DEAR ELIZABETH talks about starting your transition journey without all the answers

Dear Elizabeth,

I'm a business owner who feels genuinely stuck. After building something meaningful over 20 years, I know I need to think about transition, yet I don't even know where to begin. Who is my successor? Is it too early to start these conversations—or am I already too late? I keep waiting for clarity that never comes. Some days I think my son might be interested, other days I wonder if selling makes more sense. I worry about damaging relationships by bringing this up prematurely, yet I also fear the cost of waiting too long. How do you start when you don't have the answers?

-Overwhelmed Owner

Dear Overwhelmed Owner,

Your letter brings me right back to my own experience with Andrea. I thought bringing on a successor would slow our pace, but it's been like rocket fuel. What I've discovered is that the energy and momentum you're worried about losing actually multiplies when you approach transition thoughtfully.

Here's what I've learned after 30 years of guiding business owners and now living it myself: you don't need all the answers to begin. In fact, starting with uncertainty is often exactly where the most powerful transitions begin.

Andrea and I talk about this regularly on our podcast. How the process itself becomes the teacher. When we started our own transition journey, we had far more questions than answers. Yet through that exploration, we discovered possibilities neither of us had imagined. The business hasn't just survived the transition; it's thriving in ways that surprise us both.

The truth about starting without clarity:

Discovery IS the process. The timeline you're seeking, the successor you're wondering about, even your own readiness... these all become clear through exploration, not before it. Some of our most successful client families began exactly where you are: knowing they needed to think about transition but uncertain about every detail.

Relationships strengthen through honest conversation. Your worry about damaging relationships by bringing this up prematurely is understandable, yet in our experience, the opposite often happens. When you approach these conversations as exploration rather than decision-making, people feel invited rather than pressured. Andrea and I have seen this repeatedly, both in our client work and in our own journey.

Starting early creates options. Whether your son is interested, whether selling makes sense, whether there's a creative solution you haven't considered... all of these possibilities remain open when you give yourself time to explore. The families who feel forced into quick decisions rarely achieve the outcomes they truly want.

This is exactly why we created our Evolve program. It's designed for business owners who are ready to explore yet not ready to commit. Through our immersion experience, you'll lay everything on the table: your motivations, your options, your family dynamics, all in a safe environment that honors both your uncertainty and your wisdom.

The strongest transitions don't begin with perfect clarity. They begin with the courage to start the conversation.

Warm regards,

Elizabeth