The Romaine Lesson

September 4, 2026

3:37 pm

Dear Leah, Jack & Adam

I was fourteen years old when I got my first paying job.

This was before I launched my long and distinguished career as a dishwasher—the beginning of a journey that would eventually take me from washing dishes to owning my own restaurants.

My first paying job was as a bag boy at a small, independently owned grocery store in Reno.

It did not last long.

On my second day, the owner asked me to clean the back storeroom and dock area where deliveries were received and stored. That seemed simple enough. I wanted to do a good job, and I went to work.

Before continuing, I need to explain something about lettuce.

In the world in which I grew up, there was only one kind: iceberg. I had no idea there were other varieties of lettuce. No clue of “spring mix” or the other wonders available at Costco.

This was also almost sixty years ago. Romaine lettuce did not arrive washed, trimmed and neatly sealed inside a plastic bag. It arrived with nasty, inedible-looking outer leaves still attached, along with a nice dose of dirt.

The heads were tossed into a battered wooden crate made from moldy, rotting slats held together by rusty wire. Catching yourself on one of the wire’s sharp edges looked like an excellent way to earn a tetanus shot.

To my fourteen-year-old eyes, the entire thing looked like trash.

So I threw it out.

That was a mistake.

When the owner discovered what I had done, he came unglued. He tore into me in English and then continued in another language I could not understand.

I may not have understood all the words, but I understood the message.

I was stunned. I was embarrassed. Mostly, I was hurt.

I had not been fooling around. I had not been lazy. I had not ignored his instructions. I wanted to do a good job and had done what I sincerely believed he had asked me to do.

No one had explained that the filthy-looking contents of that broken-down crate were valuable merchandise. No one had shown me the difference between what should be thrown away and what should be saved.

The owner knew what romaine lettuce looked like. Its value was obvious to him. Because it was obvious to him, he assumed it should also have been obvious to me.

It wasn’t.

From that moment forward, it seemed I could do nothing right in his eyes. Going to work became miserable because of one mistake I never intended to make—and could easily have avoided with a few minutes of instruction.

At about the same time I applied at the grocery store, I had also submitted an application to Sambo’s. When Sambo’s called, I accepted the dishwashing job and left the grocery store behind.

As it turned out, that was a very good move.

But I never forgot the romaine lettuce.

Who Failed Whom?

When someone fails at a new task, we naturally focus on the person who made the mistake.

Why didn’t he listen?

Why didn’t she ask?

Why didn’t he use better judgment?

Sometimes those are fair questions. Students, employees and trainees have responsibilities, too. They must pay attention, make an honest effort and ask questions when they know they do not understand.

But what about the things they do not know that they do not know?

A beginner cannot ask a question about something he does not even realize is important.

That is where the teacher’s responsibility begins.

It is not enough to give someone an assignment and assume he sees what we see. It is not enough to explain something once and ask, “Do you understand?”

Most students—especially young ones—will nod yes. They may sincerely believe they understand. They may also be embarrassed to admit that they do not.

Telling someone what to do is not necessarily teaching him how to do it.

A good teacher must begin where the student is—not where the teacher assumes the student should be. That means explaining the desired outcome, demonstrating the process and pointing out the mistakes most likely to occur. It means encouraging questions and then watching the student perform the task before turning him loose.

Most importantly, it means remembering what it felt like not to know.

There is a name for our tendency to forget that others do not possess the knowledge we possess: the curse of knowledge.

Once we have done something hundreds of times, the individual steps disappear. What once required careful thought becomes automatic. We forget how much knowledge is hidden inside something we now consider simple.

To the grocery-store owner, recognizing a case of romaine was simple.

To the fourteen-year-old bag boy, it was not.

My Turn to Again Be the Teacher

Nearly sixty years later, I find myself on the other side of the lesson.

I am preparing to teach my grandson Jack about investing and, eventually, a different stock-options system than what I have used in the past. I want him to understand cash-secured puts, covered calls and, more importantly, the principles and risks behind them.

I cannot merely show Jack which buttons to push or which trades to make. If he imitates my actions without understanding the reasoning behind them, I have not taught him a system. I have taught him how to follow instructions.

My responsibility is to create a thorough outline that begins with the fundamentals and builds one idea upon another. I must explain not only what we do, but why we do it, when we should not do it and what can go wrong.

In other words, I must point out the “romaine”—the risks and distinctions Jack cannot recognize because he does not yet know they exist.

Before Jack ever risks a dollar, he should understand the risk. He should be able to explain a trade in his own words rather than simply repeat mine.

The objective is not to make money on every trade. It is to make intelligent decisions, control risk and learn from the mistakes every investor eventually makes.

There is another responsibility I have as his teacher: I must be certain that I understand the material well enough to teach it.

Teaching has a way of exposing the gaps in our own knowledge. It is easy to believe we understand something until we try to explain it clearly to someone else.

If I cannot make an idea understandable to Jack, I need to consider whether the problem is his comprehension—or my explanation.

The Lesson That Stayed With Me

The grocery-store owner and I both wanted the same outcome. He wanted the area cleaned properly, and I wanted to do the job properly. Neither of us wanted a case of romaine lettuce thrown into the trash.

Yet that is what happened because the desired outcome was clear to the teacher but not to the student.

Perhaps that is why the experience has stayed with me for almost sixty years. It taught me something that reaches well beyond lettuce, grocery stores or stock options.

Whenever we lead, manage, coach, parent or teach, our knowledge creates an obligation. We cannot expect beginners to know what experience has taught us unless we are willing to teach it to them.

That does not absolve the student of responsibility. Jack must listen, study, practice and ask questions. But as his teacher, I must go first.

My job is not to prevent him from ever making a mistake. That would be impossible—and probably undesirable. Mistakes are often part of learning.

My job is to make sure he never makes a mistake simply because I assumed he knew something I had never taught him.

Before blaming the student for getting it wrong, the teacher should ask whether he taught it right.

One Last Confession

There was one very pleasant part of my brief career at the grocery store.

The owner had a gorgeous daughter who was several years older than I was. She had two things I did not—a driver’s license and a car—and we went on several dates, with her picking me up.

Her father never knew.

I can only imagine how he would have reacted if he had discovered that the “romaine guy” was dating his daughter.

Smile…