Early in my first real conversation with any business owner, before we talk about valuation or buyers or timing, I ask a question that sometimes catches people off guard: what does your life look like the day after closing? Some owners have an answer ready. Many pause, laugh a little, and admit they have not thought about it. A few say “golf,” and I understand why. After decades of running a company, the idea of a quiet morning with nowhere to be sounds wonderful.
I ask because the answer matters as much to the success of the sale as the financials do. In my experience, the owners who know what they are moving toward are the ones who make it to the closing table with their confidence intact. The owners who only know what they are leaving behind have a much harder time.
Why this question matters to the deal
Selling a business takes time, often a year or more from the first conversation to closing. Most of the work an advisor does happens at the front of that process. We prepare the business for market, build the materials buyers will review, identify and approach potential buyers, and manage the negotiations and due diligence that follow. That work is done well before an advisor is paid, since most of our compensation comes at closing.
That arrangement means we succeed only when the seller does, and I believe in it. It also means I pay close attention to a risk that owners rarely see in themselves. A seller who has no plan for life after the sale can lose their motivation to finish it. I have seen owners receive an excellent offer from a qualified buyer, one that met or exceeded what they said they wanted and then hesitate. The offer was not the problem. The problem was that signing it meant facing an empty calendar and an unanswered question about who they would be without the business. It’s easy to do when you’ve put so much of your life into your business. When a seller backs out late in the process, everyone loses. The buyer has spent months and significant money on due diligence. The employees may have sensed that change was coming. The owner is left running a business they had already begun to let go of, often with less energy than before. Asking about life after closing at the very beginning is one of the best ways I know to prevent that outcome.
The money question comes first
Part of planning for life after a sale is financial, and it is the part owners tend to think about first. Before we go to market, I encourage every owner to work with a financial advisor to determine how much money they will need to live the way they want for the rest of their lives. That number becomes the target.
The next step is to compare that target with what the business is realistically worth today. Sometimes the value of the business comfortably exceeds the goal. Often there is a gap. Exit planning is the work of closing that gap, whether by improving the business before a sale, adjusting the timeline, or reconsidering the structure of the deal. An owner who knows their number can evaluate an offer with clarity. An owner who does not know it may turn down a good offer out of uncertainty or accept a poor one out of fatigue.
The part no one plans for
The financial plan answers the question of whether you can afford to sell. It does not answer the question of what you will do once you have. For most of the owners I work with, running their business has been the center of their working life for twenty or thirty years. It has shaped their days and their sense of who they are. Letting it go can feel like an ending.
It is not the end of anything except one chapter. But it helps to understand what the transition usually looks like, and one of the most useful frameworks I have found comes from Dr. Riley Moynes in his book The Four Phases of Retirement: What to Expect When You’re Retiring.
Moynes describes the first phase as the vacation phase. It is the early, carefree period after work ends, filled with rest and the things there was never time for before. The second phase he calls loss and lost. Once the novelty wears off, many people feel the absence of their routine and the identity that came with their work. The third phase is trial and error, a period of experimenting with new activities and commitments to find a renewed sense of purpose. The fourth phase, reinvent and rewire, is where people settle into a life that feels meaningful again, often through service or mentoring in their community.
What I appreciate most about this framework is its honesty about the second phase. Business owners are used to being needed. The phone rings and employees have questions. When that stops, the silence can be harder than anyone expects. Knowing that this feeling is normal, and that it passes, makes it far easier to move through.
Golf gets old
I have nothing against golf. But the law of diminishing returns applies to leisure as much as anything else. A round of golf on a Tuesday morning is a pleasure when you have spent thirty years unable to take one. A round of golf every day for three years tends to lose its appeal. The same is true of travel or fishing or any activity that fills time without giving it purpose.
That is why I encourage sellers to have a plan for what they want to do after closing, at least for the first year or two. It does not have to be permanent, and it does not have to be ambitious. It might be a part-time consulting role, a board seat with a nonprofit, time with grandchildren, a course they always wanted to take, or a new venture of their own. The point is to have something to move toward. There is always time to change course and find something just as fulfilling as the business was.
Starting the conversation
If you are thinking about selling your business, I would encourage you to start with the question I ask every seller. Picture the morning after closing. Where are you, and what does the rest of that year look like?
When you are ready to talk it through, meet with our advisors at Horizon M&A Advisors. We will help you understand your goals clearly, measure the gap between the value of your business and the life you want, and work with you to close it. Then, when the sale is done, you can enjoy what comes next.