Business.

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In the midst of my business building years, I had a personal encounter with the outward display of financial success. I dated a man who loved to impress. Everything was over the top, from being whisked away to NYC for front row seats at my favorite musician’s concert at Radio City Music Hall, to a marriage proposal on the helipad at the Burj Al Arab in Dubai. It felt like a fairy tale, and the seemingly financially abundant lifestyle was a jolt to my scarcity mindset. For a fleeting moment, I thought it was right for me. 

I soon recognized the façade for what it was, and faced the reality of having to carry a large portion of the financial burden to fund an unsustainable lifestyle that did not make me happy. The energy it required to keep up appearances was exhausting. The relatively short marriage taught me a lot about who I was not, and how easy it was to project wealth using credit card debt you cannot afford to repay. 

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Business success did not quench my thirst for a solid foundation and the roots I never had. Throughout the years of growing my business, I embraced the relationships and communities that became my world. I assembled my tribes of women founders and entrepreneurs committed to making a positive impact. I relished the many opportunities to bring like-minded business leaders together. Every board seat, every community role, helped me create what I craved even more than business success – belonging.

I voraciously engaged in volunteer leadership within the non-profit organization that had given me so much support along the way: a global organization created to support and uplift entrepreneurs, to give them a safe space to share their fears and vulnerabilities with peers on a similar journey. My contributions were creating the tribe I needed for my own support. Soon enough, I was serving on the Global Board of Directors of this organization of more than 20,000 members across 80 countries, providing strategy and direction for programs to better support entrepreneurs, and enable a more prominent worldwide footprint.

As I witnessed the positive impact a united community of entrepreneurs could make in the world, my passion for global connection emerged as a calling. I was enlisted to lead diplomatic and educational collaborations with the US State Department, the United Nations, and the White House, bridge-building between entrepreneurs and policymakers on a truly international scale. Witnessing the impact on hundreds of entrepreneurs who returned to their home countries feeling empowered by the programs I designed filled me with pride. Seeing the ways they took the lessons and implemented change in their own countries, was humbling and inspiring.

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By the time Sailor and I met, my identity as a global leader was well established. I was speaking at international conferences on the power of entrepreneurship to uplift societies. Organizations would invite me to facilitate workshops designed to empower youth and women entrepreneurs, to give them the confidence to take risks and follow their dreams.

I was proud of the life I had created, and the meaningful impact being made in the world. I had also become a sentimental girl – with furnishings that represented periods of my life, décor gathered from 50+ countries of travel.

While the emotional connection was undeniable, Sailor presented as poor. He lived conservatively, his suburban home was modest and sparsely furnished. He downplayed his business successes and never mentioned the word “investment”. After a few dates, he even suggested that we share expenses when going out and planning activities. It was a little unsettling to think that I was entering a relationship where I would have to carry the financial load once again. I chuckled with my girlfriends that I was used to being self-sufficient, and an authentic relationship was more important. 

Little did I know Sailor was well along the path of creating affluence. The term “stealth wealth” was new to me. I found myself in a very different situation compared to my first marriage. It was years into our relationship before I fully understood the scale of Sailor’s methodical execution towards wealth goals.

When Sailor and I combined our lives into a shared home, I had learned to nest – something I’d never had the chance to experience as a child. We spent a decade sharing our Dallas life together, each of us with our separate successful businesses, and then joining forces and our respective strengths to focus on growing and selling the company he had created long before my arrival in his life.

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My involvement in global leadership and diplomacy led to the realization that it was time to turn the page towards external impact and inner fulfillment. Running a technology company in Dallas was not the end of my story, and my heart was being pulled in new directions. The business was being challenged by having a founder, me, that was no longer 100% present as a leader for the team. The steep technology innovation curve had flattened, making it far less exciting and unable to hold my attention. 

The executive team I put in place, some through acquisition of other companies and their experienced leaders, were fully focused on day-to-day business operations. It was time to let go of the reins.

After thorough contemplation and discussion with Sailor, I decided to sell the business I had founded 19 years prior. The ownership transferred to a larger, national firm that would keep the business running under its existing name, since I had built much recognition and brand equity in the industry. The sale would also keep the existing employees gainfully employed.

