If you’re an entrepreneur, when should you begin planning for selling your business?
Most owners assume the answer is “when I’m ready.” But in reality, it’s often much earlier.
Data from the Exit Planning Institute shows that nearly 75% of business owners report some level of regret within a year of selling their business. The reasons are rarely about the decision to sell itself, but about preparation.
Many owners underestimate the time required to structure the transition properly. Without early planning, they may leave money on the table due to tax inefficiencies, rushed negotiations, or valuation gaps. Others face unexpected events like health issues, partnership disputes, and market shifts that force a sale before they’re positioned to exit on their own terms.
In some cases, the business is profitable but not transferable. The owner remains too central to operations, or the company lacks the structure and leadership depth buyers look for. In others, family or key-employee succession plans were never fully developed, limiting options at the moment they matter most.
Selling your business is not simply about timing the market. It involves keeping the company attractive, transferable, and positioned to deliver the net outcome you expect.
In our work with business owners, we encourage proactive exit planning long before a transaction is imminent. Below are several strategies we recommend to help entrepreneurs prepare thoughtfully and preserve the value they’ve worked so hard to build.
Envision the Future
What will be the legacy of the business you leave behind? Who will carry on your vision? These and many other questions—especially those that address your role (if any) in the business afterward—should be carefully considered. Imagine what the business will look like in five or ten years after you’re no longer there. Setting the foundation for this vision should be the first step.
Prepare for the Unexpected
Business owners know all too well that unexpected events can derail even the best-laid plans, so carry this tenet into planning for your business’s future. Illness or serious accidents late in life can not only affect the day-day operations if you’re not there, but the value of the business to potential buyers as well. You don’t want circumstances and tragedy to dictate the terms and conditions of your exit, so be sure to put contingency plans in place.
Develop a Succession Plan Long Before You Need It
This is especially true if you plan on transitioning your business to family members or key employees. Employees, customers, and vendors will all need assurance the business can run well with your successors, and this trust takes time. You also want to have confidence ahead of time that those who lead the business after you have the strengths and skills to continue your success.
Integrate Your Exit With Your Personal Financial Plan
For many entrepreneurs, the majority of their wealth is tied up in their business. When the company is sold, that value suddenly converts into liquidity, often more wealth than they have ever held at one time. What happens next?
Being prepared for this sudden wealth realization and incorporating this windfall into a thoughtful, carefully crafted financial and retirement plan is essential for every business owner. Without such a plan, which includes personal estate planning as well, retired entrepreneurs may feel overwhelmed and at a loss—having now relinquished their life’s work and deciding how to best reinvest or allocate the proceeds of their business sale. This is at the heart of what Anderson Financial Strategies provides to our business-owner clients.
Reinvent Yourself
As business owners ourselves, we know all too well that running an enterprise is all-consuming and it may be difficult to simply turn off that motivation and inner drive once the purchase agreement is signed and sealed. In our experience, retired entrepreneurs often need to turn their still-considerable energies toward other endeavors. This can include charitable or volunteer work or devoting time to long-awaited hobbies or time with family and loved ones. Think about your new life and sense of purpose and lay a foundation ahead of time for your legacy and what’s meaningful to you.
Don’t Be a One-Person Show: Assemble Your Team
Many entrepreneurs relish the idea of independence and being a self-made success. After all, you may have been the captain of your business ship most of your adult life. But when it comes to business transitions, assemble a team of experts to counsel and guide you through this process. This includes financial advisors, tax professionals, and qualified attorneys.
Selling Your Business? Start the Discussion Today
Selling your business is rarely just a transaction. It often represents years, sometimes decades, of personal investment, risk, and identity. Without early, strategic planning, the process can feel overwhelming, leaving owners exposed to valuation surprises, tax inefficiencies, or decisions made under pressure.
Thoughtful planning around selling your business can reduce uncertainty, shield the value you’ve created, and give you greater control over timing, structure, and legacy outcomes.
At Anderson Financial Strategies, we work closely with business owners to navigate the financial, tax, and transition considerations that come with this pivotal moment. If you’re beginning to think about selling your business we welcome the opportunity to help you approach it with clarity and confidence.
If you would like to explore our services for your family or business, call us at 855-237-4545 to schedule an executive briefing to discuss your goals.
About Shon
Shon Anderson is president and chief wealth strategist at Anderson Financial Strategies, LLC with over 20 years of experience. As a fiduciary, Shon’s mission is to provide his clients with quality financial expertise along with rapidly responsive service through an honest relationship. He specializes in providing family office-style services to help his clients organize and focus their financial life. Shon graduated from Wright State University with a bachelor’s degree in financial services and an MBA in finance. He is a CERTIFIED FINANCIAL PLANNER® practitioner and holds the Chartered Financial Analyst® (CFA®) certification. His insights have been quoted in leading financial news publications such as CNBC, Yahoo Finance, Fox Business, Consumer Reports, Forbes, Bankrate.com, Investment News, and Kiplinger. Shon serves as president of the CFA Society Dayton as well as on the boards of the Miami Valley Hospital Foundation and Wright State’s planned giving council and was appointed as a Trustee for Central State University. Shon and his wife, Jessica, reside in Sugarcreek Township, Ohio, and are blessed with triplet daughters, Elizabeth, Bridgette, and Alexandra, along with their son, Jacob, and dogs, Biscuit and Ella. To learn more about Shon, connect with him on LinkedIn.