When it comes to life’s transitions, we often focus on the destination because it feels hopeful and clear. We celebrate the promotion to the C-suite, the successful hand-off to a successor, and the travel-bug views of retirement. Those milestones matter. But the real growth often happens before the celebration, in the courageous middle where you keep moving even when the path is not fully visible.
That middle can feel messy, uncertain, and unfinished, but it is also where momentum begins.
In William Bridges’ transition model, the messy middle or the Neutral Zone is the in-between space after the old identity, routine, or role has loosened, but before the new one has fully taken shape. It can feel confusing and inefficient. Yet it can also be the most creative part of the transition, because it is where experimentation, learning, and reinvention begin. If you are there now, it does not mean you are behind. It may mean you are exactly where transformation starts.
I know this space. Not long ago, I poured time and energy into building and launching “The Next Chapter Remix” – an online game where people collaborate to invent what comes next in retirement.
It failed.
The launch missed the mark. And yes, it was painful. As a coach who guides leaders through life shifts, eventually I saw the experience not as a failure but as a live demonstration of what the messy middle of transition actually requires.
Whether you are stepping up, stepping back, or stepping away, the lesson is the same: thinking through the messy middle only gets you so far. You have to prototype your way through it too.
1. Stepping Up: Moving into an Executive Role (clarifying impact)
When you move to an executive role, your old playbook no longer carries the same weight. Execution still matters, but the work shifts. You are now expected to shape strategy, influence across the enterprise, and make decisions with less certainty and more visibility.
When I built my game, I fell into the classic builder trap. I focused intensely on mechanics, features, and getting the pieces to work. But launching a game, like stepping into the C-suite, requires a different altitude. You have to become both publisher and architect: someone who understands the larger ecosystem, not just the individual tasks.
The Messy Middle Lesson:
Your first months as a new executive role may feel like a beta test. Some decisions will land. Others will miss the mark. That does not mean you do not belong. It means you are gathering data. The messy middle asks you to loosen the identity of the expert / doer and practice the identity of the enterprise strategist. Your early choices are prototypes that help clarify where your impact truly belongs.
2. Stepping Back: Building Next-Generation Talent (transferring impact)
For seasoned leaders, the messy middle often looks like letting go. To transfer your impact, you must move from star player to coach. You have to watch others run the play, make the call, and sometimes fumble in ways you could have prevented.
Game design taught me a blunt lesson about control. I designed the rules, built the world, and set the parameters. But once the game was live, I could not control who was motivated to play, what they noticed and did, where they got stuck, or whether they stayed engaged.
The Messy Middle Lesson:
Succession is not about scripting every move. It is about building a safe sandbox where emerging talent tests judgment, practice ownership, and learn from manageable mistakes. If you over-control the process, you may protect the moment but weaken the future. Transferring impact means designing low-stakes places for others to grow before the stakes are high.
3. Stepping Away: Retirement Life Design (re-imagining impact)
For some, retirement can bring a surprising form of choice paralysis. People who have spent years operating in high-stakes environments often look at the blank canvas of retirement and freeze. Rather than choose the wrong hobby, board seat, consulting role, volunteer commitment, or daily rhythm, they get stuck and never make an intentional choice.
When my game launch failed, it was disappointing. But I also learned something freeing: I survived. My identity did not disappear because one experiment did not work. Instead it expanded because I had new information.
The Messy Middle Lesson:
Retirement is not one final decision. It is a series of beta tests. Try the class. Take the trip. Consult for a limited project. Volunteer for a defined season. Experiment with a new rhythm for 30 days. If something falls flat, it is not failure; it is feedback. Close the app. Keep the learning. Launch the next version.
The Reality of the Messy Middle
The Neutral Zone is supposed to feel uncomfortable. If every experiment succeeds, you may not be experimenting at all. You may simply be repeating what already feels safe.
My game never topped the charts, it didn’t even get close. But it gave me something more useful: tools, empathy, and resilience for helping leaders navigate the in-between with more curiosity.
So, if you are in the messy middle right now, do not wait for perfect clarity. Build a small prototype. Run the experiment. Notice what happens. Then adjust. Every small test is proof that you are not stuck; you are actively shaping what comes next.
Keep going. The messy middle is not a detour from your transition; it is the place where courage, clarity, and confidence are built one experiment at a time.
Reflections:
For the Executive: What old doer/builder habits are you still clinging to, and what small strategic experiment could help you lead from a higher altitude?
For the Succession Leader: Where are you still managing outcomes too tightly, and where could you create a safe sandbox for next-generation talent to practice real ownership?
For the Retiring Leader: If you treated the next six months as a low-stakes beta test instead of a permanent decision, what would you try first?
Carol Bergeron – Drawing on 25+ years as coach, consultant, and author, Carol Bergeron helps leaders unlock their legacy through executive branding, succession planning, and retirement life design.
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