For Business Owners, a Solid Plan Can Help Prevent Seller’s Regret

For Business Owners, a Solid Plan Can Help Prevent Seller’s Regret

September 15, 2025

Recently, we worked with a business owner who was reviewing an offer to buy his business. The business itself was ready. Its employees, processes, customers, and brand were first class. The potential buyer’s company culture was a match, and the offer was attractive.

Our role (as personal wealth advisors) in this part of the discovery process is helping clients determine if a deal works for all areas of their personal financial lives. We proved that this offer did. Ultimately, however, an agreement was not reached, and the buyer has moved on, while the owner is happily running his business. What happened?

It is not uncommon for business owners to experience seller’s regret. Any time there is a transition in life—selling a business, retirement, etc. —we face the challenges of loss of identity and loss of purpose. We wrestle with how we will structure our lives.

We advocate for clients to devote some time to developing a strategy for how they will spend their days, maintain connection, and find fulfillment. Leisure is only one area, and a bucket list is not a plan. We’ve observed that clients with successful transitions are the ones who have created a vision and action plan that addresses how they want their life to unfold in the next chapter.  

As you begin the process consider the following points, which are based on a S.T.E.P. questionnaire from the Exit Planning Institute®.  Answering them can help you create the framework to begin building a Lifestyle Action Plan.

  • SPIRITUAL

Identify the core source of your inspiration—your "center"—as it drives your motivation, security, and sense of purpose. Your center could be anything from family or work to money or self; recognizing it helps clarify what truly fuels your passion.

  • THINGS

We often strive for material possessions, but it's important to evaluate what we truly want versus what we can live without. Some things may actually hold us back, so reflecting on what to let go of is just as valuable as knowing what we desire.

  • EXPERIENCES

Life’s richness comes from meaningful experiences; reflect on those you've cherished and those you still hope to achieve. Understanding what experiences matter most helps clarify what brings personal fulfillment and joy.

  • PEOPLE

Consider the people who have impacted your life: mentors, loved ones, and those you've helped or want to help. Reflect on who you want to reconnect with, thank, or spend more meaningful time with.

I’d encourage you to find a quiet place for reflection. Take out a sheet of paper and write down your thoughts in each of the areas of personal purpose. Writing down your thoughts will help you articulate them. There are no right or wrong answers.

By Doug Feller, CFP®, Certified Exit Planner®

Financial Advisor

This material is intended for informational/educational purposes only and should not be construed as investment advice, a solicitation, or a recommendation to buy or sell any security or investment product. Please contact your financial professional for more information specific to your situation. Certain sections of this commentary contain forward-looking statements based on our reasonable expectations, estimates, projections, and assumptions. Case studies are for illustrative purposes and should not be construed as a recommendation. It may not be representative of your experience. Forward-looking statements are not guarantees of future performance and involve certain risks and uncertainties, which are difficult to predict. Past performance is not indicative of future results.

Securities and advisory services offered through Commonwealth Financial Network®, member FINRA/SIPC, a Registered Investment Adviser. Additional advisory services offered by Rea Wealth Management, a Registered Investment Adviser, and fixed insurance products and services are separate and unrelated to Commonwealth.