Jimmy Taylor has lived the thing most business owners are afraid of. Over his career he built three companies. Two ended in successful sales. One was, in his own words, a colossal collapse. He was a founding partner of Novotus, a Texas recruiting firm that grew into the number one mid-market RPO in the country. And at one point, he and his two partners had no idea what came next.
I wanted to start there, because the Novotus story is one of the clearest pictures I know of what actually frees an owner. Jimmy joined me on the Business Transition Roadmap to walk through it, and the pattern underneath his story is one I have seen in nearly every transition we guide.
When partners cannot align, every decision becomes a fight
Novotus had been in business for about 14 years and had real success. But most of the competitors they faced every day were being bought by organizations the size of IBM. The three owners, two minority partners and one majority shareholder, could not agree on what to do. Take on a partner? Take on a large investment and manage through it? Map a path to retirement when they were all ready?
Here is the part owners underestimate. That disagreement did not stay contained to the one decision. As Jimmy put it, when entrepreneurs are caught in a partnership with no alignment, everything in the business becomes stressful, and every decision can turn into a source of conflict and tension. The tension does not announce itself. It seeps into ordinary meetings about ordinary things, and over time it can take a company to its knees.
This is why I keep drawing a line between the functional side of a transition and the alignment work underneath it. The functional pieces are real and they matter. Tax, legal, the exchange of money, the closing. There are many good advisors who handle those well. But if the partners cannot get to a point where they agree on what they actually want, the functional work has nothing to stand on. The relationships fray, and the company suffers right along with them.
Most dilemmas have not happened yet
Jimmy gave the best definition of a dilemma I have heard. We tend to think a dilemma means a hard, painful decision. He reframed it. A dilemma is really just a situation where you have no good options. There are no clean choices, only hard ones, and none of them are perfect.
What I have learned in more than 30 years of this work is that the dilemma freezing an owner in place is usually not a present-day fact. It is an imagined future.
Let me give you a real example. An owner would love to bring his son into the business. It would be good for the company, good for the son, good for him. But he holds back, because he is certain that hiring his son will upset his daughter, whose husband has been out of work for 18 months and has no place in the company. So the owner decides to do nothing. He pictures two outcomes, A or B, and a loss waiting on both sides.
When that owner finally walked through the process, the conversation he was avoiding actually happened. The son came in. The daughter was not upset. Everything worked out. The dilemma he had been carrying was never solid ground. It was a story about a future that had not arrived.
That is the gray. When you are sure your only options are A or B, there is almost always space in between that you have not stopped to look at. As Jimmy said, it is a lot easier to adjust a path you are already on than to build one from scratch. Looking for the gray is how you find that path.
Write down what you actually want
The tool that opens the gray is simpler, and more uncomfortable, than most people expect. You write down what you want. We call it the objectives matrix, and it sits at the heart of the framework our Evolve members use.
I went through it myself. A few years ago I started my own transition without a successor in mind, which is the first thing I want owners to hear. You do not have to know who is going to take over to begin understanding what you want. I had built the matrix and used it constantly, so I assumed I already knew my objectives and my husband’s. When we actually sat down and wrote them out, we had some of the best conversations we have ever had. Two and a half years later, when Andrea came through the door as my successor, I pulled it back out. She did hers, I shared mine, and that became the foundation for everything that followed.
People rarely take the time to put this on paper. Not just what they want for themselves, but what they want for their family, their employees, their partners, the business itself, and the legacy they hope to leave. When you can see all of that in front of you, the path gets clearer. And the conversations you were afraid to have turn out to be the ones that solve the problem.
The mindset that built the business can be the thing that traps you in it
When I asked Jimmy what keeps owners from this work, his answer was mindset. The business cannot run without me. Nobody can do what I do. It is a box people build in their own heads.
There is real tenderness underneath it. Owners carry an enormous load, and they keep carrying it for the people around them. I picture someone walking through their day with bricks stacked on top of them, tired of the weight but unwilling to set it down, because setting it down feels like letting someone down. Jimmy named the other half of it. We believe nobody can do it the way we do. And sometimes that is true. But sometimes another person can do it just as well, or better, if we let them step in and grow into it.
What is interesting to me is that this same mindset is often the exact tenacity that made the business successful in the first place. The founder who insisted he could do it better than anyone, and then proved it. That instinct builds companies. Carried into a transition, it keeps you in the business forever.
Two things move people past it, in Jimmy’s experience: statistics and stories. The numbers are sobering. Only about 30 percent of family enterprises make it into the second generation, and only about 12 percent into the third. But numbers alone rarely change anyone. What changes people is hearing how another owner, another family, found their way through. It starts to open up a future they had not let themselves imagine.
A clear path is freedom, not a cage
For every one of us, there will be a day we step away from the business, on our own terms or someone else’s. A clear path forward is not a set of handcuffs. It is a stress reliever. It can flex when the economy shifts and conditions change, because adjusting a path you are on is far easier than starting from a blank page.
Sometimes the greatest thing you can do is help someone else carry the business forward without you, and then get to be proud of what continues on. That is not the end of the story you built. It is the part where it outlasts you.
If you have ever felt caught between two options that both look like losses, that is the conversation to start. You can find the gray. Usually it has been there the whole time.
If you would like to talk through what your own path could look like, you can schedule a discovery call at transitionstrategists.com/discovery.
This conversation is from Episode 82 of the Business Transition Roadmap with Jimmy Taylor, entrepreneur and transition guide with The Transition Strategists. You can listen to the full episode above.