Shortly after the sale of my business, it was clear that if Sailor and I were going to start a new chapter together, he would need to step back from his technology firm as well. He had the company running like a well-oiled, very profitable, machine. Selling the business outright for a meaningful sum wasn’t viable since he was such a vital part of day-to-day operations. For more than a year, he encouraged me to bring my human resources, communication, and leadership development skills to the table, to complement his analytical and highly technical focus.

On paper, it seemed like the perfect combination of strengths. Team and leadership development was exactly what was needed. I resisted. Every example of couples working together that I had seen ended in either the relationship becoming completely tactical and emotionally disconnected, or in divorce. Living together and working together would make for very unromantic pillow talk. 

On one hand, I saw the opportunity to work together to create the financial and personal freedom we both desired. On the other hand, it would put at risk the emotional safety and deep connection it took my whole life to find in an intimate relationship. Partnership and belonging was far more important than money. Sailor gently persisted. He saw a path. 

A year of my “no way” resistance was followed by a few months of “what if” and “maybe”, then a few more months of defining boundaries and roles.

The five years of collaborative work that followed, scaling and preparing the business for sale, paid off. The exit gave us a sense of shared success and teamwork, and deepened our understanding of one another. While the definition of “enough” was taking on new shapes for each of us, the proceeds from the sale forced us to internalize that it was no longer about a number in the bank account.

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For me, deconstructing our home in Dallas was more than the shedding of physical possessions. I had spent more than three decades in the same metropolitan area, building relationships and community. Every item in the home meant something. It was not about the monetary value, it was about the story behind it: what it took to earn it, the place it was acquired, or the person that gifted it to me. Distributing and dispersing things had to be done with the same level of thought and care that was taken to gather them.

Close friends were invited to claim anything to which they felt drawn. They would walk through the house, identify pieces they felt would fit well in their homes, and reconfirm over and over again that this was what I wanted. Reassuring them was easy – I would rather a close friend have things that they appreciate and love than sell it to a stranger. Things that would remind them of me from time to time while I am exploring the world thousands of miles away. Furniture, artwork, candles, household products, kitchenwares – all of it had to go. 

I set aside my most sentimental and valuable pieces of jewelry that I planned to take along into my next chapter, and had the rest organized neatly on the guestroom bed, asking each friend to pick 3-4 pieces that called to them. 

A couple of friends had adult children setting up their first apartments. The joy of being able to provide a full set of cookware and dishes for one friend’s son, or a closet full of bed linens and towels for another friend’s daughter, was worth more than any financial price.

When I received a call from a man that wanted to buy a high quality mountain bike for his wife, but could never afford one, it eased the pain of letting go of the birthday gift from Sailor when he wanted to introduce me to mountain biking a few years prior. Seeing the big smile on her face when she sat on the bike in our driveway was payment enough.

As the deconstruction progressed, piles of things laid on the dining room table that were available for sale, or that were being reconsidered as worthy of taking along. In the final two months, a collection truck was scheduled for every Tuesday, giving us a week in between to fill the front room with things to be donated to charities. Every week, the truck was full as it drove away.

After four months of the daily exercise of slowly whittling away everything we own, it was done. The home once filled with memories and emotion was now an empty house. Stripped of everything that made it mine, and the meaning it once held. I walked through each level, each room, each outdoor space. It was no longer the sanctuary I once cherished. I was moving forward into a new chapter.

Staring at the six suitcases, two carry-ons, and one backpack of remaining possessions, the feeling of freedom and untethered possibility pushed through the fear and uncertainty that filled my heart. My eyes filled with tears of release, knowing we were doing what was right for us. We shed the house, the cars, the furniture – but not our identities and not our lives. Those were just unfolding in new ways we had only begun to fully understand.

I left a single art tapestry hanging on the wall as a gift to the new homeowner. It read:

In the end, what matters most is

How well did you live

How well did you love

How well did you learn to let go.

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Those close to me know that I am not one to take the easy route in life. If circumstances get mundane, too comfortable, I stop feeling alive. Without a regular push outside my comfort zone, I get complacent. That is not good for my spirit. 

In my 20s and 30s, I often quenched that thirst with adrenaline: skydiving, deep water scuba, cliff diving, bungee jumping, motorcycle racing. In my 30s and 40s, I redirected that energy to business and social impact programs, pushing my limits and often embarking on uncertain paths that brought with them their own growth and learning. Now I am living full-time on a sailboat, discovering the next layer of me.

