I was on a call with a business owner who had done everything right. He’d read “It’s a Journey,” worked through some of the exercises, thought deeply about his transition. He has a daughter working in the business and a strong non-family employee. Both could be part of his future plan.
We were talking about my own story. Years ago, my team did a SWOT analysis and identified my lack of a transition plan as one of the biggest threats to the business. I didn’t have a successor in mind at the time. None. But I started the work anyway, built my Transition Roadmap, and about 18 months later, I met Andrea. We had a plan for how quickly we’d move through things, and then life happened. She got pregnant, which was wonderful for her but shifted our timeline. We kept going through that detour, finished the deal, and came out stronger on the other side.
When I finished telling him this, he sat back in his chair and looked at me.
“So I don’t have to know what I want before I start this journey.”
It surprised me. He’d done so much preparation already. But those words told me something important: he’d been waiting to be ready before taking the first step.
If you’d like to hear more about this concept, listen to the full episode of the Business Transition Roadmap podcast where I explore the gift of not knowing in greater depth.
The Readiness Trap
Here’s what I see all the time. Owners wait to start their transition work until they’re ready to leave. Successors wait to step up until they’re ready to lead.
The problem is that neither side is ever truly ready.
Transitioners aren’t ready to leave. They still have work they want to do, relationships they want to maintain, a role in the business that gives them purpose. Successors aren’t ready to take over. They still have skills to develop, confidence to build, and a long way to go before they can fill those shoes.
We’ve created this myth that readiness comes first, then action. In business transition, it works the other way around. Action creates readiness.
What Not Knowing Makes Possible
When you embrace not knowing, you give yourself permission to start before you have all the answers. You add time into the equation instead of trying to make transition an event that happens all at once.
Time lowers anxiety. When you’re on a journey with room to move, you can communicate better, evaluate more clearly, make real commitments rather than forced ones. You can learn and grow. The business can evolve. People can shift their thinking. All of those things happen naturally when you stop waiting for perfect clarity.
I learned this from Dan Sullivan and Strategic Coach. He talks about the gap and the gain, how entrepreneurial people tend to live in the gap, focused on what’s not done, what we haven’t accomplished, what isn’t going well. We forget to recognize the gains we’ve made along the way.
With transition, making it a journey instead of an event lets you see those gains as you go. You build confidence in yourself and in your successor. You tackle doubts through what’s possible rather than staying stuck in what’s missing. You enjoy the process because you’re not racing toward some finish line you’re afraid to cross.
The Gift in Our Story
When Andrea got pregnant during our transition, we had a choice. We could have seen it as a setback, a delay, a problem to solve. Instead, we saw it as an opportunity. She got to have her daughter and be present for that experience. She also kept contributing to the business during that time, and we learned to work together in ways we wouldn’t have otherwise.
We had more time to talk about being partners—what that really meant to us, how we wanted it to work, what we didn’t want. Neither of us anticipated that timeline when we began, but we navigated it well because we had room to adapt.
That’s what the gift of not knowing gives you. Flexibility. Options. The ability to pivot when circumstances change without feeling like you’ve failed or fallen behind.
Using Not Knowing as a Tool
I want you to think about what you don’t know right now. Maybe you don’t know when you’ll be ready to step back. Maybe you don’t know if your successor is truly capable. Maybe you don’t even have a successor in mind yet.
All of that uncertainty is not a problem. It’s a starting point.
You can begin early. You don’t have to have it all figured out. You can use the gift of not knowing to your advantage and to the advantage of the business, your family, and the community you serve.
What happens instead is that transitioners wait and avoid because they don’t know. I’d like to shift your thinking. Not knowing is a gift. It means you have time to figure things out together, to build something intentional rather than reactive.
One Small Step
If you’ve been waiting to feel ready before you start planning your transition, I’m inviting you to take one small step today. Explore what you don’t know. Think about what could be possible if you started this journey now, even without having all the answers.
Go to our website and sign up for a discovery meeting. You’ll talk with one of our guides, and I guarantee you’ll learn something that helps you move forward. It’s a no-charge conversation, and it’s worth the time to explore what you don’t know.
Your gift of not knowing can be valuable to you as you go on this journey. Let it guide you instead of holding you back.
Ready to explore what’s possible? Schedule a discovery meeting with one of our Transition Guides at transitionstrategists.com/discovery. You’ll gain clarity on your next step—no strings attached.
