Andrew Connors has spent 30 years watching high net worth clients do the same thing: sacrifice time and health building wealth, then spend that wealth trying to reclaim what they lost.
The managing director at Hightower Signature Wealth believes most financial advisors are missing a critical conversation – and a growing body of research suggests the stakes could not be higher.
A recent study by Edward Jones and Gallup, which surveyed 5,075 U.S. adults between March and April, found that only 16% of Americans have achieved genuine financial fulfillment. The largest share – a minor majority of 51% – fall somewhere in between fulfillment and financial stress, navigating a life that includes both progress and ongoing pressure.
Crucially, the research found that fulfillment predicts life outcomes more reliably than wealth alone, and that financially fulfilled adults are nearly six times as likely to rate their mental health as very good or excellent compared with those who are financially stressed.
For Connors, those numbers tie into a familiar struggle for clients: what it means to be satisfied.
"When we have these meetings and conversations around clients' goals, and ultimately the purpose is to have more – that goal line is never going to be satisfied," he said. "So at what point does time and health, while you have your wealth, become what you maximize?"
Connors has developed a way of understanding client life stages that cuts across the usual financial planning categories.
In the first phase – roughly the first decade of a professional career – clients are trading time and health simply to get started. Wealth is being built, but there are real sacrifices being made. In the second phase, the financial carrot is closer and clients begin to accelerate, still trading time and sometimes health for greater wealth accumulation.
The third and final phase is where the reckoning happens: his clients, having achieved financial security and then some, now begin trying to get back the time and health they gave up along the way.
"I think the challenge people have is understanding which phase they're in. They tend to be more reactionary," Connors said. "They are high achievers. They are wired a certain way. And when you are wired that way, it changes your DNA a little bit. It's hard, unless someone is helping you reframe your thinking."
To help guide conversations, he uses three clean definitions: time, which defines how and when you live; health, which is your capacity to live; and wealth, the financial freedom to choose how you spend both.
When asked what financial fulfillment actually means to them, Americans in the Edward Jones/Gallup research most commonly cited freedom to pursue passions (47%), less stress about money (38%), and more time with family and friends (35%). Ultimaely, the report found that financial fulfillment is less about a number and more about what money makes possible.
"If the answer to 'what is your personal benchmark for success' is a number, that's the wrong answer," he said. "The answer should be: what does that number allow me to do?"
Every client meeting at Hightower Signature Wealth opens with that benchmark question as the first agenda item. Using AI-assisted note-taking to capture responses systematically, Connors has confirmed a consistent pattern across his book of business.
"Most people's answers are usually very similar. In some shape or form, everyone is looking for freedom – the freedom to make choices of what they do, when they want to do it, how they want to do it."
Late last month, leading AI notetaking provider Zocks announced its partnership with Hightower, under which it officially became the exclusive AI assistant offered to Hightower's network of 650 advisors operating across 33 states and the District of Columbia.
Aside from recording and generating clean breakdowns of conversations, Connors says their technology lets advisors set certain key questions to cover, including how clients view and measure success. Those features allow him and other advisors to be more fully present with clients during meetings.
"I can ask a question and not have to focus on writing down the answers," he said. "I can let the AI do its thing."
The most powerful moments in Connors' practice often come not from financial planning sessions, but from unexpected life events.
In one case, he shared how a business owner's partner – a triathlete and "a specimen of health" who had competed in multiple Ironman events – died suddenly of a heart attack while walking through their plant. The shock forced his client to confront a truth Connors had been raising for years.
"He said, 'Running this business was never my dream. It's never what motivated me. I enjoyed doing it with him, but without him here, I don't want to wait,'" Connors recalled. "A year later, he sold that business. And whenever we get together now, he looks back and says, 'I can't believe I waited that long to make that decision.'"
More recently, Connors said a 60-year-old client working as a senior executive at a large public company – whom he said is in the top 1% by net worth – formally announced plans to retire by the end of 2026. That decision, effectively costing the client seven figures in future compensation, came after both of his daughters had grandchildren within the past year.
"He has reached a place where he knows how much enough is," Connors said. "He's willing to leave that money on the table to have time with his family and his grandkids, while he still has his health and wealth. And we have done significant financial planning to show him that even leaving money on the table, he is still in a position where he could potentially create generational wealth."
Planning capabilities matter for those conversations. Connors holds the CFP mark as well as the Certified Exit Planning Advisor designation, which he relies on when working with family business owners navigating ownership transitions. His technology stack also includes eMoney, Holistiplan, and Social Security planning software to make projections for clients, but he emphasized that the reports are only as good as how they are presented.
"As advisors, we often take the deliverables for granted because we see them every day," he said. "You have to put yourself in the shoes of your client and say: they might be seeing this for the first time. How do we present information so that it is so easily digestible their brain can get around it, and it can stick?"
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