My mom was an attorney.
When I was young, she used to say something that felt almost too simple to matter:
You can win most cases just by being prepared.
At the time, I thought that was a statement about law. Courtrooms are adversarial by design. Preparation makes sense there. Someone is arguing against you, facts matter, and ambiguity gets punished.
Most of life is not like that. If it were, it would be short and miserable.
But the older I get, the more I realize she was right in a broader way. Not because life is adversarial, but because ambiguity is expensive everywhere.
The quiet cost of not writing things down
Several years ago, I was part of a multi-year project with a client who had very specific expectations about how different parts of the system would work together. Multiple modules. Multiple groups of people. Lots of conversations. No hostility. Good communication. Everyone got along.
And yet, a requirement was missed.
To this day, it is hard to say exactly how. Did the client say it, but not clearly? Did we misunderstand it? Did they think they had said it? Did we all think we understood and move on?
What matters is that none of us wrote it down.
By the time the mismatch surfaced, we were far enough along that what the client really wanted was no longer realistically possible. We built something that worked. We built something close. But it was not what they had envisioned.
There was no clean way to assign fault, because there was nothing definitive to point back to. No written confirmation. No shared artifact that said, “This is what we agreed this would do.”
A simple follow-up email early on would have changed everything.
The lie we tell ourselves
Most of us believe some version of this:
I’ll remember it.
I understand it well enough.
We’re aligned.
Your mind makes this feel true. It is usually not.
Memory is not a recording. It is a reconstruction. Details blur. Confidence fills in gaps. Everyone walks away with a slightly different version of the same conversation.
When nothing is written down, misunderstanding does not look like a failure. It looks like normal progress, right up until it becomes very expensive.
What being prepared actually means
Preparation is not about assuming bad intent. It is not about treating every interaction like a courtroom. It is not about over-documenting your life.
Being prepared means walking into something with awareness of the surrounding context.
That might mean:
- Being able to clearly describe your symptoms before a doctor’s visit
- Understanding the business rules around a decision before a meeting
- Knowing that most “unique” problems are variations of things that have happened before
Preparation is about reducing avoidable ambiguity early, while change is still cheap.
Avoiding overthinking
Overthinking is easy. The difference comes down to cost.
I do not worry much about whether the dinnerware perfectly matches the meal I am serving. The cost of being wrong is low.
I worry a lot more when I am handing documents to consultants charging hundreds of dollars an hour, where mistakes translate directly into lost time and money.
Preparation should be proportional. The higher the cost of misunderstanding, the more effort it deserves.
The rule I use now
I keep it simple.
If more than two people are involved, I confirm understanding.
Sometimes that is as informal as repeating back what I heard. For decisions that matter, it means a follow-up email or a short document that says, “This is how I understand this will work. Please correct anything that is off.”
Even silence has value. It establishes what was understood at the time.
Preparation is not about being perfect. It is about anchoring reality early enough that reasonable people stay aligned.
If more than two people are involved, I confirm understanding.
When the cost of being wrong goes up, I write it down.