The Orange Peel and the Shifted Fog

Waiting for the notification bubble to pop in the #strategy channel feels like watching a slow-motion car crash where nobody is driving but everyone is screaming for the brakes. I just finished peeling an orange in one piece-a spiraling, fragrant ribbon of zest that sits on my desk as a reminder that some things, if handled with enough patience, have a clear and predictable structure. My company, however, does not. We are a ‘flat’ organization. We burned the org chart in 2019 during a retreat that involved way too much expensive bourbon and a collective, misguided belief that human ego could be solved by simply removing job titles. We were wrong. We didn’t eliminate hierarchy; we just drove it underground, where it mutated into something far more difficult to navigate than a standard reporting line.

In a traditional company, if your boss is a jerk, at least you know who the jerk is. You have a map. You know that if you need a budget approved for a $499 software license, you go to Person A, and if they say no, you can appeal to Person B. But in the flat world, the map is replaced by a shifting fog of social capital. You don’t ask a manager; you ‘socialize’ the idea. You float a trial balloon in a public channel and wait to see if the ‘Founders’ Circle’-a group of 9 people who have no official title but hold all the keys-gives it a thumbs-up emoji. If they ignore it, the project is effectively dead, but without the dignity of a formal rejection. It just withers on the vine while you wonder if you’ve somehow lost your ‘cool’ status.

The Tyranny of Structurelessness

Sky E.S., our quality control taster, is perhaps the only one who sees this clearly. Sky is the kind of person who can detect a single off-note in a batch of 199 units, and they apply that same granular scrutiny to our office politics. Last week, Sky watched a junior designer try to pitch a radical rebranding. There was no manager to tell the designer it was off-brand. Instead, the room just went silent. One of the ‘OGs’-the people who started in 2009 and therefore carry a mystical, unchallengeable authority-just tilted their head and said, ‘I’m not sure that feels like us.’ That was it. The designer didn’t get a performance review or a critique. They were just socially excommunicated from the decision-making process for the next 49 days.

This is what Jo Freeman famously called the ‘Tyranny of Structurelessness.’ When you remove formal structures, informal ones inevitably take their place. And informal structures are, by definition, unaccountable. You can’t file a grievance against a ‘vibe.’ You can’t negotiate a raise with a ‘culture.’ This is the great lie of the modern tech-inspired workplace: that by removing the ceiling, we’ve given everyone wings. In reality, we’ve just made the ceiling invisible, so you only know it’s there when you bang your head against it.

I’ve spent the last 29 hours thinking about why we crave this illusion of flatness. It’s a form of corporate narcissism. We want to believe we are so enlightened, so collaborative, that we don’t need the ‘crutch’ of management. But leadership isn’t a crutch; it’s a service. A good manager absorbs the ambiguity of the organization so their team can focus on the work. In a flat company, the ambiguity is distributed equally among everyone, which means everyone is constantly exhausted by the meta-work of figuring out who actually has the power to say ‘yes.’

The Political Wasteland

We see this dynamic play out in the way we handle conflict. In a structured environment, conflict is handled through escalation. In a flat environment, conflict is handled through gossip. Because there is no ‘judge,’ we have to build a coalition of peers to win an argument. It turns the workplace into a perpetual high school cafeteria. I saw a brilliant engineer quit last month because she couldn’t handle the ‘consensus building’ required to change a single line of legacy code. She didn’t want to be a politician; she wanted to be a coder. But in our flat world, everyone has to be a politician. If you aren’t actively managing your social standing within the 9-person inner circle, your technical skills don’t matter.

The Political Clout vs. Technical Skill Distribution

The Extrovert’s Paradise

In our office, we try to pretend that a lack of titles means we are all equal. But Sky E.S. pointed out during lunch that the person who talks the loudest in meetings is the one who usually gets their way, regardless of the data. That’s not equality; it’s an extrovert’s paradise. In a structured company, a manager’s job is often to quiet the loud voices and amplify the quiet ones. In a flat company, the quiet ones just get trampled. We have 59 different ‘internal champions’ for various causes, but none of them have the actual budget or authority to change anything. It’s all a performance of empowerment without the actual power.

I remember a project back in 2019 where we tried to launch a new product without a lead. We called it ‘The Collective.’ We spent 19 weeks in meetings trying to reach a consensus. Every time we got close, someone new would join the ‘informal’ thread and reset the clock. Because there was no designated decider, everyone felt they had a veto. We ended up launching a version of the product that was so watered down by compromise that it failed within 49 days. We lost nearly $199,000 in development costs because we were too afraid to tell someone they were in charge.

The Call for Better Managers

If I could go back to that retreat in 2019, I would have thrown my bourbon at the flipchart. I would have argued that we don’t need fewer managers; we need better ones. We need people who are willing to take the heat for a decision, who are willing to be the ‘bad guy’ so that others can be the ‘creative guy.’ We need structures that are visible enough to be criticized and modified. You can’t fix a shadow. You can’t reform a ghost.

Sky E.S. just walked past my desk and looked at the orange peel. ‘Nice work,’ Sky said. ‘Clean lines. Everything where it should be.’ I looked at the peel and then at the Slack notification on my screen. The notification was from a ‘workstream lead’ asking for a ‘pulse check’ on a project that hasn’t moved in 39 days. I realized then that the orange peel was the most honest thing in the room. It didn’t pretend to be anything other than what it was: a protective layer with a clear purpose, designed to be removed when the fruit inside was ready. It didn’t need a consensus to exist. It just needed a structure.

The Final Reckoning

We need to stop being afraid of authority. True authority isn’t about power-tripping; it’s about responsibility. It’s about being the person who says, ‘If this fails, it’s on me.’ In a flat company, if something fails, it’s on ‘the culture.’ And you can’t put ‘the culture’ on a Performance Improvement Plan. You can’t hold ‘the culture’ accountable for a $999 loss. We have traded the occasional tyranny of a bad boss for the constant, low-grade fever of a community that refuses to lead. It’s time we put the maps back on the wall, even if we have to draw them ourselves. Because without a map, we aren’t explorers; we’re just lost.