Dark Productivity

The work that keeps a business alive without moving it forward

We had to let an employee go. Their home state, North Carolina, wanted the circumstances of that departure confirmed. Reasonable enough. Someone’s access to state support depends on it.

The site didn’t load. 403. Forbidden. No explanation. Long experience told me what was happening: plenty of US state tax portals are locked to US IP addresses, and none of them think to mention it. So, VPN on, connect to a US endpoint, reload. The page appeared.

Then it wanted two-factor authentication. Also reasonable. But the only option offered was email, and the address on the registration belonged to the CEO of that company rather than a generic operations inbox. So now I needed him. In a business that runs async by default, that meant waiting for a moment when we were both live at the same time, which turned out to be five days later, at which point we burned the first seven minutes of a valuable one-on-one watching an inbox.

The code arrived. I logged in. The first thing the system showed me was an error message with the HTML unrendered, raw tags scattered across the screen. I’m convinced half of operations is simply discovering which browser a government agency accidentally tested its website in.

Five days elapsed. Perhaps half an hour of actual work. It is still sitting on my list to finish today.

That is Dark Productivity.

Naming it

If you’ve read my work before, you’ll know I like naming the quiet killers of business performance. Operations Debt. Failure Demand. Busy Ops vs Business Ops. Here is another for the family.

I’ve written before about the curse of ops people, that nobody notices when we’re doing our jobs well (https://chrismonk.substack.com/p/busy-ops-vs-business-ops-and-a-spot). Dark Productivity is that curse’s harder-edged cousin: the complex, important work that keeps a company legal, compliant and alive without ever moving it forward. Defensive rather than proactive. You are not making good things happen, you are stopping bad ones.

That distinction matters, and it is why I resist calling this work low value. The North Carolina filing is not trivial. Get it wrong and a former colleague loses access to support they are entitled to, and the company picks up fines or worse. The stakes are human and financial at the same time. But no customer will ever pay a penny more because we filed it, and no investor will ever ask.

Important. Complex. High-stakes. And it advances nothing.

I’d estimate between 10 and 20% of my working time disappears into the dark, most of it spent interacting with government agencies simply to clear the ground so the real work can happen.

The uncomfortable maths

I look after four businesses. Each one costs me at least a day a month in dark work.

That is four days a month, forty-eight days a year. At my day rate, call it around £30,000 annually. Roughly a month and a half of board-level time, gone into broken portals and hold music.

And that is before the opportunity cost of everything I am not doing while the page fails to load.

“Just automate it”

It is the obvious retort and it misunderstands the problem.

The routine work is already automated. We run Gusto and a stack of third parties precisely so that business-as-usual handles itself, and it does. What generates Dark Productivity is everything outside the pattern: the genuine exception, or the breakage that happens when several systems and a human collide. This is the US in my example, but the UK is no different. Wherever multiple systems overlap and a person has to intervene, the friction appears.

By definition, the exception is the thing that resists automation. You cannot write a rule for the case you have never seen before.

Delegation runs into a related wall. At startup scale, with small teams, the briefing cost on a task this one-off and this consequential is roughly the doing cost. Explaining the North Carolina situation to someone else, including everything that could go wrong and why it matters, takes about as long as opening the VPN and getting on with it.

So it stays with me.

Containing it

You cannot eliminate Dark Productivity. You can contain it, and you can shift some of it from reactive to proactive.

Name it and track it. Once you know how much time it actually takes, you can make decisions about it rather than letting it nibble at every day. Mine is visible, which is how I can tell you it costs around £30,000.

Give it a container. Every Monday I work through a checklist of around seventy tasks across all four companies, all of them things that cannot be automated. Mondays are carved out and protected for exactly this. The value is not that the list gets done, it is that I stop carrying it. If something needs chasing or checking, it goes on the Monday list and leaves my head.

Which sounds like a contradiction, given that Dark Productivity is the out-of-the-ordinary work and a checklist is the most ordinary thing imaginable.

The list captures categories, not tasks. The line is not “fix the North Carolina portal”, it is “any open state filings needing chasing?” I supply the specifics. And looking every week is what drags this work from reactive to proactive: you find the open loop before the penalty notice arrives rather than after.

Underneath the checklist sits a GTD ecosystem to catch everything that does not fit anywhere else. The recent upgrade there: every Otter voice note and meeting recording now gets processed by Claude twice a day, with action items dropped straight into the system. The things I notice in passing no longer depend on me remembering them.

Give it to someone who has seen the form before. Experience is genuine leverage here. The first UK HMRC PAYE Settlement Agreement takes days of reading and chasing. The tenth takes an hour. The same is true of state registrations, filing calendars, and every other piece of administrative joy.

What this is worth

All of that reads like a confession. A day a month lost to tax portals, and I’m the one billing for it.

That North Carolina saga cost me thirty minutes of real work. In less practised hands it is three hours. More likely it is not done at all, because it falls through exactly the gap it was always going to fall through, and surfaces later as a fine or a former employee who cannot access their support.

That is a large part of what I do as a fractional operator. When this work comes off a founder’s plate, they get their best hours back for the things only they can do, and it gets done faster because I have filled in that form, chased that agency and sat in that queue many times before. It also stops being an interruption tax on the whole company. Dark work handled by someone who expects it is cheap. Dark work ambushing your most expensive people is not.

If you’re a founder, try this exercise. Look at the last fortnight in your calendar and highlight every hour spent stopping bad things happening rather than building good ones. That’s your Dark Productivity bill.

Those are the open loops you can see. I’d worry more about the ones you cannot.

If this feels uncomfortably familiar, that’s usually the point where people start looking for someone who actually enjoys filling in the forms. I’m wildly busy at the moment, but I’m up for a conversation and I’ll try and show you another way.