Early in my career, I noticed something that has never stopped bothering me. I would sit across from clients who had done everything right. Just recently, a client told me, "I need you to show me that I can spend." She had spent her entire life saving because that's what she was taught to do. She had more than enough money to support her lifestyle, but the idea of spending it on herself still felt wrong.
Not because they were careless. Because every advisor they had ever worked with had told them the same thing, save more.
The financial services industry has largely been built around that one message. Save more for retirement, for healthcare, for your family, for uncertainty. Some of that advice is absolutely necessary. The Federal Reserve found that only 35% of non-retirees believe their retirement savings are on track. Disciplined saving matters.
But for families who have already built significant wealth, that same message starts doing real damage. For many people, that fear becomes most apparent at retirement, when the lifelong habit of earning and saving suddenly shifts to spending from assets they worked decades to build. They have plenty. They just cannot bring themselves to use it.
I see this especially among business owners and families whose wealth was built through sacrifice and delayed gratification. People who poured everything into building a company, a vineyard, a medical practice, or a family enterprise. They became conditioned to believe that financial success meant preserving wealth at all costs. The result is a scarcity mindset that persists long after scarcity is no longer the reality.
Behavioral economists have long documented that people experience financial losses far more intensely than gains, even when objectively secure. So, they postpone experiences they can already afford. They delay travel, time with children and grandchildren, and decisions that would genuinely improve their lives. Recently, I worked with a widow in her 80s who was considering a move to a retirement community she loved. She could comfortably afford it, but struggled with the idea of spending that much on herself. Her challenge wasn't financial. It was emotional.
Then life intervenes.
I have worked with families navigating unexpected illness, sudden deaths, and major liquidity events. One lesson becomes painfully clear. That tomorrow is never guaranteed, and too many people wait for a future they assume will always be there. Recent retirement research found that retirees often spend only about half of what they could safely withdraw.
However, that doesn’t mean that we should all be spending recklessly. There’s an opportunity for individuals to spend confidently when they have a clear plan. Often, that means helping clients understand the tradeoffs. We model different spending scenarios, identify what they want to leave behind for family or charitable causes, and establish guardrails that allow them to enjoy their wealth while still meeting those goals. In many cases, clients discover they can spend far more than they thought and still leave a meaningful legacy.
When clients can see how their investments, taxes, estate planning, cash flow, and long-term goals fit together, their relationship with money changes. The question shifts from “Can I afford this?” to “Does this support the life I actually want to build?” That means taking the family trip now instead of waiting another decade or helping children buy their first home while parents are alive to see it.
In Napa Valley, where much of my work centers on families with illiquid wealth tied to vineyards, land, or closely held companies, these conversations are especially emotional.
Their business is more than just an asset. It’s their identity, their family history, and their life’s work. I increasingly see families wrestling with whether the next generation even wants that life, and that realization forces a deeper question about what the wealth was truly meant to accomplish.
After nearly thirty years in this business, I can tell you that clients rarely look back wishing they had saved slightly more. What I hear more often is that they wish they hadn't waited. Waiting to travel. Waiting to slow down. Waiting to spend time with the people they love. Waiting for permission to enjoy the life they spent decades building.
The best financial plans should not simply protect wealth. They should help people live more fully because of it.
George McCuen, CFP, CPWA, joined The Mather Group as a wealth advisor in November 2025 following the merger of Napa Wealth Management. A Napa native, he has spent nearly three decades working with affluent families, business owners, and multi-generational households.
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