Standing in the rain outside my own car, staring at the keys resting on the passenger seat, I realize I am the living embodiment of the very problem I spent 45 minutes complaining about this morning. I am locked out of my own life because I skipped the basic process of checking my pockets. It is a small, stupid error that has cost me 25 minutes of my afternoon and a significant amount of my dignity. This is the exact sensation of working at a high-growth startup. You are promised the keys to the kingdom-freedom, autonomy, a ‘flat’ hierarchy-only to find that nobody actually gave you the code to the front door, and the person who was supposed to have it is currently on a 15-day retreat in the desert to find their ‘inner disruptor.’

Hannah is sitting inside the office, unaware of my rain-soaked existential crisis, currently engaged in her own battle. She is searching the Slack archives for the fifth time this hour. She’s looking for the returns policy. She has found three versions so far: ‘Returns_Final_2025,’ ‘Returns_NEW_V2,’ and a pinned message from 105 days ago that simply says ‘we don’t do returns anymore, just refund them lol.’ The founder, a man who wears 75-dollar t-shirts that look like rags, tells her we ‘move fast and break things.’ What we are actually breaking is Hannah’s spirit. The romanticization of chaos in the tech world is a disease. We call it entrepreneurial energy, but if you look closely, it is just an aggressive underinvestment in structure. It is a way for leadership to avoid the hard work of building a foundation while placing the burden of improvisation on the shoulders of people who are just trying to do their jobs.

I once spent 35 hours in a single week arguing about the color of a button while the underlying database was failing every 15 minutes. It’s a specific kind of insanity. You are encouraged to be a ‘self-starter,’ which is often code for ‘we don’t have a training manual and if you ask for one, we will think you aren’t a culture fit.’ This creates a landscape where the most successful employees aren’t necessarily the most competent, but rather the ones best at navigating a fog of their own making. It’s a personality test disguised as a career. If you can’t thrive in the mess, you are the problem, not the mess itself.

Rio P., a soil conservationist I met while doing a project on land management 5 years ago, understands this better than any CEO I’ve ever interviewed. Rio is a man of 65 who speaks in sentences that feel like they’ve been weathered by the wind. He once told me that you can’t force a plant to grow faster by shouting at it or by constantly moving it to ‘more exciting’ soil. ‘Soil is an infrastructure,’ Rio said, pointing to a patch of ground that looked like nothing to me but meant everything to him. ‘It needs 15 specific minerals and a structure that allows for 25% air pockets. If you ignore the structure, you just have dirt. And nothing grows in dirt that’s been trampled by people in a hurry.’

Startups are currently trampling their own soil. They treat their employees like disposable seeds, throwing them into a chaotic environment and wondering why 55% of them burn out before their first anniversary. We have normalized the idea that avoidable disorder is a sign of ambition. If you aren’t overwhelmed, you aren’t working hard enough. If you ask for a clear process, you’re ‘bureaucratic.’ But the truth is that process is what creates freedom. When you know where the returns policy is, you have the mental space to actually solve the customer’s problem. When you don’t, you spend your entire day in a state of low-level panic, clicking through 85 different tabs in a desperate search for a single source of truth.

I remember a meeting 25 days ago where the ‘Head of People’-a title that always sounds like a character from an Orwellian novel-told us that we were ‘evolving past the need for rigid documentation.’ He said it with a straight face while 15 of us sat there knowing that we hadn’t been paid on time for the last 5 months because the payroll system was ‘evolving’ too. It is a gaslighting technique. It turns the failure of the organization into a lack of flexibility in the individual. It suggests that if you were truly ‘agile,’ you wouldn’t mind that the goalposts have moved 55 yards to the left since you started your sprint.

There is a profound lack of respect in this approach. It assumes that an employee’s time is an infinite resource that can be spent on the friction of chaos. But time is the only thing we actually have. Every minute Hannah spends looking for a document that should be pinned to the top of her dashboard is a minute she isn’t growing, isn’t creating, and isn’t actually helping the company move forward. It is a slow leak in the ship’s hull that the captain refuses to acknowledge because he’s too busy giving a speech about the beauty of the ocean.

Meat For Dogs

Rio P. would laugh if he saw me now. He’d probably tell me that my internal soil is too loose. I have too many air pockets and not enough minerals. I am all ‘energy’ and no ‘retention.’ He’s right. Most of us are. We have been sold a version of success that is entirely about the ‘hustle’ and zero percent about the ‘maintenance.’ But maintenance is where the real work happens. It is the unglamorous act of updating the returns policy so Hannah doesn’t have to search Slack for 25 minutes. It is the act of setting clear expectations so a new hire doesn’t feel like they’re drowning on their first day. It is the 5 minutes of silence you take to actually think before you send an ‘urgent’ email that derails 5 people’s afternoons.

We need to stop rewarding the ‘firefighters’ in our companies and start rewarding the people who make sure the fires never start. The firefighter gets the glory, the promotion, and the 5-star review, while the person who installed the sprinkler system is ignored because ‘nothing ever happens on their watch.’ That is the ultimate startup irony. We value the person who can navigate the chaos we created, rather than the person who tried to prevent the chaos in the first place. We have built a culture that celebrates the cure but ignores the prevention, and then we wonder why we are all so sick of our jobs.

As the locksmith pulls into the parking lot-his van has a sticker on the back that says ‘Locked out? We’ve been there’-I feel a strange sense of relief. He has a process. He has a specialized tool that will slide into the gap in my window and pull the lock up in 15 seconds. He doesn’t need to ‘pivot’ his approach. He doesn’t need to brainstorm a new way to open a door. He knows exactly what to do because he has done it 555 times this year. There is a beauty in that kind of expertise. There is a dignity in being the person who knows the answer because the structure has already been established.

I’ll get home eventually. I’ll dry off, and I’ll probably go back to the office tomorrow and watch the ‘amateur hour’ continue. I’ll hear another speech about ‘radical transparency’ from a leader who hasn’t shared the budget 15 months. I’ll see Hannah stare at her screen for 25 minutes, lost in a sea of unorganized data. But maybe, just maybe, I’ll suggest we spend 35 minutes sitting down to write the actual, final, definitive version of that returns policy. Not because I’m a killjoy, but because I’m tired of being locked out of the things that matter by the things that don’t. Is structure really the enemy of your freedom, or is it the only thing that actually makes freedom possible?