Five Retirement Planning Mistakes Made by Small Business Sellers

Brad Smith • February 4, 2020
There is a common problem for business owners when selling their assets. What price, To whom? How long will the sale take? What contingencies? Advisory teams are normally the most important decision a business owner will make. A good group of advisers often includes an accountant, a merger and acquisition adviser, a business advisory board, a business attorney, a private equity company adviser, and investment banker, a commercial banker and a personal wealth management team. Even experienced advisers may overlook some long-term issues because of their focus on closing a sale.

1. Not taking into account how the income taxes of additional assets may be distributed

  • There should be a strategy when dealing with retirement assets already accumulated such as 401k, Simplified Employee Pension Plan (SEP) or Employee Stock Ownership Plan (ESOP).

2. Not understanding future living expenses

  • Business owners are in tune with their own budgeting but don’t always account for how their previously expensed items will be covered.

3. Not understanding income taxes associated with different sources of income

  • Over the years business owners accumulate wealth in various areas such as 401k, IRA plans, cash from the sale, personal savings, life insurance, asset equity and investments. Its important to align projected income tax consequences with the income sources to create tax efficiency.

4. Overlooking lifelong objectives

  • When preparing a company for sale, it can fully occupy the life of an owner. Its important to take a step back and determine why they are retiring and what they want their next step to be. A question they must ask themselves, “What will retirement for me look like? What if I change my mind and want to get back in to this industry or something else?” The business owner needs to have an idea of what to align their financial resources with their new objectives, accommodating for lifestyle, legacy and desired social impact.

5. Keeping family up to speed

  • It’s important for family members to understand how the wealth will be handled. When owners sell they tend to put all life efforts and earned money back into the company. When they sell, chances are they are going to have accessible financial resources at their disposal. Deciding how to set aside money for their spouse and children will go a long way toward family happiness.
  • If you decide to retire and sell your company, its import to avoid tunnel vision. Remember to work with your advisers and look beyond the transaction to help maximize potential benefits.

Interested in Working With Us?

If you need help with estate planning or any other legal concerns, we are here for you. Don't hesitate to contact our firm directly for assistance. Our dedicated team is ready to provide support and guidance to you and your loved ones during important life transitions.


Whether you're ready to schedule a strategy session to discuss your specific needs or if you're interested in exploring our wide range of complimentary guides and additional resources, we encourage you to get in touch with us.


With licensed attorneys and offices located in both Illinois and Missouri, we are well-equipped to serve clients in these regions. Reach out to us today and let us leverage our expertise and care to guide you through the legal process.

Helpful Guides

Begin your journey by taking advantage of our collection of complimentary guides.

View Guides

Online Documents

Simple & Convenient, Cost Effective, Attorney Reviewed Documents.

Learn More Here

Recent Posts

February 21, 2025
Estate planning is about more than just dividing assets; it’s about making sure your wishes are honored when it comes to your health, finances, and legacy.
Show More
February 21, 2025
Estate planning is about more than just dividing assets; it’s about making sure your wishes are honored when it comes to your health, finances, and legacy.
February 14, 2025
Beyond understanding the medical aspects, there are critical legal steps you should take to safeguard your rights, clarify your wishes, and prepare for any unexpected situations.
February 7, 2025
Estate planning is a sensitive and complex process that often involves difficult decisions. One of the most challenging choices parents may face is whether to leave their children unequal inheritances.
January 31, 2025
In this blog, we’ll break down inheritance and estate taxes in Illinois and Missouri, helping you understand what to expect and how to plan accordingly.
January 24, 2025
At our firm, we emphasize the importance of proper trust funding. This crucial step ensures that your trust will work for you and your loved ones when you need it most.
January 17, 2025
Estate planning often feels like an overwhelming task, conjuring images of endless paperwork, difficult decisions, and tough conversations. It’s a process that involves contemplating the future—sometimes in ways that are deeply personal and emotionally taxing.
More Posts
Share by: