In the event planning and production world where I work, project cycles are usually long, complex, and abundant with surprises. Large-scale conferences often require over a year of planning.
The process is dynamic, with so. many. moving parts and dependencies—and somewhere in the middle of it all, motivation and focus can wane.
This is the Messy Middle: the part of a long-term project where things get squishy. Priorities can get blurred, team energy can dip, and progress can feel slow or scattered.
I recently wrapped up two co-located events, for about 1,800 attendees. I definitely remember us hitting that Messy Middle during the Summer months.
So What Is the Messy Middle?
If you’ve ever worked on or led a months-long project, you’re probably familiar. It’s that time when things might get off track or lose momentum—even when there’s a meticulously crafted project plan or a framework of sprints and phases.
Humans are evolutionarily wired to move and work by the seasons (something capitalism rebranded as “quarters”). But it can be difficult to sustain energy and focus over extended timelines. These ebbs and flows are natural, but they can be challenging when you’re in the thick of your project.
Symptoms of Messy Middle Syndrome often include:
Delays or missed milestones
Blurred or shifting priorities
Wavering motivation
Communication lulls or breakdowns
Frustration or disengagement
I think athletes experience the same in a long season, musicians in the middle of a long tour, or theatre actors in a long show run — even though at the heart of it all they/you/we love what we’re doing.
Even when the work is meaningful and JOYFUL, the cumulative weight of a project can take its toll. It’s normal for teams to lose focus or energy, especially when external factors—both personal and professional—play a role.
Embracing Liminal Spaces Mid-Project
These dips are inevitable because, well, humans. Sometimes those manifest as minor disruptions, sometimes as more serious setbacks. But I’ve learned to allow for these moments to be liminal spaces of transformational possibility.
For the uninitiated, Liminal Spaces are transitional, in-between phases where the old has ended, but the new hasn't fully begun—offering potential for transformation, creativity, and realignment.
In a project expected to have continuity throughout, the idea of a project falling into periodic “liminal” periods can be scary or unsettling. They are squishy and less defined. As someone who built a career in an industry that needs structure, they still make me pretty uncomfortable. Raise a hand if you can relate.
But liminal spaces are also invitations for profound creativity and collaboration to happen.
When a project feels off track, or the team’s energy is flagging, it’s an opportunity to pause, reassess, and treat the moment as a transition into a new phase. A pause can help you:
Evaluate what’s working (and what isn’t)
Revisit assumptions or constraints that no longer serve the project
Co-create solutions to regain focus and momentum
It’s an opportunity to treat the pause or setback as a natural endpoint in the project, and discuss as a team what emerges next as a “beginning”.
Team discussions can be brief (as short as a quick check-in or as long a dedicated half-day workshopping session). Reflective questions to guide the conversation include:
“What assumptions do we need to revisit?”
“If we started this today, what would we change?”
“What’s the one most important outcome we need to achieve?”
Whether the result is a simple refocus, a significant adjustment, or even a decision to table the project, treating these moments as opportunities rather than setbacks can unlock powerful insights.
Re-Igniting Motivation
A visible drop in motivation is often a key symptom of the Messy Middle. These moments of pause are perfect for rekindling intrinsic motivation—both within the team and by its individual members.
It’s a great opportunity to reorient the team to the project’s original goals and vision—while also holding space for each person to reconnect with what excites or fulfills them about their role in the work. Even when a project isn’t particularly inspiring, a skilled lead can help team members find personal alignment within their contributions.
Questions you can discuss as a team in a liminal space include:
“What part of our work as a team feels most impactful or exciting right now?”
“Where do we feel the most aligned as a team, and where could we improve our collaboration?”
“What feels most meaningful about your role in this project right now?”
“What’s one change that could make your work feel more energizing or aligned with your strengths?”
“What’s one adjustment we could make together to reignite momentum or creativity?”
Re-Igniting Focus
When energy and momentum wane, it’s critical to re-center the team around clear priorities and a shared sense of purpose. By focusing on clear goals, connected to the larger vision, and holding space for creative, collaborative solutions, teams can regain the clarity and energy needed to move forward.
Simplify Objectives: Break larger goals into smaller, actionable steps to create momentum and help the team feel accomplishment along the way
Reconnect with the Vision: Help your team and colleagues reconnect with their intrinsic motivations and curiosity, but also what excites them about why the project matters more broadly
Collaborative, Creative Solutions: Use collaborative brainstorming sessions or constraint challenges to tackle roadblocks and inspire ownership
Balance Autonomy and Accountability: Continue fostering trust by ensuring each team member has the freedom to approach their tasks in their own way, while maintaining clear expectations and deliverables
Balance Focus with Recovery: Encourage structured deep work sessions for key tasks, paired with recovery breaks to prevent burnout and recharge focus.
These strategies provide both the clarity and flexibility needed to navigate through the Messy Middle and into the next phase, with less friction.
The messy middle of any project is an inevitable phase, but it’s also a transformative one. By viewing it as an opportunity rather than a setback, you can reframe challenges into moments of growth and alignment. Pausing to reflect, reconnect, and re-focus—both individually and as a team—allows you to navigate the squishier, less structured parts of a project with clarity and renewed energy.
Here’s to embracing the middle and the liminal spaces—and all the opportunities it holds. See you in the next edition!
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