My Why, Part Two
Written May 27, 2026
As I mentioned in Part One, after my initial years working as a fractional CFO, I chose to take a step back and study art and design. That pivot beautifully coincided with a close friend’s career taking off as a jazz singer. Because she no longer needed her day job, she asked if I would want to interview to take over her role as the personal assistant to an ultra-high-net-worth (UHNW) couple in Manhattan. I jumped at the chance to secure a well-paying role that offered the kind of flexible schedule my previous 9-to-5 roles couldn't provide. I interviewed and got the job.
Technically, I was hired to assist the wife, but over time, I truly served the whole family. I loved that job, and I respected that family deeply. I was working for a smart, intentional couple who had individually climbed the corporate ladder. They were in their 40s and were steadily moving into the top 1% of earners.
Rich vs. Wealthy
My responsibilities included managing their household and running their daily cash flow. Early on, the wife encouraged me to read one of her favorite books, The Frugal Millionaire. That book became a cornerstone for me in helping me grasp the couple’s distinct ethos and philosophy around money.
Part of my job required acting as the family bookkeeper — reconciling checking accounts, managing bill payments, tracking investments and dividends, and processing health insurance reimbursements. Consequently, I was exposed to a level of household cash flow I had never previously conceived of. Yet, simultaneously, my duties included clipping coupons and hunting down the absolute best deals on everyday groceries and toiletries.
It was in that home office — their literal family office — that I first truly understood the difference between being a high earner (the upper-middle-class path my father had trodden) and actually building multi-generational wealth. In short, I learned the difference between being rich and being wealthy.
The way I view it now: Rich describes what a person brings in and spends. Wealth describes what someone keeps and grows.
I also learned that every family carries its own distinct emotional architecture around money. My time inside their home gave me a front-row seat to the fact that wealthy families are ultimately just regular people leading regular lives with a comfortable financial cushion. They still navigate the exact same relational challenges that most couples and families face — they simply face a different tier of financial complexities. Instead of survival anxiety, their stress centers on the weight and fear of expanding financial responsibilities.
Because I operated inside their home, I witnessed these shifts firsthand. I often found myself wishing I possessed the specific psychological tools to support them through those human transitions, rather than just optimizing the operational machinery of their household.
The Mirror of the "Rising Gen"
Eventually, I moved to the West Coast to pursue graduate studies and later relocated back to the East, to Atlanta, to join a nonprofit organization I had become deeply passionate about. The short version of that chapter — which could easily fill a book — is that at its best this organization functioned as a soulful incubation center. We supported individuals in becoming social entrepreneurs, helping them connect to a deep sense of purpose and design a career or business built around service to humanity. The curriculum leaned heavily into Gestalt-style workshops, life coaching, mindfulness, and somatic practices designed to help people live guided by their intuition.
My role there quickly became threefold:
Director of Finance
Event Production (leading execution for retreats and courses)
Lead Coach (facilitating group courses and ongoing one-on-one client work)
If you have ever worked in the nonprofit sector, you know how common it is to wear multiple hats. Those were mine. I completely came alive as a coach, while simultaneously overseeing the distinct mechanics of nonprofit financial operations.
Strangely, during my eight years there, I was continuously assigned to coach students who were the adult children of exceptionally wealthy parents — most of whom possessed robust trust funds. At first, I didn't understand why the universe kept pairing me with these specific individuals. The purely mathematical side of my brain looked at our dollar-for-dollar realities and couldn't see the connection. After all, my parents were not multi-millionaires, I didn't have a trust fund, and I absolutely needed to work to survive.
It took me a long time to realize that while our financial facts were different, many of our internal feelings were the same.
In those coaching rooms, I heard them echo many of the complexities I had felt: the paralyzing fear of making a mistake with money we didn't earn; deep guilt for having an easier financial path than our peers; flashes of entitlement (feeling like the money was somehow owed to us to compensate for the emotional challenges experienced within the family), followed immediately by intense guilt for feeling entitled; and a lingering fear that we were fundamentally incapable of providing for ourselves.
Feelings of unworthiness routinely alternated with that entitlement. My clients wrestled with the belief that they weren't worth such generous investment, which was frequently followed by a manic drive to prove their individual value and worth to the world.
Walking alongside them through their journeys of creating an independent, fulfilling livelihood helped me see that while the number of zeros behind our transactions differed, the emotional shorthand was quite similar. It reconfirmed what I had suspected in Manhattan: while the math of money may be neutral, our feelings about it rarely are. It would still take me a few more years to learn that fields like wealth psychology, financial therapy, and family wealth dynamics even existed, but the seeds were planted.
Inside the House Looking Out
I ultimately left the nonprofit world because logging often up to one hundred hours a week for a maximum salary of $36,000 a year is simply unsustainable. Around that same time, my parents candidly shared that whatever inheritance would remain after their passing would not be enough to sustain me long-term. Like many of my colleagues who were not independently wealthy, it was time for me to transition.
That departure, however, opened the door to the final piece of the puzzle. A former course participant whom I had coached reached out to me after I relocated from Atlanta to rural Northwest Georgia. It turned out she lived just under an hour away from me. She reached out asking for professional help, and that request launched my next entrepreneurial endeavor: serving as an estate manager for an UHNW family navigating a profound systemic crisis.
While discretion prevents me from sharing the details of that period, three core observations completely altered the trajectory of my career and solidified my decision to enter the field of family wealth dynamics:
The Weight of the Learning Curve: I watched a family member courageously rise to the occasion, rapidly absorbing complex information about where the family wealth lived, how it was invested, and the intricate, multi-generational design for its future allocation.
Grief as a Barrier: I saw how incredibly agonizing it is for an individual to process that massive financial learning curve while actively submerged in deep grief and personal struggle during a family crisis.
The Gap in Advisory: Just as I had felt years earlier in New York, I possessed a profound desire to support her through those emotional layers, but realized my operational boundaries and standard coaching tools weren't specifically tailored to the intersection of family systems and complex wealth.
I utilized my coaching background as much as possible — acting primarily as an emotional anchor she could lean on while navigating the chaos — but I knew standard training was limited. I wasn't fully equipped to address the deep, interpersonal family dynamics she was confronting, nor did standard financial advisors have the capacity to hold space for her emotional learning curve.
That realization launched the intensive research phase to define the exact role I was evolving into. I quickly discovered that a small group of family office advisors had been identifying this exact vacuum from a different angle — viewing it from the outside of the house looking in. I was looking at it from the inside of the house looking out.
When I discovered the handful of pioneers who have built dedicated advisory practices bridging the gap between family wealth and family psychology, I knew I had found my true calling.
I am incredibly excited to use this blog to share my ongoing research and insights into the essential field of family wealth dynamics. My mission at OAOA Capital is to support families in building multi-generational legacies rooted in love, trust, and holistic health — mental, spiritual, and financial. The human capital within a family is entirely priceless, and it deserves to be protected with the same rigor we apply to the numbers.
