How to Find the Hidden Obstacle That Is Actually Preventing Progress

We were trying to build an apartment building, and the hard cost estimates came in about 20% over where they needed to be for the project to work.

The general contractor was in-house, which meant I had very little leverage and no real alternative. When I pushed back on the numbers, the answer was basically: this is what it costs.

So I did what developers do when a project is too expensive. I started value engineering. Line by line, system by system, trying to figure out where we could reduce cost without ruining the project in the process.

I spent weeks on it. And then I found something that was not really a value-engineering problem at all.

We were building too much parking.

Not a little too much. Enough that the garage was forcing us to excavate an entire half level deeper than the project actually needed. That one decision was cascading through the budget: more concrete, more structural steel, more waterproofing, more time.

The parking count had been set early based on assumptions about what the market required. By the time we were trying to solve the cost problem, nobody was really treating parking as a decision anymore. It had become part of the scenery.

That was the problem.

The team was not wrong that costs were too high, and value engineering was not the wrong response. We were just working one level too low. We were trying to make the budget work inside a set of assumptions nobody was questioning.

Once we treated the parking count as a variable again, the project changed quickly. We reduced it to what the site actually needed in an urban location with good transit access, eliminated the extra excavation, reworked the garage, and saved millions of dollars.

The project had looked unfixable because the real constraint was hiding inside something everyone had stopped recognizing as a choice.

I have thought about that project many times since, mostly because it taught me one of the simplest diagnostic moves I know: treat the given as a variable.

Most hidden obstacles are not hidden because someone is careless or dishonest. They are hidden because an assumption, decision, metric, or rule has been around long enough that everyone stops seeing it as something that could be different.

The longer that happens, the more work gets built on top of it. Eventually, the original choice disappears from view and starts functioning like reality itself.

I think about this constantly now in organizations. A board preference starts functioning like strategy. A legacy process starts functioning like a requirement. A founder's instinct starts functioning like market evidence. A cultural norm starts deciding what can and cannot be discussed.

None of those things is automatically wrong. The problem is when they acquire more authority than anyone remembers giving them.

That is where the newer jurisdiction lens in Near Enemies has become useful to me. Sometimes the issue is not that a strength or assumption is bad. It is that we have quietly allowed it to answer questions it no longer has the right to settle.

In this project, a parking assumption had somehow earned jurisdiction over the economics of the entire building without anyone going back to ask whether the assumption was still true.

Once you see that, the diagnostic question gets pretty simple: What decision, made early, is still constraining everything downstream?

It is an uncomfortable question because the answer may mean that a lot of smart, competent work has been happening at the wrong level of the problem. But in my experience, that is often exactly where progress starts.

What have you stopped questioning in your current work because it stopped feeling like a question?