The Hidden Risk of Success

By: Edward J. Leach, CFP®, MBA, CEPA

Success often creates a challenge that few people anticipate.

In fact, some of the biggest planning opportunities we encounter are not the result of poor decisions. They are the result of exceptionally good ones.

Think about a business owner who spent decades building a successful company. An executive whose employer stock appreciated dramatically. A real estate investor who has accumulated properties over many years. Or a family that inherited an asset that continued to grow over generations.

The very thing that created their wealth can eventually become one of the most important planning decisions they face.

This topic feels particularly relevant today, as headlines continue to focus on IPOs, private company valuations, and employees whose net worth has grown substantially through ownership in a single company. While those stories capture attention, the lesson is much broader.

Most people already know they have a concentrated asset.

The real question is what role that asset should play in the future they are trying to create.

Interestingly, recent research from the Exit Planning Institute found that many business owners continue to have the majority of their net worth tied up in their businesses and expect the value of those businesses to fund a significant portion of their future lifestyle.

There is nothing inherently wrong with that. The challenge is ensuring your financial future aligns with your goals, values, and priorities.

When we work with clients at HIGHLAND Financial Advisors, we typically begin with a few simple questions:

What do you want the next chapter of your life to look like?

Before discussing investments, taxes, or estate planning, we want to understand what you are actually working toward—retirement, philanthropy, family, travel, a second business, or something else entirely.

What role does this asset play in helping you get there?

Every asset should support a purpose. Understanding that purpose often helps determine whether an asset should be held, transferred, sold, gifted, or simply managed differently over time.

What risks could prevent you from achieving those goals?

This is where we evaluate factors such as concentration, liquidity, taxes, succession, estate planning, and other risks that may not be obvious at first glance.

What options do you have?

The best plans create flexibility. The earlier we understand the available options, the more control families typically have over future decisions.

As a Certified Exit Planning Advisor (CEPA), I have found that the most successful families are not necessarily those who have accumulated the most wealth.

They are the families who take the time to align their assets with the life they want to live.

Success is something to celebrate.

The key is making sure that the wealth you have built supports the future you envision for yourself and your family.

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, a professional organization dedicated to serving fee-only advisors.   

The foregoing content reflects the opinions of Highland Financial Advisors, LLC, and is subject to change at any time without notice. Content provided herein is for informational purposes only and should not be used or construed as investment advice or a recommendation regarding the purchase or sale of any security. There is no guarantee that the statements, opinions, or forecasts provided herein will prove to be correct.

Past performance may not be indicative of future results. Indices are not available for direct investment. Any investor who attempts to mimic the performance of an index would incur fees and expenses, which would reduce returns.

Securities investing involves risk, including the potential for loss of principal. There is no assurance that any investment plan or strategy will be successful or that markets will act as they have in the past.

The above article was written with the assistance of artificial intelligence (AI).