The decision to sell your business is a massive one. It will not only require practical time and energy but an emotional and financial investment. You will need to pay lawyers and other advisors, and it will demand time from your chief operators and directors. As you collectively navigate this significant transition, anxiety will heighten, and questions will fly. Many owners start down the path towards a sale, only to get cold feet and determine that “the time just wasn’t right.” This can be detrimental to the stability of the business, the team, and future sales. So before you begin the process of preparing your business to sell, pause and ask yourself these questions to make sure you’re truly ready to say goodbye.

1. How much of your personal fulfillment do you derive from your business?

Perhaps you built this business from the ground up, tooth and nail. Or maybe you purchased it in a fledgling phase and nurtured it to success. Whatever the path, you put in years of focused, dedicated energy and care into building a structure, team, and business that you are proud of, and rightfully so! It has probably become more than just your job; it is part of who you are. So how much of your self-worth, identity, and happiness comes from it? How much joy do you get from walking into work on Monday morning, solving complex problems around your conference table, or coming up with a unique solution for your clients? Would you miss the travel, the pace, or the challenge? Who are you when you aren’t at the helm? It’s essential to recognize this business’s role in your personal life – not just the time it takes but the sense of worth it brings you. If it plays a massive role in your personal life, and really defines you, actually handing it off at the end of a sales process may be a lot harder than you anticipate. 

2. What will you do with your time?

Elite athletes call this “visualization.” They imagine step by step, moment by moment, the perfect swing of the bat or spin of the dive. Being able to picture something clearly in your mind helps bring it to fruition. It allows your brain to rehearse what it will think and feel when the behavior comes to pass. Can you imagine retirement? What will you do? Where will you go? What does your family imagine? How will you fill your weekdays? What will you do with the money? If these images are vague and incomplete, it might be a sign that – when push comes to shove – you won’t follow through with a sale because you don’t know what is coming next. We are creatures of habit, innately designed to prefer routine to change. Knowing exactly what you’ll do that first Monday morning when you don’t have to set the alarm is an important step to preparing your mind for a shif

3. What problem are you solving?

Sometimes a complete sale is not the solution. But to know this, you have to articulate your problem. Do you want more time with your family? Is the leadership responsibility bringing you too much stress? Is your industry growing rapidly, and you recognize you don’t have the skills (or desire) to scale? These problems can be solved in many ways through partial sales, staffing changes, or operational restructuring to alleviate your actual pain point while retaining your involvement in the things that still bring you life. Selling your business doesn’t have to be an all-or-nothing decision. But you need to know what type of sale/transaction you are looking for before you go down the path.


As modern accountants and bookkeepers, we are here to ensure your accounts are for whatever “next step” you envision for your business. But we aren’t only your outsourced finance team – we are also trusted advisors and partners in your success. If you know you’re nearing the time to sell your business, reach out to us. Of course, we can help you prepare your financial records to ensure you get the most value from what you have worked so hard to build, but we also can help you think through some of the non-financial considerations at play when selling your business. We’ve seen it before, done it before, and are here to help.