I talk to a lot of families and business owners who tell me, “I know I should be thinking about transition, but I’m just not ready yet.” And every time I think, of course you’re not ready. Humans don’t leave something comfortable unless we believe there’s something better waiting ahead for us. And it’s not weakness that causes that. It’s just our normal human wiring. Our brains, our emotions, even our habits. They’re all designed to keep us safe and to stay in what’s familiar.
We operate our lives, if you think about it, 99% on automatic. We get up every day. We brush our teeth in the same order and the same way. We get in the car, take the same route to work or to school. Everything is very familiar. And what that means when you think about transition is that transition is real.
It’s a real transition. It isn’t just about letting go of what’s behind you. It’s about clearly seeing and believing in where you’re going. Because if you don’t have that, you’re not going to go.
What We Focus On (and What We Miss)
So too often, we tend to start our conversation focused on what we might lose. Some great examples of that are we could lose control. We could lose identity. We could lose the business we built. The leadership role that we’ve taken for decades. And almost never do we stop and really paint that clear picture of what we might gain.
Sometimes we do, a little bit, but really envisioning what we might gain. Some of it could be freedom of choice, could be impact to others. It could be leaving a legacy that’s gonna go on and be even bigger and better than what you have made so far.
And then there’s peace that comes when things are finally aligned for a next generation that you know, and you can see them doing it. You know that this is going to go as well as it can for them, because we all know there are external things in our world that change, and we have to navigate with them.
It isn’t just about letting go of what’s behind you. It’s about clearly seeing and believing in where you’re going.
You Don’t Need a Perfect Plan to Start
I’ve lived in that tension myself. There was a time when I was trying to figure out what to do with this company, with the intellectual property that I’ve built and how was it going to go forward. Or was I just going to shut it down? And I really didn’t know what’s next.
So I’ll tell you that what I did is I dove into our Evolve program. And I decided I’d been talking about it for so long that I should actually try it out and do it myself. Long before I ever even had anybody in mind who might be a successor.
And I didn’t have to have the perfect plan to start, but the truth was I had to start before I could find the plan to get clear. I had to discover before I could find. And I’ll tell you the path, it started out completely with uncertainty, and it is every bit as hard as the one that starts with a clear goal in mind.
I’ve had so many clients come in thinking they know what they’re going to do. They know they’re going to sell to a third party. And after going through the Evolve program and the discovery, they figure out that wasn’t the right thing. It was just what they had in their mind. And I have example after example of that happening with our clients. So that’s part of the beauty of the whole thing.
Transition Is a Team Sport
Transition, it’s not a solo climb. It’s actually a team sport and it’s really fun when you take it off of yourself as thinking of it’s your solo climb and you’ve got to figure it all out before you can bring anybody else in to making it a team sport. Because you can’t know every single step, but you can surround yourself with the right people who can help you see those right steps, see those possibilities and even articulate them.
And those people aren’t, it could be people like us who are running the Evolve program and guiding people through. It also though, as important is your spouse, your children, some of your key employees. And it’s terrifying to start to talk about this, because you’re so afraid as a transitioner that they’re going to think there are promises made that really weren’t, that you’re just getting yourself together here. And there really are no promises, but you’re exploring and discovering.
So others can help you protect what matters most to you, and also can be very additive to you in reimagining what’s next, even as an individual, they can be helpful there.
This Process Is Deeply Human
So this process, it isn’t theoretical. But it is emotional, it’s relational, and it’s deeply human. Because when you go through this transition discovery process and actually map out your next maybe five years, your next decade, you can really start to engage in what does it mean to you to move from where you’re comfortable right now.
I’ll say comfortable in quotes because we all know that business and assets and management, that’s not easy. But we can start to see a future that is worth moving toward, but you also start to see how it’s going to work, right? It’s not just stuff running around in your mind.
And I will tell you that in my experience, it’s such a complicated process to go through transition and then add time into it as well. Tax, estate, time, people, including clients, employees, all of that. It’s complicated enough that you, it really is helpful to have a framework to put all that information in so that you can see it.
It’s not the movement that makes it fall apart. It’s the lack of movement.
If You’re Feeling the Tension
So if you are feeling the tension and you’re knowing that right now really something is coming for you. You just don’t know what it is and you’re starting to feel that. That’s a good time to say, I’m going to dig deeper and I’m going to investigate. I’m going to explore. I don’t have to make any decisions. I don’t have to be ahead of the game.
And you can do this in a lot of ways. You could come into our Evolve program. We’ve got a lot of tools that can help you do that. But the other way that you could do it is literally by journaling, and starting to think about and ask yourself questions on what is it that’s in my Next Adventure™️ that would make me fulfilled.
In some of these conversations that we’ve had, we’ve talked about that Japanese word called Ikigai. And that is what the meaning is, your reason for getting out of bed. As you transition out of this business, you have so many choices about how you do it. And you could transition out of the equity and still be engaged in the day-to-day work. I’ve had multiple owners do that and enjoy being still active while not having the weight, not having the weight of payroll, not having the risk to themselves and to their retirement, right, and their ability to keep that retirement, that financial stability, your financial rock together. So lots and lots of options there.
What Happens When You Stay Too Long
So if you’re feeling that tension, take time to dive a little deeper and to honor that. Maybe focus and write a little bit about what you think you might leave behind just for some reflection or again, come into Evolve and you’ll do that there too. Start dreaming, start envisioning about where you’re moving and what you’re moving toward because that’s going to be your key to really being excited about leaving this business.
You’ve done a great job. You’ve had a lot of achievement. Now what?
Once you see and you feel that possibility and what’s possible for you, it’s easy to find the courage to move. And it’s actually sometimes hard not to move because you get so excited about it. And when you can’t see it yet, that’s when you need somebody around you to help you do it. Because one way or another, you are leaving this business.
And the longer you stay, while your energy is maybe declining or you’re even just at a status quo, the harder it is for those successors to come in and the more opportunity you risk. And when I talk about opportunity, what I mean by that is there’s opportunity in being with, teaching, helping others to achieve more than you ever could have imagined. So there’s opportunity there.
But there’s also opportunity for you, where you maybe kept yourself in this business, stayed in place because you didn’t see another way out, and you thought that if you started to move, everything would fall apart. And I will tell you that, at least in my experience, the people that stay, that’s when things start falling apart. It’s not the movement that makes it fall apart. It’s the lack of movement, and the lack of doing something step by step.
The Energy Shifts When the Vision Comes Into Focus
So you can chart a clear path, you can do it with others, and you can enjoy this Next Adventure™️ in your life. You won’t transition until you know where you’re going. But when you do, and when that vision comes into focus, the energy shifts. And that’s when the real work and also the real fulfillment and the fun begin.
This is a great journey. And my encouragement to you is if you’re feeling that tension of, I’m getting close, lean in soon, lean in early, and enjoy the ride because it’s a journey.
Ready to Explore What’s Next?
If you’re feeling the pull toward transition but aren’t sure where to start, our Evolve program can help you discover clarity, build your Transition Roadmap™️ and surround yourself with the right people for the journey. You don’t need to have it all figured out first. That’s what we’re here for.
Schedule a Discovery Call at transitionstrategists.com/discovery to get started.



