Retail Observer

RETAILOBSERVER.COM OCTOBER 2026 38 S everal years ago, I worked with a business owner who had operated two ice cream locations for more than 20 years. Then COVID came. Like many business owners, she became frustrated. Restrictions, staffing problems, rising costs, and the daily pressures of running the business began to take their toll. Eventually, she decided she'd had enough and sold both stores. She missed her customers. She missed her employees. She missed having somewhere to go every morning. She even missed the routine and responsibility that had frustrated her enough to sell. Financially and operationally, she may have been ready to sell. Mentally, she was not. Her experience is a reminder of something business owners often overlook when planning their exit: Preparing the business for sale is only part of the equation. You also need to prepare YOURSELF. THREE KINDS OF READINESS In a perfect world, an owner would be physically, financially, and mentally ready before selling. Unfortunately, we aren't living in a perfect world. Health changes. Families change. Markets change. Employees leave. Burnout happens. Few sellers reach the closing table with every box perfectly checked. That doesn't mean you should wait for some imagined "perfect time" to sell. It means you should begin preparing well before you intend to sell. When it comes to mental readiness, I encourage owners to consider aspects of their life: their financial situation, family, what comes after the sale, their willingness to surrender control, and perhaps most important, why they want to sell. Owners should also know what they want from the sale. The considerations to prioritize by importance should include: • Best price • Favorable terms • Minimizing taxes • Protecting employees • Preserving the company name • Making sure the business continues under an owner who shares your values Those objectives can, and often will, conflict in a business sale. Rarely will a buyer check all the boxes, so you'll have to decide what matters most. Understanding the ideal outcome before you enter the sale process will help you make rational decisions when real buyers and real dollars are on the table. UNDERSTAND WHAT THE SALE REALLY MEANS FINANCIALLY Financial uncertainty can create emotional stress. Don't wait until you receive an offer to determine whether selling will actually work for you. An expected sale price, and the amount you'll ultimately put in your pocket, are two very different numbers. Taxes, professional fees, debt, transaction structure, and financing terms can all affect the final outcome. Before going to market, develop a reasonable estimate of what the business may sell for, and work with your financial and tax advisors to understand what the net proceeds could look like. Then ask yourself the important question: Is that enough for the next phase of my life? Knowing the answer will remove one major source of uncertainty from the decision. CAN YOU REALLY LET GO? For many entrepreneurs, the business is their baby. You built it. You made the decisions. You took the risks. You survived the bad years and enjoyed the good ones. Ownership represents control, accomplishment, and sometimes, a significant part of personal identity. After the sale, somebody else gets to make the decisions – including decisions you may not agree with. Can you live with that? Owners who remain heavily involved in every aspect of their companies often have the hardest time separating after a sale. If that describes you, consider gradually stepping back before selling. Delegate decisions. Develop managers. Take longer vacations. See how the business operates without you – and equally important, see how you operate without the business. If you discover you're not ready, that's useful information. Now may not be the right time to sell. ARE YOU BEING PUSHED OR PULLED? Ultimately, I believe this is one of the best tests of mental readiness. Ask yourself honestly: Why do I want to sell? There's an S E R V I C E D E P A R T M E N T PREPARING YOUR BUSINESS FOR SALE IS IMPORTANT Preparing yourself may be even more important

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