How Do You Know If It’s Time to Sell Your Business? Answer These 3 Questions First

It is a massive wave — one that is expected to peak by 2035. According to a McKinsey report about “The Great Ownership Transfer” from February 2026, this wave encompasses “6 million businesses involving roughly five trillion in assets transitioning as baby boomers retire.” The Great Ownership Transfer is one of the most significant movements for small to medium-sized businesses we have seen in some time.

I am acutely aware of this movement because I recently sold a business I started, grew and ran for over 39 years. I learned a lot, did some things well and made my fair share of missteps.

While the report focuses on a specific demographic, the truth is that whether you are a baby boomer or a young, enterprising entrepreneur, the personal impact of a business sale is real. I know from my own experience and the stories I have gathered from fellow business owners. As a mentor of young entrepreneurs through various programs, including the American Academy of Entrepreneurs, I was surprised by the hesitation they experience even when, from the outset, the goal was to grow the business quickly, sell it to a larger entity and move on.

The traditional advice for those considering a sale is to assemble a team of advisors, do valuations, find a broker and cut the deal. Advisors can help with tax and cash flow strategies for the exit. I would argue that it is fine, but there is much more to consider. In fact, studies show there is an emotional toll and loss of purpose that entrepreneurs experience during business transition. Here are three things to consider before you begin the sales effort.

Is the timing right?

Most people think about timing in the context of their personal needs and desires. In my book, Should You Stay or Should You Go? Navigating the emotional Crossroads of Business Ownership, I look at the signs that point to an exit. Are you burned out? Bored? Have you lost your passion? These are a few things to consider.

There are other signs that point to “staying.” The most important one might be that you still have passion for the work. For many years, I stayed at my business because I still had a passion for it. Over time, the signs that I should plan to go started to mount. I no longer wanted to manage employees. I had done everything I wanted to do at my company and knew that someone else needed to take it to the next level. I needed a new challenge. Timing is critical.

Timing is also about external factors. Are you in a “hot” industry, one that is growing quickly? Selling might bring you a great deal of cash now. Maybe you should take the money and run. If you stay, the market might cool down, and the business may not retain its value. You might want to delay a sale because you are projected to increase the value significantly in the next few years. Perhaps you need an infusion of capital, and that might necessitate deeper pockets than yours. In this case, you might want to consider selling all of the business or a portion of the business. Think “Shark Tank.” The need for capital has prompted many entrepreneurs to move on.

Do you have bandwidth?

Selling a business is like having a second full-time job. I should know. To prepare for the sale of my company, I spent countless hours trying to find the right broker, analyzing data and meeting with advisors. I signed nine NDAs in about a year and a half. Each prospect required different information. It took even more hours to prepare, negotiate and respond to requests. Not to mention the onsite visits, which can be intense and draining. Once you start the process, you want to move through it as efficiently as possible because it diverts your energy and focus away from the actual work — that can negatively impact your bottom line.

The question every business owner needs to ask is, “Do I have the bandwidth to manage a sale?” Others on your team can assist with some of the work, but the owner needs to be highly involved and invested in getting it done.

It also requires additional communication with employees, suppliers and customers. You need a communication plan and working that plan takes energy.

Have you planned your next adventure?

Entrepreneurs generally have one speed: fast. That is why they are successful. They work faster. They go harder. They do not quit. They eat, sleep and dream about the business. So, what happens when they finally sell?

For many, it is not pretty.

I have seen fellow business owners go through the process of selling their business. At first, they are giddy. Several told me how it felt to “see all those zeros” behind the number deposited in their account. But the elation did not last long. Within a matter of weeks, many experienced depression and anxiety. Unsurprisingly, those who became most unhappy did not think beyond the sale. I am not one of those people because I had the benefit of learning from others.

I started to plan my next adventure almost two years before the sale. I wanted to continue to be relevant and share what I learned. That is why I applied to write for Entrepreneur.com. I set up a new LLC and began to market my communication seminars and training sessions. I started to write my fourth book, which was released recently, and have two more in process. I sought out organizations that I wanted to collaborate with and began to plant seeds.

By the time the sale was complete, I already had a full plate of work. I am on to my next adventure. I am not alone; many entrepreneurs create new entities and reinvent themselves. I believe the most successful ones devote some time to planning that adventure before an exit. They have momentum. And if retirement is the choice, plan that, too.

Timing. Bandwidth. A plan. Three things to consider carefully.