There are many aspects of this lifestyle that strike deep chords within me:

• The ocean. The idea of living on the ocean never crossed my mind. It was not a childhood dream. I never wistfully stared at sailboats, or even considered the idea of being propelled by the wind. It was not in my world. But, the ocean. The ocean was my friend, my guru, my safe place. Now I live on the ocean. It is my home.
• Wanderlust. I love travel, but not just any travel. When I travel, I want to be fully present and understand the people, the energy, the culture. Deep immersion travel. I want to explore the off-the-beaten path places, I want to linger a little longer. I know a big part of my motivation in the ways I choose to travel is related to my passion for cross-cultural human connection and diplomatic work. Our sailing life has us in countries for months at a time, collecting genuine friendships along the way.
• Self-discovery. My journey of self-discovery has been a lifelong pursuit. Since I was a child, I remember asking myself introspective questions like “Why am I here?” and “How can I ensure something meaningful and positive comes out of all of this chaos?” Life on the sea teaches me so much about myself and what I am capable of. It shows you the boundaries of my fears, and connects me with my inner wisdom. It is a self-discovery journey.
• Independence. The sense of personal pride and accomplishment I get from knowing I did something myself has often been perceived as fierce independence. I can live with that label. When it came time for Sailor to obtain an international sailing license, I knew I needed to go through the same process and be equally as trained with the same certification. The self-confidence of handling our sailing yacht reverberates in my confidence throughout my life.
• Nonconformity. I have never been one to fit into the boxes of societal norms. I have an adventurous spirit and want to do things differently. Oftentimes, I find people saying “nobody does it that way!” in response to decisions I make or paths I choose. I am grateful that my unconventional ways have created some excitement, many adventures, lots of lessons, and enough success to afford me the freedom to be living this life today.
• Minimalism. There is so much stuff in the world to buy, to store, to use (or not) and to compare to others. Don’t get me wrong, I love high quality products that are useful and bring joy. I also love 5-star Michelin dining, and first-class travel. I am okay with spending money on extraordinary experiences. I no longer have the aversion to spending I’ve had in my past. We are now selective in our purchases, and reminding ourselves to focus on quality, not quantity. Each item we bring aboard needs to find a place in our less than 500 square foot home. We focus on experiences over possessions, every day.
• Presence. In this life, presence is vital. It is the acute awareness required when things go awry, and the constant mental exercise of maintaining simultaneous alternatives to plans. Then, even in the middle of the most intense moments or conversations, everything pauses and giggles uncontrollably burst out when dolphins swim alongside and playfully jump in front of the bow. Mother Nature demands presence.

While the “dream” of sailing the world was not on my radar before meeting Sailor, there are so many things about this life that align perfectly with my own values. I know that I am tapping into something essential in me. When people ask if I am just supporting Sailor’s dream, my answer is clear: “This is my dream. Sailor’s dream. Our dream.”

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Without my identity of “business owner”, my most significant personal growth truly began. The age-old human question that has no single answer. The question that, for me, has been obscured with scarcity and survival. Who am I? 

I had spent my life overcoming adversity, and building a career and reputation to create my sense of self-worth and belonging. That self-worth was very tied to accomplishment, titles, and being seen as “important” in my roles and activities. Yet for me, “enough” isn’t about money or possessions, it’s an internal stillness. 

For the rest of my life, I could have coasted on the professional identity I had built. That was not who I am as a person, and I needed to step off the performative treadmill.

Who I am runs deeper than the constant outside affirmations. This life of living aboard gives me the perfect classroom to discover more, experience more, and open up new ways to contribute and engage with the world. I chose to strip away the external validation loop — the titles, the boards, the recognitions, the constant feedback confirming who I was — and find out what was underneath.

I am learning how to be less eager to accomplish and impress. I am recognizing how much my past success has been driven by the need to overcome scarcity. To be respected and validated. To prove my worthiness and find belonging. It worked. I accomplished a lot and I am proud of all of it. Every past experience has contributed to the person I am today, but is not the totality of who I am.

The recurring question that was driving my life choices came back with a new twist. When is enough enough? The real answer I was seeking, while complex to decipher, was simple.

I am enough.

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That’s it for today.

Stay tuned as there’s more in this series coming up soon!