The Middleman Complex: The Weight of the In-Between

Being in the middle is one of the most complex and misunderstood roles you can hold within any organization, movement, or mission-driven space. It is not the front line, and it is not the executive suite but it is where some of the most critical work happens.

When you are in the middle, you often hold Influence without authority. You can set agendas, Communicate Strategy, and even redirect direction — but you rarely have the final say.

You are trusted with the power of communication, coordination, and execution, yet not entrusted with full control over resources, policies, or ultimate outcomes. This creates a daily tension: advocating for agendas you have helped shape but cannot always protect.

The View from the Middle

What makes the middleman role even more challenging is the view: you often see the field most clearly, yet you’re still not privy to all the information at play. You watch things unfold from a unique vantage point—close enough to understand the boots-on-the-ground experience, yet expected to reflect and represent decisions coming from above.

In many cases, your voice is the voice of the organization. You carry the weight of its decisions, policies, and public perception, whether or not you agree or were consulted. You represent it in rooms where tensions are high and expectations are higher. And when mistakes are made or narratives get twisted, it’s easy for blame to land squarely on the middleman’s shoulders.

Even outside the uniform — after the event, after the contract ends, after you’ve stepped back — you’re still connected to outcomes you couldn’t fully control. This is burden that lingers.

The Weight of Duty and the Question of Trust

This position demands a deep level of trust, often in systems or leadership structures that may not offer full transparency. You're expected to carry out decisions that may not make sense to you—moves that may only reveal their logic much later, if at all.

You’re also expected to rally others—to motivate and mobilize teams, community members, or stakeholders—on behalf of strategies you had a hand in but didn’t finalize. In addition, when things go wrong, the public rarely distinguishes between the architect and the messenger. They see you.

I’ve lived this reality across a decade of work, both at the head of my own initiatives and as part of larger institutions. Even in leadership, I have chosen positions that cultivate collaboration over competition, influenced by thinkers like Minister Louis Farrakhan, who once spoke about Baltimore’s landscape of over 100 Black- and Brown-led organizations—many of which, despite shared goals, operated in silos that slowed collective progress.

That message hit me deeply. I believe someone must push from the bottom with the same force as someone pulling from the top and that both are equal. That belief has shaped my choices—and my challenges.

Living in the Tension

There is a unique pain in realizing you can represent something without being able to trust the representation being crafted behind the scenes. That’s a real tension—one that makes you second-guess yourself, overcommit your energy, and sometimes even underinvest in your own growth, believing that sacrifice will somehow balance the scales.

I’ve been through cycles—leading, stepping back, starting over, moving across industries and organizational cultures—trying to study and apply best practices while still learning, sometimes painfully, what not to repeat. My career has sharpened my skills in communication, policy writing, strategy, and relationship-building. However, it has also forced me to reckon with the limits of what any one person can carry from the middle.

The Cost of the Middleman Complex

This complex doesn’t just live in the abstract—it comes with very real costs:

• Burnout from overextension and emotional labor

• Perceived disloyalty from both sides—executives may see you as too grassroots, and grassroots may see you as too institutional

• Difficulty drawing boundaries between advocacy and appeasement

• Delayed self-investment—waiting on systems to change or people to “do right” before betting on yourself

• Misrepresentation—being the face of decisions you didn’t make, or watching your contributions be simplified, erased, or spun into narratives you can’t correct in real time

All of this is compounded by a culture that tends to undervalue bridge-builders—those who sit between worlds, trying to create cohesion without full ownership of either side.

So, What Now?

My goal in naming the Middleman Complex is not to escape accountability—it’s to own my perspective. I have made mistakes. I have misjudged timelines, extended trust where it was not earned, and sometimes stayed too long in systems that were not serving me or the people I serve.

But I’ve also gained clarity. The call of duty that led me into the middle was always rooted in something real: a commitment to collective progress, to building with others, and to believing that change requires coordination, not competition.

Going forward, I’m learning to:

• Set boundaries without shutting doors

• Trust my voice even when I’m not the loudest in the room

• Invest in myself even when systems delay their investment

• Lead with clarity about what I can and cannot control

• Document the truth—so that when the stories are told, my perspective isn’t lost

The middle is a tough place. But it’s also a sacred one—if you can navigate it with clarity, humility, and enough backbone to withstand the pressure.

So this is me, naming it. And stepping forward from it.