Mistake Stacking
Unpacking the Subtle Traps of Habit, Assumption, and Project Commitments
“Stupid program” was mistake number three.
Since my kids are half home-schooled and half in public school, a big chunk of their work is homework. The other day, my youngest was working on math through Khan Academy. Frustration was mounting.
“There’s no value in getting mad at the math program. That’s adding one mistake to the others you’ve already made.” (Said Dad the mindset coach… Oops).
Let’s unpack this for a moment, starting with different types of frustration.
Three sets of frustration
First, there’s frustration that arises from creativity. According to Kurt Lewin (as cited in The Art of the Impossible by Steven Kotler), “frustration is simply an obstruction to a goal that demands an innovative response.”
Second, there’s low-level frustration, which Ken Robinson believed was essential for sustained creativity. It’s the quiet “what if I can make it better?” itch. (Also described by Kotler.)
Third, we have frustration from mistake stacking.
In this case, frustration—rather than curiosity or learning—became mistake number three.
Mistake number two was the error in the math problem.
Mistake number one? Trying to do everything in their head instead of putting it on paper where they could see their thinking.
I’ll admit, I’m often guilty of mistake number one myself: keeping everything in my head—even though I know my writing, my creating, and my problem-solving go better when I get things out onto the page.
Here’s how it usually plays out:
- Mistake 1: Keep it all in my head.
- Mistake 2: Stare at a blank page or write sentences that don’t work.
- Mistake 3: Feel frustration, maybe even overwhelm.
All of which I solve the moment I go back and correct mistake number one – before trying to write the sentences.
The same afternoon, my youngest went back to step one—and immediately found the solution he’d been missing.
Of course, I expect we’ll revisit this conversation again soon. He’s still committed to doing the math in his head.
Mistake Stacking in Projects
Mistake stacking happens when past commitments or assumptions get in the way of current choices that might be for the better.
Prior decisions which have become integrated as commitments get in the way of changing the decision when it no longer makes sense.
- A commitment to do math in your head – maybe to avoid the writing.
- A commitment to sit down and immediately write coherent thoughts because I think I should be able to.
- A commitment to not developing technology in house – to only buy SaaS.
- A commitment to a particular project plan.
- A commitment to a favored methodology (Lean, Agile, Six Sigma, etc.).
These all represent decisions made at some point in time that have become commitments.
When something isn’t working, people double down—holding onto old decisions as if more effort will fix the underlying mismatch.
On projects it might look like this:
- Mistake 1: Choosing the standard methodology because “that’s what we do here.”
- Mistake 2: Sticking with the methodology even when it clearly isn’t working.
- Mistake 3: Adding layers of control, switching out the team, or canceling the project (sometimes stacking mistakes 3, 4, and 5).
Instead of solving the real issue, we end up stacking mistakes.
Revisit core assumptions
You can interrupt mistake stacking by revisiting your core assumptions—your underlying commitments.
To avoid mistake three, you have to notice and resolve mistake two, which is rooted in mistake one. But here’s the catch: mistake one rarely feels like a mistake. It feels like “the way we do things.”
That’s why you need feedback loops—mechanisms that tell you something isn’t working. The faster the feedback, the better—but only if you pay attention.
When something isn’t working, you have to notice it before you can do anything about it.
Engage an uncommon response
The common response to stuckness is to try harder with the same approach.
In projects, this is how you end up canceling the whole initiative when a simple change in approach—if made earlier—would have sufficed.
By the time frustration sets in, you’re already far down the road, mistake stacked upon mistake.
The math example is simple: getting a question wrong is feedback. The answer isn’t to blame the program—it’s to check your work. But you can’t check what you can’t see.
If you follow the feedback loop all the way back, it usually leads to the first mistaken commitment or assumption.
When you first notice something off in a project, the reflex is to try harder and keep quiet.
Then, when it’s too big to ignore, the next reflex is to find who or what “went wrong.”
But often, nothing “went wrong.” There’s just a faulty assumption or outdated commitment at the root.
Useful Questions for Shifting Course
When things aren’t working, ask:
- Am I doing something that doesn’t work (for this context)?
- Am I expecting results that don’t make sense here?
- Is there an assumption or commitment underneath that isn’t serving me anymore?
Use your feedback loops. Change course before mistake three.
But if you miss that, at least follow the signals all the way back to the core assumption. That’s where real change becomes possible.
– Gerrett
This was originally published on Substack in my Human Systems Playground. But I’ve decided to bring all my writing home here.
