By: Edward J. Leach, CFP®, MBA, CEPA
Most successful people spend decades preparing financially for the next chapter of life.
They build businesses. Advance their careers. Invest wisely. Save consistently. Accumulate wealth.
Far fewer spend time preparing for the chapter itself.
Whether it's retirement, selling a business, receiving an inheritance, becoming financially independent, or simply reaching a major milestone, many people assume that once they have enough money, the rest will take care of itself.
Unfortunately, that is not always the case.
One of the more interesting findings from the Exit Planning Institute's 2025 State of Owner Readiness™ Generational Report was not related to business valuations, succession plans, or financial projections.
It was the number of business owners who lacked a personal plan for what comes next.
In fact, the study found that 87% of Baby Boomer business owners have no personal post-transition plan, despite being closer to retirement or a business transition than any other generation. Even more surprising, 17% reported having no plans at all for what comes next.
At first glance, those numbers seem surprising.
After all, these are successful individuals who spent years building companies, creating jobs, growing wealth, and making important decisions.
But in many ways, the findings make perfect sense.
For many high achievers, work provides much more than income.
It provides structure.
It creates relationships.
It offers challenges to solve.
It gives people a sense of purpose and identity.
When that chapter begins to close, the question is no longer, "Do I have enough money?"
The question becomes, "What am I moving toward?"
This is one of the reasons we spend considerable time discussing life planning with clients at HIGHLAND Financial Advisors.
Before we talk about portfolios, tax strategies, estate planning, or retirement projections, we want to understand what a fulfilling future actually looks like.
Our approach has been heavily influenced by the work of George Kinder, often referred to as the father of life planning. In his book, The Seven Stages of Money Maturity, Kinder challenges individuals to think beyond their balance sheet and focus on what truly matters.
The premise is simple: financial planning should not begin with money. It should begin with understanding how you want to spend your time, who you want to spend it with, and what gives your life meaning and purpose.
While that sounds straightforward, many successful people have spent years defining themselves through their careers, businesses, and accomplishments. Taking the time to define what comes next is often a much more difficult exercise.
The financial planning industry spends a great deal of time helping people accumulate wealth.
The more interesting challenge is helping people understand what wealth is ultimately meant to accomplish.
The families who navigate major life transitions most successfully are often not the ones with the largest balance sheets.
They are the ones who have taken the time to define what they want the next chapter of life to look like before they arrive there.
Ed Leach, CFP®, MBA, CEPA, is a Partner and Wealth Advisor at HIGHLAND Financial Advisors, LLC in Wayne, NJ, and works directly with clients advising them on their financial planning and investments. Ed’s work focuses on the unique needs of business owners, helping them extract value from their businesses while creating efficiencies in their business and personal financial plans. He is also a member of NAPFA, which is dedicated to serving fee-only advisors.
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The above article was written with the assistance of artificial intelligence (AI).